Field Notes

Would you be willing to admit this to your boss?

Imagine that you made a mistake at work

Imagine that you made a mistake at work. I don’t mean a little one, I mean a real mistake, a doozy. And imagine that the mistake is entirely, and clearly –without a doubt — your fault. You can’t blame anyone else, you can’t point to mitigating factors, you can’t excuse the error: in this nightmare scenario, you screwed up in a big way, and your company or organization is exposed because of it.

How would you tell your boss? Worse, what if you are the boss…how would you tell your customers?

Steven Frank made a big mistake. Steven is the co-founder of Panic, a fairly remarkable software company that makes “super-nice” apps for MacOS and iOS. About two weeks ago, Steven screwed up and installed a malware-infested application onto his personal laptop. The details are technical and don’t matter much… the gist of the story is that, because of his boneheaded mistake, his company’s source code, the actual product they sell to their customers, was being held for ransom by internet thieves.

Here’s a piece of what he wrote on his blog:

This has been a hard post to write. I hate that this happened. I kick myself every day for not paying attention to what I was doing; the tells were obvious in hindsight. It’s a good reminder though — no matter how experienced you might be with computers, you’re human, and mistakes are easily made.

You can read Steve’s entire blog post if you’d like, but that paragraph I excerpted above is the part I want to discuss for a second. You see, I’ve made mistakes. A lot. Some real big ones, too.

It’s somewhat consoling to think, right at that moment that I realize my blunder, that, as Steven says, mistakes are easily made. But that doesn’t help much because, as much as I don’t like to admit it, deep down I believe that mistakes are for other people and I’m better than that. (I suspect that many of you feel the same way, too.)

So, if we’re going to be honest with each other, I don’t know if I would’ve had the courage to do what Steven did and admit my error to my boss (in this case, his customers, but that amounts to the same thing). That kind of transparency is worthy of respect… so I’m sharing it with you so we can both learn from it.

I’m a teacher. My colleagues and I tell our students all the time that they have to be comfortable with failure; that they can’t learn anything unless they’re willing to make mistakes; that they’ll never be able to do something right unless they’re willing to do it wrong first.

But in many classrooms, the penalty for failure is pretty steep. It’s a zero on an assignment, or a poor test grade, or a lousy outcome on a project. That’s not celebration, that’s punishment. Do we allow the student to redo the assignment, retake the test or take another stab at the project? Or do we give them some garbage like, “That’s how we learn!” and move on to the next unit?

The challenge of learning is that mistakes are easy to make and difficult to own. The more difficult challenge of teaching (or leading) is that they’re even harder to forgive.