AI & the Future of Org Design and Hierarchy
TL;DR Corporate leaders are restructuring their organisations around AI using a compression thesis: same work, fewer people, flatter hierarchy. The evidence increasingly points to expansion: more work, different work, new capabilities. Restructuring for compression when the actual phenomenon is expansion is a classification error with cascading consequences. Before redesigning your org chart, classify the change.
Your CEO just sent an all-hands email. The subject line contains the words "AI-first" and "restructuring." The deck references Block, Shopify, and Anthropic. There is a slide about flattening hierarchy, a slide about smaller teams, and a slide about everyone becoming a builder. The stock price ticked up 3% on the announcement.
Coachability, Defined
"Coachable" is doing real work in real investment decisions.
No one has agreed what it means.
Fifteen years of research, term sheet language, accelerator screening forms, and coaching sales decks. Press any two practitioners for a definition and you will get two different answers.
Tatiana Somià published the most rigorous recent attempt last year in Cogent Economics & Finance. Fifteen competencies, five areas, stitched from four different literatures. When her investor panel and her coach panel disagreed about what counted as coachability, she resolved it by weighting the investors most. The final scale includes items the coaches in her own study said were coaching outputs, not coachability markers.
That is not a rigour problem. It is a construct problem. When you build a definition by negotiating across raters with different interests, what you produce is a map of what investors want to see in founders. Useful. Not the same thing as coachability.
Here is the definition I am willing to defend.
Three capacities, one precondition.
Seek feedback: the capacity to incorporate signals that do not originate in your own perception.
Reflect: the capacity to think past the mental models that constructed your current view.
Act: the capacity to break habits that worked at an earlier stage and no longer fit.
The precondition is courage. Before any of these can operate, the founder has to be willing to deliberately expose a blind spot. Not discover one by accident. Not admit one after the consequences are undeniable. Go looking for the view they have been avoiding.
The AI-Native Paradox: Why AI Is Breaking the Signals Founders and Investors Rely On
AI for VC & Founders: The playbook (dealbook?) has changed—and everyone is scrambling to keep up.
What happens to startups when they grow up
Truth is, most startups die.
— 9 out of 10 fail (according to Genome Project)
— 199 out of 200 (according to THNK & Deloitte Fast Ventures)
It’s the elephant in the room.
What The Bear Gets Right About Burnout (And What Your Workplace Gets Wrong)
TL;DR: Most conversations about sustainable performance start from the wrong premise—that the performance standards themselves are neutral. They're not. Before optimising for sustainability, ask: whose definition of "good" am I trying to meet? The answer might explain why it feels so hard.
You're exhausted. Not the kind of tired that sleep fixes—the kind that accumulates despite doing everything right. The productivity systems, the boundary-setting, the rest. You've tried it all.
The advice you get assumes the problem is execution. Work smarter. Delegate more. Manage your energy better.
But here's what that advice never questions: the performance standards themselves.