Work Relationships

How To Make Small Talk With Your Boss

Written by Peter Jones

Stuck in the elevator or the break room when your boss comes in? Suddenly panic and get tongue-tied? Want desperately impress but not to look in any way desperate? Never fear, you’ll no longer have to spend the rest of the day regretting your awkward small talk drivel.

Here are 7 tips on how to talk to your boss without looking stupid or insane.

1. Remember their humanity.

Your boss is also a person. I know that can be hard to keep in mind, but it’s important to remember. Don’t overanalyze and read things into every single thing she says. Keep in mind she might be tired or having a bad day, or just preoccupied, and doesn’t mean anything by what she says. Bosses get to be introverted or awkward too!

2. Read the signs.

Body language is your friend here. Take note of your boss’s stance and gestures, then compare those to when he talks to other colleagues or co-workers. That furrowed brow might just be the way his face looks—not a sign he’s mad at you! If he looks really busy and closed off, leave the conversation to a minimum and try to charm him on another day.

3. Know your answer.

Guaranteed the first question you’ll be asked is “How are you?” or “How’s it going?” Don’t be caught out by this obvious first conversational parry. Have an answer ready that won’t trap you in the “Good. And you?” “Good” dead end. Pivot to a conversation about something you’re both working on, or some piece of company or industry news. Try to keep the conversation 80/20 about cool interesting work-related things, vs. personal matters—yours or hers.

4. Trader Joe it.

Ever been in a Trader Joe’s? Those employees are pathologically pleasant and instantly put customers at ease. Be easygoing and forthcoming. Throw in a few details and a charming smile and you might just make a lastingly positive impression.

5. Talk about them.

Accomplished people love nothing more than to talk about themselves. Give your boss a bit of leeway to do just that. Compliment a recent project or accomplishment of theirs, then sit back and let them direct the conversation.

6. Talk travel.

Particularly if your boss just got back from traveling or from vacation, you can always just ask how their trip went and then sit back and hear all the jealous-making details. Bonus points if you have some nice trivia or intel about the place they’ve just come from or are going next.

7. Problem solve.

If there’s a particularly stick or baffling bit of an upcoming project you’re working on, it can be a great idea to get your boss involved. Make her a part of the excitement of problem solving. Two heads are always better than one! Plus it gets your boss looking at how devoted and intent you are on doing excellent work for her and for the company. Bonus!

About the author

Peter Jones