Don’t Know What to Say? How to Survive 5 Awkward Work Conversations

Male and female employees talking at a bar

Co-workers having a conversation at a bar | Source: iStock

Saying the wrong thing at the wrong time could leave a very bad impression for a long time. This is true in both personal and work settings. It’s especially important to demonstrate good communication skills at work since a miscommunication could mean strained work relationships, a bad performance review, or even the loss of your job. Here’s a guide for what to say in each of these potentially awkward situations.

1. The elevator

It has likely made you want to become invisible at one time or another: the dreaded elevator conversation. We’ve all been there before. Your boss or a senior executive steps onto the elevator. Now you’re both standing side-by-side. Uncomfortable head nods are exchanged and then icy silence extends for what seems like hours as you inch toward your destination. How can you make a good impression in such a short amount of time? If you’re in the elevator with your supervisor or a senior manager, you’ll want to steer clear of anything personal.

John Horn, manager of banking application renewal and learning at Vancity, says it’s best to stick with work-related topics. “Are you suddenly face-to-face with a senior leader of your organization? Ask a question about the company’s three-year plan or comment on the most recent information download that you received from your boss,” said Horn. Do your best to demonstrate you’re an engaged employee who is focused on the company’s goals and excited to help your employer move forward. Just make sure to keep the conversation brief. “Whether you are asking or answering questions, when conversing in an elevator, your sentences need to be short and well-organized bullet-points. Start with what you think is the most important piece of the conversation, too, because you probably won’t have time to get through the entire list. Finally, be sure to have an exit-strategy for your chat because, before you know it, the ride is over,” adds Horn.

2. The bathroom

Do not have an important work conversation in the bathroom. It will only make an already awkward situation even more awkward. Wait until your teammate is finished answering nature’s call. And don’t follow your co-worker to his or her desk. Allow some space, and then wait a few minutes and ask your question once he or she has settled in. Michael Sykes, president of International Center for Bathroom Etiquette, says the bathroom is for doing your business, not talking business. “Do not, under any circumstances, be you man or woman, conduct any business in the bathroom. At best, participants will be distracted. More likely, they will be so busy trying to ignore you and focus on the task at hand that it’s an awkward waste of time. At worst, you are going to offend some client and blow that multi-million-dollar deal. So leave the business to the boardroom and/or golf course,” said Sykes. In short, you don’t have to worry about awkward conversations in the work bathroom, because you shouldn’t be having business conversations here at all. If you get cornered, simply say you’d rather speak at your desk or office (after you’ve thoroughly washed your hands, of course).

3. The office party

Men and women drinking at a party.

Group at a party | Source: iStock

Keep office party talk light and fun. Even though you’re at work, you can lighten up a bit and talk about hobbies or family. Again, just don’t get too personal. Author Gretchen Rubin says one key to small talk is asking open-ended questions. Raise topics that can help you learn more about the person you’re speaking with. “Ask a question that people can answer as they please. My favorite question is: ‘What’s keeping you busy these days?’ It’s useful because it allows people to choose their focus (work, volunteer, family, hobby). Also, it’s helpful if you ought to remember what the person does for a living, but can’t remember… Ask getting-to-know-you questions. ‘What Internet sites do you visit regularly?’ ‘What vacation spot would you recommend?’ These questions often reveal a hidden passion, which can make for great conversation,” said Rubin.

4. The cafeteria

The cafeteria can be a great place to catch up with work friends and relax. However, it can also be a stressful place if your boss sees you enjoying your sandwich and then proceeds to corner you to ask about the status of a project. Be polite, keep your answers short, and then remind your questioner that you’re trying to eat, check email, or finish watching cat videos. This is your time, so don’t be shy about sending a gentle reminder. If you’re the one who seeks answers to a question, just wait for a better time. If it really can’t wait, one of the big things to remember is that it’s important to read body language. If you see one of your co-workers or your boss sitting at the far end of the cafeteria, hunched over a book and a bowl of something yummy, it’s best to stay put. Walk away if it’s obvious that some serious “me time” is taking place.

5. Email

One of the trickiest office conversations you’ll have isn’t even face-to-face. Email can be a wonderful convenience or your worst enemy. If you don’t know proper email etiquette, your message could land you in hot water and become a permanent part of your employee file. Pay attention to not only content but also tone. All it takes is one strongly worded email or a misunderstanding, and you’ll be in the human resource manager’s office faster than you can blink.

If you feel an email communication is taking a wrong turn, get up and walk over to your teammate’s desk or pick up the phone and call. It’s best to clear up any issues as soon as possible before you have a big problem on your hands. Scott H. Young recommends keeping emails task-oriented.

I think best way to describe a conversational email is to look at its opposite, a task-oriented email. Task emails:

  • Get to the point quickly. More importantly, they actually have a point.
  • Separate out key ideas in bullet points or separate lines.
  • Add value to the dialog. They were written with the purpose of transferring information, not just as a knee-jerk click on the Reply button.
  • Avoid sarcasm, attempts at humor and emoticons. Some jokes stay funny after being reduced to text, most don’t.
  • Clearly either do or do not require feedback. They aren’t vague about whether a reply is required.

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