Why you need to interview your potential boss

So you are considering a new job and you are trying to figure out the infamous “workplace culture”.

Sure it’s important, but the reality is that what you are being told when you are in the interview is likely an idealized version of what it currently is or what they want it to be.

To get the most realistic preview of how your new workplace is going to run, you need to interview your boss or, better yet, your boss’ boss.


Because essentially every policy, program, perq, and expectation is going to be based on how they work and what they want.

Things to ask your potential new boss:

Are you a smoker? Because if they are, they will have no issue with fellow smokers that bugger off for 15 minute “fresh air” breaks throughout the day.

Do they take their vacation or, if they do, do they disconnect from work during their vacations? If the answer is no to either of these, then you can expect to give up the same, or made to feel like shit if you chose otherwise.

Do they work from home? Ahhh…yes, the ever popular work from home conundrum that is the topic du jour. Basically, if your boss doesn’t work from home and is vocal about the issue, don’t expect it any time soon. And if they already have this arrangement, I would expect a change in the near future.

Do they work out? Yes? Good for you – there will likely be a good fitness subsidy at the workplace and you have a great excuse for being late or ducking out early.

Do they have children? If yes, then they are likely older and you can expect some sympathy when you have to stay home to deal with a sick child, but only a little bit because either their partners/ parents/ daycare were the one to stay home.

Are they a big sports fan or former coach? If you hear things like we are in a re-building season or we are working on getting everyone on the same game plan… actually if they use more than one sports analogy in this answer…consider this a serious heads-up that you will be benched/sidelined if you are not a first line player…

Are they a former consultant turned manager? Ensure you are up to speed with the latest buzz words…repeat after me…”that is in my wheelhouse”…”you need to deal with the low-hanging fruit”…”we are timing out, so let’s take this offline”.

While this advice is somewhat tongue-in-cheek, there is definitely some truth to it. You can be shown a nice glossy brochure, a comprehensive compensation package, and an impressive Employee Handbook, but that means jack when you sit down with your boss during your first week and they say, “let me tell you how it really works around here…”

Now I bet you’re wishing you had asked a few more questions at the interview.


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