How to make alone time with your boss less awkward

Avoid stuttered phrases and prolonged silences with these tips.

How to make alone time with your boss less awkward

Show us someone who’s never felt awkward, and we’ll show you a liar.

Awkwardness, like other human qualities, is a part of everyone’s life, often rearing its ugly head in situations where you don’t feel like you can be 100% yourself. Like at work. With your boss. Alone.

Silent elevator rides, anyone?

“It’s not unusual to feel awkward with your boss; it takes building self-confidence to feel secure,” says Kathi Elster, an executive coach at K Squared Enterprises in New York City.

Luckily, you can alleviate awkward situations if you know the right techniques. We asked career experts how to make regular check-ins and random run-ins with your boss less awkward, as well as how to right the ship when those moments start to veer into cringe-worthy territory.

Awkward scenario #1: One-on-one meetings

Solution: Ask work-related questions

The primary reason for your regular one-to-one meetings with your boss is to talk about work, but sometimes the conversation may touch on non-work topics (politics, your personal life, etc.) that you’d rather not discuss. Arm yourself with questions in case you find yourself feeling put on the spot or tongue-tied.

“When those awkward moments do happen, it's appropriate to go back to confidently asking innocuous questions about the business at hand such as, ‘When do you think we may hear back from so and so?’ and ‘What are the next steps you see for this assignment?’” recommends Deborah Hankin, VP of talent at SYPartners, a consulting firm in New York.

“You and your boss both exist within the organization to accomplish its goals,” reminds Aaron Schmookler, a leadership development trainer at The Yes Works, a training and team-building company in Tacoma, Washington. “You share that purpose. Nothing dissolves awkwardness like sharing a purpose. Put your focus on purpose—on your job—instead of on how you'll come across, and you'll dissolve the awkwardness.”

Awkward scenario #2 Bathroom bump-ins

Solution: Keep it simple

No matter how amazing your weekend ski trip was, or how much you’d like feedback on your latest project, the bathroom is not the right place to yak it up. So don’t.

“The bathroom is simply not the place to relationship-build,” says Chavaz Kingman, a corporate trainer at AYF Consulting Corporation in New York City. “A nod or a smile is sufficient.”

In some cases and in some more relaxed corporate cultures, a nod and smile may seem rude—like while washing hands or fixing your hair in front of the mirror. Then, the best policy is to offer some “innocuous chit chat” and talk about the weather, sports, what the other person is wearing—and leave it at that.

Awkward scenario #3: The hallway or elevator

Solution: Ask open-ended questions

Just you and your boss in the elevator? A solo stroll with your boss down a long corridor? What do you say?

Don’t ask if they’ve lost weight. Don’t gossip about a co-worker. Don’t scream.

“Have some go-to open-ended questions in mind that you could use in these situations in case you can't think of anything off the top of your head,” says Halelly Azulay, leadership development strategist at TalentGrow, a consulting company focused on developing leaders and teams in Los Angeles.

Fill the void with simple questions, like, “How’s it going?’” or, “What are you up to this weekend?”

Awkward scenario #4 When you do or see something you shouldn’t have

Solution: Pretend it never happened

Sometimes, you’re just in the wrong place at the wrong time.

“Catch someone in an awkward private moment in the bathroom? Or catch the boss picking his nose? Turn a blind eye,” says Stacey Staaterman, founding coach at Staaterman Coaching in New York City. “Pretend it never happened and leave the area. Do not gossip about it. It will never reflect well on you to share the funny story when only two of you know its origins.”

Want the ultimate example? Staaterman shares a truly embarrassing moment that her former boss can now laugh about: “Years ago, my female boss accidentally walked into the men's room to see our CEO standing at the urinal. She made a quick exit and never told anyone one until we'd all moved on to new jobs.”