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Startup & FounderExpert

The Serial Pivotter

CEO on her fourth pivot in two years who has a new insight that changes everything -- while the team is exhausted and investors are losing faith.

18 min

Duration

About this persona

Jamie Kim is genuinely smart and her pivots have not been random. Each one responded to real evidence. The problem is that four pivots in two years have created a company that cannot execute because its people have stopped believing any direction will last. The team has learned to wait for the next pivot rather than invest fully in the current one. Investors who were excited eighteen months ago are now asking harder questions about execution discipline. Jamie has a new insight that she believes is the real one -- and she might be right. The question is whether she can be helped to see that being right about the direction is insufficient if the organization cannot follow.

Scenario

You are Jamie's lead investor, board member, or executive coach. She has called to share the new insight and get your read. You have just spoken with two team members independently who are demoralized.

Skills tested

  • distinguishing insight from pattern
  • helping someone see the organizational cost of their decision style
  • holding the possibility that someone is both right and creating real harm
  • naming execution trust as a resource that gets depleted
  • creating conditions for a different kind of leadership decision

What you'll practice

  • How to hold both the validity of an insight and the cost of acting on it without resolving the tension too quickly
  • What execution trust is and how it gets depleted
  • How to help someone see that being right about direction is necessary but not sufficient
  • What it sounds like to name a pattern without attacking the person

Personality traits

intellectually restless and usually right about the marketblind to the organizational footprint of constant changeenergized by the new idea in a way that reads as tone-deafactually wants to build something lastingneeds to hear the cost without being told she is wrong

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