196 Strategy Questions Every CEO Should Be Asking

Used by CEOs in board prep, offsites, strategic resets, and moments where clarity matters most.

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Most strategies don’t fail because the ideas are wrong.

They fail because CEOs and leadership teams aren’t asking the right questions early enough.
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1. Blind spots stay hidden.
2. Assumptions go unchallenged.
3. Risk builds quietly.
4. And the team sprints confidently in the wrong direction.

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This question bank fixes that.

A structured set of 196 questions across four sections:

Part 1 — Creating a Strategy

• What’s working
• What’s not
• Where the opportunities are
• What constraints are holding everything back

Part 2 — Stress-Testing a Strategy

• Challenge assumptions before the market, the board, or reality does.
• Find the weaknesses, the gaps, and the uncomfortable truths early.

Part 3 — Refining and Strengthening the Strategy

• A set of advanced lenses: culture, leadership, focus, calendar alignment, risk, and scenario design.
• This is where good strategies become great ones.

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​Part 4 — Suggesting M&A Moves

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• Questions that open up options:
• Buy, partner, acquire capability, or block competitors.
• For CEOs who want leverage, not just plans.

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