You Probably Aren’t Making Enough Mistakes

Work isn’t school, so especially if you’re new to work you probably aren’t making enough. Why you should make more, and why making them is good for you and your team.

Did You F**k Up Today?

One of the cool things about managing is that you get to work with a lot of people. A trend I see is that many people — especially those earlier in their career journeys — are terrified of making mistakes. I can relate. After 7 years in the post-secondary education system, I too thought that everything was about getting a good grade. I worried that if I didn’t get an A or an H or a 400,000,000 score on the SAT/LSAT/pacman, my life would be over. And then I became a first year associate and realized I was doing everything wrong. I made more mistakes than I can count, and my life didn’t end.

Why We Think This Way

In Thanks for the Feedback, Douglas Stone & Sheila Heen write about different types of evaluation. There’s praise, coaching, and evaluation. Praise is someone telling you you’re great. It’s the least controversial form of feedback, so it doesn’t get discussed much in the book. Coaching is what it sounds like — someone giving you constructive feedback designed to help you get better at something in the future. Evaluation, on the other hand, tells you where you stand based on the past. It’s a final verdict, a test score, a grade.

And there’s the problem.

If you’re good at school, or you want to be good at school, you probably work very hard at school, and probably start spending more and more time on school the further along you get. And then maybe you realize that you don’t have time for hobbies or fun anymore and school is all you’re doing. And when you’re doing school, you’re focusing on evaluation, because that is what school is good at.

You study for midterms and finals and stress out about grades and then you do it again for exams that control the key to your future as a doctor or lawyer or grad student. School gets an A++++ in evaluation.

What academic classes aren’t good at, though, is coaching. Yes, there is teaching (of varying degrees of effectiveness). But what you don’t usually have in class is a coach focused on the game of making you better at learning. There are very few low stakes opportunities for taking risks and getting better. It’d be like playing a sport where all the coach does is teach you plays. And also, your season is 3 games long. And unless you do well in games 1 and 2, you start game 3 40 points down.

Work Isn’t About Evaluation

Now, contrast that with the workplace. Once you start a job, the only forms of evaluation with any consequence are getting promoted/given a bonus, and getting fired. Sure, there’s praise, but most of the time you’ll be getting feedback from many different people with varying degrees of skill in giving feedback. And the goal of the feedback is overwhelmingly likely to be trying to get you to do better work — whether because the person cares about you, or just because you doing better work is likely to make their job easier.

And guess what? No one wants to fire you. Hiring you was hard. It took a lot of time and resources. So did training you (and this is an ongoing process, not what happens on day 1 during “onboarding”). Your manager doesn’t want to do that again; they are too busy. Plus if you are a decent human, than firing you will make everyone else at work sad. So the chances that you are being fired because you did something wrong — unless that thing was harassing/assaulting someone — are very low.

Your manager also probably remembers being new, and learning to make mistakes and not getting fired for them, and so already knows that you will make mistakes. At work, unlike in school, if you screw up it probably won’t hurt you. Instead, it will help you. More on that below. But my main takeaway from Stone & Heen’s book and from years of working and managing people is this:

Even when feedback is poorly delivered (and/or the feedback giver is an asshole), that person probably intends the feedback as coaching. They’re telling you to do X thing differently so that you will do it better next time, not to let you know that you got an F in Proofreading 101 or Intro to Writing Emails.

Getting feedback is hard. I don’t mean to make light of that. It’s still hard for me and it’s hard for all of us. But trying to take it as coaching, and learning to more clearly give feedback as a coach, can help. I’m also talking about feedback mainly to illustrate the ways work is different from school. Feedback is often the result of a mistake, but it’s not the mistake, so let’s get back to that.

Mistakes Are Inevitable

In Failure & Rescue, Atul Gawande makes a startling point about hospitals. The “best” surgical departments don’t make fewer mistakes, they are just better at course-correcting when things go wrong, or “rescue”.

No matter how hard you try, you are going to make mistakes. Instead of paralyzing yourself with fear over making mistakes, remember that they happen, and it’s what happens after that’s important.

Mistakes Are How You Learn

The great thing about mistakes is that after you make them, you learn. The surgical departments in Gawande’s article had better outcomes because people weren’t afraid to talk about mistakes or admit their mistakes, and this led to everyone learning from each other’s mistakes. And this led to better outcomes.

Learning happens when you try to do something, fail at it, and — either through your own knowledge or through coaching — you realize that there’s a different way to do it. You try again, and you may fail again and go through the cycle again. Eventually, though, doing the thing stops being hard. You master it because you have made many, many mistakes and learned from them.

If you aren’t making mistakes, you probably aren’t pushing yourself enough. Think about where you want to be 5 or 10 or 15 years from today, and where you are now. There are probably things you’ve already mastered, that you can do in your sleep. Do you want to be doing only those things for the rest of your career? If the answer is no, get ready to make a lot of mistakes.

Building a Culture With A Growth Mindset

Carol Dweck, a PhD who teaches at Stanford, has spent years studying people’s mindsets and found that people who view mistakes as evaluation, as evidence that they are or are not good at something, do much worse than people who view their mistakes as coaching; as opportunities to get better. She identifies this ability as having a growth mindset.

So, how do we as workplaces get everyone to make more mistakes and learn from them so that we can be like the hospitals Gawande writes about? To do this you need to create a safe space for people to discuss their mistakes and learn from them, and as a leader you need to talk about your own mistakes.

It’s a work in progress — we make mistakes in trying to talk about making mistakes — but soon after I started at Quill I asked everyone to read Gawande’s article and come discuss it at a lunch. This was really scary for me; I’d never asked anyone to read something before and I had no idea if it would work. But it did. We had a really good discussion about making mistakes and how we, as a team, can be better about learning from and sharing our mistakes.

One common fear was that people would be penalized in some way for mistakes. So we created a type of mistake amnesty. For mistakes that relate to how you do your work, as long as you admit them and demonstrate that you’ve learned from them, you will never be penalized for making a mistake. We enshrined this as the first Quill value we wrote down: cultivate a growth mindset.

This only works if you keep talking about mistakes and modelling that it’s ok to make them, though. Taking a cue from Radical Candor author Kim Scott’s discussion of “Whoops the Monkey,” when we first started doing this I brought in a large plastic jack-o-lantern full of candy (it was October), and told people they could have candy if they described a mistake they made and what they learned. We’ve now graduated to a “Fail Whale” I made — basically a whale-shaped post-it note on some pipe-cleaners. Yes it’s silly, but so far it’s been working.

So, here’s the easiest advice you’ll get from a blog post: make a mistake today. Try it. Even if you don’t try, you’ll probably still succeed. And when you make that mistake, remember that it’s ok, that you haven’t failed Having A Job, that you can learn from it, and that the job will still be there for you tomorrow.