Nervous Conversations With Your Boss

Making social talk with your boss is never entirely comfortable. But I used to have it worse than most.

The problem I had was that my boss had a giant painting of an undressed woman in her office, right behind her desk. I won’t get too graphic, but I will say that it wasn’t subtle in its portrayal of the female form. As Jon Lovitz would say, “it points out all the attractions”.

If my boss called you into her office, you’d be nervous enough because the boss needed a word with you. It didn’t help that when you were in her office, you had no idea where you should be looking.

It was a funny but awkward situation. Most people have an awkward time interacting with their boss at the best of times.

“My boss had a giant painting of an undressed woman in her office, right behind her desk.”

The problem is that your boss has power over you. Unless you are in the fortunate position of your boss desperately wanting to keep you, you have to be mindful of protecting your job. This means not risking a remark that may offend your boss.

Plus, you want them to like you when it comes time for a raise.

There may not be any foolproof ways to be genuinely social with your boss without reservation. But here are some hints:

1.       Develop mutual respect: Your boss isn’t going to genuinely enjoy your company if you are a groveler.
2.     Remember your boundaries: Your boss is still your boss. There are some areas that should stay off-limits.
3.     Talk to your boss about non-work things: It will help you discover who they really are and vice-versa. And if they genuinely like you, they are more likely to be forgiving of your work.
4.     Discover what your boss is quietly passion about: Many bosses will be somewhat passionate about their company. But find that part of them that lives outside the workplace – the son that overjoys them, their love of reading, their pride in tending their garden. Then for a few moments each week you’re not a boss & employee, but simply two people talking.

It’s up to you how friendly you want to be with your boss. Some bosses let their authority go to their head and they get off on having power over you. It’s hard to feel any genuine affection for a boss like this.

Other bosses genuinely care for their employees. If this is your boss, you probably already find yourself having friendly interactions with them.

It’s hard to completely avoid talking about work when in social situations with your boss. It’s essentially your common ground. But when this happens try to steer the conversation in a more fruitful direction. Step away from the details of the week, and ask your boss why they started the company, what drove their passion in that direction, and what they hope to achieve with it in the long-term.

You can also try our conversation starters to talk about non-work things. Subscribe for easier conversations.

Social interactions with your boss are often awkward, but seeing the non-workplace side of each other over time can take you from awkwardness to a genuine connection.