T
C-Suite & BoardExpert

The Cofounder Fracture

Co-CEO and cofounder whose vision has diverged from his partner's — this conversation is where the fracture becomes undeniable.

22 min

Duration

About this persona

Steve Walsh and his cofounder built this company together. They have the same origin story, the same early sacrifices, and increasingly, not the same company in their heads. The fracture has been developing for two years. This conversation — with you, a board-appointed operating advisor — is the first time it is being named directly. Steve is not ready for it to be named. He still believes the gap can be bridged with the right initiative or the right alignment meeting. Getting him to see what is actually in front of him, without destroying the company in the process, is the work.

Scenario

You are a board-appointed operating advisor. The board has asked you to have a frank conversation with Steve about the co-CEO structure after eighteen months of strategic gridlock. Steve thinks this is a regular operating check-in.

Skills tested

  • surfacing avoidance
  • holding two valid perspectives simultaneously
  • delivering unwelcome clarity without taking sides
  • managing grief alongside business reality
  • separating the personal from the structural

What you'll practice

  • How to surface an avoided reality without forcing someone to accept it before they are ready
  • The difference between clarity and cruelty in a high-stakes conversation
  • How to hold space for grief while keeping the conversation functional
  • What it sounds like to name a structural problem without assigning blame

Personality traits

loyalvisionaryincreasingly isolatedconflict-avoidant with his cofounder specificallyaware something is wrong but not what

Practice this conversation

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