or: How I Learned to Stop Worrying and Love Mistakes

5 minute read

From 2016 to 2020 I was an instructor at the Airman Leadership School (ALS) on Maxwell Air Force Base. There was a core curriculum I had to teach, but a lot of the most powerful lessons came from the students swapping stories. ALS is a prerequisite to gaining the rank of Staff Sergeant and becoming a supervisor, so none of these students had led a team before. What they ended up sharing were stories about their existing leaders.

Over and over, the same theme came up again: nobody trusts a “perfect” leader

What is a “Perfect” Leader

First of all, let me be clear: nobody is perfect. Even when you try your best, you are bound to make mistakes. Hell, sometimes you can do everything correctly and still get a bad result. That’s how life is sometimes.

When I say Perfect Leader I’m talking about that person who acts like they’re perfect. These are the ladder-climbers who got to their current rank/position very quickly. They haven’t had any negative paperwork or obvious failures, and all their stories are about their personal successes. Worst of all, when mistakes do happen around them (and they will), they shift the blame to others or double-down on bad decisions.

A Perfect Leader is a similar concept to the know-it-all from our younger years. That one kid in class who is always interjecting and throwing “well, actually” at everybody. The person who beats you upside the head with information rather than hearing you out. Like that kid, these so-called Perfect Leaders usually think they’re really good at leading - a critical oversight on their part.

Why People Try to be Perfect

Again, everybody makes mistakes. When somebody refuses to admit their mistakes, it erodes trust in that person. When a contrary opinion is presented and someone doubles down on their bad idea, it frustrates everybody around them. When a leader shifts blame to the people around them, it drives a wedge between them and their subordinates.

Every student I had understood this, and yet many went on to become this very type of leader. Why?

A phrase I often heard while teaching ALS is that people didn’t want to look weak. They felt that if they made a decision they had to stick to it. That’s what a strong leader does! they would insist. If you change your mind the Airmen you are leading will take advantage of your weakness! This would usually get the other students nodding in agreement, so I flipped it around and asked:

Imagine that your boss called the workcenter together and said “Look, yesterday I said X, but after looking into things more I realize that was incorrect. Some people pointed out that Y is actually true - thanks to those people who made me aware of the mistake.” What would you think about that boss?

The students universally agreed that this sounded like an awesome boss to work for. So I prodded, but isn’t that weak? Shouldn’t the boss have stuck to their decision? That is usually when it sunk in.

Mistakes Seem Different to the Mistake-Maker

When somebody else makes a mistake, we often shrug it off. Mistakes happen and it’s no biggie! is a typical response. They apologize and we tell them nah, don’t worry about it!

When we make a mistake, it feels like a Big Deal™. I look like such an idiot! is the immediate thought. Without anybody saying anything, we feel attacked. Why? Because we attack ourselves. And what do people do when they feel attacked? They get defensive.

It’s that defense mechanism that makes people start to build these walls around their mistakes. Excuses get generated, details are glossed over, and - if the mistake is old enough - history gets rewritten. We tell stories about our early career or our childhood, but we skip right over all the bad parts. We think it’s defending ourself, but really it makes us unrelatable and untrustworthy.

The Power of Imperfection

I’m going to say it one more time: everybody makes mistakes. It’s inevitable. When you’re a leader, you want to know about those mistakes - preferably as soon as possible - so they can be addressed. Hidden mistakes are like untreated wounds. They fester and get infected, and by the time anybody notices it’s because things have gotten so out of control that serious measures are needed. If you want to have any hope of healing these wounds early, you need people to tell you about their mistakes.

This is where imperfection shines. When you share your mistakes, your failures, your regrets, and all the things you wish you had done better, the people around you remember those stories. When they make a mistake, they will think about your stories. Maybe you already went through something similar, or maybe you had something even more egregious or embarassing. Suddenly it isn’t so scary to share a mistake with you, because you’ll understand.

I discovered this mostly by mistake, because I’m a huge fan of self-deprecating humor. I constantly make fun of myself. It started as a safety mechanism when I was a bullied little nerdy kid. Turns out it’s really hard to make fun of a guy who is already making fun of himself. I loved the disarming nature of self-deprecating humor, so I kept doing it - even after I was a Sergeant who had lower-ranking folks who looked up to me.

The effect it had on those lower-ranking folks was surprising. Over and over again, Airmen would confide in me and ask me for advice. Sometimes I wasn’t even their supervisor. They’d tell me specifically that they felt they couldn’t talk to their assigned supervisor because they just won’t understand. Truth be told, their supervisor definitely would have understood, but their attempts at seeming flawless just made them seem unapproachable. As a result, they missed out on chances to help their people with problems early on.

The Bottom Line: Be Honest

When you’re honest, people will trust you. That means being honest about everything. Want to emphasize the importance of showing up on time? Talk about that time you got in a ton of trouble because you forgot about daylight savings time. Don’t want your kids to make poor financial decisions? Show them how much you’re having to pay on those credit cards you wish you’d never opened. Your horror stories will make you seem more honest and approachable. Trying to cover that up and seem perfect will only backfire! So remember:

Don’t be “perfect” - be honest!


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