Show up ready.
Decide by the end.

1. What this call is: and isn’t

• Is: a confidential 45-60 minute working session to pressure-test your Protect / Drop / Learn bets and lock dated next steps.
• Isn’t: therapy, performance management, or legal/compliance advice.
• Confidential: what you share stays between you and your coach unless you ask otherwise.

2. What to have open

• Your client report PDF (or the browser report tab).
• Your calendar for the next 90 days.
• One decision you’re stuck on (you already named: augment current role: “Harborline is piloting copilots in finance/ops; I am asked to “champion AI” but policy is murky and my week is still 28% pack assembly. Shou…”).

3. Personal prep questions

Drawn from your runway, org signals, tools, and decision focus: jot answers before we meet.

1. Given runway 3-6 months and risk tolerance 3/5, which Learn bets stay cash-safe this quarter: and which would you delay?
2. Headcount / freeze / reorg is on the table beside AI pilots (“Ops copilots discussed in same quarter as soft hiring freeze and a quiet reorg rumor in finance/ops.”). What would make “championing AI” career-safe vs politically risky for you at Harborline Health Systems?
3. Tools touching regulated / client / patient data (ChatGPT Enterprise; Microsoft Copilot; Notion AI; CRM / client records); review status: Partial review. What must stay human-owned before any Drop experiment?
4. Your stated decision focus: “Harborline is piloting copilots in finance/ops; I am asked to “champion AI” but policy is murky and my week is still 28% pack assembly. Should I lean in as internal orchestrator or protect my seat and wait?” What evidence would falsify your current preferred option (augment current role)?
5. Success you defined: “Be the person who redesigns ops workflows around AI without burning out my team or breaking compliance.” Does that still hold after seeing exposure 47/100 and engagement 72/100?

3b. Questions that sharpen the real challenge

Short prompts to stay with the real challenge before advice. No framework homework required.

1. What is on your mind about this decision as you walk into the call?
2. You named this as the real challenge: “Whether championing AI is career-safe for me while policy is murky and a soft freeze sits next to the pilot..” What would change that answer?
3. What do you want from the call itself?
4. If you say yes to your top bet, what will you say no to on next month's calendar?

4. What we will decide by the end of the call

• Lock one dated Protect bet: Accountable ops redesign decisions and board-facing narrative.
• Lock one dated Drop bet (you keep the final say): Status packs, meeting notes, first-pass variance analysis.
• Lock one dated Learn bet sized to runway 3-6 months: Small experiments people can see (AI as junior analyst), with trust/risk/compliance checks Sequence Learn behind clarified headcount climate.
• Agree the first 30-day artifact and when you will review it.

5. What NOT to prepare

• No slide deck.
• No need to study theory or memorize framework names.
• No polished “AI strategy” narrative: bring calendar truth and one stuck decision.

6. Logistics

• Join link: arrives by email after offline payment / scheduling confirmation (pilot).
• Timezone: we will confirm against SF Bay Area; bring your local calendar.
• Recording: no recording unless we both agree at the start of the call.

7. Optional manager language