Years ago, walking through the headquarters of the company I was working for, I passed a photo shoot. The man running the company was posing for new portraits. Asked how he wanted to come across, he answered, more or less: bold and determined.
A small moment, I recall it well. In hindsight, it said a lot.
The company was going through a large transformation under his lead. In the regular briefings with the management team, the same instinct showed up in another form. He usually told us “I insist!” He told people they didn’t know. Over time, mistrust and fear grew in the leadership team. Everyone looked out for themselves. That culture did not stay at the top. Managers carried it into their teams.
Mihály Csíkszentmihályi describes the mechanism in Flow: once such practices “become part of the norms and habits of a culture, people assume that this is how things must be.”
At Thoughtworks, we talk about the courageous executive. Their courage does not come from looking bold and determined. It comes from building a culture in which they don’t control everything. They give teams room to develop their own ideas and to make mistakes.
Mistakes are not good in themselves. The freedom to make them, and to learn from them, is.
That transformation failed. There were many reasons, but the culture at the top is the one I saw up close.
In my day-to-day work, I also see the other side: leadership built on psychological safety, on leading rather than managing, on strong teams, on true empowerment, getting much further, especially in digital transformations.
Courage in leadership shows in what you are willing to let go of, not in how in control you look.
If you are in a transformation right now: How bold is your leadership team?