The biggest regrets of leaders.

I asked ChatGPT what the biggest regrets of leaders were from the last five years. And not surprisingly, the work I do every single day with organizations addresses and helps with these very concerns.

Here’s what leaders say they regret most, along with the consequences:

Not moving fast enough or being bold enough missed opportunities, loss of trust, and playing catch-up instead of leading.

Not building or investing in strong teams burnout, lack of succession, and cultures that crumble when pressure hits.

Neglecting relationships isolation at the top, low morale, and teams who feel unseen.

Work-life imbalance exhausted leaders who can’t sustain impact or model well-being for their people.

Failing to be true to values or self misalignment, regret, and cultures that learn to hide instead of live in authenticity.

Avoiding tough decisions wasted resources, stalled progress, and erosion of accountability.

Under-communicating or delaying transparency confusion, rumor mills, and broken trust.

Not investing in people development disengagement, turnover, and missed potential.

And yet here I wonder, when will organizations actually do something different and pour into their people so they don’t have to live with these regrets and the consequences of them?

Which of these regrets resonates most with your own leadership story, and what would it look like to choose differently now?

Courage is Built Here™ is about creating cultures where these regrets don’t have to be the story, and instead, where courage, clarity, and connection lead instead.