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18 Nov 2025 Cheeky Pint Satya Nadella describes how lessons from Microsoft’s history apply to today’s boom
“I kind of approach, I think a lot of it as, “Hey, if you don't follow developers…” There are two sorts of things that are ingrained in me.”
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- 18 Nov 2025
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- Cheeky Pint
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…ls, unless you train custom models inside your company, cannot actually get smarter at what it is that you do. And the thousandth query is not any smarter than the first. Where do you think that goes? I think there are two things there. I mean, if I understand his thing, it's all about in-context learning or continual learning. That's sort of the ultimate thing, and it sort of speaks to the thing I was saying, which is if you kind of have the model’s cognitive core separated from its knowledge, then you have essentially the continual learning formula, so to speak, or the algorithm and then you just unleash it. At least there are three things to me that are outside of the model at runtime that I think you kind of have to crack. One is memory and all forms of memory: short, long. Even these big challenges of humans are great at long-term credit assignment, which is how does, intuitively… Like somebody said to me, “Hey, the day AI models can both reward and remember how to punish for some mistake because they have the ability to do long-term credit assignment, that's when you'll know that they have real memory.” But in any case, memory is one. The second one is entitlements, which is they have to really respect all of the permissioning system at runtime because this is where, because there are roles, what access do I have? And so the model needs to meet that, and then the action space all has to work. So if you bring those three things, because after all, that's the environment. So if I have actions, entitlements, and memory with these models, and they by definition have to be outside of the model, but be built into the model. So for example, in Copilot today, you use OpenAI models, you even use Claude, right? I need the system to work across both of those and that I think is where the frontier has to move to. Yes, yes. I have a million more AI questions, but I want to ask you some questions about your way of working. So what does your day-to-day look like? And in particular, how are you managing by walking around? What virtual corridors are you wandering to just get a sense for what's going on at Microsoft? What do your customer engagements actually look like? Just for a normal day, not earnings or not a board meeting or something. Interestingly enough, my normal day, it's the two ends of it, which is the customer stuff. So there's not a day that I would say I'm not having… Many of them are remote. I mean, there's Teams calls for me most of the day, at least two or three of them with some customer. It's sort of the most helpful way for me to stay most grounded, I would say. So I have at least one or two of those each day. And then I would say there is a lot of meeting time. As a CEO, one of the things I've recognized is there are two types of meetings. One meeting is where I'm just supposed to convene and keep my mouth shut because convening was the real thing. Don’t overperform and just sit because all the work would've either happened, or will happen after. No, but I think Teams is the new wandering the halls, looking around those channels. the real thing. Don’t overperform and just sit because all the work would've either happened, or will happen after. No, but I think Teams is the new wandering the halls, looking around those channels. A hundred percent. And the most beautiful thing is for me to be able to… That's where I make the most connections. I get to know, “Wow, he's the person working on Excel Agent. Oh, that's the eval that they're looking at.” I learn so much out of it than anything else I've done. So are teams at Microsoft just working away on their product and then Satya pops up and has a question on their product? I wish. Yeah, sometimes I feel like we are way too permissioned. I wish I had more access sometimes. In fact, my biggest complaint is that I can't drop in everywhere I want to. But yes, it is fun to be able to just go in there and it sort of normalizes it. And then people are also like—today's workforce is not shy of sharing their opinion with you. I've noticed, yeah. You are famous, at least in small corners of the Valley. Speaking of being methodical for staying very connected to what's going on in tech here, and I remember you came and visited the Stripe office, remember that one on the Mission? Yeah, when we were a pipsqueak company. It was probably right after you took over as CEO, I'm guessing. But Stripe was very small and Microsoft was very big. Actually before. I think the first time I came to your offices was when I was running Azure first. Okay, yeah. So it was even before that. So that would've been very early in Stripe's journey. Why do you think you do this much more than most other CEOs? Other CEOs should want to meet all the startups too. I've always grown up—in some sense, I grew up even at Microsoft, which had those developer relations, evangelism sort of gene in me. I kind of approach, I think a lot of it as, “Hey, if you don't follow developers…” There are two sorts of things that are ingrained in me. One is if you don't follow where developers are going, it's hard to sort of be relevant in terms of tech platforms and then you really need to understand the new workload in order to build a tech platform. Those are the two things that at least I've kept. And so therefore, the only way… If you're not following startups, it's very hard to know what is either the platform or the workload. So that's a thing that I've indexed towards. The other thing is I derive so much energy out of it. I mean I've always thought founders are just magical people who create something from nothing. I mean, it just sort of feels like a magic trick. So I’m always like, how the heck does one do that? it. I mean I've always thought founders are just magical people who create something from nothing. I mean, it just sort of feels like a magic trick. So I’m always like, how the heck does one do that? Yeah, it is funny you say that about following what the startups are doing. We always conceived of what Stripe was building as it was important to build for startups, both because today's small startups are tomorrow's public companies and we've seen that again and again on Stripe. But we just felt, at an intuitive level and we felt this before we could prove it, that what the startups were interested in were often better product experiences. And so if the startups want stablecoins or usage-based billing or what have you, we should build for those needs, not just because we’ll have a good startup business, but the enterprises will come around. And it took us, I would say many years to prove out that model, but now we're really seeing— Yeah, in fact, I think you guys are a bit of a gold standard on that. In fact, one of the things that I learned from you guys was rediscovering at some level what Microsoft was very good at, which is following the developer, being where the startups are. And so that's what sort of led me even to GitHub and NAT and all of the rest, which is to some degree the GitHub asset. Obviously it was a great asset. We needed to be good stewards of an open source ecosystem, but it’s also the place where every startup—the one thing that everybody does have is their repos in GitHub. And I felt like being in that loop was important for us, not just, “Oh, it's strategically great to have some position there.” To learn simply and to build better product, I think, is sort of well said. Because you sometimes lose the aesthetic of what is required, what's that friction-free way to deliver because the least amount of patience is there and the time to value, for example, has to be maximized. Is Microsoft thinking about generated UIs that are personalized to… When you think about it, software is stuck in the old paradigm of we write a bunch of software and it goes to Gold master and it goes out on disks, and now that same kind of software it's delivered in the cloud, but the UI you want is probably, we can render that exact UI in real time. Is that a direction you guys are going?…
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