When is the last time you said “I’m sorry”?

In December of 2012, I officially became a parent. Thinking back on those first years of my daughter’s life (before our other kids), it’s amazing the things you remember and forget (until something reminds you).

Now that she’s a bit older, I see that one of the easy things to forget is what a handful she was as a baby and young toddler.

We learned a lot in those early years, not the least of which was the fact that love and discipline, plus consistency and patience can be a truly magical combination for helping children navigate their emotions while building a deep and lasting bond with them.

A picture of me and my daughters from 2018
My and my girls, 2018

But the ugly side of parenting is that you are forced to come face to face with your own worst flaws.

The mistakes I made as a parent are too many to count, but one thing my wife and I committed to early on was that if we made a mistake with our kids … overreacting, losing our temper, unfair punishments, misunderstanding, misapplication of blame, incorrect assumptions … we would verbally apologize to our children. We would kneel down, look them in the eye, and say the words “I’m sorry, that was wrong. I should not have done that.”

It’s such a humbling (humiliating?) thing to have to do. Me, the parent, apologizing to them, the kid … it feels strange. But it does get easier the more you do it.

Since making this a part of our family’s DNA, it’s amazing how often you notice the mental gymnastics some parents perform to avoid saying “I’m sorry” to their kids, and it’s a good reminder to me how important that small act, that simple phrase, really is.

Instruction + modeling = behavior forming

The best leaders I’ve experienced in my life were great at explaining what needed to be done, and also having the discipline and character to do it themselves.

One of Andy Grove’s 5 responsibilities as a leader in High Output Management is “being a role model”.

“Do as I say …” just doesn’t work.

If you’ve been given any leadership responsibilities, modeling the behavior you want to see from your team is absolutely essential.

Owning Our Mistakes

One quality of a healthy team is adopting a culture that encourages everyone to own their own mistakes.

Sometimes that’s missing a deadline, or shipping a bug to production, or forgetting to do something that you committed to do.

Sometimes it’s being accidentally (or purposefully) insulting, or taking something personally that you shouldn’t have, or snapping at one of your coworkers.

A team culture that allows for mistakes and encourages speedy apologies is a health metric that is at the top of my priority list as a leader.

Recommended Reading

Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong

But just wanting that kind of culture doesn’t guarantee it.

Telling your teams that’s what’s expected of them, coaching them to be generous with apologies and forgiveness, giving presentations or recommending books … none of that will be as effective as them seeing you, the leader, practicing what you preach.


So, back to the title of this post: when was the last time you said “I’m sorry”?

Guess what? You’re not perfect. You do make mistakes.

If, for some reason, you believe that the reason you haven’t apologized lately is because you’ve done nothing worth apologizing for, you have bigger problems.

If you aren’t apologizing, it’s not because there’s nothing to apologize for. You’re just so out of practice that you’re not letting things register as mistakes worth apologizing for.

Make it a practice to notice and write down every time you mess something up. Every mistake is an opportunity to learn what not to do, and to model what should be done after the mistake was made.

Own your mistakes as fast as possible, so you can mitigate and correct the damage done, improve your systems to prevent it from happening again, and try not to make the same mistake twice.

Mind how you respond to others’ mistakes

After enough time coaching your team to own their mistakes and say “I’m sorry” when they make them, and of course modeling this behavior yourself, you need to make sure you are reacting properly when people actually start to adopt the practice themselves.

Is your team safe to admit mistakes in front of you?

One of my favorite interview questions to use when chatting with potential hires is “tell me about the last time you made a mistake at work that you had to apologize for?”.

I like this better than “what’s your greatest weakness?”, because for one, it’s unexpected, and two, there’s little room to wriggle out of it with a clever answer. No “I care too much” or “I work too hard / too much” nonsense.

It sets the tone for the team they’d potentially be joining.

It’s OK to fail on this team. Expected, even.

No blame, no bravado.

We apologize, we own our mistakes, and we get better. And most importantly, having the humility to admit a mistake in front of me will never be something you have to be afraid of.

Don’t believe me? You will when you see me apologize as much or more than anyone else.

Autonomy, failure, and “pushing down”; what I’m learning about leadership

That title is a lot to digest, but as part of my (ongoing and never ending) journey to master effective leadership, it would be irresponsible not to cover the topic of autonomy.

Human beings have an innate inner drive to be autonomous, self-determined, and connected to one another. And when that drive is liberated, people achieve more and live richer lives.

Daniel Pink, Drive

I’m still very much learning about the less obvious things good leaders do, and how to integrate those things into my own approach and management philosophy.

But here is one of those obvious things that didn’t take very long to learn: few things you in a leadership position will be more patronizing, more insulting, more humiliating than micromanagement.

Nothing says “I don’t trust you” quite as effectively as looking over someone’s shoulder (physically, or virtually) while they’re working on something.

But is it a necessary evil?

Trust and Patience

Imagine being truly great at a sport. Top of your game, physically able to achieve success, game after game.

Then slowly, as you age, you begin losing the power to impose your will with a ball. No longer able to run faster or jump higher, you’re forced to move on from playing professionally. At best, it’s now a hobby.

But then you get a call. A team wants to hire you to be a coach, to help pass on your knowledge and experience to the next generation of able bodied professionals, and hopefully achieve the same level of success in coaching as you did as a player.

Unfortunately, the reality is that very few great players ever become great coaches.

Why is that?

I can’t imagine how difficult it must be to know that in the not-so-distant past, you were so instinctively great at something, having the talent to make split-second decisions with a ball in your hand, seeing what needs to be done and having the ability to execute in real time, suddenly expected to watch from the sidelines, as a coach, during pivotal moments of the game.

To execute as a player takes talent and practice.

To execute as a coach takes trust and patience.

These are skills that you just don’t naturally develop as a player, but they’re essential as a coach.

Trust: to know that when your players leave the huddle, that they remember what you said, that they have the physical ability to make it happen, that they believe you can see what they can’t and will draw up a plan that puts them in a position to win. Oh, and they won’t allow momentary hubris to take over when it comes time to execute the plan.

Patience: to have a vision for what should be. To understand that no one wins 100% of the time. Having the discipline to see failure coming, letting it happen (when appropriate), coaching through the difficulties, and pushing your team to improve iteratively.

The best time to fail

I’ll admit that I have very little tolerance for my own failure. I figure if I think long enough about all the ways something can go wrong, I can mitigate them all. If I just ask enough questions, or do the most research, or have contingency plans for every scenario, nothing could possibly go wrong.

Not only is this an unreasonably heavy burden for a single person, it doesn’t even work!

Recommended Reading

Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong

Failure is inevitable.

So when is it appropriate to let your team fail?

How do we optimize our failure for growth?

Fail when the stakes are low.

If you play sports, it’s better to fail in practice, scrimmages, pre-season, and the regular season, than it is to fail in the last seconds of the championship game.

If you’re a carpenter, it’s better to fail when building a birdhouse than it is to fail building an actual house.

You don’t run a marathon without training.

You don’t attempt to free solo El Capitan without first trying it with all the necessary safety gear.

Failure is the best teacher

I still remember the single question I got wrong on my written driver’s test when I was 15 years old. I’ll never forget it. I have no idea what questions I got right, but the one question I missed is forever carved on the inside of my skull.

Better I get it wrong at a desk at the DMV than behind the wheel, right?

And that’s the point. I missed it in the safety of a classroom. The stakes were low. If I failed the test, I’d go back home, study some more, wait a couple of weeks, and try again.

If I missed it on the road, I could end up in the hospital (or worse).

“Pushing down”

My friend Katie (who doesn’t blog) asked a great question in a recent meeting we were in.

“Is it possible to push any of these decisions one level down?”

Katie Childress

She wasn’t suggesting we push every decision all the way down. We can’t ignore the reality that not everyone in every position has all the context needed to make the right call.

Her point was that we sometimes forget to even consider if it’s possible to allow a decision (case by case) to be made by your team, rather than you, or your boss, etc.

Are we asking the right questions? What are the risks? If they fail, if they get it wrong, what’s the worst that could happen?

It’s a lot easier to “push down” a decision when the stakes are low. If they fail, so what? We learn a lesson, we course correct, and we try again. Repeat.

As repeated failure teaches us what not to do, success becomes a more and more likely outcome.

This is how your team earns trust, and learns to trust themselves, for higher stakes situations.

This is how your team can fail productively.

Which brings us back to autonomy

Throwing your team into a high stakes situation, with no experience, and expecting them to know what to do, how and when to do it, and thinking they’ll succeed (under the guise of “autonomy”) could be devastating to both your business and to the team’s confidence.

Being a good coach is about preparing and equipping your team, in low stakes situations, to have the confidence and competence to succeed in the critical moments of their work.

Don’t waste the low stakes moments.

Put ego and fear aside.

Let them try, and sometimes fail.

Then watch with pride as they pop open the Champaign bottle, hoist the trophy, and celebrate a hard earned victory.