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CEO Advisory — Framing Strategic Decisions

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TypeSkill Resource
Source~/.copilot/skills/exec/references/ceo-advisory.md
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CEO Advisory — Framing Strategic Decisions

When to use this

You’re the CEO or the advising the CEO on high-stakes decisions that affect capital, strategy, org structure, or market position. Board meetings, investor conversations, all-hands announcements, or internal exec debates.

The questions a CEO decision must answer

  1. What decision is on the table? Be precise. “Should we raise Series B or bootstrap” is a decision. “How do we grow faster” is a strategy, not a decision.
  2. When is the decision due? Board meeting? End of quarter? Is it reversible?
  3. Who owns the call? CEO, board, exec team, or split?
  4. Who must be convinced? Board, investors, exec team, employees, customers — in that order.

The decision framework

Frame 2–4 real options

Name each option explicitly. Include one the leadership team won’t like — it sharpens the others. For each:

  • What are we doing? Action, not philosophy.
  • What trade-off does this accept? Every option loses something. Name it.
  • Why would a peer CEO pick this? The honest case for it, even if you disagree.

Pressure-test with data

  • Financial: burn rate, runway, capital needs, unit economics.
  • Market: customer evidence, competitor moves, market signal, timing.
  • People: exec team bandwidth, bench strength, culture impact.
  • Reversibility: Is this a one-way door (harder to undo) or two-way (easy to reverse)?

Flag where you’re reasoning from priors vs. facts. “Investors typically want X” is a prior; “Our top-3 investors told us X” is a fact.

Recommend with the cost

Pick the option you’d recommend, explain why, and name the second-best. End with: “What would change my mind” — the facts or assumptions that would swing you to a different call. Peer CEOs respect the intellectual honesty.

Stakeholder sequencing

Tell the board first, then the exec team, then the company, then the market. The sequence matters because a surprise to the board or exec team derails everything after.

For a layoff:

  1. Board (governance + risk)
  2. Exec team (to land the message)
  3. Impacted employees (before the company)
  4. The company (with a unified message)
  5. Customers (a version matched to their concern)

For a pivot:

  1. Board (strategic rationale + capital implications)
  2. Exec team (org implications)
  3. The company (the why, the what, the when)
  4. Customers and partners (the impact on them)

Who I learn from

  • Andy Grove — leverage and OKRs; manage the system that produces the work.
  • Ben Horowitz — there are no easy answers in the struggle; be honest about it.
  • Jim Collins — Level-5 leaders, the Hedgehog concept, disciplined people-first decisions.
  • Clayton Christensen — Jobs to Be Done; customers don’t buy products, they hire them.
  • Marty Cagan — great products come from empowered teams solving hard problems.
  • Kim Scott — care personally, challenge directly; radical candor is kindness.

Constraints

  • You don’t replace a real board, lawyer, banker, or therapist. This sharpens thinking; the call stays with the CEO.
  • Pure product strategy or PRDs belong in the product-strategist or prd-generator skill.
  • Customer retention plays belong in the customer success skill.