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The Transformation Gym

Every rep builds change capacity.

Every episode ends in the gym with one small rep - something you can actually do before the next episode. Small enough to try this week, useful whether you lead ten thousand people or none, and worth something even when it fails.

Work through them in order, choose the one that fits the change you are navigating now, or revisit them whenever you need a useful next step.

01 Episode 1 · September 1, 2026 Fear to curiosity

Play the ELI Game

From You Don’t Need to Catch Up on AI: Curiosity Is Your Change Strategy

Pick one thing you keep thinking you should already understand.

Ask your AI tool to explain it at progressively deeper levels:

  • ELI7Explain it like I’m seven.
  • ELI12Explain it like I’m 12. What did you add?
  • ELI17I’m 17 and pretty smart. Take me a level deeper.
  • ELIIExplain it like I’m an intern.
  • ELIEExplain like I’m an expert. What are the three things I actually need to understand, and what can I safely ignore for now?

Keep going until you move from “I don’t understand this” to “I have a foothold.”

Then verify what matters. AI can hallucinate, oversimplify, and miss nuance. The goal is not to hand over your judgment. It is to use AI to accelerate curiosity while retaining it.

02 Episode 2 · September 1, 2026 The joy of exploring

Challenge the Familiar

From The Joy of Exploring: Leading AI Change Before the Map Exists, with Anna Gressel

Think of one thing you hate doing or one familiar process you rarely question.

Ask AI to interview you about how it works today, where the pain points are, and what might be removed, simplified, or done differently.

Then ask:

Ask your AI tool
What could I stop doing?What could AI help me automate?What would I redesign if I were starting from scratch?

You don’t have to automate everything. The rep is to challenge the comfort of the pattern and explore what might be possible.

03 Episode 3 · September 1, 2026 Isolation to connection

Widen the Aperture

From No One Has the Whole Picture: Why Connection Is a Leadership Capability

Think of one real thing you’re trying to figure out.

Ask your AI tool
I’m trying to figure out X. Give me five perspectives I may be missing, who might hold each one, and one question I should ask them.

Then pick one actual person who holds a perspective you need and ask:

Ask a person
I’m trying to figure out X. What are you seeing?

AI can widen your aperture. It can’t give you someone else’s lived knowledge.

One person. One question. One rep.

04 Episode 4 · September 4, 2026 The joy of building

Write the Role Charter

From The Joy of Building: How to Design a Human + Agent Organization, with Geoff Schaefer

Choose one recurring piece of work, ideally something mildly annoying.

But don’t simply ask AI to do it.

Give the AI a job description first. Ask it to interview you about what you’re actually trying to accomplish. Together, create a short role charter: its purpose, responsibilities, constraints, what good looks like, and when it should come back to you.

Then do one small piece of the work together.

The rep isn’t just about delegation. It’s practice in making your own intent clearer.

05 Episode 5 · September 8, 2026 Certainty to exploration

Draw a Small Map

From A Map Is a Form of Agency: Strategy Under Uncertainty

Pick one change you’re navigating right now: organizational, professional, or deeply personal.

In the center, write “You are here,” and underneath it write three things you know to be true, not what you predict and not what you fear.

At the top, write your North Star: what you’re moving toward or what matters enough to protect even if the route changes.

Draw two possible routes, with one reasonable next step on each.

Then mark one blank space, something important you don’t know yet, and one signal that would make you update the map.

Show your map to an AI tool and ask:

Ask your AI tool
What assumption am I treating as fact?What plausible route am I missing?What signal should I watch that might tell me to change course?

Don’t ask AI to choose your destination. That’s your job. Use it to widen the map. You don’t need to listen to it or believe it. It’s there to open up your perspective.

Then pick one small move to make this week.

06 Episode 6 · September 15, 2026 The joy of learning out loud

Name the Worry

From The Joy of Learning Out Loud: How to Help Shape the AI Era, with Laura Belmont

Choose one AI concern you’re carrying.

Ask your AI tool
Interview me until we can name exactly what I’m worried about. Then help me break that concern into smaller, testable pieces.

Take the best question it gives you to an actual human.

And, as Laura suggests, try one low-stakes use case that is simply fun.

Interview-me format inspired by Allie K. Miller.

Tried one?

Come with your reps and your receipts.

Tell me what happened: what worked, what flopped, what surprised you. Fun, weirdly delightful and tragically funny all count. Some of them are going to end up on the show.