Dear Work It Out,

What do you do if your boss (accidentally) adds mistakes into your work after you've turned it in and they're supposed to be correcting it? How do you address it without making things awkward?

Similarly, how do you bring up difficult topics with your boss in general?

Afraid to be awkward

*

Dear ATBA,

I'll admit, this is a difficult needle to thread. The way you approach it will depend a lot on your relationship with your boss and their personality. My answer assumes that your boss is a reasonable person with whom you have a relatively good working relationship.

The good news is that you've said this is an accident. We all make mistakes, even those of us tasked with finding others' errors. Your boss is not trying to sabotage you and that's the first thing you should remember when talking to them.

This is a chance to work together toward what is a common goal: accuracy in your work benefits both of you and makes both of you look good. Inaccuracy does the opposite. So treat this like you're on the same team and not adversaries.

There's a couple of ways I would deal with this. First, I would treat it as a personal development opportunity.

Ask to understand your boss's process better by seeing the changes they've made to your work before it goes to whatever the next step is, whether that's being posted somewhere publicly or just being sent on to another person or team within your company. From that you get two benefits: the ability to learn from the edits they're making to improve your own process (how you can frame it in your conversation), and the ability to catch any missteps.

If you see an error, the way you deal with it will vary depending on what it is. If it's a typo or a misspelled word, just change it. If you can't change it yourself, say to them, "I noticed a small mistake can we change it before it goes out?"

Pointing it out without assigning blame might be enough to make them realize that they were the one just tinkering with that particular word and take responsibility. Even if they don't, the flub gets fixed.

If your boss made a change that is inaccurate, that's where things might feel a little more awkward. Say, "I noticed this changed from the draft I sent you, and I want to make sure I understand why," and then explain how it differs from what you believe to be accurate. That way you can work together to figure out if they just made a mistake or believed they were correcting something.

Hopefully you get on the same page and, again, everything gets fixed before the work goes to anyone else.

If this is a one-off or only happens a couple of times, you should be all good with this process. If you see this happening repeatedly or your boss isn't willing to put an extra step into the process, it could be time for a more serious conversation.

And okay, yes, that may feel awkward. But if you have a reasonable manager, they'll understand that you're only trying to make things better for both of you.

Don't just go to them with the problem, though. Have solutions in mind before you raise the issue. That way you're not giving them just something to solve, you're showing that you're already thinking about how to make things better for the both of you and the work you're putting out together.

This three-step approach works for a lot of difficult conversations you may need to have with your boss.

If you still feel uncomfortable going to your boss in difficult situations, it could be time to find an ally. If there's another manager on your team you feel more comfortable talking to, get their insight on how to bring up your concerns with your manager.

Ultimately, being able to bring up difficult topics with your manager should be a win for both of you, because you get the chance to work together to create a better working situation. If you can see these conversations through the lens of them being an opportunity to build something great, over time, they should become less awkward.

Work it Out is Make It's revived advice column for employment-related conundrums. Have a pressing career concern or question? Email me anonymously ataskmakeit@cnbc.com. Submissions may be edited for length and clarity.

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Help! I'm afraid to tell my boss they've added mistakes to my workhow do I keep things from getting awkward? - CNBC