What's the Biggest Mistake You've Made at Work?

Our readers share the biggest mistakes they have made in their careers, from personally mortifying to costly, and get insights on the most challenging problems.

At some point in your career, it’s probably going to happen: The stomach-churning, blood-running-cold, dizzying realization that you’ve just made a major mistake. 

We asked our readers for the biggest blunders of their careers and got tales ranging from personally mortifying to costly. Our workplace guru, Justin Kerr, author of How to Be Great at Your Job and How to Be a Boss, shares his insights on some of the most challenging problems.

I lost a grant at a previous job. 

Q: I had to own up to the mistake, but I wish my boss had given more direction to help me not make that mistake again and figure out how to make up for the lost funding. I was able to secure alternative grants, but I was left on my own through a lot of that process. It was a horrible experience I hope never to relive. How can I get more help to solve problems like this? —Ashley L., administrative specialist 

A: Bosses aren’t mind-readers, so the first and most important thing to do is explicitly ask for help—meaning you need to say the words out loud: “I’d like your help with (insert specific request here).” You’d be surprised how often this crucial step is skipped.

Bosses, co-workers and mentors all respond well to flattery, so be sure your request is laced with the right amount of ego-boosting context, such as, “You’ve won so many grants—have you ever seen this type of thing happen before? Is there any advice you can give me or people you recommend I speak with?” 

Lastly, it’s important that you’re actively cultivating your network of mentors, peers and even past co-workers so that you have a bigger pool to draw on for advice and support because, unfortunately, it is a fact of life that we will all have bad bosses who may not be able to help us in our moment of need. 

My boss made me pay for a mistake.

Q: When I started my previous job, I got one of those scam phone calls about our “printer order.” Since I was fresh out of college and this was my first time in that kind of job, I fell for it hook, line and sinker. It ended up costing the company a good bit of money, but we were able to get most of it back. My boss made me pay the difference between what was spent and what monies we got back. Since I was so young and scared, I didn’t even think twice about it. I had to fork out $1,000 to pay for my mistake. Lesson learned, but I question everyone who calls now. What do you think about me having had to pay for the mistake myself? —Danielle G., administrative assistant

A: Did they also give you the profits when you saved the company money with other phone calls or decisions?

This strikes me as supremely unfair and unethical. As it relates to how you could handle similar situations in the future, I’d recommend an approach where you offer extra effort to find other cost savings to make up the difference within six months. I would also encourage you to ask a lot of questions (and get HR involved): Is it company policy that employees pay for any errors made in the workplace?

Part of the cost of doing business is absorbing losses from employee (human) error. Unless you were formally trained and specifically warned not to do something, you have a lot of room to find alternative solutions that don’t involve paying $1,000 for every mistake. I’d be broke if I was held to that standard!

Bosses aren’t mind-readers, so the first and most important thing to do is explicitly ask for help.
— Justin Kerr
workplace expert author

Incessant teasing

Q: My bosses are pretty forgiving and allow us to fix our mistakes. They do love to remind us of them, sometimes for a bit too long—in a joking way, of course. It’s amazing how one boss in particular loves to tease whoever made the mistake, sometimes all day long. I love it when he makes a mistake. It is so much fun to keep bringing it up as many times as it conveniently works into the conversation. What are your thoughts on this type of work environment? —Gail G., staff assistant

A: Teasing is often a substitute for someone trying to establish a relationship but not knowing how. So as silly as it sounds, you and your co-workers should get to know each other better so that you have other things to talk about instead of the boring topic of workplace mistakes.

Your approach of mercilessly teasing the boss when they make a mistake is only perpetuating the problem, so I’d encourage you to take the higher ground and stop the cycle of psychological abuse. It may seem like fun and games “in a joking way,” but this isn’t healthy for anyone.

If all else fails, I’d recommend you speak with them directly, point out their behavior and explain its impact on you. That should do the trick.

Follow Justin Kerr on Instagram @mrcorpo or visit mrcorpo.com.