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9 of the Most Awkward Work Situations—And How to Handle Each

Tips for (delicately) handling work situations we've all experienced.

We can all admit that awkward situations are a natural, unavoidable part of life. Remember that seventh grade dance or, if we’re being honest, pretty much the entirety of high school? But when awkward experiences happen at work, an environment where our actions affect how we’re perceived by those we need to work with, and our livelihoods depend on our performance, those cringe-worthy moments sometimes come with extra consequences.

Can you just laugh off that time you assumed a mistake was someone else’s fault and confronted them, only to receive a polite reminder that you, in fact, were the culprit? Or when you sent a scathing email about your boss to…your boss? Not exactly. At Career Contessa, we’ve pretty much seen it all. The good news is that there are ways to recover gracefully and professionally. Here’s how to handle the most awkward work situations we’ve seen come across our desk.

a coworker steals3

I’m all for working in groups to help the company reach its goals— it’s a necessary way to get projects done at work most days, but team performance is rarely a factor during your performance reviews. It’s your special projects, well-written articles, and presentations that prove you’re a valuable member of the team so when a co-worker takes credit, or even steals your idea, it can sting. Badly. So what to do?

First, make sure you’re keeping track of your accomplishments (this free worksheet can help you assess your career so far, but you might also want to consider starting a work journal) and referencing these throughout your job. It’s a good reminder of what you’ve done so far and the type of worker you are.

Next, to protect yourself in the future, start going public with your ideas in your team meetings with your boss before you share it with anyone. I know we all like to get feedback and approval before we put ourselves out there, but embrace the vulnerability. If you’re the first to share the idea and put in the extra effort to also plot the details around how you’ll execute it, then there’s no way a co-worker can take credit without at least mentioning that it was yours in the first place.

your boss blames you

Battling a boss can be a risky proposition, so you’ll first want to consider if it’s a battle worth picking. If it’s something small and inconsequential, maybe just accept the blame and move on. If not, try not to publicly accuse her or get emotional. Instead, ask for a private meeting, stick to the facts, and keep your message professional. Ask your boss if she noticed the issue or mistake, and explain that you’re talking to her because you want to make sure she’s in the loop. By “bringing it to her attention,” it lets her stay in control, thus avoiding too much tension, but also forces her to act. Hopefully that action is an apology, but if not, she now understands she didn’t get away with blaming you for her mistake and (hopefully) won’t try that in the future.

work late

First, get clarity about why. Why does your boss need you to work late? What, specifically, is the outcome that you need to accomplish before you leave? Once you establish an understanding of what your boss needs from you, you can work backwards to a solution. Maybe you compromise and promise your boss you’ll finish your part of the project by coming back (or getting online) later that night or you’ll wake up extra early. Maybe you ask a co-worker who’s already up to speed on the project to help you with a future I.O.U offer. In an ideal environment, it would be best to establish guidelines around working hours before this situation, but when you’re in it, it’s your responsibility to offer workable solutions if you really want to get out of there. 

you cried at work

Haven’t we all?! Obviously it’s best to keep it together until you make it to the private bathroom. But we all know that feeling when you can’t stop the tears from rolling. When this rush of emotions happens, you’ll need to calm yourself. Repeating a positive motto and breathing can help slow that rush that you felt takeover (even just saying “You are OK,” repeatedly in your head will help). Another great idea is to start building a support group at work, so you have safe community to bounce ideas off and vent as long as it’s not destructive venting. Crying at work can be the outcome of bottled up emotions, surprises, or even from personal stress that rolls over. Find what you need support-wise so you can avoid a next time. 

in the bag

So your company was hiring for your dream job, you put your name into the hat, had a great interview and basically thought you were a shoe-in when…BAM. That email announcing a new external hire lands in your inbox. Yup, it hurts. First, take a day or two to let your emotions subside (call your mom if you want to). On day three, it’s time to act and have that conversation with your boss.

Start by setting up a meeting and give them advance notice about what you want to cover (so they can give you thoughtful answers). Come prepared with facts—why you were a fit for the role, your history with the company, the positive feedback you've received—and reiterate why you wanted it. Keep emotions out of it. Then, finish it off with, “Given all that, could you give me your reasons for not selecting me for the position?”

Bring a notebook so you can write out their response because you may forget it later, and it will help calm the awkwardness. Take those facts and decide if you want to stay, go, or do something in-between like learn the skills you lacked to ask for a promotion in the future. Skillshare is an easy and affordable place to start with skill-building classes.

mental health day

As a manager, I totally understand the need for mental health days, which is why I prefer employees to be upfront with the team and me before they take one. But if you really don’t feel like you can share this ahead of time and get caught, you’ll need to confess to your boss the next day that you took a mental health day and ran into a colleague. You can explain—but not give excuses— that you should have been upfront about your need for a day to clear your head and will do so in the future. I’d also prove that a mental health day was great for your headspace by coming to work prepared the rest of the week—come early, stay a bit later, produce great work, etc. And in the future, honesty really is the best policy.

spreading a rumor

Your hallway reputation is everything these days so I get why a rumor would be a really kicker in the workplace. First, find the root of the rumor. What is it and who started it? Compile the facts and then set up a team meeting with any key players, either part of the rumor or affected by it. Before you address the group, decide what your one ask is going to be. Do you want them to know it’s not true? Do you want them to help you in stopping this rumor by not mentioning it again? Addressing the issues head-on is best and controlling the setting—like having everyone in one meeting—allows you to mitigate anyone twisting your words or how you reacted later on because you are all there together. 


A dream opportunity popped up that doesn’t compete with work (i.e. working with a competitor) that you really want to take part in. The catch is that it’s within the next 24-hours. Think a free vacation with your bestie because they suddenly broke up with their boyfriend. First, consider if this opportunity is shaking the nest. Which co-workers will be affected by you taking a few days off, or are you right in the middle of a big project? If you think you can swing it, put together a plan to present to your boss that outlines how you’ll be able to take the time off without letting something slip at work. By the way, this works best if you’ve proven yourself already to the team. 

youre being left out

Everyone will or has experienced being left out of something social at work. It’s just a fact. Start by giving them the benefit of the doubt—they probably have no idea they’re doing this. When they get up at noon to start walking to lunch—the one they didn’t invite you to yesterday—you can pipe up with “Hey are you guys off to lunch? Mind if I join you? I’ve got to buy lunch today, too.” Speak up more often and see what happens. If you’re truly experiencing a mean girl situation and it’s affecting your work or making you want to look for a new job, schedule a meeting with your manager. If it’s not affecting your work, though, consider just focusing your social efforts elsewhere. Create your own girl squad. It’s OK—and might even be better— if you find a work buddy that’s not in the same department.

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