• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI

2

Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 

3

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises

1

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI

2

Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 

3

The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Career Advice

How to Make Alone Time With Your Boss Less Awkward

By
Jon Simmons
Jon Simmons
and
Monster
Monster
Down Arrow Button Icon
By
Jon Simmons
Jon Simmons
and
Monster
Monster
Down Arrow Button Icon
June 22, 2017, 5:00 PM ET
Woman standing outside of elevator full of business people
Neil Webb — Getty Images/Ikon Images

This article originally appeared on Monster.com.

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.

More from Monster.com:

100 companies hiring now

Follow us on the path to finding your first job out of college

Everything you need to know to get a new job—in just 5 minutes

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.”

About the Authors
By Jon Simmons
See full bioRight Arrow Button Icon
By Monster
See full bioRight Arrow Button Icon

Latest in Careers

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Careers

Financial advisor presents a graph to her client.
Career HubEducation
How to become a financial advisor: 4 steps to a life-long career
By Preston ForeJanuary 2, 2025
1 year ago
Group of business people look at charts and graphs.
Career HubEducation
How to become an actuary: 4 steps to earn six figures
By Preston ForeOctober 21, 2024
2 years ago
Woman analyzes a chart with a laptop next to her.
Career HubEducation
How to become a CPA
By Preston ForeSeptember 27, 2024
2 years ago
Woman explains a concept to a woman sitting next to her.
Career HubEducation
How to become an accountant
By Preston ForeSeptember 20, 2024
2 years ago
Group of varied professionals stand looking toward the camera.
Career HubEducation
These are the nation’s fastest growing jobs—and many pay $100k
By Preston ForeSeptember 13, 2024
2 years ago
Nurse pulls cash out of the front pocket of their scrubs.
Career HubEducation
A guide to a nurse’s salary: Broken down by all 50 states and industry type
By Preston ForeAugust 7, 2024
2 years ago

Most Popular

Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
AI
Microsoft AI chief gives it 18 months—for all white-collar work to be automated by AI
By Jake AngeloMay 16, 2026
1 day ago
Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 
Politics
Former top Russian official admits the country is over Putin and can 'imagine a future without him' — even elites bail as Kremlin seizes their assets 
By Jason MaMay 16, 2026
21 hours ago
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
Politics
The Bezos family just donated $100 million to help achieve one of Mayor Zohran Mamdani’s top campaign promises
By Jake AngeloMay 12, 2026
5 days ago
SpaceX heads into a record-shattering IPO with the 'deepest moat that exists today' as investors vow to 'never bet against Elon'
Innovation
SpaceX heads into a record-shattering IPO with the 'deepest moat that exists today' as investors vow to 'never bet against Elon'
By Jason MaMay 16, 2026
1 day ago
Oil markets could be a month away from the moment of truth. Brace for a 'non-linear' price spike and panic buying, analysts warn
Energy
Oil markets could be a month away from the moment of truth. Brace for a 'non-linear' price spike and panic buying, analysts warn
By Jason MaMay 16, 2026
1 day ago
Meet the 20-year-old CEO who launched a company in high school to solve Gen Z's entry-level job crisis
Future of Work
Meet the 20-year-old CEO who launched a company in high school to solve Gen Z's entry-level job crisis
By Jake AngeloMay 16, 2026
1 day ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.