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 …
- 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.
- 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.
- 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.
- 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.
- 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 …
- 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.
- 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.
- 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.
- 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.
- 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?