Director Readiness Advisor
Coach the PM-to-Director transition with 4 situational branches — preparing, interviewing, newly landed, or recalibrating — and deliver war-story-backed guidance calibrated to your specific stage.
Generic leadership books can't tell you whether you're still an IC with a Director title at 18 months, or a senior PM overreaching at 3 months. A branching diagnostic can. One diagnostic question + 3 adaptive follow-ups → coaching calibrated to exactly where you are, not where the org chart says you should be.
Who it's for: senior PMs preparing for Director roles, PMs actively interviewing, newly promoted Directors in first 6 months, struggling Directors 12+ months in, CPOs coaching their bench, exec recruiters vetting candidates
Example
"I've been a Director 18 months and my exec relationships aren't working" → Q4 branch → recalibrating + exec relationships + 1-2 years → 5 targeted recommendations on stakeholder mapping, rebuilding trust, reframing updates, shifting from feature status to portfolio narratives, and honest self-assessment about fit
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npx ccplaybooks add director-readiness-advisor# Director Readiness Advisor
Guide PMs and Directors through the specific challenges of the PM-to-Director transition using adaptive questions and targeted coaching. Diagnose where you are in the journey and deliver practical, war-story-backed guidance calibrated to your situation — not generic leadership advice.
This is not a readiness checklist. It's a coaching conversation that names what's actually hard, why it's hard, and what to do about it.
## The Four Transition Situations
The PM → Director transition looks different depending on where you are:
1. **Preparing to make the leap** — Still a PM, actively developing toward the role
2. **Interviewing for Director roles** — In an active internal or external searchGet new playbooks like this one
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What This Does
Diagnoses which of four PM→Director transition situations you're in (preparing, interviewing, newly landed, recalibrating), then asks 3 adaptive follow-ups to deliver 3–5 targeted, war-story-backed recommendations. Not a readiness checklist — a coaching conversation calibrated to your exact stage.
Built on the Altitude & Horizon Framework. Pairs with altitude-horizon-framework and workshop-facilitation.
Quick Start
mkdir -p ~/Documents/DirectorReadiness
mv ~/Downloads/CLAUDE.md ~/Documents/DirectorReadiness/
cd ~/Documents/DirectorReadiness
claude
Describe your situation. Claude asks the 1 diagnostic + 3 adaptive questions and delivers targeted coaching.
Four Situational Branches
- Preparing to make the leap — Still a PM. Close gaps in thinking altitude, stakeholder navigation, strategic narrative, or direction creation.
- Interviewing for Director roles — Internal, external, or both. Build stories for each transition zone; reframe PM wins in Director language.
- Newly landed — First 6 months. Address thinking-like-a-PM, Hero Syndrome, unclear direction, or stakeholder shift. Calibrated to inherited vs. new team.
- Recalibrating — 1–2+ years in. Diagnose persistent patterns: still acting like a PM, team not performing, exec relationships broken, or no portfolio clarity.
Key Coaching Principles
- Don't over-index on Director thinking while still a PM — Serve your current role fully.
- The transition is a decision, not a graduation — There's no readiness test.
- Inherited teams: wait 60–90 days before reorganizing — The monkeys in the room aren't always wrong.
- Change the reward loop — Director wins are quieter and delayed; IC praise doesn't come anymore.
- Honesty beats avoidance — "Here's the gap + how I'm developing + what I'd focus on in 90 days" lands better in interviews than dodging.
Named Failure Modes
- Hero Syndrome — Regressing to old IC reward loops
- Allergic to Process — Protecting star-PM exceptions, creating coordination chaos
- People-Pleaser Leadership — Confusing popular with effective
- Instant Gratification Trap — Reading leadership books to shortcut war-story experience
Common Pitfalls
- Treating preparation like a checklist — optimizes for appearances, not muscles
- Misidentifying your situation ("preparing" when actually mid-interview, or "newly landed" at 18 months)
- Looking for permission — there's no readiness test
- Applying "first 90 days" advice when you've been in the role two years