coaching-pms

Coaching Product Managers

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Install skill "coaching-pms" with this command: npx skills add oldwinter/skills/oldwinter-skills-coaching-pms

Coaching Product Managers

Scope

Covers

  • Coaching a PM (direct report or mentee) to improve product craft, leadership, and decision quality

  • Converting “be better at X” into a measurable development plan with weekly reps + follow-ups

  • Defining what “good PM” means in your context and diagnosing skill depth using Bloom’s Taxonomy

  • Building a coaching cadence that scales (coaching as the primary job of product leadership)

When to use

  • “Coach my PM on strategic thinking / product sense / execution.”

  • “Create a PM development plan / growth plan for the next 8–12 weeks.”

  • “Assess a PM’s current level and decide what to coach next.”

  • “Define what ‘good PM’ means here and align on expectations.”

When NOT to use

  • You need a formal performance-management process (PIP, HR documentation, investigation) — use your company/HR process.

  • You only need 1:1 meeting design (use running-effective-1-1s ).

  • The situation is primarily a conflict/difficult feedback moment (use having-difficult-conversations ).

  • You need org-wide leveling/comp framework design (this pack can seed inputs, but it’s not the full program).

Inputs

Minimum required

  • Your context: role (PM manager/product leader), team/product, stage, constraints

  • The PM: level/title, scope, tenure, strengths, current challenges

  • Coaching goal: what must be more true in 4–12 weeks (outcomes + behaviors)

  • Evidence: 2–5 examples of work (PRDs, launches, decisions, stakeholder feedback) — anonymized

  • Any existing ladder/role expectations/values (if available)

Missing-info strategy

  • Ask up to 5 questions from references/INTAKE.md (3–5 at a time).

  • If role expectations or evidence are missing, proceed with explicit assumptions and label unknowns.

  • Do not request sensitive personal data; use behavior/evidence summaries.

Outputs (deliverables)

Produce a PM Coaching Pack (Markdown in-chat; or files if requested) in this order:

  • Definition of “Good PM” (in this context)

  • Competency model + observable behaviors + Bloom depth ladder

  • Current Assessment (evidence-based)

  • Strengths, gaps, current level per competency, evidence notes, constraints vs skill gaps

  • Shared Vision (1–3 growth bets)

  • Target level, success signals, why it matters, timeframe

  • Development Plan (practice loops + stretch work)

  • Weekly reps, stretch assignment(s), required artifacts, coaching support, timeline, measurement

  • Coaching Cadence + Session Toolkit

  • 1:1 structure, coaching prompts, feedback moments, artifact review points

  • Follow-up Tracker + Review Plan

  • Checkpoints, how to evaluate progress, how to adjust the plan

  • Risks / Open questions / Next steps (always included)

Templates: references/TEMPLATES.md

Expanded guidance: references/WORKFLOW.md

Workflow (8 steps)

  1. Intake + boundaries + coaching goal
  • Inputs: user context; references/INTAKE.md.

  • Actions: Confirm this is a coaching engagement (not HR/PIP). Define timeframe and outcomes. Choose whether to output the full pack or a subset.

  • Outputs: Context snapshot + assumptions/unknowns.

  • Checks: Goal is stated as observable outcomes/behaviors (not personality traits).

  1. Define “good PM” for this role (Petra step 1)
  • Inputs: PM role scope; company context; any existing ladder/values.

  • Actions: Draft a context-specific competency model. For each competency, define behaviors and a Bloom ladder for skill depth (know → understand → apply → analyze → synthesize → evaluate).

  • Outputs: Definition of “Good PM” (competencies + behaviors + Bloom levels).

  • Checks: Expectations are observable; avoids vague labels like “be more strategic” without behaviors.

  1. Assess current capability using evidence (Petra step 2)
  • Inputs: work examples; feedback; self-assessment (optional).

  • Actions: Map evidence to competencies. Assign a current Bloom level per competency. Separate skill gaps from constraints (scope, unclear mandate, lack of data/authority).

  • Outputs: Current Assessment table.

  • Checks: Each claimed gap has at least 1 concrete evidence bullet; uncertainties are labeled.

  1. Choose 1–3 growth bets + shared vision (Petra step 3)
  • Inputs: assessment; business priorities; PM aspirations (if known).

  • Actions: Pick the highest-leverage competencies. Define target Bloom level + success signals. Align on what “good” looks like for this coaching cycle.

  • Outputs: Shared Vision (growth bets + targets).

  • Checks: Bets are achievable in timeframe; limit to 1–3 to avoid thrash.

  1. Build a development plan with “reps” (Petra step 4 + Bloom)
  • Inputs: growth bets; upcoming work; available support (mentors, tools, stakeholders).

  • Actions: Turn each bet into practice loops: weekly reps + a stretch assignment + required artifacts. Choose reps that deliberately move up Bloom levels.

  • Outputs: Development Plan.

  • Checks: Every bet has (a) reps, (b) artifacts, (c) a measurement signal, (d) a coach commitment.

  1. Design coaching cadence + session toolkit
  • Inputs: time budget; existing 1:1 cadence; tool constraints.

  • Actions: Propose cadence and meeting design (pre-work, agenda, artifact review points). Add coaching prompts that develop independent reasoning. Define “when to be directive” exceptions (risk/time-critical).

  • Outputs: Coaching Cadence + Session Toolkit.

  • Checks: Cadence is sustainable; coaching promotes autonomy (not dependency).

  1. Follow-up loop + measurement (Petra step 5)
  • Inputs: development plan + cadence.

  • Actions: Create a tracker and review checkpoints. Decide how progress will be evaluated (rubric + evidence). Define how/when to adjust bets if constraints change.

  • Outputs: Follow-up Tracker + Review Plan.

  • Checks: Progress is measured via artifacts and behaviors, not vibes.

  1. Quality gate + finalize pack
  • Inputs: full draft pack.

  • Actions: Run references/CHECKLISTS.md and score with references/RUBRIC.md. Add Risks / Open questions / Next steps.

  • Outputs: Final PM Coaching Pack.

  • Checks: The next coaching session can be run using the toolkit without additional invention.

Quality gate (required)

  • Use references/CHECKLISTS.md and references/RUBRIC.md.

  • Always include: Risks, Open questions, Next steps.

Examples

Example 1 (strategic thinking): “My PM is strong at execution but weak at strategy. Build an 8-week coaching plan, including an assessment and weekly reps.”

Expected: growth bet around problem framing/insight synthesis; Bloom ladder; stretch work (opportunity assessment); cadence + artifact reviews.

Example 2 (stakeholder leadership): “Coach a senior PM to lead cross-functional alignment and improve exec comms.”

Expected: bet on stakeholder mapping + decision briefs; practice reps (pre-reads, narratives); coaching prompts; review checkpoints.

Boundary example: “I need to start a PIP and document underperformance.”

Response: recommend HR/performance process; optionally provide a coaching-focused development plan template only, clearly labeled as non-HR.

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