Your AI strategy has a trust problem, not a tooling problem

Agency > Agents

Jun 05, 2026

∙ Paid

"This piece from Elena gets at one of the most under-discussed parts of AI transformation: that AI tools can make people faster, but only if they have the the autonomy, trust, and context to actually use them. Otherwise, you’re just giving more tools to people who are still stuck waiting for permission."

- Lenny Rachitsky

When I talk about things like High-impact ICs and speed as a moat, everyone gets excited. But you don’t get those through ‘AI transformation initiatives.’ (Yuck)

Sure, having the right AI tools and skills is part of the equation. But even the best employees with all the most magical tools will get trapped… if your org structure and culture don’t adjust.

Right now, many companies already have the technology they need to go much faster. The blocker is company systems that are mostly designed to prevent things from happening. The power is centralized and all the team members are treated like a risk vector. Exhausting approval cycles, super tight boundaries on roles, unbreakable title-based hierarchies, and a whole tier of middle managers whose main job is to keep everyone in line.

All of this pretty much screams at employees, ‘We don’t trust you, stay in your lane.’

And it should be obvious: Rapid innovation cannot happen in that kind of environment. Super high-impact individuals and high-ve…

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