Answer Three Questions per Part, Out Loud, in the Same Room

Work through one part per session. Answer the three questions out loud, in the same room, and don’t let anyone answer for anyone else.

The CTO Sets the Standard the Team Works To#

• If you disappeared for ninety days starting tomorrow, which parts of your standard would keep running, and which exist only because you enforce them in person?
• Which decisions route through the CTO out of habit, and what does that cost?
• When did this team last re-test the founding premise of the business against the market rather than its own slide decks?

Write the Playbook Down and Keep It Current#

• Which play could nobody in this room explain the “why” of without looking it up, and why is it still a play?
• Which part of your process survives because it works, and which survives because nobody wants the argument that removing it would start?
• The last time your playbook changed, did someone read the market, or did something break loudly enough that you couldn’t ignore it?

Lead by Placing and Developing People Well#

• Who on your team is in the wrong seat, and how long have you known?
• Which skills gap are you hiring for urgently that you could have started building eighteen months ago, and what has the wait cost?
• In your last crisis, what did your silence tell the team before your first message did?

Earn Trust by Showing How the Work Is Going#

• Which people, or AI agents, hold autonomy they haven’t earned, and which have earned autonomy you still haven’t granted?
• What claim did this team repeat to the board last quarter that no instrument in the company can verify?
• How much credibility did you spend this year that you never built first?

Growth Needs Decisions Made Ahead of Demand#

• Which growth threshold did you cross without re-teaching the playbook, and where is that omission showing up now?
• Which architecture decision are you letting whoever ships first make by default, because this team hasn’t made it deliberately?
• Which decision have you kept “open” as a form of safety when it’s actually a cost nobody has priced?

Build a Team That Keeps Working Without You#

• When generation got cheap, where did your bottleneck relocate to, and who owns that stage today?
• Name your successor. If you can’t, what does that say about how you’ve spent the last three years?
• Which recent technical decision would embarrass you if the customer it affects were sitting in this meeting?

Tie the Playbook to What the Business Earns#

• Which request did you price as a ticket this quarter that was actually a capability, and what did the underpricing cost?
• When did each person here last watch a real customer use what you shipped, without an account manager translating?
• What are you building right now that clears your economics but not the customer’s, and how long will you keep pretending the two-sided test doesn’t apply?

Try this with AI.

“Pick the three questions in this guide my leadership team is most likely to answer dishonestly, and tell me why. Then rehearse the hardest one with me: you ask, I answer, and you keep pressing until I stop giving the version I’d give the board.”