No-Regrets Leadership

My daughter has a desk calendar with an African proverb for each day. I often steal the proverbs to use as tweets; this morning I posted one from Kenya:  “One does not regret helping another.”

This little piece of wisdom strikes me as profound and pithy advice for leaders. Because it’s true: As I look back on my 20+ years of managing and leading, I can’t think of a single time when I helped someone—with information, moral support, resources, or time—and later regretted it.

I got to thinking: What do I regret having done, as a leader? And what have I never regretted?  Here are my two short lists.


I regret …

  1. Not taking advice from people who’d been there. I’ve made three or four major screw-ups in my management career.  In every case, a more-experienced friend or mentor advised me beforehand to take a different course. Too caught up in my own knitting, I didn’t listen.
  1. Caring too much about sunk costs. One of the classic cognitive biases, the sunk-cost effect is when you think, “I’ve gone so far down this road; I can’t turn back now.” Well, today I can confidently say that on about 20 percent of those roads—yep—I should’ve turned back.
  1. Trying to be “Mom.” One of my strengths is taking responsibility. That’s great, but sometimes I carried it too far. It may be Mom’s job to make sure the kids are happy, successful, and playing nicely together at all times, but it wasn’t my job as a leader.
  1. Assuming I was indispensable. Sometimes (ok, often) I fell into the common leadership trap of believing my own press. As it turns out, “You’re great” doesn’t mean “We can’t live without you.” Guess what: They can, and they will.
  1. Being confrontational. My old employer had a values code that included “Confront with respect.” Sounds like good advice, but I can’t say it’s foolproof; at least, it wasn’t proof against this fool. There’s a world of difference between truth spoken with love (see #4, below) and truth spoken with anger, defensiveness, or cold respect. I regret the times I’ve led with the latter.

I’ve never regretted …

  1. Stepping up to a challenge. You’ve probably heard the adage, “Every day, do one thing that scares you.” Well, I don’t know about every day; I will say, however, that any time I’ve thought, “I’m scared to death … but I’ll do it anyway,” I’ve never regretted it.
  1. Trusting my team. Whether it was a complex project, sensitive information, or a stretch assignment, I tended to trust my team members to handle it. There were a few times when this policy backfired, but it’s really an either-or thing: either A) you trust your team, or B) you don’t. I’ve never regretted choosing Door A.
  1. Prioritizing family, health, and happiness. I spent too many hours worrying my career would suffer because I’d stayed home to watch my daughter dance in The Nutcracker instead of getting on a plane for a sales pitch. I needn’t have worried. Every minute with my family (or just looking after myself) was a no-regrets minute.
  1. Speaking the truth with love. Here’s the flip side of #5, above. I’ve learned that directness is neither good nor bad; it’s the intent behind it that counts. Merely respectful intent isn’t enough. But truth with loving intent—it’s a rare thing, and you can’t go wrong when you speak it.
  1. Helping anybody: probably the one behavior that is absolutely regret-proof. One of my old bosses used to say, “Err on the side of generosity.” It’s a good principle, and I will add a corollary: “Generosity knows no regrets.”

What about you? What do you regret doing, as a leader? What have you never regretted doing? And what does all this say about guiding principles for leadership?

About Jocelyn R Davis

Jocelyn Davis is Principal of Seven Learning, a leadership development firm that creates a lasting lift in leaders' effectiveness using classic books, films, and stories.
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3 Responses to No-Regrets Leadership

  1. Kate says:

    Being unkind. I justified it at the time as truth-telling and directness, but the truth is I was hurt and I lashed out. I *was* being direct and telling the truth, but I didn’t have to be harsh. It still feels awful to think about. It really doesn’t take any more time to be kind than otherwise (once you learn to end conversations graciously, which can be challenging)… and it’s worth a few moments of my time to lift someone up instead of grind them down.

    • Indeed. It usually doesn’t take any more time to behave well as opposed to badly. Just more courage, I think. Hmm … maybe it takes LESS time to behave well, because then we don’t have to spend a lot of time covering up, justifying, regretting, making amends, and so on. Good behavior as a productivity strategy?

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