A complete question bank to sharpen, pressure-test, and strengthen your strategy. Used by CEOs in board prep, off-sites, strategic resets, and moments where clarity matters most.
Why this matters
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.
- Blind spots stay hidden.
- Assumptions go unchallenged.
- Risk builds quietly.
- And the team sprints confidently in the wrong direction.
This question bank fixes that.
What you’ll get
A structured set of 197 questions across four sections:
| Part 1 Creating a Strategy Expose the real conditions of the business: – 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. | 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. |
Who this is for
This question bank is built for leaders who want to:
- Sharpen a draft strategy
- Review a strategy written by someone else
- Lead a board-level conversation with confidence
- Run an effective leadership offsite
- Break through confusion and see the whole picture
- Explore whether to build, partner, or acquire
- Push ambition without losing clarity
What makes this different
These are the exact questions I use with CEOs of growing and established companies — questions that create insight, focus, alignment, and hard decisions.
197 questions that will change the way you think about strategy — and the way your team executes it.
Used in coaching sessions with CEOs of SaaS companies, global enterprises, and businesses preparing for scale, transformation, or exit.