Microsoft has a problem: lack of demand for its AI products

Well, the major problem Microsoft is facing is that its AI products are not only shoddier than average, which is nothing new for them in many categories, but that this time the competition can actually easily leapfrog them.

Like, I have a 'Copilot' button prominently displayed in my New Outlook on MacOS (the only platform where the app-with-that-designation is sort-of usable), and it's a dropdown menu, and it has... zero items when expanded.

I asked my 'Microsoft 365 Bing Chat AI Bot Powered By ChatGPT<tm>' about that, and it wasn't able to tell me how to make that button actually do something, ending the conversation with "yeah, that's sort-of a tease, isn't it?"...

Oh, well, and I actually also have a dedicated Copilot button on my new Lenovo laptop powered-by-Windows-11. And, guess what, it does exactly nothing! I can elect to either assign this button to 'Search', which opens a WebView2 to bing.com (ehhm, yeah, sure, thanks!) or to 'Custom', in which case it informs me that 'nothing' meets the hardware requirements to actually enable that.

So, my question to anyone in the Microsoft C-suite: have you ever tried to, like, actually use, like anything that you're selling? Because if you would have, the failings would have been obvious, right? Right??

The other day I've clicked on one of Outlook calendar's copilot prefilled questions: "who are the main attendees of this meeting". It started a long winding speech that went nowhere, so I typed in "but WHO are the attendees" and finally it admitted "I don't know, I can't see that".

I bet c-suite uses Mac

> Like, I have a 'Copilot' button prominently displayed in my New Outlook on MacOS (the only platform where the app-with-that-designation is sort-of usable), and it's a dropdown menu, and it has... zero items when expanded.

I guess that's worse than the Gemini button in Google Sheets that asks me to subscribe to AI services. I have multiple times been in a sheet and thought "asking an LLM how to do this thing I want to do right here in this product would actually be great if it works", remembered there was an AI-looking button in the top right, clicked it, and nope'd out of the subscription.

I just want to know if it works or not before I buy it.

Absolutely! There are so many scenarios where they could actually add some value, and they're fulfilling, like, exactly none of those?

Even in Visual Studio Enterprise, their flagship developer product, the GPT integration mostly just destroys code regardless of model output. I truly cannot fathom how any of that made it past even a cursory review. Or how that situation would last for over 6 months, but, yet, here we are.

And, again, it's fine with me: I'll just use Claude Code, but if I were a Microsoft VP-or-above, the lack of execution would sort-of, well concern me? But maybe I'm just focused on the wrong things. I mean, Cloudflare brought down, like, half the Internet twice in the past two weeks, and they're still a tech darling, so possibly incompetence is the new hotness now?

Yeah, and I also bet their Outlook 'Copilot' button has more-than-zero options in its dropdown menu.

But I'd actually love to know how to achieve that, and so far Microsoft AI is awfully silent on the subject...

> Oh, well, and I actually also have a dedicated Copilot button on my new Lenovo laptop powered-by-Windows-11. And, guess what, it does exactly nothing! I can elect to either assign this button to 'Search', which opens a WebView2 to bing.com (ehhm, yeah, sure, thanks!) or to 'Custom', in which case it informs me that 'nothing' meets the hardware requirements to actually enable that.

How did you manage this? Probably some company-wide group policy saves you. It keeps starting copilot for me, drives me crazy.

There's AI in Teams to. I wanted to use it to recolect info from my chats but apparently it's unable to do so.

> So, my question to anyone in the Microsoft C-suite: have you ever tried to, like, actually use, like anything that you're selling?

Satya Nadella insists that Bing365Pilot has supercharged his productivity, but determining if he's high on his own supply or lying through his teeth is an exercise for the reader.

> Copilot consumes Nadella’s life outside the office as well. He likes podcasts, but instead of listening to them, he loads transcripts into the Copilot app on his iPhone so he can chat with the voice assistant about the content of an episode in the car on his commute to Redmond. At the office, he relies on Copilot to deliver summaries of messages he receives in Outlook and Teams and toggles among at least 10 custom agents from Copilot Studio. He views them as his AI chiefs of staff, delegating meeting prep, research and other tasks to the bots. “I’m an email typist,” Nadella jokes of his job, noting that Copilot is thankfully very good at triaging his messages.

https://www.bloomberg.com/news/features/2025-05-15/microsoft...

Nah, they probably just have Copilot as a bullet point on a slide, count that as "using AI", and are psyched for their next board meeting.

Nadella has to have his own custom agents. It isn't even possible for an enterprise like MSFT to not have custom agents that are still remotely useful.

So, his experience with Copilot agents != Average Customer's experience

And everything aimed at developers assumes you're using Unix.

I have Copilot at work, it feels so useless sometimes. As an example, I had a report which I needed to make some batch edits to. I figured why not let the robot take a crack at it, so I clicked the Copilot button and spent a couple minutes describing what I needed changed.

Copilot tells me it can't edit my current document, but it can create a new one. I figured okay, Microsoft doesn't want to set it loose on the original, guess it makes sense that it requires a copy. So I said yes.

Nope. Instead of creating a copy of my document and editing it, it created an entirely new document which excised basically everything in the original report and replaced it with a very short summary - I'm talking 5000 words down to 500. All my tables and figures were gone, as was the standard report template my employer uses.

What utter garbage. Office productivity is a major use case for LLMs, and here the largest vendor of productivity software on the planet is happy to fuck it up.

> He likes podcasts, but instead of listening to them, he loads transcripts into the Copilot app on his iPhone so he can chat with the voice assistant about the content of an episode in the car on his commute to Redmond.

I remember reading that when it first came out and all I can think is: No, he doesn't like podcasts, if you like podcasts you listen to them.

That's like saying "He loves food, but instead of eating it he feeds it to an analyzer that tells him what elements were detected in it".

I have to assume it's all BS/lies because if that's a truthful statement (about podcasts and the other things) then I really question wtf they are doing over there. None of that sounds like "the future", it sounds like hell. I cannot imagine how shitty it would be to have all my emails/messages to the CEO being filtered through an AI and getting AI slop back in return.

Sounds like Siri - unable to control much of anything on the iPhone outside of reading/sending text messages and setting alarms.

> How did you manage this?

I did absolutely nothing special, other than running the latest-and-greatest Windows 11 Enterprise, which is what we put on most of our laptops without any customizations other than "require 2FA and some antivirus and firewalling" via Intune.

And I just went into our Azure admin portal, looking for any AI goodies to enable, and... there just doesn't seem to be anything there? And we have an Enterprise P2 subscription, which is usually where all the good stuff is, but, yeah...

Hard disagree: there is a whole universe of Windows-based developers. But even for them, the best offer seems to be a frequently-updated but still-entirely-underwhelming Visual Studio Enterprise plug-in that after 6 months (or so) can't even show proposed changes in response to a prompt without destroying surrounding code...

I've fooled around with some vibe coding on several LLM's like Claude, Gemini, and ChatGPT with some pretty decent results.

Since I have a full Copilot license at my corporate day gig, I figured I would try using Copilot for a basic static site. Nothing too hard, and something that's been handled easily with the other LLM's.

The prompt was pretty basic just to get something to start working with. "Build a four page template. With a home or index page, two pages of content and a contact page with a responsive slide out menu from the left hand side of the page."

It ran and put everything in a folder. I open the home page and everything was broken. I opened the files in VS Code and saw this:

    <ul class="drawer__list">
      <li>index.htmlHome</a></li>
      <li>services.htmlServices</a></li>
      <li><a class="nav-linkeduling</a></li>
      <li>contact.htmlContact</a></li>
    </ul>

And then this:

    <head>
    <meta charset="utf-8" />
    <meta name="viewport" content="width=device-width, initial-scale=1" />
    <title>Home · Acme Web</title>
    <meta name="description" content="Accessible, responsive starter template with a slide-out menu."/>
    <linkts/css/styles.css
    /assets/css/styles.css
    </head>

I mean, if you can't even this right, I don't have much hope it can do anything more complicated. To say this was pretty sad is an understatement and clarified how far Microsoft is behind other LLM's.

This is just him aping every other AI CEO. Every single one has to act like the agents are super-geniuses mere moments away from achieving the singularity like people can't try them out themselves and be disappointed. Some of it is "we think this will work soon so it's ok if we pretend like it's working now", but I think a lot is just needing to constantly shove hot air into the balloon before it pops.

> he loads transcripts into the Copilot app on his iPhone so he can chat with the voice assistant about the content of an episode in the car on his commute to Redmond.

What a dorky thing to do. Does the CEO have some concept he's living a life that precisely _zero_ of his customers do? Who would even think to do this?

> “I’m an email typist,” Nadella jokes of his job

Yea, I have actual work to do, perhaps you should familiarize yourself with this?

I've always suspected Microsoft is a front for an ineffable cosmic evil that is trying to crush the human spirit into bewildered, abject despair.

How else do you explain Teams and the Hotmail UI?

And that’s ok. Those are core features of the phone that absolutely must work reliably and consistently. Far better to do a few important things really well than a hundred things execrably.

Kudos to you. I never use new buttons out of fear of something irreversible happening, like sending a random email or deleting something. I still feel uncomfortable with the Gmail UX, I would _never_ use a ”hello iz magic ai”-button.

I asked Microsoft 365 Copilot to create a new word document for me (since they have hidden the link on office.com) and... it refused to do that.

Edit: Just tried again. It refused to do it. I mean WTF.

This is what move fast and break things looks like in a enterprise the size of microsoft.

It's mostly break things and little moving fast.

But the idea is that it's AI or death, so some broken buttons seems of less importances than the buttons itself being there, because the button working is a problem involving several teams, so no one is actually responsible, but the button being there is some team problem, and hell yeah they solved in the first sprint.

> in the car on his commute to Redmond

This was funny to me, because he lives like 8 minutes away.

However the other day I asked the Gemini assistant on my phone to check the birthdays in my calendar, get all their dates, then make a graph of how many fall in each period with a 15-day moving average. It did everything as instructed including writing a python script to generate the graph, then discussed the results with me :)

The only good feature about copilot in Microsoft 365 is that if you ask it to delete itself enough times eventually some other app will eventually be promoted to the most prominent when you first login.

You're thinking of Larry Ellison.

I’ve found it fairly useful in Excel. The suggestions to clean up data are pretty good and it’s spat out some quite gnarly formula on request

So it’s like Copilot in Excel, that can’t interact with or seemingly even see the contents of the spreadsheet that’s in focus.

That would certainly explain the Loop UI

I would expect Siri to be able to do anything on the iPhone that I can - change settings, report stats, kill/launch apps, etc.

It would be nice if it could control 3rd party apps too, like GMail, but being able to control the stuff that Apple themselves have built doesn't seem a lot to ask.

> So, my question to anyone in the Microsoft C-suite: have you ever tried to, like, actually use, like anything that you're selling? Because if you would have, the failings would have been obvious, right? Right??

They all use Macs lol.

I bet they use iphones and leave computers to their underlings/assistants.

It's so easy to ship completely broken AI features because you can't really unit test them and unit tests have been the main standard for whether code is working for a long time now.

The most successful AI companies (OpenAI, Anthropic, Cursor) are all dogfooding their products as far as I can tell, and I don't really see any other reliable way to make sure the AI feature you ship actually works.

Microsoft: What? You want us to eat this slop? Are you crazy?!

"Compute? Think with own brain? Our servants do that for us."

On new-outlook-on-Windows there’s an option to disable the copilot button. Wanna take a guess what that does?

Me: Can you access my inbox and Teams messages?

Copilot: Yep!

Me: Please find any items in my inbox or sent items indicating (a) that I have agreed to take on a task or (b) identifying me as the person responsible for a task, removing duplicates and any items that I have unambiguously replied to via email or Teams. Time window is preceding 7 days.

Copilot: Prints a list with, at best, 5% accuracy

I know some folks have the peculiar idea that search is dead in favor of AI, but if AI can't accurately find information, it is useless. As near as I can tell, Copilot finds 3-4 items (but rarely the SAME 3-4 items across runs) and calls it a day. It just seems like nobody is actually testing any of this stuff. Microsoft is actively destroying its credibility because it's offering a tool with a party trick but is utterly unreliable. I will, therefore, not rely on it.

On the other hand, if it's true, it explains a LOT about Microsoft's silly AI strategy.

Are you kidding? You get to be the star guest of every podcast you listen to and everything you say is amazingly witty and insightful.

I know exactly the kind of people who would think to do this. Unfortunately. :)

It's a generalization problem. We can train LLMs that 'know' a lot of stuff in the global sense but the tasks that are interesting to people require the LLM to know a lot about you and your world in a very specific sense. The technical problem is that it's all corner cases and that's impossible to scale right now. No amount of context window is going to get you there either.

Imagine a circumstance where Windows Search was as good as Apple's Spotlight, and could integrate with cloud services to index documents, browser bookmarks, web history, maybe podcasts, etc.)

Hey Copilot, where is that document I was reading about the new network diagramming software Jacob is testing out?

Or Hey Copilot, my disk is getting pretty full. What software is taking up a lot of space that I haven't used for a while? Or are there any files I can move to cloud storage to free up space?

But no, instead it's just 'we're going to take screenshots of all your windows, OCR it, and index it, so that when someone infects your machine they can see your credit card numbers and pornography habits.'

At what point does Charlie Brown not kick at the ball Lucy offers?

It's been 19 years since "Microsoft Re-Designs the iPod Packaging". [0] Is the disconnect displayed in this message thread that there's always 10,000 new people discovering a fact? [1]

0. https://www.youtube.com/watch?v=EUXnJraKM3k

1. https://xkcd.com/1053/

50% of our code is being written by AI! Or at least, autocompleted by AI. And then our developers have to fix 50% of THAT code so that it does what they actually wanted to do in the first place. But boy, it sure produces a lot of words!

"Move fast and break things" is fine if you're a social networking site and breaking things means people can't get their racist memes or browse marketplace for twenty minutes until you push a change.

It's less fine if the things you're breaking are your core operating systems and the office suite that makes you most of your money and it takes you months to get the relevant teams aligned to push out a fix for the bad idea your execs pushed.

> I truly cannot fathom how any of that made it past even a cursory review.

Maybe it's a fifth column group working to destroy Microsoft.

Honestly, I can't tell if you're being sarcastic and it actually does disable the button, or if you're being jaded and cynical and it just hides it for six hours then it comes back. Either option seems equally likely at this point.

Tests are called "evals" (evaluations) in the AI product development world. Basically you let humans review LLM output or feed it to another LLM with instructions how to evaluate it.

https://www.lennysnewsletter.com/p/beyond-vibe-checks-a-pms-...

Maybe he has Microsoft Copilot Full-Self-Driving

Look, if the CEO of a five trillion dollar company investing hundreds of billions into AI can come up with some custom agents to handle every aspect of the CEO's work, surely your average Microsoft 365-subscribing corporation can do the same.

It's just another example of the rich being wildly out of touch. Yes, Beyonce has the same 24 hours in a day that the rest of us have, but she also has enough money to pay people to do every aspect of her life that isn't bringing her joy or wealth. Yes, AI can be used to streamline workflows or help you find signal in the noise so you can focus on the important things better, but if every company has to build that themselves then no company is going to see the value of spending a bunch of extra money on something that they can only get benefit from if they spend even more money.

If the 'AI agents' that Nadella is talking about were part of Copilot then sure, okay, I could see a benefit, but when people in this thread are saying that Outlook can't even tell you who is in a meeting then it certainly explains why Nadella doesn't understand the lack of value.