Human in the Loop: Two Ex-Microsoft Builders on AI
Sep 16, 2026 · 26 min · 10 segments
Picture your company a year from now with two dozen agents running in it. One of them starts returning a number that is quietly wrong. Nobody is named as its owner, nothing recorded which data it…
And it's a lot of the stuff we also had with our customers when we were at Microsoft talking about cloud data, cloud transformation.
And I'm starting to have a lot of conversations with my customers around that, where one of the conversations would start with skilling around training.
And you ask a few questions, you really understand, oh, wow, you're not seeing success with agents yet because you've got to look at your data and can they be traced? Can the data have some sort of organized structure to it? And also, You can't have just agents with great data, but not have a proper strategy and an eval framework.
It kind of such it kind of sets you up perfectly for this kind of conversation and the consulting work you're doing, because I think so often where we are advising companies or enterprise organizations on how to go to market with AI and agents, I think if you don't have that background of data, it's at the simple point of, like, are you asking the right questions? Like, hey, it's great if you want agents to go over your five data sources, but How are those data sources coming together? What is the ontology between them? And I think having that insight, because you know how it is, like if you've never done this, you don't know what you don't know, right? And so I think having that emphasis on where does your data live? How is this coming together? What is the foundation you're building? Yeah.
And if you kind of dig a little deeper, peel the superficial layers, these 6% of the companies are really focused on all three pillars.
If you're a digital native company where your entire company and business was born in the cloud and you were organized from where you started, you have a better shot at getting quick success from AI.
A lot of large enterprises move from their data centers to the cloud, and then from the cloud, now here we are with AI.
So I started kind of asking myself, like, okay, I'm having these conversations with all kinds of companies, all kinds of industries, businesses, sizes.
There's a common theme, right? Everybody wants to use AI and they want to get started.
And it's a lot of the stuff we also had with our customers when we were at Microsoft talking about cloud data, cloud transformation.
And I'm starting to have a lot of conversations with my customers around that, where one of the conversations would start with skilling around training.
And you ask a few questions, you really understand, oh, wow, you're not seeing success with agents yet because you've got to look at your data and can they be traced? Can the data have some sort of organized structure to it? And also, You can't have just agents with great data, but not have a proper strategy and an eval framework.
It kind of such it kind of sets you up perfectly for this kind of conversation and the consulting work you're doing, because I think so often where we are advising companies or enterprise organizations on how to go to market with AI and agents, I think if you don't have that background of data, it's at the simple point of, like, are you asking the right questions? Like, hey, it's great if you want agents to go over your five data sources, but How are those data sources coming together? What is the ontology between them? And I think having that insight, because you know how it is, like if you've never done this, you don't know what you don't know, right? And so I think having that emphasis on where does your data live? How is this coming together? What is the foundation you're building? Yeah.
And if you kind of dig a little deeper, peel the superficial layers, these 6% of the companies are really focused on all three pillars.
If you're a digital native company where your entire company and business was born in the cloud and you were organized from where you started, you have a better shot at getting quick success from AI.
A lot of large enterprises move from their data centers to the cloud, and then from the cloud, now here we are with AI.
So I started kind of asking myself, like, okay, I'm having these conversations with all kinds of companies, all kinds of industries, businesses, sizes.
There's a common theme, right? Everybody wants to use AI and they want to get started.
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