intermediate · 54–72 min

The Strategy De-Risking Workshop

Is your new strategy doomed to fail? Identify hidden blind spots and sabotage points before you launch.

About this session

A new strategy often looks flawless on slides while hiding operational gaps and cultural friction that can derail it after launch. This session forces leadership teams to stop pitching the plan and start hunting for the specific factors that will likely cause it to fail. You leave with a list of documented sabotage points and a concrete plan to mitigate them before the first milestone.

Why it works

By shifting the focus from strategy defense to intentional sabotage, the workshop bypasses the optimism bias that usually prevents senior leaders from voicing skepticism. The four-step structure creates a safe environment for participants to surface hidden risks, turning vague anxieties into specific, solvable problems that the team can align on immediately.

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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