Hi Reader,

I was talking with someone who spent two decades leading large engineering teams, hundreds of people at peak. She's figuring out what's next, and she said something I keep hearing:

"The thing I got good at was managing people. Delegating, figuring out who does what. But teams keep getting smaller and flatter, and I'm not sure that matters anymore."

I told her the opposite is true.

What I'm noticing

As AI agents start doing real work, drafting, analyzing, handling customer questions, someone has to decide what the agent owns, what the human owns, and how the handoff works when it breaks.

That's org design. It always has been.

What surprised me: the failure modes of AI agents look almost identical to the failure modes of junior hires. They do exactly what you told them, not what you meant. You find out once the output is wrong, long after the work got handed off.

The person who knows how to structure work clearly, set checkpoints, and diagnose where a handoff went sideways? That skill compounds over the next five years. It doesn't fade.

Your next move

Three ways to put it to work this week:

1. Map one repeating workflow to who (or what) does each step. If you can't write it down, you can't delegate it, to a human or an agent.
2. Treat your first AI agent like a new hire. Define what success looks like before you hand the task off, not after.
3. Build in a mid-task check. An end-of-task quality review catches problems too late. A checkpoint partway through catches misalignment before you are cleaning up the output.

Life beyond the screen

I do a version of this with my kids. When I hand off a chore, the ones that go sideways are always the ones where I assumed they knew what "done" looked like. Clean your room means one thing to me and something very different to a six-year-old. The fix is the same as with an agent: say what done looks like, up front.

A question for this week: What's one decision on your team that only lives in someone's head right now, that an agent could take over if someone set it up right?

Work with me directly. If you want a thinking partner on your product strategy, AI rollout, or building your fractional practice, here's how I work with people: https://gamma.app/docs/Chill-Labs-Coaching-Information-ifjuyb0hjgw9xtb​

Come to the Water Cooler 🚰 I host a free monthly gathering for people building fractional and independent practices - honest conversations on positioning, pricing, and pipeline, plus recaps when you can't make it. Join here: https://chillaborate.com/fractional-water-cooler​

Let's Chillaborate,

Dina

Founder, Chill Labs

PS: New to the Automate Yourself podcast? There are plenty of episodes worth digging into - start anywhere: https://chillaborate.com/podcast 💙