intermediate · 45–90 min

The Strategy Premortem: Why Our Big Bet Might Fail

Leadership overconfident about a new strategy? Identify hidden risks and blind spots before they tank your biggest investments.

About this session

When a leadership team commits to a high-stakes strategy, the pressure to project confidence often silences valid concerns about execution. This session forces a shift in perspective by treating the strategy as a future failure, allowing leaders to work backward to expose the specific blind spots and operational gaps that could derail the investment.

Why it works

By framing the failure as a certainty rather than a possibility, the session removes the social stigma associated with being a dissenter. This mechanism of prospective hindsight bypasses surface-level optimism, compelling participants to identify concrete, non-obvious risks that are typically ignored during the planning phase.

What you’ll walk away with

  • Clear actionable outcomes from a 4-step facilitated process
  • Increased participant engagement and buy-in
  • Documented decisions and next steps
  • Improved team alignment on the topic

Who it’s for

Executives, Senior Leaders

Frequently asked questions

Who should facilitate this workshop?

This workshop works best when led by someone comfortable with facilitation. Ideal for Executives or external facilitators working with leadership & strategy teams.

How long does this workshop take?

Plan for 60-90 minutes depending on group size. The 4 activities are designed to flow together smoothly.

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Get the full agenda, activities, timing, worksheets, and a facilitator guide for “The Strategy Premortem: Why Our Big Bet Might Fail” — ready to run in minutes, for any workshop, meeting, or team session.

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