intermediate · 90–90 min

How to Stress-Test Your Strategy in 90 Minutes

Avoid costly mistakes by identifying potential failures before they happen with this strategic stress test.

About this session

Most strategic plans look perfect on paper but crumble when they encounter real-world friction or overlooked internal constraints. This session forces leadership teams to stop defending their roadmap and instead systematically identify the specific points where their strategy is most likely to fail. You move from a state of optimistic planning to a concrete understanding of your biggest risks and how to mitigate them.

Why it works

The structure utilizes a pre-mortem framework that gives participants permission to be critical without appearing unsupportive of the team's goals. By operating under the assumption that the plan has already failed, the group bypasses the pressure to stay positive, surfacing hard truths and blind spots that usually only emerge during a post-project autopsy.

What you’ll walk away with

  • Clear actionable outcomes from a 3-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 3 activities are designed to flow together smoothly.

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Get the full agenda, activities, timing, worksheets, and a facilitator guide for “How to Stress-Test Your Strategy in 90 Minutes” — ready to run in minutes, for any workshop, meeting, or team session.

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