How to Make it Less Awkward When You and Your Boss are Alone

Maybe the two of you took a ride together to go grab Chipotle for lunch, or perhaps you shared a long elevator ride – at some point, you probably found yourself alone with your boss and surely there were one or two awkward moments.

It’s completely normal to feel awkward or even a bit nervous around someone who has influence over your station in life. It’s also very possible to overcome that awkwardness and actually enjoy alone-time with your boss.

There are a few basic and simple ways to reduce the awkwardness of finding yourself alone with your supervisor. In fact, these steps can lead to making a great impression, which could lead to good things down the road.

Talk shop

A big reason for awkwardness with your boss is not knowing the non-work topics, like personal life or politics, to avoid. For instance, you don’t want to ask your boss about his father if he is currently struggling with a serious illness. Therefore, it’s a good idea to come up with work-related questions that have zero risk of being offensive.

Questions like, “What’s the deadline on that project?” or “Do you think we’ll be busy next week?” are great ways to get the conversation started or fill in awkward silences.

Furthermore, working together to achieve the same goals is something the two of you have in common. Even if you have completely different personalities and interests, you have a shared purpose getting work done for your company. Focusing on that shared purpose, as opposed to on how you’re being judged, will help you break down most awkward situations.

Ask open-ended questions

Open-ended questions are questions that don’t lead to a yes-or-no answer. These questions give people permission to talk about themselves, something most of us like doing. Questions like, “How was your weekend?” or “What did you do to deal with that storm last night?” are also a subtle form of flattery because they indicate that you are curious about your boss as a person.

Throw softballs

If you’re in an elevator or in the bathroom with your boss, the situation doesn’t call for a lengthy in-depth conversation. This isn’t the time to ask about their ski trip to Aspen or plans for the holidays. However, you also don’t want to just nod and stand there in awkward silence.

Softball questions are a great way to make conversation without asking the other person to do any heavy-lifting. Questions like, “Did you see that singer on The Voice last night?” or “Where did you get those shoes?” offer a quick back-and-forth that you can walk away from with confidence.

Ask for career advice

Asking for advice is another way to subtly flatter your boss while possibly getting good career information at the same time.

While you want to avoid suggesting that your gunning for your boss’s job, questions like, “Do you any of any certification classes I should take?” or “Are there any great networking events coming up?” are non-threatening and let your boss know you think of her or him as a mentor.

At Labor Temps, we help determined professionals take the next step on their career path every day. Please contact us to find out how we can help your career.