Awkward Work Situations: How to Handle Them With Style

Every workplace has its own peculiar holiday customs

Holiday color drinks with ice
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We spend a lot of time at work with colleagues, and this time of year tends to be rife with opportunities to experience the awkward. With the gift-giving and holiday party season just around the corner, use these tips to prepare for those inevitable awkward moments at work that could otherwise leave you in a bad mood.

People asking for money

Whether it's to support their favorite charity or for a gift for the boss or a co-worker, it can be uncomfortable to tell someone you don't want to support his or her cause or pay for a gift for someone you don't even like. How you respond will depend on the situation. If it's a gift for the boss or a colleague, you may be best off giving something than taking a stand and being labeled uncooperative. However, you can always say you are taking care of your own gift, or, in the case of a charity, explain that you've already maxed out your quarterly charitable contributions.


Whether a co-worker gives you a gift and you don't have one in return, or you're deciding if you should buy the boss a gift, the gift-giving season can be awkward. While you shouldn't feel obligated to give anyone a gift, it's a good idea to identify the workplace rituals before it's too late if you want to give a good impression. If everyone exchanges presents, you may want to just go along and avoid discomfort. If you have financial issues, give something homemade or thoughtful that isn't expensive. If you feel strongly and don't want to participate for religious reasons simply explain why you aren't able to participate.

Colleagues asking you to support their kids' fundraisers

In many companies, it is actually against policy to ask co-workers to purchase items, especially if it is a supervisor asking an employee. However, if you don't want to pull the, "it's wrong of you to even ask me" excuse, you can still easily beg off by saying that you "already got your share of (wrapping paper, cookie dough or other trinket) from the neighbor's kid."

Conversations about salaries or bonuses

If your company gives holiday bonuses or raises at this time of year, it can be awkward to answer a colleague's question about what you received. Whether it's because you think you may have earned more or less, it can be a difficult conversation either way. If you're not comfortable discussing it, you can always demur and say you've found it's a good policy not to discuss money with colleagues and leave it at that.

Office parties

It's not bad enough that you have to spend all day with colleagues who have gross habits. At this time of year, they expect you to prepare to enjoy evenings socializing with them, too. Even if your colleagues aren't your favorite people, it's still a good idea to extend yourself and join in the fun – even if it isn't that much fun for you. Make a point to limit or avoid alcohol consumption and keep the conversations casual and pleasant. You never know, an office party may provide an introduction to someone you've been wanting to meet; never ignore the networking potential.


For the non-religious or those in minority religions, saying grace before work events can be very awkward. Usually, your best bet is to be respectful, but don't feel compelled to bow your head or say "amen" if you don't want to participate.

Share your own stories of awkward work moments and how you handled them in the comments section below.

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when I was laid off from a big law firm -- they did not include my 1-1/2 hour over time with the final check--the next monday I was at the labor board filing for that 1-1/2 hour overtime -- it took the company 11 days to get that check to me and I was given $1100 for their stupid-ass omission --so much for being $500/hour labor/employment law attorneys.

November 14 2013 at 7:16 AM Report abuse rate up rate down Reply

Although I don't think we should go back to the sexist "Mad-Men" attitudes of the sixties, I wish men and women could compliment and joke casually with each other without being accused of sexual harrassment. It just makes the day go faster and more pleasantly

November 09 2013 at 5:25 PM Report abuse rate up rate down Reply

I had someone say "You liberals believe that Obama is the black Messiah" and I said that I did not believe that Obama was the Messiah but that I could see how someone would make that mistake. According to the Bible the messiah would come shortly after Armageddon and Obama came shortly after George Bush.

November 09 2013 at 4:40 PM Report abuse +1 rate up rate down Reply
1 reply to bjwtex's comment

I should not be doing this but ... tee hee hee hee hee

November 09 2013 at 10:49 PM Report abuse rate up rate down Reply

I handled all the above with one simple answer: You are a co-worker, not a friend.

November 09 2013 at 12:58 PM Report abuse rate up rate down Reply

My late sister was mildly retarded. She worked in a jewelry factory. She mostly could dothe job , but was weak in social skills. But, she knew enough to show good will to bring presents to co-workers on their birthdays and at holidays, to come to a baby shower with a gift, and to compliment people.
When she died of a massive stroke, her supervisor told me that the bosses wanted to fire her many times due to less than perfect work. But all the supervisors and workers defended her and she was kept on until her death.
And I was touched by how much her workers had cared for her.

November 09 2013 at 9:38 AM Report abuse rate up rate down Reply

AND: Start a petition in YOUR office for fresh air, open windows (on occasion), and real know, from the sun? It's good for your health. And that will increase productivity. Bosses and management really need to recognize....

November 08 2013 at 2:47 AM Report abuse rate up rate down Reply

Wow, work is hard enough...let alone having to suck up at the office. These "traditions" and rules really make office life lame. Just be honest w/ people and tell them to get out of your cube!

November 08 2013 at 2:42 AM Report abuse rate up rate down Reply

Actually, there are a few more "awkward" work situations that you didn't seem to feel needed discussion. Workplace violence makes the news today, but in the 'good old days' things went a little differently. Many years ago, I was bodily shoved against a wall, my glasses slapped from my face, and slugged in the stomach by my boss, who was also the owner of the company. He was upset because the monthly profit/loss figures I had prepared for him weren't what he was expecting. I contacted the police after he left, and was flatly told "Look, you can quit your job right now, or you can wait until he fires you if we come over's up to you." My wife was expecting our first child, and I couldn't afford to lose my job and health insurance at that I declined to do anything about it, or him, through the police. Instead, I walked over to his office, closed the door, and quietly told him "You ever put your hands on me again, I'll put a bullet in your gut." He looked at me hard for a moment and said "Ok...fair enough." I found another job shortly afterwards.

November 08 2013 at 12:33 AM Report abuse +1 rate up rate down Reply
1 reply to Ed's comment

Good for you man!!! I have had a similar experience at "work" aka the office...minus the physical abuse. In today's day and age (w/ lawsuits and all the politically correct mumbo jumbo tiptoeing) office workplaces now are more like a mind fck. Hostile work environments and workplace bullying...yep, that's how they run the show these days....and they get away w/ it all the time more so than in any other career. I also quit my job. It's not worth the life is like swimming w/ sharks.

November 08 2013 at 2:57 AM Report abuse rate up rate down Reply

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