← index updated 2026-09-08 3 min 644 words leadership reflection founders

The dent and the crater

How a bad year can change the way you lead, and how to keep your team talking to you.

"The world breaks every one and afterward many are strong at the broken places. But those that will not break it kills."

Ernest Hemingway, A Farewell to Arms (1929)

Some of the senior leaders I've worked with changed after a bad year. A board turned against them, a launch failed, or a cofounder left. Months later, they were still organising their work around making sure it couldn't happen again.

You can see it in small decisions. A leader adds another approval because the last launch went wrong. They dismiss a pitch because it resembles a company they once backed. They stop asking for advice on the decision that hurt them. Each choice has an explanation, and experience gives them plenty of reasons to sound convincing.

I think of the original setback as a dent. The crater develops when avoiding another setback starts to determine how you work. You spend less time asking whether a new idea is good and more time looking for the part that could hurt you again.

Some caution makes sense. You should understand why a launch failed and change the things that contributed to it. The difficulty is noticing when you've extended that caution to decisions that have little to do with the failure.

A new hire brings an idea and you tell them you've seen it before. You close your door and call it focus. You put another review on the calendar without asking what the existing review missed. From your side, you're applying what you've learned. The people working with you may experience it as a growing reluctance to hear them out.

You might not notice until they stop bringing you rough ideas. They wait until they can defend a proposal before sharing it, or they ask someone else. You get fewer opportunities to help while the work is taking shape. If you've also pulled back from customer calls, you can be making decisions with less information while feeling more certain about them.

The leaders I've seen stay open over time have people they can talk to about this. Some use a coach. Others meet with a few peers who know enough about the job to challenge their account of a difficult quarter. A partner or a mate outside the industry can help too, especially if they aren't impressed by your title and will tell you when you're being unreasonable.

Those conversations need room for the part you're embarrassed about. You might have handled the board meeting well and still be afraid of going through it again. You might know the team needs more autonomy and find yourself checking their work anyway. Saying that to someone gives you a chance to examine it.

It also helps to have something outside work where your role carries no weight. The leaders I know who ride, surf or build things make time for an activity where they can be a beginner, get something wrong, and carry on. You need some part of your life that doesn't depend on being the person with the answer.

This takes attention because your team will adapt to how you behave. If you cut people off, they learn to keep difficult conversations short. If you dismiss an idea before asking a question, they get more cautious about suggesting one. They have work to get through and will find a way to do it with the leader they have.

That adaptation can make the problem harder to spot. Meetings become smoother. People bring fewer disagreements to you. You may take that as evidence that the team is working well together, especially after a period when everything felt difficult.

Meanwhile, the people closest to the work are choosing what to tell you based on the reaction they expect. By the time a problem reaches your desk, they may have spent weeks trying to solve it without involving you.