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Invite dissent about your projects. Ask people around you for what could go wrong. Many of us want to be optimistic about everything we do and the projects we run. We are delaying our failure and inviting it. Ask the right questions to invite the bad news. Here is what you are doing. “Team, how confident are we about this release tomorrow?" The eyes of your team dart around the room. Their heads nod and bob in agreement that everything is fine.

Here’s the secret. Give room for nuance. Ask a better question. “Rate your confidence, on a scale from 1 to 5, we should ship this tomorrow?” Look at that. You are receiving much better information on the state of your project. Here’s another secret. “What is being left unsaid?” Then pause for a long time until it starts bubbling forth. Here is where you take it to the next level, use the “and what else?” question from the coaching habit to draw it out everything else.

Reflect on projects of the past the failed. “How come they did not tell me sooner?" Leaders invite negative feedback. Start practicing asking these questions.

  • On a scale, how confident are we about this deadline?
  • What is being left unsaid?
  • And what else?
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