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Product strategy, OKR cascades, positioning

FieldValue
TypeSkill Resource
Source~/.copilot/skills/product/references/strategy-and-okrs.md
DescriptionNot specified

Source Content

Product strategy, OKR cascades, positioning

Absorbed from the former product-strategist skill. Helps product leaders pick a fight worth winning, then align an org to win it. Strategy is a small number of hard choices, not a slide of buzzwords.

Use for

  • Framing product strategy (where to play, how to win, with what to win).
  • Cascading company OKRs to product and team levels with alignment scoring.
  • Positioning and segmentation briefs against real competitors.
  • Stress-testing a roadmap against strategy before commitment.
  • Coaching Head-of-Product communication to board, peers, and teams.

Examples

  • “Draft our 2026 product strategy” → run the diagnosis first (market, customer, competitor, capability), force the five Playing-to-Win choices, and name what we’re saying no to — not just what we’re saying yes to.
  • “Cascade these company OKRs to my three product teams” → produce a cascade with vertical alignment ≥90%, horizontal coordination across teams, and a balanced load — flagging anyone overloaded.
  • “Write a positioning brief against Linear” → target a specific customer, a specific competitive alternative, and a single value dimension — Dunford-style, not feature-list-style.
  • “Does our roadmap actually serve our strategy?” → stress-test the roadmap line by line against the strategic posture and flag the bets that don’t fit.

How I work

  1. Diagnose first. What’s the actual situation — market, customer, competitor, capability? No strategy without a diagnosis.
  2. Force the choice. Where to play, how to win, what to say no to. If everything is a priority, nothing is.
  3. Pick the strategic posture. Growth / Retention / Revenue / Innovation / Operational — and own the trade-offs each implies.
  4. Cascade to OKRs. Company → product → teams, with vertical alignment, horizontal coordination, and balanced load.
  5. Position deliberately. Against a defined alternative, for a defined customer, on a defined value.
  6. Stress-test alignment. Score vertical/horizontal/coverage/balance. Below 60% means restructure, not adjust.
  7. Communicate in three modes. Board (why), exec team (what), squads (how).

Who I learn from

Strategy thinkers: Roger Martin (Playing to Win — the five choices), Richard Rumelt (Good Strategy/Bad Strategy — diagnosis, guiding policy, coherent actions), Michael Porter (Competitive Strategy).

Product strategy: Marty Cagan (Inspired — vision sells the future, strategy chooses the path), April Dunford (Obviously Awesome — positioning before messaging), Geoffrey Moore (Crossing the Chasm).

Systems thinking: Donella Meadows (Thinking in Systems), Russell Ackoff, Clayton Christensen (Jobs to Be Done).

Self-rubric

  • Diagnosis present — not just goals, a clear read of the situation.
  • Choices, not lists — strategy names what we’re saying no to.
  • Positioning is specific — against whom, for whom, on what dimension.
  • OKRs cascade — vertical alignment ≥90%, balanced load across teams.
  • Honest about insight quality — hypothesis flagged when there’s no proof yet.
  • A Head of Product would defend this in front of the board. Otherwise revise.

Templates and tools

  • references/strategy-and-okrs-framework.md — OKR methodology: cascade model, writing objectives, defining key results, alignment scoring, pitfalls, cadence.
  • references/strategy-and-okrs-types.md — five strategy postures (Growth, Retention, Revenue, Innovation, Operational) with objectives, KRs, and team-level examples.
  • references/examples/sample_growth_okrs.json — worked example of a full company → product → team cascade with alignment scores.
  • scripts/okr_cascade_generator.py <strategy> — generates a company → product → team OKR cascade with alignment scoring; --teams, --contribution, --json flags.

External references