What to Do: When You See Your Boss Outside of Work

Author: The Job Window |

The Job Window

When I was in the 6th grade, my mom took my sister and I to the mall. I think it was to get a new pair of shoes. Even when you’re in the 6th grade, some things are irrevocably true. Being with your family is lame, the mall is awesome and you won’t be allowed to get any of the toys you ask for. There are older kids leaning on stuff and you can’t wait to grow up and be like them.

It was on this day that I saw the strangest thing. My 6th grade teacher was walking right towards us. My first thought was “How did he get out of the school?” It was a Saturday. Then he waved and my mom waved back! How does my mom know my teacher? I know they’ve had like one parent-teacher conference, but now they’re friends or something? My 6th grade brain couldn’t not handle the idea that my teacher existed in the real word. You’ve probably had a similar experience.

The workplace is not so different from school. You have your coworkers who you make friends with and see socially. It’s not a stretch to think of them as having fully formed lives and running into them on the street. But your boss, now that’s different. They clearly live in the office talking about memos and TPS reports forever. You leave on Friday and they are there. You come back on Monday morning and they are there, right where you left them.

What do you do then, if you encounter your boss in the real world? Don’t do what 6th grade me did, stand still with a furrowed brow and stare at the person with a look of confusion and dismay. Give a slight head nod. More than likely your boss will give you a slight head nod in return, and you’ll both carry on your ways. Don’t forget that as much as you might not want to see your boss in real life, they feel the same way.

If your boss sees your head nod, smiles and starts walking towards you. Do not run away. No good can come from that. Stand your ground and smile back. Your boss may try to make a small joke, it’s best to chuckle. There will be a long silence. Break this silence by saying you’re on your way to wherever you are going, and start to go in that direction.

You’re boss might say “See you Monday” but then it’ll be over. That wasn’t so bad was it? If it happens again maybe you could muster up the courage to ask how your boss’ day is going… but we don’t recommend it.