Tell Me About a Time You Made a Mistake

This is one of the scariest interview questions. In an interview, you always want to show yourself in the best light. You want to show how perfect you are. But here’s a secret. Interviewers know that you’re not perfect, and that’s OK. It’s more important that you learn from your mistakes and try to get better. This requires you to be honest about where you went wrong in the past and what you’ve done to fix it. If you can’t admit your mistakes, how can you grow?

Many people think of this question as, “Give me a reason not to hire you?” Or they think about a horrible mistake they’ve made it the past, like when they had just started their summer job at the local caterer and completely misinterpreted the instructions for their first order, like:

The fear comes from the way the question is phrased. Anytime something is phrased in the negative, we immediately jump to dark thoughts. You can do yourself a favor by reframing it in the positive form like, “Tell me about a situation where you made a decision and after it was over, you’d learned something surprising?” This happens all the time. There’s rarely a time when a business decision goes exactly as planned because customers never behave the way they are supposed to.

Here’s one time I discovered something surprising at work after initially making the wrong decision.

I was a product manager for a large financial services company. We would release features to our customers on a quarterly basis.

One day, I get an email from my colleague Tom. It said, “I have an idea. Before we send out any emails to clients, we should make sure that we run them by a ‘Virtual Correspondence Committee’ or VCC a week before we send communications to customers. This would help to make all of our correspondence to clients quicker and easier.”

I saw this email and thought “Wait. What? There’s no way this is going to work. We’re such a big and crazy organization. The last thing we need is more bureaucracy.” I was about to send him an email telling him this.

Then I took a step back. I’ve sent emails like this in the past and it never went well. It escalates with both sides getting defensive. Instead of sending the email, I said to myself, “Tom has been here for 30 years. I bet he’s seeing something that I don’t.”

So I called him up. After some chitchat, I said, “So I got your email. Tell me more about this new committee.”

He said, “Well, I’ve been hearing some things from the service desk. When we send out emails to clients, they’ll call up their service teams and ask for more information. But the service teams hadn’t even seen the emails.”

“Do the service teams need to give comments back to us?” I said.

“No,” he said.

“And how much time would the service teams need?” I asked.

“About a week,” he said.

“So you’re saying that a week before we send out the email to clients we should make sure to send a heads up to the service team?

“Yes! That’s it!” Tom said.

So instead of having a battle about who was right, we ended up coming up with a solution to a problem that I didn’t even know existed.

Sometimes the question of self-knowledge is phrased as a weakness rather than a mistake. The interviewer may ask “What is your greatest weakness?” The classic bad answer here is to evade it as in, “My greatest weakness is that I’m a perfectionist.” This basically tells the interviewer that you think you’re perfect and there’s nothing to improve. So the conversation might go like this:

“Tell me about a weakness that you have?” says the interviewer.

“I’m a perfectionist,” you say.

“So how does that work as a weakness?”

“Well, I always spend lots of time making sure that everything is perfect. I never hand in work if it’s not 100% right.”

“That sounds very difficult. Does that mean that you can’t get much done because you’re always checking your work? Or does it mean that you’re not prioritizing the most valuable work first? Or maybe you don’t share interim work products with stakeholders. How does the weakness affect your work”

“Ummm…,” you trail off.

As you can see, you don’t want to evade the question or focus on the weakness. You want to focus on how you’re improving. Instead of answering that question about your weakness, but it’s often better to answer “What are you working to improve?”

Learning is all about making mistakes⁽¹⁾In The Last Lecture, Randy Pausch summed it up well, saying, “Experience is what you get when you don’t get what you wanted.”. We imagine that learning will be easy and simple. We think that we should be able to learn something quickly and immediately implement it—like in the Matrix. But in the real world, you can’t learn without making mistakes. When you go to the gym you get stronger by making your muscles a little weaker. Then they grow back stronger. ⁽²⁾I wrote about how Amazon institutionalizes this idea in my article Amazon article No Pain.

One of the best ways to learn is to look for things that don’t make sense. Whether it’s what someone said or the way you interpret it, there are lots of times when things just don’t compute.⁽³⁾Many people have talked about this idea before. Stephen Covey calls it Habit 5: Seek First to Understand, Then to Be Understood from The Seven Habits of Highly Effective People. When looking at Habit 5, notice that the woman in the video It’s Not About the Nail won’t even talk about solving the problem until she feels understood. These are uncomfortable situations and your first instinct is to judge the other person as wrong. But slowing down and getting clarification makes for a wonderful learning opportunity. So the next time your thinking is going along on its merry way and someone throws you for a loop, take a step back and say, “Wait! What?”