Want to Be Less Awkward Around Your Boss? Try These 11 Tips

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Carly Williams
Carly Williams



Ever misjudge a hug for a handshake and wind up trapped in some sort of unforgivable in-between? I have.

Ever stumble your way through a few floors of elevator small talk, only to regret 99% of what you said upon returning to your desk? Yup. Guilty of that, too. 

While these confessions don't appear to give me much ground to stand on when writing a post about being "less awkward" with your boss, just hear me out. Navigating your relationship with your boss can prove complicated for anyone -- from the graceless (like me) to the smoothest of smooth talkers. 

To develop a rewarding and productive relationship with them, you've got to find a way to overcome those confusing non-verbal cues, painfully awkward silences, and overly formal conversations. But how?

To help shed some light on the situation, I turned to my boss, my boss' boss, my boss' boss' boss, and a few of my trusted colleagues to come up with a list of tips that'll have you feeling (and acting) less awkward with the person you report to. 

11 Tips for Being Less Awkward Around Your Boss

1) Remember that they're human, too.

We'll be the first to admit, it's hard not to read into every comment your boss makes -- both good and bad. But overanalyzing their word choice and tone can lead us down a bad path. 

Did she really think I was doing a good job? Was she being sarcastic? Should I be worried about my job security?

Overanalyzing feedback will often make your interactions with them more awkward than they need to be. So before you go overthinking things, remind yourself that your boss is only human.

"If they respond awkwardly from time to time, don't read into it. They could've just come from a stressful conversation. They could be distracted. Or maybe they just slept poorly last night. Push past those instances and don't let the awkwardness build on itself," explains HubSpot's Director of Content Corey Wainwright.

2) Learn to read body language.

When you're talking to your boss, tune into their non-verbal communication. What kind of hand gestures do they make? Do they typically fold their arms? Do they use these same mannerisms when speaking with your other colleagues?

Many times, people read into their boss' body language and assume that it's a direct reflection of their performance. For example, if they notice their boss furrows his brow, they're quick to assume he's displeased with their work. However, the simple truth is, that may just be how he acts. In fact, he may furrow his brow when he finds something particularly interesting. 

It's equally as important to be aware of your own body language when communicating with your boss. Depending on how you act, it's easy for your body language and your words to send conflicting messages, which is a recipe for misunderstanding.

To learn even more about body language in the workplace, check out this helpful infographic.

3) Follow the 80/20 rule.

There's nothing worse than an awkward silence -- especially with your boss. And while it's tempting to fill those conversation gaps with small talk about the weather, having a meaningful conversation is a better use of both their time and yours. 

But what constitutes a meaningful conversation? And how does one approach the situation?

"Keep it to an 80/20 rule in conversations -- 80% about successes, interesting projects, things you've read that are work-related, and 20% about how that bleeds into you or him/her as a person," Wainwright explains. "Not only does that open up the conversation to go into that personal direction if you're both up for it, but over time, these nuggets of personal information can add up to a more well-rounded picture of one another as a person."

And when they do share personal information with you, make note of it. "Memorize the names of their spouse, girlfriend/boyfriend, kids, pets ... anyone they talk about on a regular basis. That way, in an effort to build a connection (or break a silence), you can ask how someone important in their life is doing," advises my colleague, Lindsay Kolowich.

4) Have an answer for "How's it going?"

When we're asked general questions, we tend to fall back on general answers. For example, we've all experienced a conversation like this:

"How's it going?"
"Good, and you?"

Trouble is, having dead-end conversations like this with your boss can draw attention to your level of discomfort. 

"'How's it going?' is really an invitation for you to give them some insight into what you're thinking about or what's worrying you. Take advantage of it. You can start with the standard, 'Good,' but pivot that into a conversation," explains HubSpot's VP of Marketing Meghan Anderson.

The more you put yourself out there, the easier it will be for your boss to get to know you, your interests, and your abilities. 

5) Be on time. 

Have you ever showed up to a party or event too early and found yourself struggling to make small talk with the host? What about showing up late? Often times, that can be even more painful, as you're forced to poke around the room trying to make your way into someone else's conversation. 

Well, the same can be said for a meeting with your boss. While you'd think that showing up early is a sign that you're prepared or punctual, resume consultant Adam Sterling suggests that showing up too early to a meeting actually implies you're disruptive to other people's work schedules. Awkward.

And if you thought that was bad, try showing up late. While situational tardiness is forgivable, making a habit of it will signal to your boss that you struggle with organization and responsibility.

Need help showing up on time? Try limiting distractions (television, radio, text messages, etc.) while you get ready, prepping your belongings the night before, or setting reminders on your phone or work calendar to leave a few minutes early.

6) Talk about something that excites you.

When in doubt, talk about something that you're excited about -- whether it be a change in the industry, a book you're reading, or a project you just completed.

Many people tend to shy away from sharing their passions or big ideas for fear that they'll be judged or misunderstood, but your boss wants to see that you're enjoying what you're doing.

"Unabashed interest is the best way to get past polite or overly formal conversations," explains Anderson. "Share something your working on or -- and sometimes this is even better -- it could be something you've seen in the field that you think is really interesting and worth emulating. Excitement is infectious. Share yours."

7) Cap yourself at two drinks.

While drinking too much in front of your co-workers is a slippery slope, drinking too much in front of your boss is best classified as an egregious offense.

It's okay to have a drink (or two) as a way to break the ice, but don't exceed that. If you do, you're opening up the door for yourself to say things you don't mean -- or say things you do mean, but you don't want your boss to hear.

Thought you felt awkward around him or her before? Well, drunken confessions will only make it worse. A lot worse.

So next time you're out in a drinking situation with your boss, have a couple drinks. Loosen up and talk shop. But be sure to politely excuse yourself -- or switch to water or soda -- after that. You'll be happy you did.

8) Try solving a problem together.

When we achieve something truly awesome at work, it's typically easy for us to convey these wins to our boss. We're proud of our accomplishments, and we want them to be proud of us, too. However, when it comes to hashing out problems we're facing, we tend to be more reserved. We beat around the bush.

While letting your boss know that things are going south isn't ideal, it does present an opportunity for the two of you to work on the problem together.

"Stronger relationships are forged when there are problems you have to overcome than when everything's coming up roses," Anderson told me. 

Working towards a solution together will help you get to know your boss better, as it'll reveal a lot about how they think, handle stress, and arrive at solutions. Just make sure that you bring a few ideas to the table when you present the issue. This will help to show your value and reinforce why you've been hired to do your job in the first place. 

9) Brush up on your business meal etiquette.

I've flung quinoa, flailed noodles, and mishandled table bread one too many times to not include this tip on the list. 

When dining with your boss, there's a lot to keep in mind. But if you spend the majority of the meal silently freaking out about what to order or how you should place your napkin, you'll run the risk of not being present -- and they'll notice.

Luckily, my colleague Lindsay put together an awesome guide to business dinner etiquette to help you get acquainted with how you should behave next time you share a meal with your boss. With tips on what to wear, when to arrive, how to handle your utensils, and more, you'll learn the insights you need to make a great impression. 

10) Set up more face-to-face time. 

If you work at a large company -- or you or your boss works remotely -- scoring face-to-face time can be challenge. Thanks to email and internal messaging apps, it's easy to stay in touch, but without that real in-person interaction, it can be kind of awkward when you're trying to get to know one another.

If you work in the same building, make an effort to check in with them more often, suggests Mike Renehan, a writer for the HubSpot Sales Blog. If their schedule permits, set up time to touch base with them every other week. If they're really tied up, seek other opportunities to score some time with them. For example, you may want to volunteer for a project that requires one on one time with them, or attend an event they'll also be heading to. 

If you work remotely or in a separate office from your boss, try video calls. While it's slightly less natural than real face-to-face time, it's a close second. And if you're struggling to learn more about them, follow them on Twitter and be sure to connect with them on LinkedIn, too. 

“Simply reading his LinkedIn profile may help you find common ground if you know where he went to school and companies where he used to work,” explains Ellie Eckhoff, VP of ClearRock, a leadership development and executive coaching firm.

11) Read up on their personality profile.

Does your company issue a workplace personality profile such as DiSC?

A DiSC assessment -- short for dominance, influence, steadiness, and conscientiousness -- is designed to help you increase your self-knowledge by highlighting "how you respond to conflict, what motivates you, what causes you stress, and how you solve problems."

"It's a great way to learn more about your boss' communication style," suggest Emma Snider, Section Editor for the HubSpot Sales Blog.

If you find it's difficult to resolve conflicts with your boss or communicate challenges without upsetting them, try taking a look at their profile to reveal more effective ways to approach these situations that better align with their personality type.

How do you overcome awkwardness with your boss? Share your tips in the comments section below.

Want to learn more about office politics? Check out The Art of Being a Great Coworker: 13 Ways to Improve Your Work Relationships.

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Topics: Office Politics

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