Episode 429: Getting started with LLM Wikis

by [Scott](/content/author/scottmsclouditpro/ "Posts by Scott"/index.html) | Jun 4, 2026 | Podcast

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- Welcome to episode 429 - of the Microsoft Cloud IT Pro podcast recorded - live on 05/29/2026. - This is a show about Microsoft three sixty - five and Azure from the perspective of IT - pros and end users, where we discuss a - topic or recent news and how it relates - to you. - In this episode, Ben and Scott dig into - the concept of LLM wikis, specifically - building - personal knowledge management vault using Obsidian, - markdown, and AI tooling like Cloud Code, GitHub - Copilot CLI, and Copilot Cowork. - Scott walks through how he wired up Obsidian - Web Clipper and an RSS dashboard plugin to - feed articles into his vault automatically, - then had the LLM help build a Python - script to automate the ingestion workflow and cut - down on token usage. - Then he expands into how Copilot Cowork fits - into this workflow as a scheduling harness with - practical examples of using it to pull email - from an inbox daily, convert messages to markdown, - and generate a prioritized to do list. Let's - dive into the world of LLM wikis. - I have a theory. Windows? No. I mean, - yes. I run too much stuff. Yes. But - no. Well, I think we all run too - much stuff. I've noticed lately that and I - think I talked about this a couple weeks - ago, the whole I've got cotypist on my - Mac doing type ahead prediction - with with a locally downloaded model. - I've got - Type Whisper - running in the background with a model loaded - in case I just wanna do text dictation. - Like, I I I I was thinking about - it the other day. At any given time, - local model running, I probably have at least - four instances of the same model or a - similar model all loaded up because these apps - don't have, like, a common cache interface. Like, - they don't use, like, hugging face cache or - things like that. They all download, like, locally - into their packages and their directories. - So at least - for me, I think a lot of the - things that I'm running into lately are actually - resource contention. Like, I haven't materially changed my - workloads - or my workflows, but I have a bunch - of the bunch more of these apps running - in the background that I didn't have before. - I was trying to do a little bit - of an audit, and it's not driving, like, - crazy memory pressure, crazy CPU pressure. - But, like, when some of these models load - and unload, like, you've got, like, I don't - know, like, Gemma four sitting there ready to - go. It's like, oh, hey. I had four - gigs of RAM that just got evicted for - this thing over here, and then it's gotta - reload rapidly for this like, it I don't - know. That that would be my guess is - we're all running, like, so much, like, local - AI slops that we don't even know it. - So little of it we can control. Like, - I don't remember if we talked about this - or when this came out, but Google Chrome - now downloading, what, a four gig - LLM model in the background as part of - the browser? The Gemma model in the background. - Yep. Yep. So that same model is the - same model that I'm using in Cotypeist, which - is - similar to what I'm so so, like, I've - got this app called Type Whisper. - Anyhoo. So Type Whisper is one of the - dictation apps. But rather than using, like, Whisperflow - or Super Whisper, - everything - processed locally on device, you can choose, like, - hey. I I wanna use Parakeet. But the - cool thing it does is it does - live processing, like live transcription, - and then it does post processing as well, - which is nice. So you can do that - thing where you're just saying, hey. I'd like - to make a list. Number one is this. - Number two is this. Number three is this. - And, normally, that would just be a big - flat wall of text going across. But if - you post process it and it gets smarter, - it actually renders, like, one, two, three, and - four into a list, and that's the text - that is expressed that you just dictated. - But I was thinking about that one the - other day. I was like, oh, this is - getting slower and slower. And I went and - looked, and I turned on, like, the pre - integration, - the Run It thing, the post integration. - So that one had to get kicked to - the curb. It was nice, but - it was it was slowing things down for - sure. Yeah. - All these things. - You know what other things well, nope. I - won't go down that rabbit hole. We can - talk about other things. But speaking of more - things we're running, you and I both started - playing with something within the last I don't - know when you started. I started, like, a - week and a half ago - playing with more things to run on our - computers. - Yes. And this is not maybe we should - preface this. This is not specifically, I would - say, Microsoft or March - Microsoft three sixty five or Azure episode. However, - it incorporates into our work with Microsoft three - sixty five and Azure and how we're starting - to track some of our resources. I have - a tie in I have a tie in - for you there. I'm actually gonna yeah. Do - you have a tie in for me? Yep. - Okay. So if you're listening and you're like, - there's not gonna be a tie in, Scott - has a tie in. I don't know when - it's gonna drop. So you better listen to - the whole episode - to figure out the tie in. Stick around. - Okay. I've been playing around - and been watching all these just videos fly - by and articles fly by - around the concept - of LLM wikis - and - leveraging - LLMs - to - manage a wiki resource for you. And, specifically, - like, I've been doing this with Obsidian Vaults. - So Obsidian Vaults work very nicely here. They're - marked down plain text. LLMs process plain text - pretty darn well. They understand markdown pretty well. - It's kinda, like, a a de facto standard - for authoring these things. Right? All the skills, - agents, you write everything. Everything you do is - in markdown. - So an LLM Wiki, if - you have a compendium of knowledge that you - wanna put together, and that could be around - anything. It could be maybe around a topic - that you're researching. - So I don't know. Let's say you want - to - in M 365 Land, do you want to - go explore the current single the current licensing - constructs and compare this e SKU to this - business premium SKU or to this add on? - You could go and take, like, all those - pricing pages and all the documentation around that, - and you could put it in just a - big dumping ground of markdown, just a raw - source. And then you can have an LLM - reason across that data - and extract information around it. So understand - what was the source data that came with - it, maybe what are the general concepts around - it, entities, - all these different - sorts of things that are out there. - So Andrew Kapathy, who's kinda, like, one of - the original or or original researchers over at - OpenAI, - I believe he's also the person who coined - the term vibe coding. So he's kinda pretty - close to - it. He's been in this space for a - little bit? Been in this space for a - little bit. Was recently hired by Anthropic - post - getting out there and putting some of these - things out. But I'll have a link in - the show notes for everybody to - a gist - that he posted. - And - and this gist - is just an LLM Wiki. - So you go and kinda read through this - thing, and it's just llm-wiki.md. - And - the core idea - of this whole thing, like I said, is - you kinda have a big dumping ground. - You could think about it as maybe, like, - a folder that you called raw or you - called ingest, - you called it clippings, - something like that. - And what you do is you keep putting - articles in there, reference materials, - but you put it in as markdown. - So this whole thing just becomes - a big bank of markdown that's sitting out - there. And - you direct the LLM that anytime - a new thing shows up in my raw - directory - to reason over it and then extract that - information, extract entities, extract core concepts, tell me - what the source of it is, and put - it all together. - And this is the nice thing about something - like Obsidian. So Obsidian, a personal knowledge management - tool, PKM, - But Obsidian - does - Wiki style links, so you can have all - these things start to relate to each other. - And then you get the kinda graph based - views that that come along with that as - well. - So it takes almost nothing to wire it - up, first of all, to get started. So - it's pretty much go out and take this - gist, - and, yes, you need to have access to - some kind of LLM interface. Now that LLM - interface - could be hang with me here. Could be - quad code, could be Gemini CLI. Well, actually, - Gemini do CLI just went away. Anti anti - gravity, but there's also anti gravity CLI. - It could be GitHub Copilot CLI, codex, - whatever that is. Or if you have access - to, I don't know, say, Copilot Cowork - and in in and the Frontier agent because - you're in the Frontier program, - you can also run an LLM Wiki inside - of Copilot Coburg. Have you tried this? I'm - curious to see. Did and it works? Oh, - yeah. It opens up a whole interesting world - of possibilities here. Hold on. Stick with me. - Now you have me curious. - If you're managing file storage today, you've probably - felt the pressure. Refresh cycles are harder to - plan, costs and complexity are increasing, especially as - file workloads scale across regions. - That's why Microsoft customers trust Nasuni. As an - Azure certified software, - Nasuni provides a global file system designed for - enterprise scale environments, keeping file data secure, governed, - and accessible across Azure environments without added infrastructure - complexity. - It's the foundation to keep your unstructured data - stable even as your infrastructure evolves. To see - how much you could save while keeping your - initiatives on track, visit nasuni.com/tco. - That's nasuni.com/tco. - So let's talk about wiring all this up. - So so you basically go out the and - I've done a couple of these now, like, - and been kinda playing around. And you've been - playing around with one to build, like, a - basically, an Obsidian Vault for us around the - podcast. We can go back and say podcast - stuff in. It's fascinating. When did we talk - about this? On what date this happened? How - many times did we have this guest on? - And now you've got all that information in - text in one place. Show me all the - episodes where we talked about a specific topic. - Like, it's been really interesting. Go show me - what topics. We've pulled analytics into it. Go - show me what topics - tied into - analytics. Yeah. All the things. Go take this - gist, and you can literally copy and paste - it. I don't know if this is how - you started with the one that you worked - on. I'm curious how you started, and I'll - tell you how I started. So I took - this gist, and I copied and pasted it - straight into a CLI. I took it and - put it right into actually, you know what - I did? Because I wanted to do this, - like, a freeway that anybody could get started - with. So I did it in cloud code, - but I did it in cloud code tied - to - OpenRouter - and the free models in OpenRouter. So I - wasn't using a paid anthropic or cloud plan. - I wasn't using, like, pay per token. I - did all this stuff for free. You could - do it free for free with anti gravity - and things like that. It gets a little - harder to do free later, like, once the - vaults get a little bit bigger, but you - can totally start out Really hard to do - free later. But you can start out for - free. So you take this gist - and you put it into your LLM interface, - in this case, let me say, like, Claude - code. Just paste it straight into the terminal - and add a line at the end - that says, I want you to turn this - into - a context file for this vault, or, like, - I want you to create the second brain - for Scott that manages - everything he finds on the Internet wants to - read about later. Right? So you give it - a little bit of context. That's it. You - just put in that one little sentence at - the end, fire it off. It will create - a Claude in the case of Claude, it - will create a claude dot MD. You did - this in GitHub Copilot. It'll create you, like, - a Copilot instructions dot MD. I recommend doing - a claud dot MD as a context file, - and then you can just pull it from, - like, LLM to LLM because all the various - or, I guess, from agent to harness to - harness. Because you can take a claud dot - MD and use it in claud. You can - take a clog dot m d and use - it in anti gravity CLI. You can take - it using GitHub Copilot CI. So so that - context file becomes very portable. So you do - that, and that's where you - start. And then it's gonna create your, in - my case, a clog dot m d. - And in my Cloud dot md, I said, - okay. I'm gonna go do a little bit - of light iteration here on some of the - instructions - that that I want this thing to have, - right, and have for its context. - So that was I've got a root folder - called clippings. - I believe in the original gist, it's called, - like, raw. I don't know. It didn't sit - well with me. I was like, yeah. I'm - gonna put Obsidian clippings in here, like Obsidian - web clipper, so I call mine clippings. And - then I added a couple different Wiki directories, - so it automatically does one for it does, - like, Wiki slash sources, - entities, Wiki slash concepts. - I wanted Wiki slash people because I knew - I was gonna be putting things in there - about, like, the podcast and you and I, - so I wanted it to extract, like, Ben - and Scott or Ben and Scott together, - kinds of things. And then - all you do is go out and start - putting some markdown in that in my case, - my clippings directory. So the way I did - that is with Obsidian Web Clipper. So Obsidian - Web Clipper is available on every platform. It's - there on iOS and Android, so you can - use it on your mobile. It's there - on Edge and Chrome and Safari. - So any kind of thing that you end - up looking at on the web, all of - a sudden becomes a resource that you can - take and you could say, hey. I wanna - reason over this later in my Wiki. So - maybe you start small. Go grab, like, five - articles that you're interested in and put them - in there. And then all you do is, - say, ingest my clippings or ingest my raw - stuff, depending on how you set up that - directory and how you framed out your ingest - flow. And then it'll go, and it'll just - build this stuff out. I went and iterated - over mine a little bit. So I I - because I was using - Obsidian Web Clipper uses a template when it - loads data in, so I wanted - all my reasoned over data to also follow - a similar template. So it had a title, - a publish date, a create a date, tags, - reference resources, things like that. So I actually - created a template dot m d file, and - then I went back and I modified my - cloud context. And I said, okay. Hey. When - you ingest things, - make sure that the outputs - use this template. Super easy. Right? - So and you just start right there. - And - you start to get this little bit of, - like, this is interesting. - And then you start wondering what else you - can do with it. But it runs away - from you very fast because - you're ingesting text and maybe not just a - couple lines of text, but let's take that - m $3.65 pricing example. Right? I I wanna - build something that can go reason over that. - You're going and grabbing every pricing page, potentially - the images off those pages and doing, like, - OCR and computer vision over them. So it's - pages and hundreds of kilobytes of text that - you're putting in, which is heavy on the - token side, both on input and output. Yes. - So this is where something like maybe like - OpenRouter and a free solution - starts to run away from you a little - bit. So I did OpenRouter. I got by - with maybe, like, my first 10 clippings in - doing this. And when I ran out of - stuff in OpenRouter, I was like, well, I - just wanna see, like, how far I can - push this free thing. So I went over - to Anti Gravity, which was recently released, and - that uses Gemini and Gemini Flash under the - hood. Let me tell you, anti gravity burns - some tokens. I think I burned through all - my tokens in anti gravity, like, on my - after, like, my first two ingests, - and it burned them for, like, six days. - You have no more usage for the next - six days. - But what you do there is - LLMs, - they really like to overthink things. Right? And - so they'll start to do things like, you'll - notice these patterns when, in my case, I - was saying ingest my clippings. - I noticed every single time, no matter - which harness I was using or which model - I was using, all of them were doing - similar things. They would say, like, oh, well, - I need to go figure out how to - list your ingest directory. So every single one - was saying, thinking thinking thinking. Okay. I'm gonna - list your your ingest directory. So I'm gonna - go do, like, an lsstar.md - kinda thing. You can automate all that stuff. - You don't have to have the LLM do - it. So the trick is you come back - or you or you don't have to harness - and the model do it. So you come - back and you say, hey. I've got this - context file now, and we've come up with - a workflow. How can I automate this workflow? - Can we make parts of this workflow scriptable? - Just ask the question. - And in my case, like, the one that - I've been really living in, I called it - my brain bank. I said, hey. This is - Scott's second brain. - So it created me a Python script called - brain dot p y. - And off brain dot p y, it created - a number of subarguments. - So it took my ingest flow, and after, - like, three ingests and it had all the - context, and it kinda knew what it was - doing repeatedly, it built me a brain dot - p y, - slash - ingest or, like, dash ingest command. And then - I said, oh, hey. You're doing this. Why - don't you build me, like, a like a - linting command to make sure that you're always - matching up to my template? Because I used - to use spinning a lot of tokens trying - to go back and read that template dot - MD and then get it back rear. So - it made me brain dot p y lint, - made me brain dot p y organize, - made me brain dot p y, - clean up any old clippings, maybe, like, organize - them into subfolders, - things like that, link them back to sources. - So over time, I've been on this journey - of saying, hey. All the stuff that you're - doing that I see you're repeating yourself doing, - but it's you as, like, the LLM thinking - about it, just go slam that in my - script. Just keep putting it in there, putting - it in there, putting it in there. So - then you're not burning all the tokens. Like, - it doesn't have to and then you tell - it, go update my context file. So if - I look at how I started from, let's - say, like, my ingest flow in my claw.md, - originally, - that was - something like - go - it said, hey. Your vault structure for clippings, - things like that. So my operations for ingest - was, like, step one, go list this directory. - Now step one has turned into research. - Run Python three scripts - brain dot p y scan ingest, - and then - take that output and then go check this. - Go run brain dot p y again, get - this list output, compare those two things. So - that way, it doesn't have to, you know, - start immediately every single time enumerating a whole - directory and running over it - and being very heavy. So you can start - to very quickly, like, drive it down into, - like, scriptability and less and that was the - part that I kind of enjoyed. Right? Like, - IT pro hat. Like, hey. Let's go get - this going. I think you were doing some - PowerShell scripts and things on your side, - on the Windows side. But you just kinda - keep going down that path, going down that - path, going down that path. And then - because you're doing this all in an Obsidian - markdown style, now you go and open it - up in Obsidian. Just go open your project - directory and what you're doing in there, - and you'll get access to - all the features of Obsidian. So that includes - tagging. It includes searching. It includes the PKM - with the knowledge graph. - Obsidian's - like a canonical markdown editor. It's really darn - good at it. You and I had been - chatting about one of the ways we do - research for the podcast is by following a - bunch of RSS feeds. What's the easiest way - to ingest the RSS feed? Well, I've been - going through, like, Feedly or Reader and opening - it in a website and then hitting the - Obsidian web clipper and doing things like that. - There's this really cool plugin for Obsidian called - RSS dashboard where you can just follow an - RSS feed. And as you follow, it's - it and now because it's an Obsidian vault - and it's just marked down, and I can - have it in my OneDrive - or you can have it in your Google - Drive or whatever, - It's actually kinda like Feedly, and that suddenly - it's a cloud sync service. Right? It's following - you around in your configuration. - But RSS dashboard is really cool because every - feed article that comes through, you can just - click a red or an unread button to - to flag it or get rid of it. - But if you click save on it, it - has a really nifty templating system. So I - was able to take my template dot m - d, which, again, was just based on an - Obsidian web clipper kinda default template. But I - was able to make that my template for - RSS dashboard - and have it every time I saved an - article from RSS, - it saves it as markdown over in my - clippings directory automatically. Right? Like like like, yes, - I have to click save on the article, - but it gives me this kind of, like, - one stop shop - ingest flow to get those things kind kinda - through. - So really interesting way to go and kind - of reason over personal data, - really any kind of project that you're doing. - I I would recommend constraining this stuff. Think - about it maybe like, if you're coming from, - like, - if you're coming from Claude Land, maybe think - about it as, like, project based. Or if - you're coming from, like, the cowork side of - the house, - maybe you use, like, notebooks in cowork, things - like that. Like, let me group these documents - together so that I can go do some - research on them kinda thing. I do find - that, like, I I I think that they - do a lot better when it's kind of - same knowledge area to reason over rather than - having a whole bunch of different things there. - Because, again, you could see eventually, you get - back to, like, really heavy context windows and - and things like that that happen along the - way. But so let's talk about now hey. - Great. You did this in our RSS feed. - Or, alright. You told me that, like, I - could dig an article from the web, and - I can clip it in here. Sure. Whatever. - Copilot cowork. - And Copilot cowork, - the Frontier agent. So the Frontier agent that's - out there has custom skills. So you can - take - the very same - kind of flow - around - having a context, - in this case, like, the claw.md. - You can actually take everything that's in your - claw.md - and put it in a skill.md - inside Cowork. And you go, oh, well, that's - not helpful. Like, you're all you're doing is - telling me that I'm just using co work - to process my clippings and things like that. - I actually recommend going a step further. Create - yourself skills - that do things like - take take the emails in my inbox - and - save them into my ingest directory as markdown, - and it'll take all your emails for that - day. Like, I've I've somebody on my team - did this, and it's super cool. He has - it so Cowork - looks at his inbox every day. It takes - all the items in his inbox, - and it turns them into markdown. And then - once they've been turned into markdown, they just - get marked as read and archived because now - they're sitting over in markdown, right, just in - in his OneDrive. - And then he runs an LLM Wiki style - kinda thing on top of it to - extract what are his priorities for the day. - Maybe he got an email from me or - he got an email from a coworker or - he's got specific projects that he flagged, things - like that. And then he has this set - of skills that iterate over it, and I've - been playing with this too. It actually works - really darn well. - You can take those things, - reason over them, create your own personal knowledge - management vault just inside of your OneDrive for - business. Obsidian's free. You're effectively getting cloud sync - because you got markdowns. So if you're in, - like, you're in, like, oh, hey. I need - to get to this on my work phone - or things like that, run Obsidian on your - work phone. Just point it at your One - OneDrive directory. It's okay. - It it'll all work. And then you get - to start thinking about, like, richer functionality within - Obsidian. So this was the thing that unlocked - it for me in the Copilot Cowork scenario - was not just, like, reason over what happened - today and maybe give me a, like, a - table. Like, tell me, like, the top three - people who emailed me or things like that. - But Obsidian has plugins - and - Wiki style markdown for things like task lists. - So you can actually have it, like, take - if you got 50 emails last night and - you walk in the morning, - you can have it take those 50 emails, - reason over them, do whatever it needs to - do, and create, like, your to do list - for the day. And then you actually get, - like, a clickable to do list, not in - Planner or anything like that. Like, you can - just put it in Obsidian and have it - there and ready to go, and it's very, - very portable. And because Copilot Cowork - has access to, like, your team's messages and - your inbox and all these things, You can - have it, like, mark your email as read - and archive it. You can have it organize - your email for it as it's doing this - extraction and pushing things out. You might have - it like, in my case, I get a - lot of, like, junk mail and newsletters. - So no matter how hard I try and - filter those things out, some always make it - into my inbox or my inbox other things - like that. So I can have that flow - come back and - clean that up as well. Right? Like, say, - hey. It notices there's a newsletter there. I - don't have to worry about creating a custom - rule for it anymore. I've just got Cowork - dumping that stuff off to a newsletter directory. - And then part of my ingest flow, because - it's still ingesting those things into my Wiki, - is telling me what newsletters I got that - day just in case there was something there - that I wanted to read or or things - like that. So you can absolutely take this - concept - and pull it over to - the world of things like Copilot, Cowork, - and all of that. Or if you wanted - to yeah. I've seen a couple folks do - this with - just something like GitHub Copilot and WorkIQ - or - Copilot - CLI, - Claude with the, like, the WorkIQ MCP and - things like that as well. The problem with - the WorkIQ MCP is I've had way better - luck with, like, Copilot coworkers saying, actually, like, - move this message from here to here. WorkIQ - is, like, glorified graph reader. So you end - up in some weird throttling scenarios and other - things that CoPilot CoWorks seems to generally skirt - around. - You're out of time. CoPilot needs to be - deployed ASAP, but is your tenant really ready - for it? Years of data, permissions, and users - lurk in its shadows, ready to be exposed - by AI. - Sharegate Protect sees it all, so you can - find the exposure risks, fix them fast, and - deploy AI with confidence. - Microsoft - three sixty five governance. We got this. Learn - more at sharegate.com/governance. - Have you tried it the other way where - once you have your Obsidian Vault and you're - syncing it down with OneDrive, - you save articles - into your raw folder in OneDrive - and have Copilot Cowork actually ingest all the - stuff you're saving locally - Yeah. And then just use - so you use Copilot Cowork for everything. Yes. - Use Copilot Cowork as the harness. As the - LLM, the harness. Yep. Where I said, hey. - When we started in the beginning, I said, - hey. I was doing this in Claude with - open router. Replace Claude and open router with - CoPilot CoWork, - the Frontier agent. And then you just switch - from doing everything in the CLI to going - into Cowork and starting - conversations - in Cowork in the browser for all the - ingesting and - processing that raw data. Yes to starting. But - once you're like - let's do, like, the crawl, walk, run thing. - So I think crawl is us walking in - there and typing all the time and kicking - these things off. Once you have a refined - workflow, Copilot Cowork lets you schedule this stuff. - And if you're structuring it in a way - where you're being principled, like in my case, - with my local - vault here that I was using for, like, - ingesting RSS feed articles and things like that. - So in that one, - I'm sitting in, - I'm sitting in a world of that workflow. - That's really like an on demand thing. Right? - Like, I don't always have clippings in there. - I don't need it to be looking once - an hour or anything like that. Emails are - coming in all day. So I can have - that skill - run every hour and do that ingest - hourly. So I don't even have to live - in Outlook. I can just go live in - Obsidian. It's kinda kinda kinda nice. The other - thing too is - I talked about the concept of, like, taking - some of the heavier operations and going and - putting those in scripts and things like that, - you can still do that in co work - because co work can execute local flows. - Or the other approach that you could take - would be - to really think about maybe rather than, like, - scripts and functions - to just skills and functions. - So having kind of the building blocks sitting - inside of composable skills - that then you can stack per scheduled task - or whatever you wanna do on on on - the CoWork side. Interesting. There was another question - I was gonna ask about this, and I - can't remember what it was. Adjusting, scheduling, - oh, - have you compared - so this has always been a debate too, - right, is how - Copilot does in terms of responses versus something - like Claude or - any of those. Have you compared the LLM - that gets built or the Wiki that gets - built by Cowork versus a Wiki that gets - built by Claude - just to see - side by side - how I know CoWork is different because a - lot of it I don't know that there's - as many system prompts injected into - CoWork - given that things like DLP don't even work - in it versus the normal Copilot. I feel - like the system prompts are are still there. - You do have - depending on your tenant configuration, - you do have model selection or at least - model I would call it model selection light. - Like, in my case, I can choose a - couple variants of GPT - and a couple - anthropic models. - You do get much richer model selection when - you're over on a CLI - or, like, a GitHub Copilot chat kind of - experience. - But the nice thing is - you're talking one vault that just lives out - or a series of vaults. It's all just - text, right, that that lives out here in - a side card. So you're not restricted - to - just Copilot co work or just GitHub Copilot - CLI. You could augment this. Yeah. You can - augment this and kind of go in. So, - like, for me, I tend to live in - the terminal. - So I'm not going in, like, during the - day. I don't actually, like, worry about going - into cowork and to ever typing a question - in a cowork. Cowork's a harness for me - to go and run skills, do the extraction, - kinda Right. Compound value and compound knowledge over - the course of a day, a week, a - month, things like that. - But when I'm going in and I'm going - across - and I'm saying, hey. Look at this stuff. - I'm typically doing that through - the CLI or, like, just just, like, GitHub - Copilot chat, things like that. Now the other - interesting thing that I found here is - it starts to make the data that you - extract - a little bit more deterministic. - So - it's a weird black box when you go - into Copilot - or you go into co Copilot cowork, and - you say, take a look at all my - emails from today - and - extract StackRank my top three priorities. Right? You - never know. Is it actually gonna search all - my emails for the day? What is what - does it consider an email for a day? - Is it only looking at my inbox? Is - it looking at my inbox plus my inbox - other? In my case, I run inbox inbox - other, and I do the Scott Hanselman inbox - cc things. I got I really got three - inboxes. Right? So I never know, like, what - it's looking at and what it's doing. But - by extracting the data and pulling it out - and sidecarring it, when I say go look - at today, today is a very real thing. - It's a discrete set of data that sits - out there and is available. - And and I found that accuracy has kind - of improved there. I have, like, far more - confidence that it - can can do what it needs to do. - Have you run into - anything, - like, using co work to your point earlier - about it can be expensive? Sorry. I think - I have a meeting up. - This episode is brought to you by Trusted - Tech. If you're managing Microsoft three sixty five, - you already know licensing isn't simple. - E three versus e five, the brand new - e seven licenses, - Copilot security bundles, and with price changes coming - in July - 2026, the stakes are getting higher. Trusted Tech - helps IT leaders make sense of their Microsoft - three sixty five environment with a free licensing - consultation. - Their engineers analyze what you're licensed for and - what you're actually using and where you can - optimize, whether that means consolidating - security tools, preparing for Copilot, or eliminating wasted - spend. Plus, they offer proactive - and reactive support, which has been awarded yet - another solution partner designation from Microsoft - for support services. - If you want a clear, data backed plan - that has helped over 7,500 - subscribing - customers - save up to 20% on Microsoft three sixty - five before your next renewal, - visit trustedtech.team/mscloudprom365 - and schedule your free consultation - today. - Okay. I have a meeting at four. Where - you run into some of that quotas and - stuff? Like, I did mine. I did the - podcast. It was granted, it was 400 and, - what, 28 episodes. - I had all the transcripts, - so it was some big text documents, like - thirty minutes of talking turns into a lot - of text. And I was using - Claude, and I was doing the - Claude Max - five x. So this is the $100 a - month plan on Claude, and you get, like, - a five hour quota. When I started ingesting - podcast episodes, - and even I experienced this even. I tried - to put a bunch of stuff in Python, - do as much as I could still burn - through my five hours of quota in, like, - twelve minutes. - It was crazy how quick I burned through - tokens. - Did you - how much did you test cohort to see - if during the ingest or have you noticed - do you start getting - throttled or limited where it's like, okay. Go - use something else to your point for that - initial if you're gonna ingest a bunch of - stuff, or do you have to start being - careful about how often or how much you're - ingesting yet? - I can imagine it might you might start - getting limits eventually. Yes. You do have to - be careful. So so I think the - interesting thing here and the callout that I - keep coming back to is - and you're nailing it, is the context windows - and the token usage, both on inputs and - output, does get very heavy. - So - I I think this is someplace - where I would be inclined to think that - folks in our community would be able to - wrangle this pretty well given kind of their - backgrounds as - developers, - IT pros, more experienced end users. You have - to think a little bit like that scriptwriter - or that programmer. - So your job isn't just - to have a big context window that you're - firing off every single time. It's kinda like - ruthless optimization. - Get this down to here. Get this down - to here. Get this down to here. So - so what I realized was - when I went and did this on my - own, just kinda same thing over in, like, - Claude with open router, blah blah blah, and - I too had to switch over to my - paid Claude plan. Don't get me wrong. Like, - it it it didn't get me all the - way there. It's expensive. - I think one of the reasons it didn't - get me all there all the way there - because I didn't think about, like, a programmer - from the start. - And I I just kind of approached as, - like, the spirit of what mister Kabathea put - out there of, hey. Here's an LL on - Wiki, and you give it a simple set - of instructions, - which I I recognize a lot of these - folks who are putting these things out there. - They do live in a world of unlimited - tokens. Right? They work at Anthropic, and they - work at OpenAI - and things like that, and not all of - us have that luxury. - So you do have to kinda think about - that and start to refine things. I have - noticed - I I will say so I I mentioned - I've built a couple of these now. - So the first one, I really went down - that refine refine path. Now I have this - really solid - templated thing that already has the scripts from - day zero. So when it starts, - it's already starting in a more optimized state - rather than having to start from scratch every - single time. So you kinda carry that knowledge - forward, and that helped me a whole bunch - when I was thinking about the Copilot Cowork - side of it. And then it really started - to click for me when I saw one - of my coworkers - who was in the mixed modality of Copilot - Cowork - for things like email extraction, - but then they were on they were still - on the CLI and doing, like, native Obsidian - Web Clipper things and all that stuff. Right? - Like, they were kinda using multiple tools - all to have the data coalesced - into - a single source. - And, effectively, like - I mean, Obsidian's markdown, you can make it - look pretty, all those things. It has checkboxes - and tables, and you can put images in. - Like, is it as rich text as something - like OneNote is? Absolutely not. But when you - start to get this flexibility of having, like, - multiple ingest points, multiple output points, - and kind of the capabilities that come with - the plugins in Obsidian, - all for free, - it kinda just works. Right? It's a very - it's it's a very cool system. - And once you start to go down this - path, like, for me, I, like, I'm one - of those people, like, I hate to admit - it, but I can live in email. Right? - It's pretty easy to get 50 emails overnight, - then you just get stuck in it. You're - like, I don't really live in email as - much anymore. - Email has just turned into I've got this - other thing over here that's taking a look - at it. I had to refine it. I - had to take some time put time into - automating that process and - automating myself out of that job of living - in email, - but it - it helps on the other side. And I - think, like like, the thing that really, like, - kicked my butt was - this team teammate of mine who, - he lives in the chaos that I live - in - and the rest of our team lives in. - And he has this - super awesome - I hesitate to call it a demo because - he showed his real workflow for how he - manages all this stuff. He put it all - in a Git repo for us so we - could just pick up skills - and run with them. And he's one of - the first people that I'd seen who successfully, - like, - navigated - inbox zero - at Microsoft - without feeling like he was missing out on - something or feeling like you're not just doing, - like, the - control a, delete, or control a, archive, and - I'll hope they email me again tomorrow - kind of thing. - It it was also very interesting to me - to see the way that - this individual managed tasks in Obsidian, like, how - they weren't trying, like, a forcing function of, - like I've seen a lot of people use, - like, Copilot cowork and and integrate it with - Planner and things like that. They put together - their Kanban boards, and I I feel like - the process runs away from you. It gets - a little too fancy at some point. I - I think - we're much better served when stuff becomes nice, - simple. Like, here's a to do list. I've - got a checkbox. I check that thing off, - and it gets a strike through it. - And you get to feel good about that. - Like like, there's a little there's a little - rush of endorphins, - right, when you when you check that checkbox - and have that - sense of accomplishment that's out there. And because - this stuff is all text, you can do - things because, again, LLM Wiki style Obsidian, you - don't even have to check the checkbox. - I would imagine I haven't done this, but - I think this would be totally doable. Like, - I could go into GitHub Copilot CLI, and - I could say, - my my task for today - to email Jack is done. Can you just - check that off for me? And I would - go check it off for me. Right? I - don't have to - worry about actually even opening a vault or - looking at anything and - running that way. - Like, the the elephant in the room, which - I don't think anybody could address at this - point, - and, I mean, it it is there, is - your like, this stuff's all plain text. Right? - You are extracting it out and and kinda - putting it down to your, - your OneDrive and things like that. So stuff - like - IRM and MIP - really don't apply to markdown files. - So it certainly, like, don't break, - like, organizational constraints - or things like that. Pay attention to sensitivity - labels and all that stuff. Those types of - things? Well, Cowork doesn't pay attention to sensitivity - labels, so why should I? No. It does. - It can't read any MIP file. It's kinda - useless. So Yeah. If you're actually encrypting it. - Yeah. No. I'm gonna have to play with - this too because I'm doing all my meeting - I'm doing this with meeting notes, and I - created a Wiki for meeting notes. So, like, - meeting notes out of people, so I have, - like, people and topic and all of that - meeting notes. It would be really interesting to - take this into Cowork and actually, like, now - I can correlate meeting notes with emails, with - all of that. How about just meeting notes, - but meeting notes with transcripts? So go create - yourself a skill, load it into co work, - have it extract your meetings transcripts - from the prior day, ingest them in, and - then go run this over them. Right? Like - like, that's just a super Yeah. I see. - I'm already doing that part of it. Now - we just have to tie in the emails. - So it is. This it's it is definitely - interesting to start tying all this together. - Again, those are the two I've done is - emails. I did the podcast. - I've started to do just references, but I'm - gonna go play with blog posts and figure - out how to incorporate some of that other - stuff in with Cowork. But I just gotta - chat that my other meetings started. World of - possibilities here. Absolutely. So I'll put a bunch - of links in the show notes to kinda - the original gist and things that came out - here. Yeah. There's some good YouTube videos out - there we can post in the show notes - too, - walking through how different people have done this - and showing how some of it's set up - too. I haven't seen a lot of people - who have done - Copilot Cowork. There's a lot of Claude. There's - a lot of good reference implementations. - Yeah. Claude's out there. Super easy to, like, - Google, Bing, DuckDuckGo, Kagi, whatever your search engine - choices. - I will put out some examples for those - who are in the Microsoft ecosystem. - So So there's a pretty good one out - here that I'll put in. It's called the - GitHub Copilot Wiki, an AI powered second brain - template. - So it that's it's kinda like a forkable - template that you can start with. So it - already has the wiki structure. - It has a template dot m d. - It has a lot of these constructs, right, - that I talked about here, and it can - just kinda, like, bootstrap you if you didn't - want to - if you didn't wanna start start for yourself - links a template too. So we'll drop those - in the show notes. Cool. Perfect. Well, thanks, - Scott. Yeah. Enjoy your weekend, and I'm gonna - go jump on my next meeting. Perfect. Me - too. - Life life is on. Alright. Thanks, Ben. Alright. - We'll talk to you next time. Yep. Bye - bye, Scott. - If you enjoyed the podcast, go leave us - a five star rating in iTunes. It helps - to get the word out so more IT - pros can learn about Office three sixty five - and Azure. - If you have any questions you want us - to address on the show or feedback about - the show, feel free to reach out via - our website, Twitter, or Facebook. - Thanks again for listening, and have a great - day.

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Episode 429: Getting started with LLM Wikis

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Welcome to Episode 429 of the Microsoft Cloud IT Pro Podcast. In this episode, Scott and Ben dig into the concept of LLM wikis, specifically building personal knowledge management vaults using Obsidian, markdown, and AI tooling like Claude Code, GitHub Copilot CLI, and Copilot Cowork. The core idea comes from a gist by Andrej Karpathy and involves creating a structured folder of markdown clippings that an LLM can reason over to extract entities, concepts, and sources, building a searchable, graph-linked knowledge base over time. Scott walks through how he wired up Obsidian Web Clipper and an RSS Dashboard plugin to feed articles into his vault automatically, then had the LLM help build a Python script to automate the ingest workflow and cut down on token usage.

The conversation expands into how Copilot Cowork fits into this workflow as a scheduling harness, with practical examples of using it to pull email from an inbox daily, convert messages to markdown, and generate a prioritized to-do list. Ben shares how he applied the same approach to 428 episodes of podcast transcripts, and both hosts note that token costs can run high fast without some upfront thinking about optimization. Scott closes with a reminder that pulling data into plain markdown sidecars outside of IRM and sensitivity label protections means teams should stay mindful of organizational data policies.

Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options.

Show Notes

• LLM Wiki
• GitHub Copilot Wiki: An AI-Powered Second Brain Template
• Karpathy’s LLM Knowledge Base Wiki for Enterprise
• Karpathy’s LLM Wiki? No Code with Claude or Github Copilot!
• sametbrr/llm-wiki-manager

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Episode 428: Migrating Group Policy to Microsoft Intune

by [Scott](/content/author/scottmsclouditpro/ "Posts by Scott"/index.html) | May 21, 2026 | Podcast

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Episode 428: Migrating Group Policy to Microsoft Intune

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Welcome to Episode 428 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott unlock the secrets to modernizing your IT management by ditching pesky on-prem GPOs and embracing the future with Intune. They discuss how savvy IT pros are migrating thousands of GPOs into clean, manageable cloud policies. Dive into real-world workflows: from exporting and analyzing legacy GPOs with AI tools, to recreating policies in Entra ID, and finally decommissioning AD. You’ll discover how to think through the migration, avoid common pitfalls like leftover legacy configs, and implement a phased migration that minimizes disruption.

Show Notes

• DiskPrices.com
• These HDD prices are getting crazy. An increase of 96.4% in 1 month for the same 26TB drive. $279.99 a month ago to $549.99 today. Where are we buying hard drives now?
• Import and analyze your on-premises GPOs using Group Policy analytics in Microsoft Intune
• Microsoft Copilot in Intune
• Policy CSP
• Use the Intune settings catalog to configure settings
• Use the Intune properties catalog to get device hardware properties
• Create a Settings Catalog policy using your imported GPOs in Microsoft Intune

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Episode 427: Copilot Cowork Hands-On Experiences

by [Scott](/content/author/scottmsclouditpro/ "Posts by Scott"/index.html) | May 7, 2026 | Podcast

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Welcome to episode 427 of the Microsoft Cloud IT Pro podcast, recorded live on 04/30/2026. This is a show about Microsoft three sixty five and Azure from the perspective of IT pros and end users, where we discuss a topic or recent news and how it relates to you. In this episode, Ben and Scott open with a quick peek at Merrill's latest project, Yako, a browser extension to make navigating to your Microsoft three sixty five services quicker. Then they move into an extended follow-up on Copilot CoWork and some of the recent hands on hardships, artifact management, and integration with Anthropic, including a potential security risk related to sensitive data. So we're trying something new today, Scott. We are recording in Riverside so that we can maybe try to do some shorts. And who knows? Maybe we'll even broadcast live to LinkedIn and YouTube here in the future. Start incorporating some video. I've been told we should do actually, nobody's told me we should do video. The SEO people and everybody that grows podcasts tell me we should do video. Our AI overlords are back. They're just gonna have us do this until we're done with it. We've tried it before and then quit. I don't know, Scott. Maybe this time it'll stick. Maybe Riverside will make it easier. The AI has definitely made some of it. It's compelling stuff here. We we should probably get into, get get into our topic of the day. Yeah. Before we get into our topic, though, did you see Merrill's latest invention development project, etcetera? I have not. Okay. So go into whatever browser you use and go search for Yako, y a c o, or you can go to the website, get Yako, yaya, not c,yako,.com. I'll send you a link. I should've done this earlier because now I don't know where our Teams chat is. It is a browser extension that changes the home page of your browser. So he created it for Edge, Chrome, and Firefox. And now when you click a new tab in your browser, it gives you the like, it gives you a bunch of links that you can customize to whatever Office March well, Microsoft Cloud, really, Cloud links. So, like, mine, I hit a new tab, and I can pick OneDrive, Outlook, Loop, Copilot, Azure, Sentinel, Intune, Admin Center, all the different things. Then I can customize what I want on there. That's a nifty one. I can see how that would be helpful in a work context. I I don't know that I'd use it too much on my personal one, but def definitely on the work side of things. Yeah. I don't know that it's a personal one, but for work and, frankly, I don't really care about the news that normally pops up, and I know you can tweak it. And I don't really wanna set portal to office.com since that doesn't even get me to my apps anymore. It just gets me to Copilot chat. Admin.microsoft.com. Yeah. Or use, like, Copilot or quad or chat GPT or whatever and pin pin that one in there. I use the Copilot one on personal edge. Like, it tends to do pretty good. The only thing I hate about it is it uses Bing as the search engine. So if it can't, like, auto resolve to yako.com or get yako.com, it fires me off into Bing. Then I'm left with Bing search results. I don't I don't need Bing search results in my life. But yeah. No. Cool. I'll have to try this one out, and we'll put a link to gityako.com. G, yeah, getyako.com by Merrill. Nice one. Again, probably more for work than personal because it doesn't have any of the well, I can't remember. Does it have personal m three sixty five stuff in there? I would have to go look. Oh, you can also switch it from classic icons. I know we've talked about these before if you want a new tab to be like msportals.io or cmd.ms. Yeah. I did see that. So so that's another project that Merrill has out there with the with the short links and things like that. So that that could be a helpful one as well. Oh, it does have some of the consumer stuff. So if you are just at home and you wanna do consumer stuff in it, you can do that as well. You're out of time. Copilot needs to be deployed ASAP, but is your tenant really ready for it? Years of data, permissions, and users lurk in its shadows, ready to be exposed by AI. Sharegate Protect sees it all, so you can find the exposure risks, fix them fast, and deploy AI with confidence. Microsoft three sixty five governance. We got this. Learn more at sharegate.com/governance. Now we can get into our topic if you want. That was just a nifty thing that popped up in my feed the other day and I was been playing with. And maybe a little bit of follow-up. So last time we recorded, we kinda talked about the co work situation and Claude co work and CoPilot co work. And that definitely sent me down the path of, like, hey. Let me play a little bit more with CoPilot CoWork and kinda see where I could see how far I could get with some of the stuff we had talked about, like, maybe, like, the limitations of not being able to interact with your local desktop or or local resources, all that kind of stuff. So custom skills in Copilot Cowork are kind of broken right now. They're they're a little frustrating to to work with along the way. Definitely ran into the I'm very used to kinda prompting LLMs at this point or a lot of these tools with questions to kinda help me refine a prompt and come up with a way to generate, like, the artifacts that you want. So rather than saying go in and build me this, it's ask me a couple questions that are gonna help. Like, here's the outcome I wanna achieve. So in, like, in the case of, say, like, Claude Code or GitHub Copilot CLI, things like that, or GitHub Copilot chat, it's very easy to go in and say, I would like to build a new skill that does blah blah blah. And then it will actually kinda ask you a couple questions, and it will frame out the markdown for you, and it will write it to the right directory for you, like, to the point where it where you can do install to just my local session or install this globally kinda thing. And Copilot Coburg kinda surprised me. It walked me in and it said, oh, you wanna create a new skill. This is great. I'll go create a new skill for you. What do you wanna call it? What do you want the description to be? And I already had all this markdown and stuff that I wanted to pump into it. So boom. Great. Click the go button, does its cheeky. I'm thinking about it and thinking and spinning the gears. And then it spits out an output for me, which is a skill quality report. So it gave me this very nice HTML file that said, I created your skill, and your skill has an 83, 84% score or whatever it is. Right? So it gave me this, like, nice dashboard that said, your skill is gonna be awesome and it passes. I don't know what it passes because it just generated me an HTML file that said my my my skill was really good. But it also hallucinated that it had ever created the skill. So it never actually went and created, like, the skill dot m d and put it in the right folder in my OneDrive and did all that stuff. So great that it told me my skill was awesome, and it generated a report that my skill was awesome. Not so great that it didn't actually generate my skill. It didn't actually create a skill? Maybe it did. Maybe it's in someone else's OneDrive. That was number one. Number two is actually finally did get that skill created. Had to go do it manually, provision it into my OneDrive. It's a little weird in the cowork frontier agent today because sometimes it sees your skills in your OneDrive, and sometimes it does not. So when you go and you do, like, slash commands in Copilot co work, you're presented with an interface of, like, people, skills, files, and these various things. So the very first time I created this skill, I went out there and I went and I just popped it into my OneDrive. I closed Copilot down, just the Copilot m three sixty five Copilot app, which I was just happened to be using, but it's that web wrapper. Loaded it back up, slash command. Oh, look. There's my skill. That's awesome. Like, didn't need to navigate around a bunch or do anything. Came back and so I did a quick chat with it just to see, like, okay. Does this work? Cool. It generated some output. Looks like it did the right thing that I wanted it to do. So then I spun up a new chat. Now mind you, I didn't close m three sixty five chat down. I didn't change anything in my OneDrive. Okay. Just a new session. Just a new chat session because now I'm like, oh, cool. This still works. Let me actually go, like, fire off and do what I wanted to do. New chat? I don't know about your skill. I've never seen this thing in the world, like, in my life. I I don't know what it is and what's going on. So you do the slash command, not there in the slash command. You actually knit browse straight over to the skills tab from the slash command, not there. But you I was able to say in my co work session, do you know about this skill? Can you please, like, use it when I put this what I wanna do in here? So it it eventually kinda wrangled itself. So I think that skills experience has a little bit of refinement to do, maybe something for folks to watch out for. The other thing that's been, I think, kind of getting on my nerves a little bit is as you're in Copilot Cowork and you're generating artifacts, so like in that very first run where it generated a skill report for me or or what I was trying to do with this custom skill that I spun out, it was ultimately spitting out some HTML files and some markdown for me as, like, an output. So those all go into your session, and you see them kind of in the Cowork, in in the co work frontier agent interface, like, it has a little bit of a different interface than the chat interface, and it says, here's your inputs, here's your outputs, blah blah blah. Good luck because well, at least in whatever build I'm on that's pushed out today or as of today, you cannot, like, right click those things and open in OneDrive. There is a little drop down like like an ellipsis there to click it and say open in OneDrive. Doesn't work for me at all. So then you gotta go manually browse your OneDrive. So you go into your OneDrive, you go into your documents folder, you go into your co work folder. And then in your co work folder, well, you've got skills, which is where you load your custom skill, and then you've got sessions. And then each session is a GUID. So if you do multiple chats per day or anything more than, like, one or two with co work for the day, now you have these folders that are just GUIDs. And, hopefully, you can figure out by timestamp which one is the right folder because you have to browse into that GUID folder, and then there's an outputs folder in there, and then that's where your artifacts end up. So it's a it's got some rough edges and some friction today. And it immediately drew drove me back to GitHub Copilot CLI, at least, because I I have access to that or GitHub Copilot, I guess. And the other thing is I was hoping that because Cowork is in the cloud ecosystem to start, that it would be able to get by some limitations that I potentially run into in my day to day being on the CLI or the desktop. And probably one of the biggest ones is I often have, like, multiple artifacts, could be presentations, Word documents, excels, things like that, that I kinda wanna, like, iterate over and riff on and come out with those ideas and go back and forth on my thinking around them. So on the desktop, I run into a lot of issues because I have my OneDrive and I have things synced and both my work OneDrive and then I use shortcuts a bunch too, so I have shortcuts back to SharePoint sites. A lot of the content that I iterate on day over day and throughout my day is IRM ed. So it has some kind of information rights management or, like, MIP information protection. Encryption on the files. Yep. Yeah. So when you're on your desktop and you're sitting there in, like, GitHub Copilot CLI, well, it's got a skill to read Word documents. Just uses the anthropic word skill, but that can only read nonencrypted content. It can't even though it has your user contacts and you're saying do this or go into my, like, physical folder on my OneDrive kinda thing, it can't do it. So I was kinda hoping that, like, Cowork would maybe help solve that for me, and I could just rethink some of the skills I use in the cloud world. Cowork can't read my protected documents either. It just blows up and says, sorry. I can't do this. Is it because it's sending it over to Anthropic into Claude versus when you use the GPT models that's staying in the Azure data centers and it's going to the models internally? That would be my assumption if that's the case because those MIP protected documents, I can use in things like Copilot notebooks when I'm in GPT mode. And then, oh, yeah. We should also talk about so, Anthropic had an outage earlier this week on their API surface, and it happened to be when I was in the middle of one of my Copilot co work sessions, completely bombed out. Like, the session crashed, and if I try and go back into that chat now, I just end up on a page that says, sorry, like, sorry, Dave. I can't do this right now. Can you sign back in? Like, I am signed in. But I I basically just lost the ability to go back in and see any of that chat history or anything for that session that's out there. So that that that was an interesting moment for me as well because I was trying to debug it. Like, what happened and what's going on? Is m three sixty five down right now? Like, why is just this one chat broken? And it turns out it coincided exactly with the anthropic API outage. So it was a good reminder for me of, like, that mental model of, like, when you're in Copilot Cowork, you are, I I guess, using just the anthropic APIs. So a lot of that stuff does start to click then about, like, oh, hey. I can't read and or open that IRM document and all those kinds of things. So that that's a, like, funny, like, I guess, limitation, but that I just I was not prepared for and I did not have in my head to even think about, here's one more modality or, like, mental model that I need to carry as a user into leveraging these tools. If you're managing file storage today, you've probably felt the pressure. Refresh cycles are harder to plan, costs and complexity are increasing, especially as file workloads scale across regions. That's why Microsoft customers trust Nasuni as an Azure certified software. Nasuni provides a global file system designed for enterprise scale environments, keeping file data secure, governed, and accessible across Azure environments without added infrastructure complexity. It's the foundation to keep your unstructured data stable even as your infrastructure evolves. To see how much you could save while keeping your initiatives on track, visit nasuni.com/tco. That's nasuni.com/tco. So do you want to talk about our topic, or do you want me to bring up something that popped into my head since we're on this topic and you brought that up? I mean, it's your show. Not really. Keep going with this. So this brings up an interesting thought then. Right? Because that would also seem to imply that your chat session, is it not being stored in Microsoft three sixty five? So then, like, did that get corrupted in Microsoft three sixty five data, or is it the fact that Microsoft three sixty five to earlier point can't reach back out to the API to grab that session from Claude? In which case, if all that data's in Claude, what does that start implying for things like auditing and retention and sensitivity labels when it comes to chat? Like, this is something, and I don't know if I should go pop open mine while we're talking, is do your clogged conversations in Cowork function the same way that a conversation would in a GPT model when it comes to sensitive information and sensitive content and, I guess, almost like that data sovereign sovereignty data sovereignty type scenario. I would imagine, and this is conjecture because I haven't seen it, like, formally documented. But today, when you're in an m three sixty five tenant, you can have the OpenAI and GPT models kinda, like, by default. That's your default mode. You have to go and explicitly enable anthropic and basically sign the legalese that you're good with your data You're using that. Leaving the boundary of Microsoft's cloud because you are chatting with a model that at least is hosted. So even if you're not sending the data out, you're still sending the chat out. So if you're chatting about something that's potentially sensitive to your business, that would just be passed in natural language, right, via your prompt over to over to that side of things. So I I know, you know, organizationally where I am, like, there there is a big difference in functionality between folks in The US and Europe because we haven't lit up anthropic due to GDPR and things like that for those for that set of users. So that that that does make it tough. Like, some things potentially aren't available to some folks based on, like you said, data sovereignty, data residency, GDPR, various legal requirements, things like that that that are out there. And you asked, like, where are the chats stored? I have no idea. I would hope that they're stored in the same place as, like, my, like, grounded memory for, like, my m three sixty five chats. But when is that? I I don't know. Like, that chat that crashed for me, and it just happened to be I I was in there prompt in a way and firing off requests, like, just when that anthropic API went down. That that thing, like I said, I can still get to the files because they're in my OneDrive. I can see the session ID and, like, I can map back to the GUID and the day and the time when that thing happened. So that's good. Like, the file storage is still there. I lost all the chat history. I've I have no idea where that is and what that looks like, along the way. So there is a little bit in the docs around, like, how does Cowork handle data. So authentication, super easy. Right? That's just your m three sixty five credentials and your org ID. Tenant isolation, so you can only work with data within your organization's tenant. Easy enough, because you can't access data cross tenant. And because you can only work with cloud data, like data in SharePoint or OneDrive, well, that that kinda takes care of it because you don't have to worry about the local access thing or anything like that. And if you did upload some data to the chat, it would get uploaded to your OneDrive and be part of the the session and all that. So file storage taken care of. You you're you're in OneDrive or SharePoint within your tenant. What's not clear is there's a little bullet when you go into the co work docs that says data subject rights. Access deletion, rectification, and portability requests are supported in accordance with Microsoft's privacy standards. Okay. So I would imagine that's, hey. I went into the m three sixty five admin portal and I clicked yes. Users within geo x y zed can get access to anthropic models, and then it's just off to the races from there. So, Scott, while you were talking, I just did a fascinating test on Copilot in my environment. Oh, you just asked it just to see if you could get it to leak again? No. We're not talking about what I got it to leak before. That's secret. If you run into me at a conference, come ask me. I am not recording when I got it to leak. I went into cowork. So I have a document in my environment. Let me preface this. I will more than happily give you these screenshots too if we wanna put them in the show notes. I have a document in my environment that I put a sensitivity label on. Mhmm. I did not encrypt it, so it's not using AIP or MIP or any of those, just a sensitivity label that's for labeling purposes. And then in my DLP policies, I put a policy or a Copilot and Copilot chat blocking Copilot from essentially accessing the content in this document or doing anything with the document. So it's just a simple test document. Like, in it, I wrote the color of the chair is blue, the color of the ocean is red, or something just something goofy like that. So if I go into Copilot chat, just normal Copilot chat session, make sure I'm on the work tab so I can get to my data, and I just do a slash command DLP policy test doc, what color is the chair based on this file, and Copilot returns to me, I attempted to open DLP policy test, but the content is blocked due to your organization's data loss prevention policies. Because of that, I don't have any visibility into the file's content, can't determine the color of the chair, blah blah blah blah blah blah blah. So works just like it intended. I did I wasn't paying attention. I had it on the web chat for a little bit too. I can still do a slash command and reference the document. And I asked it the same thing, and it just said it can't determine the color of the chair because there's no image content associated with it. It's text only, no description. I guess it kinda makes sense. It must be the difference that a web Copilot chat, how it interacts with the document versus on the work tab. Interesting that it didn't reference the DLP policy even though I added the document to the chat, but it still couldn't get to it. Then I went into Cowork and did the same thing. DLP policy, test doc, what is the color of the chair based on the file? Based on the document, the chair is blue. Cowork does not respect Copilot DLP policies. You turn this stuff on. You you use it. User discretion is advised. Yeah. And if you are doing DLP policies, you may want to and I get, like, Cowork's still frontier. Right? It still preview all the normal stuff, but CoWork at this point in time does bypass some of those security features that, I guess, I feel like by default, it would have been on that if we're gonna if I'm gonna go in and configure sensitivity labels and security and exclude certain things from Copilot, that it wouldn't be able to bypass it in that type of scenario. Maybe it gives a little credence to the do use things. Like, like, I can tell you, if you use MIP and it's encrypted, it's like, you're not get you're not getting that thing. You're safe there. I will say you're safe ish there. Like, you're as a user, there's still things that you can potentially do. So so for example, like, you can copy and paste data out of a a Word document. Right? And LLMs speak markdown. So while I was looking to see, okay, is there a way that I, like, I can make all this stuff work? I'm trying to, like, Google Bing, DuckDuckGo my way through life and see if I can figure this out. I did see some articles out there from folks who were talking about kinda markdown as the language of LLMs, which is true. And there's all these, like, just open websites that have fancy JavaScript engines, or there's a really nifty extension for Versus Code, which does paste as markdown. So you can copy your Word doc, just control c, give me all this content, and you can go and paste it into a markdown file. And then it's just out in the wild. Mark markdown's not getting a sensitivity label and IRM'd and all that stuff. So And all those. That's another thing I think that maybe, like, folks gotta think about. Like, it it's really just exciting, scary, interesting to kinda see the evolution of these things and see where the gaps and things come up all along the way. Like, I I don't envy, like, because I'm talking through these situations. Like, I don't envy, like, CSOs or things like that or chief information officers having to or legal. Right? Like, trying to figure out, hey, what do we do in our organization when it comes to the use of these models and these systems and contracting with these various vendors and things that are out there? Because in a world of just anything can be converted to raw text, then you you can just egress it and have it out there kinda thing. And so, like, I was playing around with that paste to markdown extension of Versus Code. Super cool, like I said, but you can do things like you can paste, say like an image from a website or from a document, and when you paste it in, it gets pasted as a base 64 encoded just native image in there. So it it's not even like, if you had, like, sensitive data in a flowchart or something like that coming through, you could potentially leak that into an LLM or something like that. So def definitely some stuff to think about. Yeah. This episode is brought to you by Trusted Tech. If you're managing Microsoft three sixty five, you already know licensing isn't simple. E three versus e five, the brand new e seven licenses, Copilot security bundles, and with price changes coming in July 2026, the stakes are getting higher. Trusted Tech helps IT leaders make sense of their Microsoft three sixty five environment with a free licensing consultation. Their engineers analyze what you're licensed for and what you're actually using and where you can optimize, whether that means consolidating security tools, preparing for Copilot, or eliminating wasted spend. Plus, they offer proactive and reactive support, which has been awarded yet another solution partner designation from Microsoft for support services. If you want a clear, data backed plan that has helped over 7,500 subscribing customers save up to 20% on Microsoft three sixty five before your next renewal, visit trustedtech.team/mscloudprom365 and schedule free consultation today. I was playing around with this a little bit more. Like, if I use the Claude model like Opus in chat, DLP works. I just tried it with another agent that I built that uses, like, WorkIQ and all the different m three sixty five ones. And that one, it does pick up that the file has a sensitivity label on it, and it says access to the files with the sensitivity label will be as per org policy. So it doesn't look like it's necessarily even tied to agents or the specific model because this agent I did set to use, I think it was Claude 4.6. It does look to be very at least a DLP policy workaround does appear to be something cowork specific and not necessarily agent or model based. Now we don't know how the data necessarily flows to Claude and the cowork agent versus an agent I built versus Opus in a Copilot chat. I don't know. I think it gets to some of what we've talked about before is Copilot feels overly complex, I guess, when it comes to some of this stuff. Like, this feels like something I shouldn't have to be I shouldn't have to have five different ways to five different places I have to validate that my sensitivity labels work. Like, if I say this is excluded from Copilot, it shouldn't matter what I'm doing in Copilot. It should be uniform across the entire platform. We could go down this rabbit hole for a long time. Right? So think about we've talked in the past about, like, declarative agents. So great. Super easy to spin up. I wanna give this thing a description. There's also going down the path of, like, full foundry agent that you can, like, publish as a native agent out to Copilot and to Teams and all those other kinds of things that are out there. So that's another interesting scenario because now I'm not, like, in a declarative agent. I'm in an agent that sits over in Foundry, which is in Azure land. Sure. Still still within the boundary of my tenant for identity and all that kind of stuff, but not necessarily within the boundary of my tenant as far as, like, m three sixty five is hosted and not, like like it's not Azure. It's m three sixty five and Azure kind of thing. So you can also kinda have, like, that just have to think through, like like, alright. What does that mean? And, like I said, it's not I and maybe it's me. And I totally they get this could be a me thing, but I also think it's a little bit of, like, a Microsoft thing and just how it's presented, documented, pushed out there. Like, I spent a decent amount of time trying to go out and find and tell me, like, how some of this stuff works, where does sensitivity of labels lie, where does DLP apply, all these things. And it's not, like, well done, I guess. Like, you can go with, like, into the purview docs, like, for sensitivity labels, and it'll tell you, like, hey. This works with Copilot chat and Copilot agents. But is that true? Is that just Copilot declarative agents, or is that Copilot Foundry agents that then that agent in Foundry could have access to other tools? It could have, like, logic that potentially ships your data between different tools and has different integrations. Like, I don't know. The whole thing weaves in weird ways. So much like I'm, like, just delighted by, like, being back in terminals and CLI experiences and things like that, you can see all this potential there, but the rough edges, the friction, just the mental overhead, I think, for users, and I'll I'll totally admit, like, you and I are probably more on the advanced side where we're thinking about these things where most other people aren't. They're just hopping through life going like, oh, researcher, help desk, a new chat, word and web. I don't know the difference. So I was just start or work in web. I was just starting work, or I was just starting web. Oh, I didn't know you could select a model, any anything like that. So you've got that full spectrum too of, I I think just kinda personas and folks that are gonna be out there using these things. Wild times. We'll see. This will be interesting to keep coming back to, and I promise we'll get to our topic that we were gonna talk about eventually. Someday, we'll get there. We'll see. That that was a backup anyway, but thank thanks for letting me rant a little bit or at least do some follow-up on co work. No. I think it's how we all learn. Right? Like, some say, hope if one person out there listens to this and their takeaway is, I was thinking about playing with it, but maybe I'm gonna wait a couple weeks until it refines a little bit more. Maybe we save somebody else a a little bit of toil and overhead. Even you and I talking about it and starting to think through, again, like, the DLP policies and sensitivity labels, and I hadn't even thought about that before until you brought up that thing about it crashing and losing your session of where is this, and how is this looking at those. So appreciate it. If you come back and listen to this, here's your thing. Right? We'll dump the transcript out, throw this through an LLM, and have this just write your next m three sixty five Copilot whatever security workshop for you. Exactly. That's it, Scott. Podcast, we're gonna multipurpose this content. That's the plan. Right? I will let you go get to your weekend. I'm gonna go try to get a few more things done before my weekend, and my wife is standing outside the door texting me for my order for dinner. Alright. I'll let you go. Thanks as always, Ben. Appreciate it. Thanks, Scott. We'll talk to you later. Bye. Bye bye. If you enjoyed the podcast, go leave us a five star rating in iTunes. It helps to get the word out so more IT pros can learn about Office three sixty sixty five and Azure. If you have any questions you want us to address on the show, or feedback about the show, feel free to reach out via our website, Twitter, or Facebook. Thanks again for listening, and have a great day.

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Episode 427: Copilot Cowork Hands-On Experiences

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Welcome to Episode 427 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott open with a quick look at YAKO (getyako.com), a browser extension built by community member Merrill that replaces the new tab page with a customizable dashboard of Microsoft 365 and cloud links. From there, the conversation turns into an extended follow-up on Copilot Cowork, covering some of their recent hands-on experience with custom skills, artifact management, session crashes tied to an Anthropic API outage, and the friction of working with IRM-protected documents in Copilot Cowork.

The bigger thread running through the episode is data security. Listen in to hear more about considerations for onboarding to Copilot Cowork in its early days.

Show Notes

• Yako
• Get started with Cowork (Frontier)
• How does Cowork handle my data?
• Does Cowork connect to external models for processing?
• Are there unsupported countries/regions?
• Sensitivity labels for Microsoft 365 Copilot and Microsoft 365 Copilot Chat

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Episode 426: Claude Cowork vs Microsoft 365 Copilot Cowork

by [Scott](/content/author/scottmsclouditpro/ "Posts by Scott"/index.html) | Apr 23, 2026 | Podcast

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Welcome to episode 426 of the Microsoft Cloud IT Pro podcast recorded live on 04/17/2026. This is a show about Microsoft three sixty five and Azure from the perspective of IT pros and end users, where we discuss the topic or recent news and how it relates to you. In this episode, Ben and Scott dig into the world of co work, comparing Anthropic's Claude co work and Microsoft three sixty five Copilot co work across desktop versus cloud, local file access versus native graph data, context windows, models, and regional availability. They also dig into the hidden skills menu in Microsoft three sixty five Cowork, building custom skills with markdown in OneDrive, the missing MCP story, and how Cowork fits alongside regular Copilot chat. If you want, stick around for the after show where Scott vents about Gemma four eating all his storage. Another episode. Scott, you decided to join me for this episode after you I was gonna say left me with joy, but you really didn't leave me with joy. You delegated your responsibilities of the last episode to joy. And you missed out. Some joy to your life. You did be some more joy to my life. No. Thank thanks to Joy Apple for stepping in. I had a scheduling snafu. I had to go do some round tables at Azure MVP Summit and ended up having some discussions around how folks are using AI to transform their careers. And actually, that kinda, like, intersects with our conversation today because we're gonna be back to the whole AI thing. Yeah. And Yeah. So today, let's chat co work. Co work. Like the building where I go get a co work co workers? A co work subscription. Co work versus co work kinda thing. Yeah. So so one of the things that I've been on lately, this path I've been down, and this was definitely, like, a theme that I picked up a couple weeks ago with the MVPs at Summit, is the kind of pace of things continues to accelerate. There's always new tools, all that coming out. Yep. But also the methodology for existing tools is changing over time. So there are things that maybe somebody's been like, we talked about CLIs, things like quad code and Gemini code and help copilot CLI and all that and, like, getting back to the terminal. That approach that exists in those ecosystems of creating agents and creating skills and kind of going down the stack, it's it's rapidly changing over time. So one of the discussions we're having was like, hey, you potentially actually are in a worse place today if you're starting out with, let's say, in, like, claud and claud code. You know, you've got a claud MD or maybe you're in GitHub Copilot CLI and you have a Copilot MD, whatever it happens to be, and you've set this, like, grounded set of instructions. Well, maybe you had to set that grounded set of instructions because six months ago, the models weren't that good. But today, they're actually just better at less you telling them what to do and more asking them questions and then letting them kinda come to these frameworks on their own, things like agents and skills. So we're in this weird world of markdown rules today. I didn't see this one coming. Right? They didn't have it in my bingo card where markdown would be like the new programming language of the future, but it is. It unlocks a bunch of stuff. So today, we're gonna talk about rather than the CLI side of things, we're gonna talk about the co work side of things. So a little bit about kinda Claude CoWork, what that does, and more specifically, m three sixty five cowork and where that sits in, I think, the kinda agentic ecosystem of being able to perform tasks, schedule work, more than single things. Like, it's less write this report for me, spit the report out, more like go actually action something, like go triage my mailbox for me kinds of things. And how those are powerful and how they form up and how you can kinda customize them and take them a little bit more forward with things like markdown files that just equate to skills that you can go and deploy out there. Yeah. You mean co work is kind of like a co worker that can go do stuff alongside me? It's like Kinda. Kinda. Yeah. It's tough with the naming here. So Really? Yeah. Yeah. Maybe it's tough. Shocker. Shocker. I mean, it is hard because there's Claude CoWork, and Yep. That's the anthropic or the folks who run that. It's been out there for a while if you are some kind of paid Claude subscriber. So if you're either in, like, the Pro or the Max plans or things like that. And then Microsoft also has anthropic models. Like, you can go and run SONNET and things like that inside of m three sixty five if you're in the right geos and you have, like, the responsible AI access and governance and all that around it. But you can go run anthropic things, but then there's also this anthropic ish thing in Copilot cowork, but fundamentally different set of behaviors just because of the way these two things are wired up. Right? So maybe we should kinda like walk the stack of, like, how these work and where they're different, and then we can get into m three sixty five co work and a little bit about I would you say they're different, but looking at it, as I played with it, there are absolutely some similarities here too In terms of Yeah. It's I guess similarities, yes. But I think from the start, they're very different. So if you think about yes. I have a coworker that can go and perform tasks for me. Certain actions. Sounds simple on the surface. Yep. Both of these things do this, but the modalities are very different. Right? Desktop versus cloud. The connectivity and the ecosystem is very different. Again, things like access to maybe model context protocol, MCP servers, Both local and remote can be different based on that whole local versus cloud experience. There's also things like differences in the models that run from the cells, which then hits like context window limits and some other things that that are out there. So there's like this it's weird. There's two things with the same name that kind of, like, one sits in the Microsoft ecosystem, but uses clod models under the hood. And then there's the anthropic clod side of things, where it has its set of capabilities, and it does what it needs to do. But, you know, as similar as they look on the surface, I think they are bifurcated in that one is gonna do one thing better than the other. So now you're at a point where if you're in both ecosystems, like me, but you're there as well, now you gotta choose the right tool for the job, which is becoming a little bit of a mental burden. But if we just start at the top, so thinking through the modality of where these things run, Claude CoWork runs on your desktop. So it runs in an application that sits on your desktop, macOS, Windows, and you're there and ready to go. And Microsoft three sixty five co work runs in the cloud because there is no local like, real, like, local experience Right. Or at least an app that can talk and interact with local resources, things like that. And that becomes impactful. Like, so one of the very first things that I did when I sat down and I said, Oh, M365 co work is here, and it's available in the Frontier program. Let me go light this up and play with it, was I wanted it to organize some files that were in a folder on my PC, local folder. I've done this by a 100 plus times with Claude Cowork at this point. Right? Hey, take this folder of receipts and categorize it for me. Take this folder of blah blah blah. Help me organize my Obsidian vault. Like, just point at this folder and go. Let it do its thing. And when it the very first time I went to use m three sixty five co work, I immediately hit a blocker in that the data that I wanted to organize wasn't in the cloud. It it did not reside in in OneDrive. So I had to go and upload all this stuff, kick it up there, kinda wait until I could get, like, the ability for, like, that file picker that's in the m three sixty sixty five Copilot app to finally, like, refresh itself and grab what it needs to and see that stuff out there. But that that modality of, like, desktop app and local connectivity versus what's ultimately a web app sitting in a desktop wrapper with no local connectivity. It is something to think about and kinda just hits you right in the face. Yeah. The other thing I would say about that, kind of on the flip side, is I've also run into things. I've used Cloud Cowork. I've scheduled tasks in there. But because it's all local, guess what has to happen for my scheduled task to actually run when it's scheduled? The machine has to be on. It has to be booted up, etcetera. So there's some of them I that I have to do on macOS for different reasons. It has my laptop is my Mac device. My desktop is Windows. I have to have my laptop on for that to run. Or there's some things I do have running in Windows on my desktop. If I'm gonna be out on vacation or I'm gonna be traveling, have to leave my desktop on for those to run versus the nice thing about Cowork and when it is in the cloud like that is, yeah, maybe I don't have some of my local desktop access. But now if I am doing scheduled things, I'm not necessarily relying on my machine to be on because those tasks can run up in the cloud, all of that. So to your point, it's interesting as we look at these and as I've been playing with these of, to your earlier point, they're not the same. There's pros and cons to each one of these. Yeah. It's I mean, it's just the mental friction. And, like I said, I think for me, it's kinda getting into the modality and thinking, am I in the right place? Right. And because of the names having certain expectations, because Claude Cowork has been around for so much longer. Yes. Well, I think, yeah, there there's definitely some inherent bias there. Just having been in kinda the that ecosystem and getting used to things like Cloud cowork before being introduced to m three sixty five cowork. Yep. Alright. What else is on here? Local file access, that was, like, the first three. M three sixty five data, I mean, this one's kind of apparent, obvious, maybe, is that Microsoft Co Works, you're gonna have all the graph data. You have all the WorkIQ stuff that's available just natively right there. You don't have to do anything. You don't have to wire it up. It's gonna run-in a secure in that security boundary versus Cloud Cowork, and I've done all this. You can just wire up all these MCP connectors to get that data, but there's a little bit more work there on the Cloud Cowork side if you're in the Microsoft three sixty five world. If you have multiple tenants, this is one thing, Scott. Both with Cloud CoWork and Microsoft three sixty five Copilot CoWork, I wish I could live in just a single Microsoft three sixty five tenant because having meetings and team conversations and emails and all of this in four or five different tenants for reasons that are very valid based on the clients I work for, these tools do not help me consolidate all of that stuff stuff across multiple m three sixty five tenants no matter which one I use. But that m three sixty five data is another interesting one to think about as you work through it think through it. Yes. So I have been doing this with Claude Cowork, at least as far as my organization, like my work data. Yep. But OneDrive and Dropbox and Google Drive are all connected locally for me. Okay. So I remember, like, one of the one of the very first things that I did with Cloud Cowork is I have a a Dropbox folder that's full of just receipts. It's where I dump every receipt that I scan, whether it's for work, for life, whatever it is. And it's been this dumping ground for years. And it lives in the cloud. It lives in Dropbox. But because Dropbox syncs to my desktop, I didn't need any kind of special connector or anything. It was just Yep. Just there. Connect to a file system and let it run. So I think even, like, for me, once you understand, like, the particular model you're working with or you get used to it, you kind of, like, want that as well. So there would still be some things where it says, like, oh, in an m three sixty five co work land, it connects to your m three sixty five data. Well, I can connect to the graph with WorkIQ and and the MCB that's available there. So saying, like, m three sixty five Cowork does graph access and Claude Cowork doesn't, that doesn't really fly. Granted, one is way faster than the other. I will say, like, m three sixty five cowork, way faster than doing things in WorkIQ and the MCP. Same thing for, like, access to data. If I have OneDrive and I can sync that stuff and bring it down, I can still I can still manipulate it. So it many times as I'm, like, working with m three sixty five co work, in the back of my head, I'm also thinking about the ways to just work around it with Claude co work so that in the event, like, my employer should give me Claude someday, cross my fingers, I would just be able to go back into that ecosystem, not only for my personal stuff, but for my work stuff as well. Yeah. And that I've done that. Like, I'm in the same boat where it's files on the local computer. I think for some, and this is some of my clients, it's not even so much, can you do it? It's in this comparison that we have that we'll post in the show notes talks about, some of it's a little bit more the security side of things too. Like, I have certain clients that are like, we are going to use Copilot because for certain compliance reasons, regulatory reasons, or just general what IT is comfortable with for various reasons, they do shut down all these other ones. And having Cowork, having Purview there for auditing, being able to put a few more of those security controls around it, have security around it does make a difference for them. Oh, I'm I yeah. Absolutely. No argument there that, like, being in the ecosystem is part of the value prop that you get out of it. What other ones on here do you wanna talk about? There's a whole list. Again, we'll put it out there. Yeah. I can check all those, like, add add What about the context window? That's an interesting one on here. Yeah. So Claude CoWork, again, back to, like, the model things, uses Claude Opus 4.6. I don't think they've switched it to 4.7. Like, that just came out. They I I did. I I don't CoWork has 4.7 in there already. They came out with it yesterday. I wasn't impressed with it. Yesterday. I haven't had anything to do in co hitting Claude CoWork today, so I haven't been in there. So so, yeah, you kinda get, like, latest and greatest model, which means you also get these, like, for better or worse, larger context windows to work with tokens. So the data that you're passing in, I mean, well, at least in Opus four six, you had up to a million tokens in a context window. And it looks like Copilot Cowork is 16,000 characters, which is a little a little limiting in the grand scheme of things. So that that's another modality thing where you have to think about what's the story and context window that you're building in that you're kinda grounding into this coworker to go do something for you? Like, how complex is the thing that I'm asking it to do, and how much of that do I need to teach it in the form of, like, defining the agent or defining the piece set of work that needs to be done, agent skill, whatever, that you're gonna pop in there. So it's not something I've ever really thought about with Claude Cowork, And I haven't run into any inherent limitations with m three sixty five CoWork yet, but I'm sure there's gonna be some rough under the edge, like, just hidden on the edge thing that hurts just a little bit at some point because of that. Yeah. This episode is brought to you by Trusted Tech. If you're managing Microsoft three sixty five, you already know licensing isn't simple. E three versus e five, the brand new e seven licenses, Copilot security bundles, and with price changes coming in July 2026, the stakes are getting higher. Trusted tech helps IT leaders make sense of their Microsoft three sixty five environment with a free licensing consultation. Their engineers analyze what you're licensed for and what you're actually using and where you can optimize, whether that means consolidating security tools, preparing for Copilot, or eliminating wasted spend. Plus, they offer proactive and reactive support, which has been awarded yet another solution partner designation from Microsoft for support services. If you want a clear, data backed plan that has helped over 7,500 subscribing customers save up to 20% on Microsoft three sixty five before your next renewal, visit trustedtech.team/mscloudprom365 and schedule your free consultation today. And going back to the models too, just this document or this image does say Opus 4.6 for Cloud Cowork. Four seven is there now. But it says it's version not disclosed for Copilot Cowork. And I actually just looked in mine, and I have both Sonnet 4.6 and Opus 4.7 that I can select in Microsoft three sixty five Co Works. So I was actually surprised to see Microsoft add the model to Copilot the same day it came out. Like, Claude came out with four dot seven, and it showed up in Claude and CoWork almost, Or not Claude and Cowork. Claude and Copilot almost simultaneously. But Microsoft, that's one area I would say too that they've I feel like they've listened a little bit. By default, they still go to auto, but they are letting you have a lot more control over being able to select the model you wanna use. Yep. Which is best. You can get in there and play with it. It's, so this is another interesting one and a little bit of like a double edged sword, and I've been running into this for a while. So I work in a global organization, global team, particularly like my team members and my coworkers over in Europe. Uh-huh. We'll be on a call and we'll be doing something. And I like, I remember the first time I did this with Researcher hopping in and I was like, Oh, this is really cool. Like they get they give us access to to Claude models, anthropic models inside Researcher. And everybody's like, yes. And then they're like, no, because I don't get that because I'm in Europe, and it's locked out Oh, interesting. Due to tenant configuration and things like that. So back to the whole, like, where you are in the world and things like GDPR boundaries and tenant configuration, like Yep. May or may not be available to you. And so far, like, because it's all built on anthropic models as far as the Cowork Frontier agent that's there today, same thing. It's locked out and not the not the most viable thing. Which that's interesting. You brought it up. Let's dive into Cowork a little bit. So Microsoft cowork. Yes. You just said one of the key things there is the Microsoft three sixty five cowork agent because that is what it is an agent that you go into your Microsoft three sixty five Copilot, go find the agents, and you install this you install Cowork as an agent into Copilot, which is different than I get at least how it appears in Claude where it's just a toggle between two different things. Yeah. I think Claude ultimately has, like, chat, co work, code. Yep. So you've got these kinda, like, three modalities, and you can go across them or three kinda main interaction pillars. And once you learn them, you kinda pick and choose and go to the right one. M three sixty five Copilot's a little bit different in that it tries to drive you into, like, the search hub for everything. So they're just thinking down, like, your hamburger menu on the left, right, your set of options. You've got search, you've got agents, you've got chats, and just running down the gamut of things. So I think it is an interesting decision to say rather than, like, being, like, right in your face, like m three sixty five Copilot is always gonna be here kind of thing, that it's, to a certain degree, demoted, like, as an agent and just sitting down a little bit further in the stack. So for me, I've got, like, tens of agents installed right now in, like, M three sixty five Copilot. So it's, like, depending on how that list shifts over time as I'm adding agents, taking things out, can be like a little bit, like, of a chore just in the UI to get down there and find it. You need to start pinning them, Scott. Pin your agents and I don't know why pin them. They're just gonna go away, and I'm gonna find a new one, or is it gonna move my cheese, or what whatever it is. Kinda like they moved to apps again? That's another conversation. Apps moved again. Okay. Squirrel. Apps. S. Apps. Apps was the other part that's up there. Yeah. Yeah. So it's it is a little bit different to go and find it. So like you said, so you gotta be to bootstrap. You have to be in the Frontier program. Yep. You have to have the anthropic models, like the governance controls in the m three six five admin center lit up for your tenant saying like, hey. This is okay for folks to use. And then you've gotta go the extra step. I don't I'd like, I don't think you can can you automate this as an admin, like, deploying agents to all your users? Like, I'd I had to go in and find it, like, in the the agent store, go add it manually kinda thing. I went and found it. I'm trying to remember. I think you can. I think I did push out agents to everybody in my tenant. So I believe there are admin controls where you can go say, go push this agent out to all these different people and publish it to these people and all that. But Gotcha. Yep. Yeah. I'm not a 100% sure on that. Alright. Yes. So so, like, you kinda get through the installation gauntlet as a user, and then you've got m three sixty five Cowork. I think it's also interesting that the way Cowork presents to a user. So the very first time you go into just about any agent in m three sixty five, you've got a set of, like, suggested prompts and what this agent can do and how is it how is it going. So it looks very similar to some of the other, like, default prompts in in the prompt library for an m 365 tenant. It's got stuff like, catch me up, organize my inbox, organize my week, help me prep for a meeting, plan for an event, prepare my one on ones. And funny enough that the other default prompt is research a company. Like Yeah. Okay. That that's in CoWork, not in researchers. So there's a little bit of nuance there. That is true. But I do use Co claw Cowork a lot for researching a company before I have a call with them. I should make sure that it's too. Because in Claude Land, in Cowork Land, I can also bring projects into Cowork, like collections of documents and all those kinds of things. So similar thing I can do over in M 365 Co Copilot. I could bring, like, a collection of documents together, like, maybe, like, research from Gartner, IDC, something. It depends on what you're going at and what you're really kinda trying to get it to do and get out of it. But those things are all there for you. And I think the natural inclination is just to kinda go in there and, like, pick one and see how it does and what it's got going on. So back to, like, first experiences. So, like, my first experience with m three sixty five Copilot was help me organize my inbox. So just that default prompt that's there. So it kinda wants to go through, and it does the typical thing that I think most of these, like, reasoning models are doing now. It churns for a little while. It sinks. It goes out, reads your inbox. And then I found it to be, like, oddly inflexible. Like, I couldn't get it to do what I want, right? And sitting here saying, like, I found a bunch of newsletters. Okay, great. You want me to delete all your newsletters? No. Don't delete my newsletters. Take the newsletters from the information and business insider and put them in my inbox other, archive the rest, and then delete these two kinda thing, right, which should just work. It didn't. It it it it didn't like me at all in that model. I also found, like, through that one and a couple of the other, I I guess, system prompts, default prompts that are there, because it's erring towards the side of, like, human in the loop and human interaction, you still end up doing a lot of clicking. So those things, like, organize my inbox. Like, if it makes the wrong decision, like, Scott, I wanna delete all your newsletters, and I'm like, I don't wanna delete all my newsletters. I you still need to go and individually triage them, and it's a 100,000 times faster to just open your inbox and do it there than it is like clicking the buttons and the little drop downs and the little action notifiers that come up inside of a m three sixty five co works. So it's a like, I think it presents that it does what it, like, says on the tin, but the interaction for it is a little bit strange. But I'm sure that'll improve over time. Probably one of those benefits to just saying, hey. It's in an agent, so they can iterate on it a little more rapidly. Right. Well and I would say from that, like, telling an agent to go organize my inbox would inherently make me nervous. So I do appreciate that they are a little bit on the side of caution, but it would be nice that if you told it to do something, it actually did it. To be fair, Claude's done the same thing to me, and it's interesting. So how often have you found yourself using AI? And then after, like, fifteen or twenty minutes of arguing with it to try to get it to do something, you have that realization of this would have been quicker for me to just go do it. I'm getting there a lot quicker these days. My my patience is just that much shorter. And I think, like, some tools like CloudCoWork and m three sixty fiveCoWork, they don't help with that frustration. So one of the things that I've been doing more and more on the CLI side, at least in, like, CloudCoord land, is you can do things like when you're on that path and you start banging your head against the wall, maybe the context is poisoned a little bit too much. Right? Like, the task has gotten too big or it's just gone off the rails, is you can do things like you can rewind. Right? I just wanna I wanna step back and history before the con go back before the context was poisoned or we got off the rails, and I kinda wanna explore a different path. So I've gotten, like, really spoiled by that in the CLI experiences where it doesn't exist in co work land. So at least, like, CloudCoWork versus CloudCode, like we discussed a couple weeks ago about the CLIs. Like, I just default to the CLIs. But you really don't have that option with m three sixty five Copilot. There there is no CLI for it. Right? There's just a web app or the desktop app and the web wrapper, and you kinda get in there and get going with it. But I think generally, like, I ran into the same thing with a lot of just the default prompts that were there. In sure, they were pointy and opinionated, which I think is good for anybody who's just starting out. And maybe you don't have a workflow or you're open to having this thing come back to you with, like for your mailbox, like a different categorization system. It's really hard when it's yours and it's all out there. But I think we'll have a workaround there because we were going through and talking about this one and getting ready, and we both realized that m three sixty five Copilot does something that we didn't know. Yes. Are we gonna dive into that? To work. Well, before we do that, there's one thing I wanna call out because I missed it the first time I was looking at this too in terms of getting started. As you get that prompt, and this will even lead into what you just said too a little bit. And you have your get to work, organize my inbox, my week, but then it asks, how can I help you today? And you can start typing. And part of my first thought was, okay. This, like, organize my week is doing maybe a little bit more than just typing. There's a button next to how can I help you today that says add attachments? And if you well, if you hover over it, like, the info box is just add attachments. I'm like, okay. Great. So I can add a file or a PowerPoint. If you click that, you get attach cloud files, upload images and files. But then there's this other one right above it that's add work context, and it has files, peoples, and meetings. And if you click that, it gives you a whole another set of menus where you can go in and it'll give you where you can select people from your contacts. You can select files. You can actually select meetings, so it'll surface your whole calendar in there. So if you wanna add a specific meeting context in there, certain emails, chats. So I could go add, like, our chat from this podcast recording in there, channels, sites. So all of these different things, I guess, you could say from inside of Microsoft three sixty five. But then another one here is skills, and it has PDF, where the PDF skill will create, read, and manipulate PDF documents. Has the same thing for Word, Excel, calendar management. So if you're trying to recreate some of these, there's a lot of these there's a lot of nuances and tweaks that you can make that are kinda hiding, in my opinion, under the add attachments. Not a place that would maybe go look to add all these skills in or add these different options? Missed it. So I'm so used to when I'm in m three sixty five Copilot. Like I said, like, you get kinda, like, in your, like, way of work in these ecosystems. Yep. I'm pretty much down to I know in, like, every chat window that's there, I can just type a forward slash, and all my recent documents and everything are there, and I can just attach my cloud files. So, like, for me, embarrassingly, like, I was not inquisitive enough to click the add attachment button and see that underneath there. So so, like, that whole set of skills is interesting, and I kinda ran into this when we were going through and planning and reading the documentation, stuff like that. But some of these skills that are there, like, there's an email skill. Bet you that ties back directly to that that other Right. That that other prompt that's up there. And maybe, like, the thing I'm gonna have to go and play with this next week after the weekend and get in there and play with it, is I didn't realize that you could create custom skills as well. Yes. So so so that's very interesting to me. Like, I would actually like, I I don't know if you can do this because you're in there right now. Can you take any of the co work skills that are there, like the email skill? Can you go grab, like, the markdown for that and then be able to edit it and make your own email skill? Or you just gotta start from scratch? I don't know. Let me go see because so I'm gonna go look somewhere because you're right. You have all these skills that are in there, and then you have your custom skill and where are those custom skills, Scott? Because we looked at this. I would because I saw this. I saw, like, custom skills starting to pop up, and I'm like, So I can have custom skills, but I where are they? Which led me to the documentation. Imagine that. I read documentation. Here we are back at the beginning. Yeah. So they just live in your they live in your OneDrive. Yeah. So specifically in your documents folder, you can create a subfolder for co work and then a skills subfolder under that. So effectively, forward slash documents, forward slash co work, forward slash skills. And then within that folder, same thing, subfolder per skill. So the example in the docs is just weekly report. And then within that folder, a skill dot md, which is really cool. Like, at least they're not, like, reinventing the ecosystem. Like, they're just using markdown here. And now the immediate thought I had as I was going through this, I'm gonna have to play around a bunch next week, is I do have some, like, skills that today, I run-in things like Copilot CLI. And like I said, they're all hooked up. They have access to these MCP servers, WorkIQ, and Azure DevOps, and kinda kind of all the tools that I need that are out there and available. So I might have to take a couple of those and pop them over and just see, like, where the friction is in the modality difference between can't interact with my local desktop anymore, but can interact with can interact with certainly files in OneDrive. I think it's gonna be a real limiter in that there's no MCP connectivity inside m three sixty five Copilot, which means there's no MCP connectivity within m three sixty five Copilot co work either. So you're kinda baked in with the set of connectivity that's there and kind of boxed in and gated by just what they offer there today. So I couldn't extend it with, say, like like in my world, one of the things, like I have a skill that goes out and kind of very similar to their example in the docs, creates my weekly report, but it's not based off of just my inbox. It's based off of things like things like Azure DevOps where we're tracking work items and work item management or like GitHub projects and things like that. So it's a little bit of a limiting factor, but I'm I'm gonna have to go play around, I think, with some of those and see. But, like, I think the real power there becomes that much like you've had access to scheduled prompts, so you can do the same thing here in m three sixty five Copilot Cowork. You can absolutely schedule your prompts. But because they also have access to that set of skills that are baked in, PDF, Excel, Word, email, enterprise research, enterprise search, deep research, calendar management, all that stuff, and then extending with your own skills, well, like, that could be a pretty powerful thing. You're out of time. Copilot needs to be deployed ASAP, but is your tenant really ready for it? Years of data, permissions, and users lurk in its shadows, ready to be exposed by AI. Sharegate Protect sees it all, so you can find the exposure risks, fix them fast, and deploy AI with confidence. Microsoft three sixty five governance. We got this. Learn more at sharegate.com/governance. I did go look while you were talking, and I cannot find a way to see the markdown or whatever they're using for those skills that they have built in. I have the folder in OneDrive. If I go to that folder, files that are created as a part of a chat conversation in Cowork are stored there. So it will generate output if you ask it to create a file or a PowerPoint presentation or anything like that. It gets you'll see it in the details about your chat conversation, but then that's where that file will live after the fact too. I would say not necessarily super easy to navigate to because it's under the documents co work, but then it's sessions. And the session folder under there is a GUID. So you have to know the GUID for your session if you're looking for the file or you search. And then once you go into there, then you have, like, your output folder. Yeah. See, you fire research your agent off, see if it can figure out the GUIDs, and then come back in. There you go. And then map it in. Yeah. So you get to play with chat and the other agents and then agent take But there are no markdown skills in there, and I haven't found a way in the UI to, like it'll show me what skill it's using. And I can pick a skill, but I can't see anything behind the scenes of what that was like. Like, it's hard to do. Like like, my example of organizing my inbox my way, like, I could go document that. Like, I can absolutely put that in markdown. But it'd be nice to see, like, potentially, like, just that system prompt or, like, how they're calling their underlying scale or what their underlying scale does just so you can, like, mock it in and potentially map it the same way or remap it over to your workload versus reinventing the wheel kind of thing. Same thing for, like, calendar management, help me prep for my one on one kind of thing. Like like, I found it wasn't very good with the helping me prep for my one on one because my conversation with my manager for my one on one isn't just about the work that I do. It's about the work that my team does. It's about the work that my teams do. Right? So, like, you can pull, like, all my interactions with my manager over the course of the week. But over the course of the week, that's probably, like, 25% of what's top of mind for me and walking in and where I need to be next. So, yeah, I think there are some rough edges here, but I'm excited to go try these custom skill things and see how those go. Yeah. In theory, though, you could pull in chats from your team members. Like, if you prepared Yes. If you went and recreated the prepare for your meeting instead of using theirs and pulled in chats from your various team members, chats with your manager, and all of that, in theory, I think you could probably improve that way better than Microsoft could just because of that knowledge that you have when you build your skill. I'd have to play around with it and see. Like, today, from what I've seen, and I think it's gonna be a limiting factor here as well, is I already tried to create, like, declarative agents for these things that that have access to my email, my calendar, my chats, things like that. I think they're just severely limited by the context windows and the amount of data that they can pull in and reason across Got it. Gonna actually tie back together. Yeah. I think if you're somebody who's, like, working the same things, same area, and it can kinda learn a little bit or have some memory, great. But I I can have hundreds of conversations in teams and they're all split brained and all over the place. Yeah. So somebody could be like, somebody could be I've had this happen a lot. Someone's, like, emailing me or chatting me about an issue for a customer. Yep. But it's not actually, like, a product area that I own. They just know to reach out to me because I'm part of this organization and this product. So then I have to come back and redirect it, and then I end up in these chats that just run forever for, like, customer escalation. But, like, it looks important when, like, something comes across and says, oh, you were on this, like, high severity incident. It's like, well, no. I just connected customer who had the incident to the right engineering team or things like that. How do you filter that out? I just sent you an email, Scott. I used the stakeholder comms skill, and I said I wanted to communicate with you. And it asked me if I wanted to communicate about what I wanted to communicate about, so I sent the podcast. And then it asked what it was. And I said a guest or topic idea and then to email it to you, and it wrote a whole email. Put, like, the to, the from, the subject, the whole body of the email in, like, essentially, in a window inside of the chat, and I just hit send and sent you the email. So some of that I tend to see if it's still cool. Active windows. I think it it is nifty. Like, that one's probably not a ton of friction, but now try imagine triaging your inbox with the 40 things that it's in here. You're trying to click each little drop down. No. Don't do this with this one moving over here kinda thing. Let's see. What else can we chat about with coworkers? So we talked we kinda opened with how Claude coworkers in similar but different and what some of those modalities were and some of those feature differences, it's probably worth talking about a little bit about, like, how Copilot chat and how Copilot co work are also different because you're ultimately, like, in a chat interface for both of them. So I think as a user or somebody who's getting started with it, you kinda look at it and go, Like, what is this thing? So co work is gonna fill that niche of being able to do multistep work. So not only go read my inbox, not only categorize my inbox, but then also provide me the ability to actually take action on it, kind of category by category or things like that. You can work across multiple applications because of the skills that are there. So having access to, like, a Word, Excel, PDF skill, things like that. So you can kind of work with it in maybe I would think of it as, like, notebook mode. Like, let me bring a bunch of artifacts in and then have it generate a new artifact based on those and have it come out the other side. Because it's we talked about some of the scheduling things, all that. It means you get more like asynchronous or autonomous, I guess, execution versus just having to sit and wait for a chat, which is kinda synchronous and right in front of you. And, yeah, I think we talked about, like, the action stuff and the kinda connectivity and what's there. So you kinda got chat sitting there. Hey. These are my quick one offs and or just single part workflows, and then you've got coworkers sitting there with longer autonomous execution and multipart workflows. Yeah. If you're managing file storage today, you've probably felt the pressure. Refresh cycles are harder to plan, costs and complexity are increasing, especially as file workloads scale across regions. That's why Microsoft customers trust Nasuni. 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Co work can actually go that extra step and use things like the PDF or the PowerPoint skill. And it's a little bit more I don't wanna say deterministic. It's just better at, like, generating those outputs based on the set of inputs that you give it. So when you think about having access to, like, a deep research skill, So, sure, there's research agent over here or there's this deep researcher over here. They're gonna, like, on the tin, look very similar, but one's gonna give you a different set of outputs versus the other. So back to, like, you gotta think about, like, right tool for the right job kind of thing. Once you kinda get into that, you can figure out where you need to be. But Yep. You still have to know where you need to be upfront. Right. It can continues to be one of the problems with with all this AI stuff. It's just Yeah. Because the mental overhead. Right. With co work, when I would I generated a company research. It gives me the option. Do you wanna email it? Do you wanna create a Word document? Do you wanna do all this? Copilot chat, it's just like just spits everything out. Prepare for meeting with something similar. It's like, what topics are we gonna talk about? Do you want me to create a PowerPoint presentation that you can use for the meeting? A lot more interactive and work focused versus the chat would just yeah. Having a conversation with somebody versus generating tangible outputs, maybe. Mhmm. Yeah. So Yeah. It's yet another thing to add to the list. Right? And and go play around with a little bit. Yeah. I'm absolutely gonna play around with it. I am still absolutely missing. I would love to see, to your point earlier, them add the ability to tie an MCP servers to this somehow. I still feel like that's a big gap between It it would just unlock so much. I I use them all the time. Like, I am in my role and for what I do, I'm dead in the water without Azure DevOps and without the the fabric slash Kusto MCP. Like, I very much need those two things. I use I use them all day in my job. Therefore, I need access to them through these kinds of tools. So having the ability to do that without having to go and create my own agent and connect into Foundry and then, like, yes, you can go down that path and you can do those things, but, yeah, not the most fun path to go down when you're just looking to get something done quickly. Yeah. And even if you went in and created your own agent right now, I don't think you could pull those MCP servers into co work with it. You could go create an agent. Maybe you could recreate co work with MCP servers, but not at all. Well, I'd have to go into Foundry, and then I'd have to use Foundry tools and connectors that are there. Again, different ecosystem, different language. Like, it's just hard. Right? Like and I get this stuff takes time, but, oh, man. I think you just, like, unlock so much if you made Copilot, like, a local app that had access to MCP servers. Yeah. Well, they're redoing Windows 11 this year. Right? Massive changes to Windows 11 to make it better and faster and less web app heavy and more native apps and Yep. Maybe we'll get, better Copilot app as part of that. I'm not holding my breath. We'll see. I think there's a bunch, like, the OS vendors can do to improve the space. May may maybe we'll close on this one, like, this will be, like, our after hours chat here. So, hey, thanks for sticking around everybody. That was that was coworkers with coworkers and all that. Yeah. We went long today, Scott. Yeah. We did. I I gotta give you one of my, like, my pet peeves before I leave, and maybe you can solve this for me and make me, like, be able to sleep over the weekend. So what was it? This week, last week? I forget. It all flies by. Gemma four came out, the new model, the multimodal re reasoning model from Google. So that came out with a couple different modes. It came out with, I think, a 2,000,000,000 parameter, a 4,000,000,000 parameter, and a 26,000,000,000 parameter. So immediately, a bunch of application developers kinda slurp this up and said, oh, this is awesome. Like, I can get, like, a 2,000,000,000 parameter model that can run on things like an iPhone or an Android device or your tablet or your computer and all that. So for me, I have like, let me give you the use case. So I have several applications on my computer that all use underlying local models that have been downloaded, like the model weights, either MLX or g g u s that are out there, but now they're all using the same one. So I use this really cool app called Coteypist, which does basically, like, tries to complete your sentences for you as you're typing them on the keyboard. And it's super nifty and super cool, lets you pick your model that you wanna use in there, and they added Gemma to that. So I'm like, okay, cool. I'm gonna get off Quinn, and I'm gonna go to a Gemma. So I go grab the GEMMA 4,000,000,000 parameter model, which is about five and a half, six gigs. K? Okay. So no no problem. I got five and a half, six gigs of free space. I'll delete that GEMMA model that was taking up three and a half, four gigs, and and I'll make a little bit of room. But then I also had a need to hook up I I was doing a little thing on the side trying to play around with, like, local LLMs and so with quad code. So I took LM Studio, which is, similar to, like, Oh, Llama. Like, Hey, go download the model. So downloaded the same exact model. Now I have two copies of it because it lives in two different apps. Because it's, like, bundled with the app and in, like, an app bundle. And so and recently, I ran into, this week, a third one that I also use where it I can see I can't even select the model. It's baked into the app just as part of the functionality of it. So, like, the app bundles are, like, blowing up in size. So I like, I was complaining to somebody at work about this. Like, the OS vendors, I think, really need to carve out a space for application developers to host model weights, like, to download, like, all those h e g u f or in the case of, like, Apple Silicon, MLX2, and store it side by side. So if I've already downloaded the QEN or the general 4,000,000,000 parameter model Don't download it again. And tie into the existing one. Gigs of space, I should just have that five and a half, whatever, once and let everybody read out of it and have it come together. It's been killing me because, like like, my Mac has a terabyte hard drive, generally big enough. I am running out of space constantly over the last couple weeks because of this. Like, as these new things are coming, they're being pitched out there free, open source, like Gemma four. They're just getting integrated into everything, and it's blowing it up. I'm starting to notice the same thing on my phone, like, where you have even, like, less head less headroom, yeah, to go ahead and do that. So I do think, like, the OS vendors need to solve for that space, and they should also start to kind of think about, like, the new world of agentic workflows and surfacing things like local MCPs. So, like, in Windows land, a lot of that stuff's been around like, oh, hey, we'll have an MCP for file explorer. Yep. I I think Apple should do the same thing on macOS, just have a local file system MCP with its own guardrails, security model, any authentication it needs, those kinds of things. So, yeah, my so so my pet peeve, like I said this week, is I got all this cool functionality that's coming into all these apps because now it's kind of like, quote unquote, free for developers to do, but it's leading to just like me For the infrastructure space. How to solve that one, I would love to do it. Other than me hunting down a remodel and creating creating like sim links and trying to figure out, like, what the canonical place I wanna store it is. And some of these applications don't like the the they don't like the sim link thing, so it doesn't always work. I don't know that I'm gonna let you sleep over the weekend. I don't have a solution. I'm not an OS developer. You you just you're just like, hey, Scott. Be like me. You just go grab a four terabyte or an eight terabyte Mac, and you'll be done. No. Because you can't buy those anymore because we have no more storage that's available to buy anywhere ever again. This is true too. We are out of technology. Technology is sold out, Scott. That is an interesting problem, though, but I do agree. You just need to be able to download the model once and somehow recognize you know what that gets away from, though. It gets away from Apple's home whole model of that's how Windows ended up the mess it is. Right? Because they wanted to have shared libraries that these applications can all leverage shared libraries. MacOS said, no. That's stupid. We're gonna make everything in a self contained package. Yep. So here we are now wanting Apple to be more like Microsoft is essentially what you just said. Yeah. To to a certain degree. So but I think it does make sense. We'll see who gets there. Right? I think there's it's just more of that continuum as these things start to get adopted. Like, I wouldn't be surprised if six months from now, like, the majority of applications that have things like text inputs or take voice inputs or do, like, computer vision on top of these things, like, if they don't just start to really, like, glom on to things like Gemma four and the and these OSS things that are out there because, like, they just work, and they're free, and they're licensable. Like like, they're just in the right right right place at the right time. So we'll see what vendors do. But like I said, if anybody's got a creative way to solve this one, and don't come back to me if I answer SIM links because that doesn't work for all of them. I I would love to hear it because maybe I'm missing something. Alright. And reach out to Scott on LinkedIn if you're still listening to the after show with Ben and Scott complaining about technology and solving or solving the world's problems. This should be Ben and Scott solving the technology problems of the world, the after show. Alright. The after show. Well, with that, it is 90 degrees in Florida. Go enjoy your weekend? I don't know. It's getting hot already for me. I'm ready to go back to the 75, 80. Yeah. It's like that at about 6AM. After that, it's it's all off the rails. Yes. The gym has still been okay at 05:30 in the morning, but I'm dreading the next several months because this isn't gonna last long. But enjoy. I will be oh, by the time people listen to this, the conference will have come and gone. I'm headed down to the Microsoft three sixty five community conference tomorrow, the day after we're recording this, not the day after people are listening to this. Well, enjoy your conference. Hope you come back with some good information. And Alright. We'll see you when you're back. Sounds good. Thanks, Scott. We'll talk to you later. Yep. Thanks, Ben. Have a good one. If you enjoyed the podcast, go leave us a five star rating in iTunes. It helps Thanks again for listening, and have a great day. Thanks again for listening, and have a great day.

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Microsoft Cloud IT Pro Podcast

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Episode 426: Claude Cowork vs Microsoft 365 Copilot Cowork

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Welcome to Episode 426 of the Microsoft Cloud IT Pro Podcast.Ben and Scott are back together this week to talk through Microsoft 365 Copilot Cowork, including how it compares to Claude Cowork and where each one makes sense. The two products share a name but work pretty differently. Claude Cowork runs locally on your desktop and can access files on your machine, supports MCP server connections while M365 Copilot Cowork runs in the cloud, requires files to be in OneDrive, and does not support MCP connectors yet. On the flip side, the Microsoft version runs scheduled tasks without needing your machine to be on, has native access to all your M365 data through Graph, and fits inside your existing compliance and security controls through Purview, which matters a lot for regulated organizations.

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Episode 425 – Exploring Collaboration and Governance at the MVP Summit with Joy Apple

by [Scott](/content/author/scottmsclouditpro/ "Posts by Scott"/index.html) | Apr 9, 2026 | Podcast

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Welcome to episode 425 of the Microsoft Cloud IT Pro podcast recorded live 03/27/2026 from the Microsoft Studios at the Microsoft MVP Summit. This is a show about Microsoft three sixty five and Azure from the perspective of IT pros and end users, where we discuss a topic or recent news and how it relates to you. In this episode, Scott quadruple books himself with meetings, and Joy Apple joins Ben once again on the show. It's the end of MVP summit, and Joy and Ben are a little short on sleep, but have a great time learning a bit more about Joy Apple and her road to becoming a Microsoft MVP. We also spent some time chatting about SharePoint, OneDrive, Teams, and the importance of governance in Microsoft March, especially in this age of AI. And finally, we wrap up just talking a bit about the community around around Microsoft three '65 at the MVP summit, at conferences, and that family atmosphere that we enjoy so much at these events. Let's dive into the show. We are here for another episode of the Microsoft Cloud IT Pro podcast with Joy, and we are we're in a fancy studio. It is so fancy. It is. We're at the Microsoft I was gonna say, I was gonna name the podcast. We're at the MVP summit in Redmond at Microsoft headquarters at the mothership as people like to say. Right? Yes. Right. We are at the Microsoft mothership. And they offered up the opportunity for podcasters to, like, sit down Mhmm. And record podcasts in fancy studios. So this one's audio and video, and I know most people listen to the podcast on audio. We will put up the video probably on at least the podcast YouTube channel, and we'll put links in the show notes if people wanna actually go see Joy and I. And Who wouldn't wanna do that? You'll have the video. I don't know. You may put stuff up some places too. But I've been known to do it. You have. I will let you most people know me. I mean, you've been on the podcast once or twice? Is it just been once? This is twice. So do you wanna tell us a little bit about Joy Apple? Who Joy Apple is? What Joy Apple does? Where Joy works? I can do that. All of that? All the things. But first, I have to be paranoid because we had to put a push a button to turn on the video, but the audio is just going. Right? The audio is going. I can see we can see it over here. See the little green lights? They're, like, flickering on the bottom there. Okay. Do you feel better? Perfect. I'm good. So hi. I'm Joy Apple. I'm paranoid. But let me see. Who am I? What do I do? Where do I do it? So Joy Apple, I've been in the Microsoft space. This year turns over to twenty official years. Does it really? Where did you get your start? In a bank. In the Microsoft role in a bank? Nope. Oh. So I was in the financial industry. Did you know that human beings in general are really uptight about their money in their houses? Yes. Imagine that. Imagine. Just those things. I didn't love it, but it was fine. Okay. When I was the self taught geek nerd, if something didn't work, I was not, but I was the on-site IT person because our IT was two hours away. And you weren't scared to push a button? I'm not scared to push a button. Even at a bank. There are destroyed household appliances from when I was a child. Because before Joy could walk, she would crawl and push buttons. And a microwave with metal in it? Yeah. So I had an opportunity. I was approached by someone who was helping to write a book with Microsoft Press, and they asked them to do some copy editing. It was for the Microsoft Office SharePoint Server Administrator's pocket consultant. That is a mouthful. I know. And if you had a pocket that was, like, 10 by five by three, the pocket consultant would fit into that. That's a really big pocket. Really big pocket. Was it because the title had to fit on the front of the book so that I had to make the book that big? And I think it was like a some kind of a that was when they would put, like, tool images on the front of the book. So it was like a pneumatic handle or I don't know. I don't know. But I was like, this is really cool because the bank at that time used Lotus and that which was like, that's some of the OG collaborate software. Right? And I was trying to convince them, like, we could see each other's calendars. We could manage mortgage appointments and things like that. We could do that. And they're like, that's so complicated. Just print the calendar out. So all those kinds of things. But going through this book, I was like, this is it's really interesting. I I wanna know more. Well, if you've ever written a book, probably does it, like, make you rich instantly, if ever? You know what? I have heard this. I have never written a book, but I have talked to enough people writing books. It's always so it's always in my the back of my mind, it would be really cool to, like, have a book with my name on it. And then I talk to anybody that's ever written a book and they're like Don't do it. Don't do it. Like, okay? Don't do it. No. It was fun, but I wasn't paid in money. I was paid in training. Oh, interesting. Because I was like, this is and I look. Because I wasn't a cover author. I wasn't contributing content. I was taking engineering words and putting them into sentences. Engineers don't talk Shocking. Sentences. We love you. You engineers. Understandable words. We love you. I was raised by an engineer. We love you. I'm an engineer. You can make fun of me. I would have to completely rewrite everything. So I learned SharePoint. I went to web content management training. I went to end user training. I went to admin training. And within two years of that, I moved to an official IT role at a government contracting facility in Huntsville, Alabama. Then I became a trainer. Does it have a name? We are just gonna leave that alone. Then became a trainer and then a consultant. So, like, literally, it was right time, right place, grace of God, the right opportunity, because I don't think any of us grew up wanting to be SharePoint professionals when I did not. Well, SharePoint didn't exist when I was a kid. Fair. But I also did not grow up with these aspirations of Oh, but it was as amazing journey. And thinking back, like, holy moly, twenty years. Like, we got to see some really cool stuff today Yes. That I couldn't have imagined twenty years ago. When you were right? When you were doing SharePoint 2007 because yeah. Yeah. It's wild to think about all the changes in SharePoint It's amazing. Over the last twenty years. And it what, like, is it was this year earlier in March. Well, it's March now. A week or two ago was, like, SharePoint's 20 birthday. Yep. Growing up. So we have almost been with it the entire time. I got my start about the same time you did. It was, like, 02/1956. It was sometime I did stuff with SharePoint 2003. Mhmm. Old. That'd be a success. But it was about the time 2,007 was coming out. Yeah. Okay. So I think it was somewhere between it was, like, 02/1956 time frame that I got my introduction to it. Yeah. It's an amazing journey. I mean, you always take turns as you're going down your career path and sometimes, like, why did I do that or I wish I'd done this different. But in like, for me personally, at my third or fourth in person MVP summit. Okay. So did you go to any of the in person ones? Like, the what? The first one or two right after COVID Mhmm. People I I heard feedback that it wasn't great those first year. I didn't have anything to compare it to because I was a woman during COVID. Did you go then as soon as it was back in person after? Maybe I did you know what? Maybe it was Ignite that I didn't go to. I think I did go to the first person in Ignite. First in person in Ignite too. Also, I mean, we were figuring things out and doing the best we could. Yes. Very true. Right. But no. It's been fantastic. Oh, so, yeah, twenty years, Microsoft, firmly on the collaboration side of the house. Right now, I am with Orchestra Tree Software now. So that is where I have expanded, and I've been there for about three and a half years. It's been three and a half years already? It's man, the stuff we're doing, also exciting and fabulous. So I love governance. We can say that now with our head held high. We can say govern yes. We used to be like, okay. I wanna say this word. It's the g word. It don't hit me now. It's like, y'all gotta do your governance. You need to do governance. And I feel like you need to do governance. I mean, we both been in SharePoint line. If we've seen SharePoint site sprawl, I feel like governance is even more important now. People create it's kinda like AI. Right? AI helps you find things faster, easier, all of that, but I also feel like it helps you create things It does. Faster and it expedites the ability to have sprawl or for content to get where it shouldn't be or all of that. So Yeah. Yeah, I feel like governance is way more important now. It's very important. My colleague, Reyna O'Neil, wrote a little article on LinkedIn the other day. I've got my phone on airplane mode, so it doesn't make noise. So now I can't remember the type. Something like your AI isn't broken your processes or something like that. Right? And she saw about the fact that AI amplifies whatever practices you have in place. Oh, yeah. That's right. Yep. So if it's just the gates wide open, anyone could do anything, anytime, any place, anywhere, just go nuts. Or we talked about a lot this week, YOLO mode. Right? If you're if everything in your tenant is YOLO, AI is gonna it's gonna be so bad because, right, everything's there. Nothing gets cleaned up. You just put things wherever you want. You don't really approach things with a process. AI can't magically fix that for you because it's feeding off of what we give it. So if we're giving it chaos, it's gonna amplify that chaos. Yeah. You're out of time. Copilot needs to be deployed ASAP, but is your tenant really ready for it? Years of data, permissions, and users lurk in its shadows, ready to be exposed by AI. Sharegate Protect sees it all, so you can find the exposure risks, fix them fast, and deploy AI with confidence. Microsoft three sixty five governance. We got this. Learn more at sharegate.com/governance. It's similar. We talked about this a lot even in the years with like, when Power BI and business intelligence and data warehouses and all those are coming out. Right. You give it bad data, you're gonna get bad reports. Input output. Yeah. You give Copilot bad data, incorrect data, old data, whatever data. It's yeah. It's just gonna amplify the bad the badness. So Buckley Christian Buckley and I were talking about this recently. So we're dusting off our old presentations because they're relevant again. Right? Because we're we have to talk the fundamentals this is a bold statement. But it's like the fundamentals are so much more important now, it feels like, than they ever were. Now I've got a talking heads song in my head. Do you guys sing for us? Maybe not right now. This is only coffee. It's only coffee. They're not recording this late in the day when their beverage requires a switch. Just the ammo bets are off. But, yeah, it's like information architecture. How many times have we said that phrase this week going, hey, Microsofts, don't forget about information architecture. Hey, folks using m three six five, don't forget. And if you're not really familiar with that, we have so many good resources in the community. Information architecture is so important. Data hygiene is so important. The concept of archiving things, setting permissions right. Oh, so important. And this is a lot of stuff. I'll let you do a little bit of a orchestrate pitch here. Okay. Alright. Because a lot of this stuff is stuff you're building into orchestrate Yep. Now. Right? There's a lot of that governance Totally. Controls, reporting. My my little elevator pitch is that Orchestrein is a governance automation layer for Microsoft three sixty five. Okay. Right? Yeah. Load it in. It's great from a user perspective because the apps right there, pen it to the left rail in Teams because that's where we all are all the time. So templated provisioning, it it it's one of the one of the things I never appreciated when we switched to modern experience inside of SharePoint is it was so difficult, if not impossible, to have a cookie cutter homepage template. Right? It's very difficult. Yep. My favorite thing about orchestra, I think, still to this day is the fact that you can point orchestra at what we call a live template and say, I wanna use this every time something new is created. Mhmm. Pages, web part layouts, links, icons, images, lists, libraries, columns, JSON formatting. Boom. Go. Yeah. And it's not even just SharePoint sites, but, like, teams. Because I Teams. I use orchestrate. Communication sites to even engage communities. Right. Like, I create a team for every client I have in consulting, and that's how I do it with orchestra. I'm like, I want this team, these channels. I want it set up this way for every client team and SharePoint site and structured this way and Yeah. Yeah. So that we've had archiving in the product for years. When Microsoft released m three six five archive, we have added that to our archive suite. So you can make that policy driven now. So you can go in and say every time this template is used, this is the archive policy. If it goes, let's make it up. If it goes inactive for ninety consecutive days, reach out to the owner. And maybe for some sites, we don't wanna delete anything yet, but let's keep it in place, make it read only, set the group to archive, prune the drafts, and reclaim some storage. Alright. There's things you can do. Yeah. There's a variety of options there to get that rot out of the way. A redundant outdated and trivial content, if that's a new acronym for you. Secure guest management. I don't know that I've heard that acronym before. ROT yesterday. I had to do it. I don't know that I don't know that I have. Vlad said it today. Did he? Yeah. You don't listen to Vlad though. No. I think he just let it just wash our feet up. Because Vlad did not come say hi to me the other night. You did. You came down when you got back and said hi. Vlad blew me a kiss and got on the elevator. I don't That was a brush off of it. It was. I don't yeah. Anyways So much love in this community. Yes. This is the best. This is Which we'll have to come back to that here in a minute. Well, yes. It will. But no. Not to get salesy or pushy or anything about that, but this is a topic and a passion that I've always had around the technology stack. So I get to work at a company where that's what we do. And I think my favorite thing about Orchestra is the creators of the product are founders, our director of product, David Ferencore. Shout out David. You do amazing work. They've lived it since the early days. They've been the developers. They've been the consultants. So it's not just making a product to do a thing. It's like, this is the pain. Let's go fix it. Right. I've lived this pain. I've been in this world long enough. I know what hurts. Let's make it. Like, we just really solution. We just released our phase one of OneDrive governance. Because if you have your point's bad, OneDrive is horrible. Have I told you the story about my OneDrive? Well, this was OneDrive and SharePoint. I think I've I think I've told it on the podcast before. But I'm I'll tell it to you just, again, from your perspective. I have some client I've had a lot of work lately around people running to roll out Copilot and do governance. Mhmm. On their data, they're like, what do I need to do to roll out Copilot? I'm like, you should really make sure how your stuff is in SharePoint. Put your bare fist on speed dial. Yes. And then And I did it. Like, I'm sure I could do this with our history. I have my own PowerShell script that I point at SharePoint and just say, go find me all the sharing links and how they're shared and who they're shared with and all of that. Yeah. It's already built in. I built a PowerShell script. You don't need it? We can do it for you. Well, I did not build a PowerShell script. Claude built a PowerShell script. Thank you, Claude. But, anyways, I ran it against one client. They had 25,000 links in their SharePoint environment that were shared with the entire organization. I believe it. That's probably their default. Yeah. It was their default, and then we went in and switched their default and all of that. This was a new one for me. One of their users, OneDrives, it gave you this was one of the built in SharePoint reports in SharePoint advanced management, the same reports For data access governance, do you need to tighten your Yeah. I feel like it's you know, we're having to Go higher. Technical difficulties will drive. Okay. I'll keep going, though. Yes, sir. But I looked at this report, and one of the items in there is how many users is your content shared with. This one user, one user's OneDrive, 2,500 different people had content to or access to some content in his OneDrive. That's cool. Going back right? Going back to your OneDrive governance, it's like, how because of sharing is great. I love the ability to share, but there is absolutely that governance need. Like, you cannot have that many people having access to somebody's OneDrive without realizing what and how, especially folders. That's the other aspect. Someone shares a folder and all of a sudden they, like, start dropping content in it without realizing that the folder is shared. For long. Yeah. Yep. Because that content grows because it's what we do. We create content. And, yeah, it part of that comes back to us. And I'm saying us as, like, the broader admins, subject matter experts, whatever your role may be. We've got to convince our organizations to do proper training. Yes. Got to. Because just because you can share everything out of your OneDrive, it does not mean you should Right. That should be in a team with the proper audience, guardrails, what have you. I can let anybody into my house, but should I let anybody into my house? I don't know. Sharing is caring. I'm not that sharing with my house. No. Going back to your early statement about the bank. I care about my house. Right. We can't tie it about the house. I am not sharing my house with everybody and anybody. I have proper governance around who's allowed in my house. External users. Yeah. What's an internal my family is are those my internal users in my house? We. My coffee cup is a leak. This is a problem. Oh, I'm sorry. I don't have I'm gonna look like the messiest guest ever by the time. It's fine. Okay. Anyway, so yeah. It's proper go over there. Stuff. Yeah. I get to have great conversations. And part of my role, it's like one of those other duties is assigned just because I decided I wanted it to be. I get to be that kind of strategist for a lot of our customers too. It's like, look, I know you know what you're doing, but if you need to brainstorm, if you need I call it corporate therapy. If you just need someone that's been there, done that, has the shared trauma, set up a call. Let's hop on Teams. Talk it through. So again, I get to help be an unofficial adviser in some ways. Therapy. I think there is someone out there on the socials that is a SharePoint therapist. I should know who that is. I can't think of it right now. I don't know who that is. Yeah. I'm no. I'm not gonna look. I'm gonna stay focused. Resist resist the ADD. Yes. I will do it. Squirrel. Yeah. So, anyways Tell me. This week, tell you, we're at the MVP summit. Yeah. We mentioned that earlier. We did. And this is we've both been have you been an MVP have we been MVPs for about the same amount of time? I think I'm on year three or four. Four? I am on year five. I just got a five puck. Oh, yeah. Last week. So you're ahead of me. I think I can't remember how many clicks I have. That is cool. That was very exciting. But this is one of you said it earlier, your favorite week. This is a lot of people's favorite weeks. It is. And it's not we can't really talk about The details. The details. There are a lot of details. We wouldn't get to be invited back. Yeah. We would lose that MVP. But I think we can talk about just the experiences and even why it's our favorite week. Mhmm. And a lot of it has to do with, like, what I for me, it's like what I said about Vlad. Just Yes. The feel of it almost being like a family out here. It's, yeah, it's like a family reunion every year. It really is. And people are like, oh, it's lame or roll their eyes, but no, really. When I was in my Uber pulling up to Building 30 3 on Tuesday, my driver saw the lines because it was before the keynote, right? That was the official day, right? Yeah. So people everywhere, shuttles were dropping, all this stuff. And he was like, oh my gosh, what is happening? I was like, today is the first day of MVP summit. I said there are people we're here coming in from all over the world, and I said this is the one time of year if you get to come, you might only see your friends this one time a year. Yeah. And I think that's the first bit of excitement is that. But then, I mean, we're MVPs because somehow, someway, we got on the right radar or whatever, but it's because we love to share and to talk and to explore and to experiment with this technology. So now we get to come to the mothership once a year. Yeah. Talk to the builders, talk to the program managers. They do a little bit of show and tell. We get to give them feedback. We may or may not have bingo cards for those conversations about things. Fuzzwords. Yeah. No. I think you're right as you were talking about it, it's we love to share, go talk to people, go show people all the cool stuff. Yeah. But a lot of times, we go to conferences, different events, all of that. We see each other there, but we're also there presenting Yes. Talking to people, showing people how to do it. This week, it, like, it's a week where it gets to flip. We're the attendees. We're the attendees. We're just here seeing our friends that we only see. It's funny. There's someone that lives in Jacksonville, same city as me. Okay. He and I played ultimate Frisbee together for years and years. Like, five or six years in Jacksonville. I had not seen him in, like, five years. He became an MVP, and I saw him last year. Didn't see him for a whole year. Saw him again this year. It's like we live in the same city. We're different No. It's categories. Right. We're different categories of MVPs. Like, he does a lot with he works at a company doing path building a password manager. Okay. You would think me being in security, we'd see each other more, but he's a lot more on, like, the development side of it, the product side of it. I'm doing consulting. But we see each other, like, once a year at MVP Summit. But it is it's that it's flipped. We're the attendees. We just get to hang out, spend time with people, spend time be sassy. Spend time with other people we maybe see at conferences. But at conferences, we are busy writing our presentations that we have to give the next day because we plan ahead. Yeah. Like, conferences those conferences feel busier. They're very busy. Is it's still busy, but it's different. It's relaxed for the attendees. We get to be the people being talked to, shown Yep. The new buttons, the new things Yep. All of the stuff we have to talk about really vaguely like that. Yeah. And it's great. Though I was just thinking as we were talking through that, I was like, what would it be like to turn our conference presentations into feedback sessions? And now I would like to gather your feedback on that. Yeah. Because I would say this, if if anyone at Microsoft can hear me now, it's still dropping. It is still dropping. Crazy. When you stand up in front of us as engineers, as program managers, project managers, and you open yourself up to that feedback, thank you for doing that. Yes. We really appreciate it. And we apologize for the brutal honesty that we can give sometimes. Yeah. Like, this was funny. I will talk about this. This is one session. It is not crank that thing down, Joy. There you go. One of the sessions I was in, it was all the questions that you how did they phrase it? Now I'm gonna blank out. It was something about oh, it was all the questions about a certain product that you're afraid to ask. Oh, that's bold. They crossed off the you're afraid to ask and just x it out and said, we have very quickly realized that MVPs are not afraid to ask anything. That's weird. But it is. To that point of we appreciate it is I appreciate those sessions when it really is. Like, just come in and ask us if you are from Microsoft and you're listening. Really, don't take it personally. We just No. We're very opinionated about the products we love. Well, I so few years ago, there was a sneak peek of some things that they were working on, and 99% of us in the room lost our minds over it. In fact, Jonathan Weaver said, I wish I had a video of how fast your hand went up. I'm like, oh. So we stayed after because you gotta get out of the room because other things are going on. People gotta get playing. Another session. Just like a typical conference, there's another session coming in. People are coming in. Yeah. Yeah. Yeah. But But we kinda hung out in the room for a few minutes. I was talking with a gentleman who, again, he gave some great presentations and took some good feedback yesterday too. Very much appreciated. I was like, well, I don't understand why you would do it this way. He said, well, this is what our customers want. But I think from our perspective as consultant because we've been the consultants. Like, you don't have to have MVP after your name to live to be this valuable resource for your customers because sometimes our customers think they want something, so they go do it or they hire someone to do it for them. And then as consultants, we get brought in to fix it later because they didn't really understand what they were asking for or the ramifications of going down a certain path. Yep. So this is that chance to have that conversation with the product makers. Yeah. And that is amazing. And it's so it's kind of fun too. It's like I was joking the other day. It's like, well, I asked a question, I couldn't really get them to answer it. But sometimes it's like, well, I wasn't asking it the right way. Yeah. Or the terminology is a little different from one side of the table to the other. Or you ask a question, you see them go, oh, when you think about that. Yes. Right? Because they're not out in the field working with the customers as much as we are. So you just see this massive collaboration happening real time. 100%. So good. And then sometimes they truly just have no idea. I've been in a few of those where it's like, what about this or this? And I don't know. We don't know yet. And that's fair, especially as fast as things change now. It is. And I think from a consultant perspective, that honesty feels good because that's what I hope we bring to our clients too is I should not be making up answers to my clients, and I appreciate not having answers made up to me. Like, just I don't know is a perfectly valid answer. And it's the right answer because and this was a piece of advice given to me in my early consulting days. Some of us tend to have some overachieving tendencies and we just feel like if we don't immediately know what to do, when to do it and do it right all the time, we're failing. Right? But my mentor pulled me aside and said, your job is not to know everything. Your job is to figure it out. So or find someone who knows to help you figure it out. Yeah. He said, so stop putting so much pressure on yourself. If you don't know the answer, you are allowed to gracefully say, I don't know, but I will find out. He said, then go figure it out. Yeah. 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But at the same time, I'm like, I kinda wanna see who's down there because it's the last night to hang out. And you did it the other night. I had gone out to dinner. I came back. You were out at another event, and I was down at the bar there. And Uh-huh. You looked over and you're like That was what you did. Because if you've never seen him stand up, he's tall. He's so tall. Yes. I was standing up and you saw me, and I was about to go back to my it was 11:30 at night. I was about to go back to my room. I had literally just said, okay. I'm going back to the room. I'm going to sleep. I turned around to walk out, and you walked down the steps, and I'm like, I'm not going back to my room. Well, yeah. Because it yeah. I'd left one of the one of the various kind of party meetup things. And I thought, well, I'll just at least see who's here. I don't really wanna hang out because it was late. I'm gonna be good. I'm gonna be disciplined, and I'm not gonna be so it's like, well, I see. But there was Ben standing up in a very bright blue hoodie, so it was hard to mix. I was like, well, crap. I guess I have to go talk to Ben. So I go down the stairs and then, like, it was probably an hour. Yeah. I think it was, like, 12:30 or something. Talking and you're like, I was gonna go. You walk down the stairs. I was like, well, I was gonna go, but you were standing here. But at the same time, I don't know that either of us we say we were gonna go to bed, but it's so much fun. It's so much fun. And I was thinking that, like, the other night when I was getting ready for bed and everything, I was like, it's it's a interesting combination of exhausted, depleted, but so full. Yes. It's like your your social, your community, your family cup, oops, gets filled up, but you're so tired. Like, my husband, he's like, I'm gonna pick you up at what time? I was like, 04:30, five. He said, maybe you wanna go to dinner? I said, yes. And then I'm gonna go to bed. And then to bed. Yeah. And then Vlad I mean, Vlad did a good job the other night. Like I said, he came in and he made eye contact with me, and I yelled something to him across the hotel lobby. And he blew me a kiss and turned around and Yeah. Because it was Vlad. Yes. Vlad, I have That's disappointing. Things I can learn from you beyond just SharePoint is how to get to my room on time. How does this go? Nope. Yes. But it is fun. So other people, like, this is always an interesting conversations. I've done other interviews at MVP Summit as well is, like, if people are listening, they're like, oh, this really sounds like fun. I wanna be there. Obviously, the first requirement to doing this is being an MVP, but what was your journey to being an MVP? Like, how did you go from I'm doing consulting, I'm Mhmm. Helping out at Bucks, now I'm doing SharePoint consulting to the MVP. Because I feel everybody's journey seems to be different. It's a little different. It it's interesting. Because so that's one thing to call out. It is different for everybody because there's no checklist that says do these 10 things, and you two will be an MVP. It's not a certification. It's an award. Yep. I am a communicator, trainer, teacher, sharer at heart. Right? Like, if I know something, I want everyone to know it because it's amazing. Consulting and I was really interested way earlier in trying to figure out what this MVP thing was and what these what conferences and speaking and all that is. I have a drama and theater background. Obviously, I mean, you don't come into IT with anything normal. Right? So I did. But, apparently, I'm abnormal. I mean I've been told that multiple times. My family tells me I'm not normal. I'm the not normal one in my home, and I embrace it. But So was that your educate was you went to school for drama and theater? I went to school on a drama and theater scholarship. Okay. Yeah. But then I became a star for admin, and it was like Natural career progression. As one does. Because I got married very young the first time around. So that straight, I'm gonna go to college for four years, I wanna go get this degree, I knew that didn't happen. So there was a lot of, like, turn left, turn right, zigzag, zigzag. When it was my turn to go through school, right, because I had to go work jobs to live, landed the IT job, and I was like, do I wanna keep paying for my college a semester at a time now because I dropped out of college, did this thing, or do I wanna invest in learning this technology? Okay. I chose the technology. I'm so glad I did. But the community stuff wasn't encouraged at that point in my life. So I'm basically living joy two point o. Okay. So I took some pivots. Part of that included relocating from Alabama to Oklahoma. Okay. So various things happened. My first SharePoint Saturday was in 2010 Alright. In Dallas at the Microsoft campus. And it was my first taste of it, but then I had to, like, reboot. So things happen and then, oh gosh, eight years. I can't do math. We're just gonna say at some point later, years later, someone approached me and said, hey, there's a SharePoint Saturday happening in Atlanta. They need speakers. I think you should do this. And it had been a couple of years, a few years in between 2010 and that. It's like, okay. So I just started speaking because I I love to be on the stage. I love to share. I love to teach. Social media, speaking, the occasional blogs here and there, writing articles if somebody asks, consulting and things like that. Okay. But then in 2019, there was an MVP dinner, and Joel Olsen asked me where I was gonna go. Oh. Was like, no. Was this like after a conference where it was a bunch of MVPs going out for dinner? Or six five Friday or Saturday, San Diego. Okay. Right? Yep. Joel's like, are you gonna come to the dinner? I was like, no. He's like, why not? He's like, well, I'm not an MVP. He's like, you're not? I was like, no. He's like, you need to fix that. I'm like, okay. So I talked with him, Rob Windsor, wonderful, good mentor. Thank you, Rob. I love Rob. He's the best laugh in the industry too. Yes. Rob, we love you so much, man. But I had some mentorship. Time was right. I was told, yep, you're good to go. And my application was approved. Did you get it the first time? Yeah. Congratulations. Oh, thank you. But I I had some very wise counsel, right, of, like, wait. Because there was a few moments, like, am I ready now? No. Wait. Yeah. Wait. But yeah. And it's been amazing. Some people are like, what did you do to get it? It's like, I talk too much. That's what I do. I don't. Well, it's interesting comparing your story how you got there to mine because I had several similar experiences where I would go speak at a conference or I'd go do something. And there was one in particular I remember. I think it was I was talking to Stephen Rose. Another guy, everyone. He's in? Stephen. Yeah. Again, we're all just one big happy, lovable family. The best. And it was at a conference, and he's like we were saying, bye. See you later. He's like, I'll see you in March. I'm like, what's in March? What's in March? In March? MVP Summit. And, like, I'm not an MVP. And he same response. You're not an MVP? And I had that response from multiple people at different events, but I think what that illustrates is that it's not something you get that checklist to. Most MVPs are MVPs because we love what we're doing to the point that people are surprised we're not MVPs because you're already doing the MVP stuff. You love doing the MVP stuff. Yes. So you're doing it to the extent that people are surprised you're not MVPs. Right. And then it just happens. I would say my number one thing about the whole program is if you approach it from what do I have to do to be an MVP, don't proceed. If that's the mindset, don't proceed because it's not what you do for your job. It's not your nine to five. In fact, it's your everything that happens Outside of your nine to five. Nine to five. It's a lot of meetings, it's a lot of calls, it's a lot of work, but it's the kind of thing like if I found out tomorrow we decided, Joy, you're not part of the MVP program anymore, it would not change what I do. Right. Because I didn't do these things to get it. I love the technology. I love the product. I love helping people have a better experience at work, and we're at work so much. Right? The technology needs to work. That's what we do. Right? We make it work. Right. And we love going to conferences and hanging out and With friends. The podcast, doing this. Like, this was one of the things that I think helped with my MVP. Sure. But I had done the podcast, what, I think I said four years. This is year nine of the podcast. Congratulations. Thanks. But it illustrates that point. I did this for five years. Before there was an acronym. Before there was an acronym Yeah. Yeah. By my name for doing that, for speaking at conferences. My first conference was 2009, 2010, something like that. Yep. Yeah. So it is. It's not something and there were times it was a mix for me. There were times where I actually I legitimately got frustrated because I've done all these conferences and everybody's like, you're not an MVP? I'm like, no. What am I doing wrong? Yeah. Yeah. And I did not have the experience of my first nomination getting it. It took me, like, two or three. Okay. Okay. No. You haven't done enough. And I'm like, I What more can I do? Right? Like, what more can I do? And it's not that it was again, it wasn't like there was a checklist, but it was like It's not. I don't know. I'm doing enough that everybody thinks I'm an MVP except for the people that are approving the MVP. I think that's where my frustration was coming from was all these people are like right. All these people are like, why aren't you an MVP? Why aren't you an MVP? I'm like I don't. I don't really know because you all think I should be. Apparently, there's somebody over here that doesn't think I do enough, and it's I still kept doing it because I loved doing it, and eventually it happened. And that's the thing. We do what we do because we just love it. And I joke all the time. My husband thinks I'm the not normal one. I say all the time, I could win the lottery tomorrow, like, the lottery, and I would buy a home in Bora. But I would do the fun stuff for free. A 100%. 100%. It would be John White. Yeah. Right? I Are you saying John White won the millionaire? No. But I just He's another good guy. Right? So he supposedly retired, I thought, but he says a free conference. Yeah. No. I don't know. No. He's not. I'm not even retiring. No. You know what? Do it for fun. Do you feel overwhelmed by trying to manage your Office three sixty five environment? 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I'm gonna get old and I'm not gonna be remember stuff, and already I'm like, I'm tired. I can't keep up with all this change. Thanks. Like yeah. This gen whatever? It was there's an MVP. Another MVP story. I was at a conference recently, and we were all sitting down and chatting, and there was another m b a new MVP there. And it came out that this individual was born in 2001. Ouch. I we yeah. Like, now I don't feel like I'm so young anymore because Yes. That reminds me I need to go get a bone density test soon, probably. Oh. Because we're just so old now. These young kids. These young whippersnappers. No. It was funny because earlier in that week too, someone had made a reference to a movie, to The Matrix. And in that session, it was like, if you haven't seen The Matrix and you're in IT, and I've looked, I'm like, wait. Where did that come out? That came out two years before this individual was born. It was 99. And I'm like, oh, now we're really old. We're referencing movies and saying every IT person should watch it, but there are IT people that were born They were toddlers. Years after this movie was released. Well, I'll say this. Like, okay. Yes. The Matrix. I mean, it's so relevant, especially now, right, with all with the AI. Right? We were yeah. The Office Space. We were talking we the other day, I was talking to different TV shows and movies that are really funny to go watch now that came out years and years ago. But, yes, you're matrixing the Office space is one, and I probably haven't seen it in three or four years now. I need to go with your ride. Now we're gonna go watch it, like, on the plane. It's not on is it on the plane? I don't know. I don't think my airline that flies direct to Tulsa and Seattle has seatback entertainment, but I maybe I should. I've got that little thing where I can clip my phone to the back of the seat. Okay. Right? Thanks, Jay, for that recommendation. Yep. So, yeah, I should download that, and I'll watch it on my if I don't just conk out. I'm so tired. It has been so fun. Yeah. I'm taking a red eye home. I will absolutely conk out. I don't I try not to do those. I going all the way to the East Coast from Seattle, it's a five hour flight to Atlanta Mhmm. An hour flight to Jacksonville, a three hour time change. And then you have to fit a layover in there too, so it's like five, seven. It's like a ten day. It's a difference of ten hours. Yeah. If I don't take the red eye on Fridays, I feel like I miss the weekend with my family. Because I do have the four kids. They, like, see me on the weekend. Props for that. Like, okay. I can take the red eye. Can you sleep on a plane? An okay. So here's the other aspect of it. I kinda like, I can sleep. I don't sleep great. Yeah. I sleep enough that I can get through I'll get through the day tomorrow without taking a nap. Yeah. I'll be dead tired though by, like, 10PM. So I can actually fall asleep Okay. At a normal time for eastern time zone. Force yourself to adjust. Right. And force myself to adjust rather quickly instead of if I left tomorrow morning after a full night's sleep, I would not be tired tomorrow night till, like, 3AM. Got you. So I respect it. There are it it's rough, but it does help with that adjustment. So Yeah. I used to have the deal with going from Seattle to Atlanta then back to Tulsa, but thank you for Alaska Air for having direct now from Tulsa to Seattle and back. That is a quality of life improvement for me. Nice. Yeah. Yeah. See if they wanna sponsor the podcast. Alaska Airlines? Yes. We appreciate you, That would be interesting. Swag. I'm shameless. You're shameless in your promotion of everybody. Alright. With that, we've been talking for, like, forty five minutes. It's what we do. It is what we do. The I think you made this comment the other day. Somebody asked if we could talk for twenty minutes. You're like, we're consult. We can talk about absolutely nothing for twenty minutes. Twenty minutes? Yeah. And make it seem like Let me show you. But we have there is a little bit more of a session we could go to, and our listeners might want to yeah. Yeah. You might have other things to do. They might have other things to do. There was something else I was gonna say, oh, we would get kicked out of here if we keep talking too long because there's someone else returning a podcast after us. Unless that door locks. Does it? Yeah. I feel like that might be the end of our MVP status when we lock ourselves in the studio. Why did you lose your status? Well, we barricaded ourselves in the recording studio. Yeah. Oh my. Alright. Awesome. Well, thank you. You're welcome. Thanks for coming on. It's been fun. Scott, you missed out. Sorry. You triple booked yourself today. Yeah. Maybe you should learn how to use a calendar in Outlook. Do we have the technology? We do. Like, there are ways to make sure you don't triple book yourself. Pretty soon, AI will make sure we don't. I don't know that I'm ready for that, to be honest. Don't know. Because I don't know that it'll depend on how smart AI is because I very much will get triple booked, and there is quite a process I go through to decide which the one. Of the one I'm gonna keep because it is not always the first one in. Agree. It could be how easy one is to reschedule versus another, deadlines that AI may not know anything about. Yeah. Yeah. But it should because it's all on the graph. Are my deadlines on the graph, or are they in my head? That's a you problem. That is a me problem. Thanks. I have lots of me problems. Y'all do. But Okay. Yes. With that, thank you again for My pleasure. Joining me last minute due to Scott's faux pas. Yeah. Thanks, Scott. It was fun. So good. Yes. Enjoy. Safe flight home. Same to you. We'll see you in April. Right? Orlando? Are you coming to Orlando? You be determined. TBD. I found out yesterday there's a 20% chance I might get drop shipped there. Okay. In a cardboard box? Like, would you really get shipped in a cardboard box with little air holes in it? And If they put a mattress and I could lay down and just, like, conk out, yeah, I would be down for that. That's probably better Right. So where are you gonna be if people do want to yeah. If people wanna go find you or see you in person or you're on so where's your social media of choice? Is it LinkedIn? It's pretty much LinkedIn these days. That is Sure. That's where we've done. So, yes, they can go find you on LinkedIn or what conferences do you have coming up? I'm gonna be at Comms v Next in Denver. If you've never checked that out, do it. Do it. Do it. If you have a passion for unified communications and or collaboration, they will have you covered. So that's a May, I think. That sounds right. I'm not gonna be there, but those dates sound right. It should be there. I have been told I need to go there. Every year, I end up with so much that time of year, and it hasn't worked out. But I don't have a worry. See, I'll make you do it next year. I'm also gonna be at TechCon three six five in Chicago in June. Okay. Tech mentor back here in Seattle in August. Alright. Maybe Techcom three six five Seattle also in August. I just can't remember if they've started accepting or if I could have accepted. Not started accepting. I do know that because I submitted for that one, and I talked to people that said Okay. They have not started Okay. Accepting yet. Cool. So you have not been rejected. Yes. I hope it's still alive. Right? That's always I wish yeah. Anyways, side topic. Yeah. That one. Ignite, maybe. Two big meetings. Okay. November. And Sandy Branson. I'm gonna be yep. I'm gonna be in Branson. September. Yes. Yes. Early September. Early September. So, yeah, we're gonna be everywhere. I might even be at ESPC. Oh, that one's coming up soon. Right? Since it Or as soon as that one? You'll leave the weekend of Thanksgiving. Okay. That one's November. Mhmm. Late November. Alright. That's right. Because that one's right by night. Yeah. Like, there are people that, like, go from Which is why I did it last year, I think. I don't know. Okay. It would just, like if my calendar says to be there, I book a flight and I go. Got it. It's kinda how my world works. Perfect. Alright. So, yes, if you wanna go connect with Joy, find Joy. I would say the other thing, some people say, I felt this before I was an MVP. I was I'm an introvert. I am not one to, like, go up and talk to I was always like, oh, they're speakers, they're MVPs. I was intimidated. Yeah. I get that. Don't be intimidated. No. Yes. Come, like this, I would say, is another good thing about if you think this is something you'd wanna do, one, let's do what you love, but come talk to us. Like, MVPs, introverts or not, we genuinely love talking to other people, helping other people, giving other people advice. I've had people reach out to me at conferences and said, I'm not an MVP. I would love to just talk to you about being an MVP. Yeah. It's like not we're not gonna give you a checklist of how to get there, but we'll talk to you about our experience about Right. We've had other MVPs tell us, to your point, you haven't done, go do this, go Yes. Here's guidance that might help get you closer. We just can't guarantee anything. Right. And we love doing it. MvB stuff aside, if you wanna be involved in the community, that does not mean standing on stage as speaking. It could be. It could also mean just help doing behind the scenes organizing or if you want to write or if you wanna do something like this. I mean Yep. We have thoughts, we have ideas. It is not a cool kids club. It's a nerd kids club, and everyone is welcome. It's a cool kids club, but, you know, it's because it's just a cool club. It is cool. You don't have to be cool to be in the cool kids club. Like, I feel like that's it. Like, it is absolutely a cool club. Yeah. Maybe that's the better phrase. It's not a cool kids club, club, but it's a cool club. It is a cool club. And just And you don't even have to be an MVP to hang out with the speakers too. There's lots of speakers that aren't MVPs. Yes. Again, I hung out with speakers and MVPs for, like, five or six years before I was an MVP. Yep. Yep. And they are they're all very friendly. It's just fun. Yeah. We enjoy being Just fun. We like to talk. We like to share. We like to hang out. We like to hang out at the bar till We like to stay up past the time. Way later than we should. Yeah. Alright. With that Yes. Squirrel. Jacqueline, we're gonna wrap up, like, ten minutes ago. Yes. Good. Alright. Until then, thanks again for joining us. Always Join us, and we'll see you again soon. See you soon. Bye. Bye bye. If you enjoyed the podcast, go leave us a five star rating in iTunes. It helps to get the word out so more IT pros can learn about Office three sixty five and Azure. If you have any questions you want us to address on the show, or feedback about the show, feel free to reach out via our website, Twitter, or Facebook. Thanks again for listening, and have a great day.

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Microsoft Cloud IT Pro Podcast

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Episode 425 – Exploring Collaboration and Governance at the MVP Summit with Joy Apple

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Welcome to Episode 425 of the Microsoft Cloud IT Pro Podcast. In this audio and video episode recorded live at Microsoft headquarters during the MVP Summit, Ben welcomes a return guest, Joy Apple, to the Microsoft Cloud IT Pro Podcast and discuss her 20-year career in the Microsoft collaboration space, from financial services to SharePoint training, consulting, and her current role at Orchestry Software. Joy explains Orchestry as a Microsoft 365 governance automation layer covering templated provisioning for SharePoint and Teams, archiving policies (including Microsoft 365 Archive), guest management, and OneDrive governance. They emphasize that AI and Copilot amplify existing information architecture, permissions, and data hygiene issues, making governance more critical. They describe the MVP Summit as a “family reunion” where MVPs attend sessions and reconnect with peers. Joy and Ben also spend some time describing paths becoming an MVP and how much they just enjoy the community around the Microsoft 365 ecosystem and connecting with people both at MVP Summit as well as various conferences throughout the year.

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