Can a Leader Use a Mistake as a Teaching Story?

The uncomfortable question

A leader may hesitate to discuss a decision that went poorly. Will the story weaken confidence or make a colleague feel exposed? Dr. Tom DePaoli’s Leadership Stories from the Corporate Jungle and Navy Deck Plates presentation includes mistakes alongside accomplishments because both can teach. The value of a candid account is not that every failure becomes inspiring. It is that people can examine the conditions, the judgment, and the consequences more carefully than they can examine a rule stated without context. A leader who tells the story should begin by owning their part, especially when other people had to carry the result. Turning someone else’s difficulty into the leader’s anecdote would teach the wrong lesson.

What to include

Describe the decision the team faced, the information available at the time, and what the leader expected to happen. Explain what actually happened and what became clear only afterward. Tom’s stories cross Navy service, business, and teaching; their settings differ, but each invites a reader to ask how responsibility was handled. A useful telling should leave room for a colleague to disagree with the leader’s interpretation. Avoid smoothing away the uncertainty that made the choice hard, or claiming that the outcome was obvious in advance. If the story involves another person’s private situation, protect it or choose a different example. Honesty is not permission to expose a teammate.

Turn the story into a conversation

Ask listeners what they noticed and what question they would have asked before the decision. Someone close to the daily work may see a warning sign the leader missed. Another person may explain why the chosen option made sense under the circumstances. The point is to practice judgment together, not to script the right answer after the fact. Tom’s presentation repeatedly returns to caring for people and learning from those around him. A discussion of a mistake should do the same. If the account points to a process problem, identify the change and who will test it. If it points to a communication failure, decide how the next team will hear a concern sooner.

A limit worth keeping

Do not demand that employees offer up mistakes merely because a manager has shared one. Safety is built over time, and a leader’s response to the next problem will matter more than the warmth of a single meeting. Share a story when it serves a concrete learning purpose, take responsibility without theatrical self-criticism, and let colleagues draw their own conclusions. The book offers more of Tom’s lived episodes, and the video lets readers hear why he chose storytelling as a way to teach leadership. A practical starting question is whether there is one choice you would handle differently now and what information you wish you had asked for then. That question can lead to a better decision process for the team today.

A good ending may be a question rather than a moral. What would you have noticed if you had been doing the work at the time? Which signal did we ignore, and who might see it sooner next time? Those questions make the story useful beyond the person telling it. They also invite expertise from people whose roles are absent from most leadership accounts. The story becomes a way to improve attention.

Hear Dr. Tom explain the idea in the book presentation, then explore the book for the full account.