So, You Made a Mistake at Work. Should You Tell Your Boss?
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Workplace mistakes happen to the best of us. Sometimes they take the form of a typo in an important email while other times they take the form of a conversation with a client gone wrong, but the real dilemma occurs after the mistake itself has actually been made: Should you or shouldn’t you tell your boss?

The internal struggle between wanting to handle things on our own and knowing that bigger problems require a little help from the higher powers is a real one, says Adam Smiley Poswolsky, a career expert and author of The Quarter-Life Breakthrough, a guidebook to help Millennials find meaningful work. We, as Millennials, often want to be able to solve things ourselves, after all, and that’s a really awesome instinct to have—but within reason.

“The intention behind wanting to solve something yourself is really good; it means you’re good at your job and you’re a professional,” Poswolsky says. “But there are always things where the proper action is to tell somebody else, because honesty is really important, too.”

So, the “Should I tell my boss?” question is a complicated one. The good news is that it will become easier to answer as you get older and become more experienced, but if you need a little guidance now? Read on for three situations in which you can totally handle things on your own and three situations in which cluing in your boss is a must.

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1. You sent the wrong date on an invitation or the wrong attachment in an email to clients.
So you went back to read over an email you sent earlier today and found an error, and now you’re feeling pretty embarrassed. But have no fear: This situation has an easy fix. Follow up the first email with a second email in which you apologize to the clients and include the correct date or attachment, and voila—problem solved.

Now that the situation is handled, give yourself a pat on the back: Your boss might not know it, but by calmly and maturely handling an easily fixable situation like this one, you just saved her a serious hit to her productivity. “By handling it yourself, you keep someone who’s very busy from having something else to deal with,” Poswolsky says. “If you think of it in terms of email communication, that could be one forwarded email, an email back, and then you have to have a meeting about it. That already could be 20 minutes wasted.”

2. You accidentally deleted important data in a company Google doc.
Gulp—just like that, with one swift push of a button, three weeks of your team’s hard work has been lost. While your first reaction might be to go into full-on panic mode, take a deep breath and remember that Google docs provide an option to view revision history and restore old versions of documents. Read: You’ll have the doc back up and running again in no time. And if a coworker happened to notice your mistake in the split second that the info was gone? Send her a quick apology via Gchat.

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Believe it or not, fixing a mistake like this on your own can result in a mini-boost of confidence. “You’re gaining experience by just taking care of business,” Poswolsky says. “You’ll think, ‘Oh, I handled that. I’ve got this.’ So, when another challenge comes up that might be even a little more complicated, you’ll know that you did it the last time so you can do it again.”

3. You and a coworker had a minor misunderstanding.
After a slight miscommunication via email, you and a coworker are feeling, well, pretty frustrated with one another. While it might be tempting to bring in someone else to mediate, take a minute to step back and evaluate the situation. If it really is just a matter of miscommunication (and this is the first time this has ever happened), you can handle it on your own. Start a calm, in-person conversation with your coworker and use those excellent people skills of yours to resolve the conflict—all without getting your boss involved.

The ability to handle tough situations like this one is something that comes with time and experience, but it can also be made easier by talking with your boss directly about how to handle these when they happen. “A periodic check-in conversation with your boss about your performance is a great time to bring this up,” Poswolsky says. “You might say, ‘Hey. This situation is something that came up. Is that something you would want to be notified about or can I just handle it on my own?’” Knowing for sure what your boss wants you to do when a problem arises? Major win.

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