On Regret and Leadership

In developing current and future leaders, I’m fascinated by the role regret plays in leadership maturity — and how it shapes who we become.

Frank Sinatra once sang, “Regrets, I’ve had a few… but then again, too few to mention.”

In reading today’s ABC interview with Kamala Harris, she admits she regrets not challenging Joe Biden’s decision to seek re-election in 2024 — a decision she now calls “reckless.”

“𝘞𝘢𝘴 𝘪𝘵 𝘨𝘳𝘢𝘤𝘦, 𝘰𝘳 𝘸𝘢𝘴 𝘪𝘵 𝘳𝘦𝘤𝘬𝘭𝘦𝘴𝘴𝘯𝘦𝘴𝘴? 𝘐𝘯 𝘳𝘦𝘵𝘳𝘰𝘴𝘱𝘦𝘤𝘵, 𝘐 𝘵𝘩𝘪𝘯𝘬 𝘪𝘵 𝘸𝘢𝘴 𝘳𝘦𝘤𝘬𝘭𝘦𝘴𝘴𝘯𝘦𝘴𝘴. 𝘛𝘩𝘦 𝘴𝘵𝘢𝘬𝘦𝘴 𝘸𝘦𝘳𝘦 𝘴𝘪𝘮𝘱𝘭𝘺 𝘵𝘰𝘰 𝘩𝘪𝘨𝘩. 𝘛𝘩𝘪𝘴 𝘸𝘢𝘴𝘯’𝘵 𝘢 𝘤𝘩𝘰𝘪𝘤𝘦 𝘵𝘩𝘢𝘵 𝘴𝘩𝘰𝘶𝘭𝘥 𝘩𝘢𝘷𝘦 𝘣𝘦𝘦𝘯 𝘭𝘦𝘧𝘵 𝘵𝘰 𝘢𝘯 𝘪𝘯𝘥𝘪𝘷𝘪𝘥𝘶𝘢𝘭’𝘴 𝘦𝘨𝘰, 𝘢𝘯 𝘪𝘯𝘥𝘪𝘷𝘪𝘥𝘶𝘢𝘭’𝘴 𝘢𝘮𝘣𝘪𝘵𝘪𝘰𝘯. 𝘐𝘵 𝘴𝘩𝘰𝘶𝘭𝘥 𝘩𝘢𝘷𝘦 𝘣𝘦𝘦𝘯 𝘮𝘰𝘳𝘦 𝘵𝘩𝘢𝘯 𝘢 𝘱𝘦𝘳𝘴𝘰𝘯𝘢𝘭 𝘥𝘦𝘤𝘪𝘴𝘪𝘰𝘯.”

“𝘐 𝘩𝘢𝘷𝘦 𝘢𝘯𝘥 𝘩𝘢𝘥 𝘢 𝘤𝘦𝘳𝘵𝘢𝘪𝘯 𝘳𝘦𝘴𝘱𝘰𝘯𝘴𝘪𝘣𝘪𝘭𝘪𝘵𝘺 𝘵𝘩𝘢𝘵 𝘐 𝘴𝘩𝘰𝘶𝘭𝘥 𝘩𝘢𝘷𝘦 𝘧𝘰𝘭𝘭𝘰𝘸𝘦𝘥 𝘵𝘩𝘳𝘰𝘶𝘨𝘩 𝘰𝘯.”

That’s the thing about regret. It’s uncomfortable, but it also points us to what we value most and where we’ve strayed from it.

As a coach, I find that reflecting and learning from regret is one of the most powerful tools we have. It reveals what truly matters: values, resilience, and self-awareness.

Over the years, I’ve heard leaders share regrets like these:

• I put work ahead of family.

• I should have acted sooner.

• I stayed too long in the job.

• I didn’t act when I should have.

As Lucille Ball once said, “I’d rather regret the things I’ve done than the things I haven’t done.”

In coaching, the aim isn’t to dismiss or erase regret but to use it. Regret shows us where our decisions didn’t align with who we are or who we aspire to be.

Regret, when used well, becomes one of the most honest teachers we have.

Finally, when leaders admit their regrets and show what they’ve learned, trust builds. Their story becomes a bridge to others’ growth.

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