May 21, 2026 · 24 min · 8 segments
Brian Evergreen worked in AI at Microsoft from 2016 to 2023, including a role helping Fortune 500 executives develop their AI strategies. He kept seeing the same pattern: most of those projects were…
When you talk about it that way, you're resigning and saying, "I hope that whoever builds that future, that there's a good place for me and my organization in it." So instead I say, no, we're at a moment in time where we all know there's this inflection point where we need to make some strategic decisions.
So what is the future that you want to be, and what future of work do you want to build for yourself and your organization or your department? And then what would have to be true for you to be able to do that?
[audience applauds] I am GeekWire co-founder Todd Bishop, and we are coming to you this week from El Gaucho restaurant in Bellevue, Washington.
At Microsoft, you served as US AI strategy lead and later ran autonomous AI co-innovation in Microsoft Research.
He wrote the book Autonomous Transformation: Creating a More Human Future in the Era of AI, which will form the basis for much of our conversation tonight.
And the thing that makes his perspective in the book especially interesting right now is that you actually wrote this before ChatGPT launched.
You were making the case for rethinking how organizations approach AI before the rest of the world was losing its mind.
So today he runs the Future Solving Company, advising Fortune 500 executives, and he's got a sharp and sometimes provocative take on what companies are getting wrong, and right, as they rush to adopt AI and agents.
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When you talk about it that way, you're resigning and saying, "I hope that whoever builds that future, that there's a good place for me and my organization in it." So instead I say, no, we're at a moment in time where we all know there's this inflection point where we need to make some strategic decisions.
So what is the future that you want to be, and what future of work do you want to build for yourself and your organization or your department? And then what would have to be true for you to be able to do that?
[audience applauds] I am GeekWire co-founder Todd Bishop, and we are coming to you this week from El Gaucho restaurant in Bellevue, Washington.
At Microsoft, you served as US AI strategy lead and later ran autonomous AI co-innovation in Microsoft Research.
He wrote the book Autonomous Transformation: Creating a More Human Future in the Era of AI, which will form the basis for much of our conversation tonight.
And the thing that makes his perspective in the book especially interesting right now is that you actually wrote this before ChatGPT launched.
You were making the case for rethinking how organizations approach AI before the rest of the world was losing its mind.
So today he runs the Future Solving Company, advising Fortune 500 executives, and he's got a sharp and sometimes provocative take on what companies are getting wrong, and right, as they rush to adopt AI and agents.