intermediate · 90–90 min

The Strategy Insurance Policy: A Premortem Workshop

Identify hidden risks before they tank your strategy. A structured way for leaders to voice concerns without being seen as 'negative.'

About this session

Strategy launches often fail because senior leaders hesitate to voice private doubts for fear of appearing unsupportive or pessimistic. This workshop flips the perspective by asking the group to imagine the plan has already collapsed, providing a safe space to identify the specific cracks that will actually break it.

Why it works

Treating failure as a certainty rather than a possibility removes the social pressure to be optimistic, which usually silences critical thinking in executive meetings. This shift in perspective transforms vague anxieties into a prioritized list of specific safeguards that can be integrated into the strategy 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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