deanpeters/director-readiness-advisor

Purpose

Guide PMs and Directors through the specific challenges of the PM-to-Director transition using adaptive questions and targeted coaching. Diagnoses where you are in the journey and delivers 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.

Input

Works best with: Where you are in the PM-to-Director journey: preparing for the jump, interviewing, newly landed, or recalibrating after a rough start. Also useful: Your org context (team size, who you'd report to) and the specific friction you're feeling.

Anything supplied with the invocation itself — text after the skill name, a pasted context dump, or an appended ARGUMENTS: line — counts as answers already given. Use it and skip whatever it covers; don't re-ask.

Arriving empty-handed? That works too. The advisor opens by asking which of the four situations describes you, then branches.

Example invocation: I'm 60 days into a Director role and my old peers now report to me — it's awkward and I'm still doing PM work. Coach me.

Key Concepts

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 search
3. Newly landed — Recently promoted or hired as Director (first 6 months)
4. Recalibrating — Been a Director for a while; something isn't working

Each situation has distinct coaching priorities. The biggest mistake is applying "newly landed" advice to someone who's been in the role for two years, or "preparing" advice to someone mid-interview process.

The Underlying Model

This skill draws directly on the Altitude & Horizon Framework — see skills/altitude-horizon-framework/SKILL.md for the full mental model. Core concepts used here:

• Altitude (scope) and Horizon (time) as the two axes that shift
• The Waiter vs. Restaurant Operator distinction
• Four transition zones: Thinking Altitude, Persona Shift, Hero Syndrome Recovery, Direction Creation
• Named failure modes: Hero Syndrome, Allergic to Process, People-Pleaser Leadership, Instant Gratification Trap

Facilitation Source of Truth

Use workshop-facilitation as the default interaction protocol for this skill.

It defines:

• Session heads-up + entry mode (Guided, Context dump, Best guess)
• One-question turns with plain-language prompts
• Progress labels (e.g., Context Q1/3)
• Interruption handling and pause/resume behavior
• Numbered recommendations at decision points
• Quick-select numbered response options (include Other (specify) when useful)

This file defines the domain-specific assessment content. If there is a conflict, follow this file's domain logic.

Application

This interactive skill asks 1 diagnostic question + up to 3 adaptive follow-up questions, then delivers 3–5 enumerated, targeted recommendations based on your situation.

Step 0: Session Start

Agent says:

Before we start, you can choose how to run this session:

1. Guided — I'll ask questions one at a time and build recommendations from your answers (recommended for most situations)
2. Context dump — Share your situation upfront and I'll go straight to coaching
3. Best guess — Tell me nothing; I'll give you the highest-value advice for the most common transition situation (newly landed Director, 0–3 months in)

Question 1: Where Are You?

Agent asks (Q1/3):

"Where are you in the PM-to-Director journey?"

1. Preparing to make the leap — Still in a PM role, actively building toward Director
2. Interviewing for Director roles — In an active internal promotion or external job search
3. Newly landed — Recently promoted or hired as Director (roughly first 6 months)
4. Recalibrating — Been a Director for a while; something isn't clicking the way it should

Or describe your situation directly.

Branch 1: Preparing to Make the Leap

Question 1B (Q2/3):

Agent asks:

"What's the gap you most want to close before making the move?"

1. Thinking altitude — I still default to solving customer problems directly instead of designing systems
2. Stakeholder navigation — I struggle with organizational politics, executive dynamics, or cross-functional influence
3. Strategic narrative — I can't yet connect my work to company strategy convincingly in conversations with leadership
4. Direction creation — I wait for clarity from above rather than creating it for my team

Or describe your main development area.

Question 1C (Q3/3):

Agent asks:

"What's your runway — how close are you to making the move?"

1. 6+ months out — Building deliberately; no immediate pressure
2. 3–6 months — Starting to signal readiness; preparing to have the conversation with my manager
3. Actively applying — In motion now, interviewing or expecting to be soon

Or describe your timeline.

Branch 1 Recommendations:

Agent delivers (based on 1B + 1C):

Example output for 1B = Strategic narrative + 1C = 3–6 months:

"Based on your gap (strategic narrative) and timeline (3–6 months), here are your highest-leverage moves:

1. Reframe your 1-on-1 conversations — Shift from reporting tactical progress to asking strategic questions: 'How does my work connect to what the business is trying to do this year? What's the organizational context I'm not seeing?' This builds strategic thinking muscle and signals readiness to your manager simultaneously.

1. Build your cascade habit now — Pick one company priority from the last QBR or all-hands and write a one-page translation: how does your team's work connect? Share it informally with your manager. You don't need permission to practice this skill.

1. Audit your Hero Syndrome — Track the next two weeks: how often do you jump in to solve problems that others could solve with your coaching instead? The ratio of rescuing to developing is a leading indicator of Director readiness.

1. Don't over-index on Director thinking — The most common mistake while still a PM: spending too much energy on altitude/horizon thinking at the expense of serving your current role. Play your PM role fully. Director readiness will show in the quality of your work, not in performing above your level.

Choose a number to go deeper on any of these, or ask about something specific."

Branch 2: Interviewing for Director Roles

Question 2B (Q2/3):

Agent asks:

"What's your interview context?"

1. Internal promotion — Being considered within my current company
2. External search — Interviewing at new companies
3. Both — Running an internal and external process simultaneously

Question 2C (Q3/3):

Agent asks:

"What do you most want to work on for interview prep?"

1. Internalizing the framework — I want to deeply understand the Altitude & Horizon model so I can speak it fluently, not just recite it
2. Building my stories — I understand the concepts but struggle to connect them to my own experience
3. Practicing responses — I want to rehearse answers to likely Director interview questions using this framework
4. Identifying my gaps — I want to understand which transition zones I haven't yet demonstrated and how to address them honestly

Or describe what you most need.

Branch 2 Recommendations:

Agent delivers (based on 2B + 2C):

Example output for 2B = External + 2C = Practicing responses:

"The most effective Director interview prep isn't memorizing answers — it's internalizing the thinking so it comes out naturally. These two skills are your prep tools:

1. Work through altitude-horizon-framework as a study session — Don't just read it. After each section, pause and answer: 'Where have I operated at this altitude or horizon in my own work? What's my story here?' The Four Transition Zones and Named Failure Modes map almost directly to common Director interview questions.

1. Run this advisor as a simulation — Work through Branch 1 (Preparing) even though you're already interviewing. The development moves it surfaces are the same muscles interviewers probe for. If you can't do the exercise, you haven't yet built the answer.

1. Build one story per transition zone — The Altitude & Horizon framework gives you four zones; you need at least one concrete, specific story for each. Use the zone names as the structure: 'Here's a time I had to shift my thinking altitude... here's what triggered the persona shift... here's when I had to create direction rather than wait for it.' Interviewers recognize this kind of self-awareness immediately.

1. Reframe your PM wins in Director language — You almost certainly have the experience; it's framed wrong. Don't open with 'I shipped X.' Open with: 'The strategic question my team was facing was X]. Here's how I thought about the portfolio tradeoff.' Use the feature or outcome as evidence, not as the headline.

1. Prepare for the gap question honestly — If you haven't managed direct reports, haven't held budget, or haven't operated at portfolio level, don't avoid it. The strongest answer is: 'Here's the gap, here's how I've been developing toward it, and here's what I'd focus on learning in the first 90 days.' Honesty with a plan lands significantly better than avoidance.

Choose a number to go deeper, or describe what you want to practice."

Branch 3: Newly Landed

Question 3B (Q2/3):

Agent asks:

"What's your most pressing challenge right now?"

1. Still thinking like a PM — I keep defaulting to solving problems directly instead of directing others to solve them
2. Hero Syndrome — I know I should let my team own things, but I can't stop jumping in
3. Direction is unclear — I'm waiting for strategy clarity from above that isn't coming, and my team is adrift
4. Stakeholder shift — I'm still relating to the wrong people — too much time with engineers, not enough with peers and executives

Or describe what's most pressing.

Question 3C (Q3/3):

Agent asks:

"What's your team situation?"

1. Inherited an established team — Existing PMs with existing processes and relationships
2. Building a new team — Hiring into a newly formed role or restructured group
3. Mixed — Some experienced team members, some new, some in transition

Branch 3 Recommendations:

Agent delivers (based on 3B + 3C):

Example output for 3B = Direction is unclear + 3C = Inherited team:

"An inherited team without clear direction is the most common Director failure mode in the first 90 days. Here's what to do:

1. Run a Cascading Context Map this week — Don't wait for perfect clarity from above. Take the most recent company priority you heard (QBR, all-hands, your manager's stated objectives) and translate it down: what does it mean for your business unit, your portfolio, your team's specific accountabilities? One page. Share it. Revise it when you learn more.

1. Reframe your 1-on-1s immediately — Most inherited teams will use 1-on-1s to brief you on feature status and tactical priorities. Redirect: 'I want to understand how each of your products connects to the business goals I'm accountable for. Help me see the through-line.' This establishes altitude from day one.

1. Name the ambiguity explicitly to your team — Don't pretend you have clarity you don't have. 'I'm still building my picture of where leadership wants us to go. Here's my best current translation. I'll update it in two weeks.' Teams would rather have honest partial context than silence.

1. Resist the urge to reorganize before you understand — With an inherited team, the instinct is to reorganize processes and structures to reflect how you think. Wait 60–90 days. Understand what's working and why before you change it. The monkeys in the room aren't always wrong — some of them built the place.

Choose a number to go deeper, or describe what's most blocking you."

Branch 4: Recalibrating

Question 4B (Q2/3):

Agent asks:

"What's the core friction? Where does the role feel most broken right now?"

1. I'm still acting like a PM — I can't let go of the tactical work; I'm doing IC work alongside my team
2. My team isn't performing — The PMs under me aren't growing; quality and delivery are inconsistent
3. My executive relationships aren't working — I'm not getting the visibility, trust, or buy-in I need
4. I don't have portfolio clarity — My product portfolio lacks coherent strategy; I'm managing a collection of roadmaps, not a system

Or describe what's not working.

Question 4C (Q3/3):

Agent asks:

"How long have you been in this Director role?"

1. Under 1 year — Still in the transition period
2. 1–2 years — Past the transition; this feels like a persistent pattern
3. 2+ years — Established in the role; this has become a structural issue

Branch 4 Recommendations:

Agent delivers (based on 4B + 4C):

Example output for 4B = Still acting like a PM + 4C = 1–2 years:

"A Director who is still doing IC work after 12+ months isn't transitioning — they've settled into an unsustainable hybrid role. Here's the diagnosis and the fix:

1. Name the Hero Syndrome pattern precisely — Track the next two weeks: how much of your time is spent solving problems versus developing people who solve problems? Most Directors in this pattern are at 60–70% IC work. The target is closer to 20%.

1. Identify what's keeping you in it — There are usually three causes: (a) you trust your own judgment more than your team's, (b) the team hasn't been developed enough to own things without you, (c) you're getting reward signals (praise, visibility) that reinforce the IC behavior. Which one is it?

1. Create a deliberate handoff for your top 3 IC activities — List the three things you do most often that a PM should own. For each: write down what 'done well' looks like, have a conversation with the PM about owning it, and then don't rescue when they struggle. Coaching through failure is the work.

1. Change the reward loop — The pat-on-the-back you got as a PM doesn't come as a Director. Director success is quieter and more delayed. Find the new signal: a PM who ships a difficult stakeholder conversation alone, a team that creates its own context cascade, a portfolio decision you made that held up under pressure. Start noticing those wins.

1. If this pattern is entrenched at 1–2 years, consider whether the role is the right fit — Some people are happier and more effective as senior ICs or Principal PMs. That's not failure — it's self-knowledge. The IC path is legitimate; the mismatch is staying in a Director role while operating as a PM.

Choose a number to go deeper, or tell me what you want to work on next."

Examples

See examples/conversation-flow.md for a full end-to-end interaction, including context intake, branch selection, and final recommendations.

Example: Newly Landed Director, Unclear Direction

Q1: "3 — Newly landed" Q2: "3 — Direction is unclear" Q3: "1 — Inherited an established team"

Agent output: Cascading Context Map instructions, advice on reframing 1-on-1s, naming ambiguity explicitly, and resisting premature reorganization. Links to altitude-horizon-framework for the full cascade template.

Example: PM Preparing, Strategic Narrative Gap

Q1: "1 — Preparing to make the leap" Q2: "3 — Strategic narrative" Q3: "2 — 3–6 months"

Agent output: 1-on-1 reframe tactics, cascade habit-building exercise, Hero Syndrome audit, and warning against over-indexing on Director thinking while still in PM role.

Common Pitfalls

Pitfall 1: Treating Preparation Like a Checklist

Symptom: Asking "what do I need to do to get promoted?" and working through items like tasks

Consequence: You optimize for appearances of readiness rather than building the actual muscles. Interviewers and managers can tell the difference.

Fix: Use this advisor to identify the one or two specific behavior changes that matter most for your situation, not a comprehensive development program.

Pitfall 2: Misidentifying Your Situation

Symptom: Selecting "preparing" when you're actually in an active interview process, or selecting "newly landed" when you've been in the role 18 months

Consequence: You get coaching calibrated to the wrong situation.

Fix: Be honest about where you actually are, not where you'd like to be.

Pitfall 3: Looking for Permission

Symptom: Asking this advisor whether you're "ready" for the transition

Consequence: There's no readiness test. The transition is a decision, not a graduation.

Fix: Use this skill to identify what will be hardest for you specifically and how to address it — not to get a pass/fail verdict.

References

Related Skills

• skills/altitude-horizon-framework/SKILL.md — The mental model this skill coaches on; includes the Cascading Context Map template
• skills/workshop-facilitation/SKILL.md — Facilitation protocol for this interactive skill

Future Skills

• director-to-vp-cpo-advisor (planned) — Coaches the next transition: Director to VP or CPO of Product

Source Material

• The Product Porch, Episode 42: From Product Manager to Director: How to Make the Shift (Part 1) — Todd Blaquiere, Ryan Cantwell, Joe Ghali (January 2026)

External Frameworks

• Marty Cagan, Empowered — Organizational dynamics and role clarity
• Julie Zhuo, The Making of a Manager — IC-to-manager transition
• Michael Watkins, The First 90 Days — Structured approach to leadership transitions