Guide the PM-to-Director transition across preparing, interviewing, landing, and recalibrating. Use when leadership scope is changing and you need practical coaching.

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 ](../workshop facilitation/SKILL.md) 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. 2. 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. 3. 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. 4. 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. 2. 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. 3. 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. 4. 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. 5. 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. 2. 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. 3. 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. 4. 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

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