How Can I Tell If My Prospective Boss Is a Jerk?

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How Can I Tell If My Prospective Boss Is a Jerk?

We’ve all been there: You’re sitting in an interview with your would-be boss and you can’t quiiiiiite tell if he or she would be a big ol’ jerk. The words coming out of his mouth sound good but there’s something you can’t quite put your finger on that makes you want to run out of the building like your hair’s on fire.

So how do you turn your hunch into more than a feeling?

how do I tell if my prospective boss is a jerk?

Don’t want this to be you? Keep reading for tips on how to avoid it below.


A lot of times you can suss a lot out by reading between the lines in terms of environment and general presentation. And don’t let ‘gut feelings’ fall by the wayside! Take note of them in your notebook, if you can do so discreetly, so you can weigh this later.

  • Is the would-be boss prepared for the interview? Does it look like their read your resume?
  • Is their desk a mess?
  • Do they allow themselves to be constantly interrupted by their manager or peers?
  • Do they seem not ‘in the moment’ or present? Do they seem distracted?

Those things could be an indication that the environment is chaotic and lacks clear priorities and boundaries and they are prone to the insanity as much as the next person, meaning they wouldn’t be an effective shield from any potential sh*tstorms. (Not that you want those kinds of storms, but they can happen at even the good companies, so you want a boss who can have your back)


You want to suss out whether they’re going to be the right manager for you.  You want to think of ways to be able to figure this out without asking, “So what’s the culture like here?” Questions like, “What is the on boarding process like and how do you handle beginner mistakes?” can give you insight into how they value their training and how they handle new employees making errors. (Hint: You don’t want them to say, “Well, we certainly hope people don’t make mistakes!”). Ask how they are involved with career progression and how they personally gauge development and progress. What are some of their personal metrics for success for their direct reports? What about the company’s metrics?

If anything sounds fishy or off to you, it probably is. Trust your gut and/or seek the advice of a trusted advisor or colleague (hopefully someone with experience interviewing). There’s a difference between ‘fast paced environment’ (which everyone says they are now- have you ever seen a job posting that said, “we take things slow”? No.) and “CRAZY TOWN!”


When I was a young newly minted manager/boss, I took the tell-it-like-it-is approach. Not at the beginning. At the beginning, I was more how I described the boss above in the “presentation section”. But once I found my footing, I explained exactly the type of environment it was and the expectations the position had and left it up to the candidate to self-select in or out. That could actually be a green flag (I’m making that a thing) regarding a company. If you know what you’re getting yourself into, then you can make the best decision for yourself based on your values and priorities.

If the company has craptastic Glassdoor review, ask! Don’t be afraid of ‘offending’ someone. Imagine if you found yourself in a terrible work situation because you were afraid to ask about the elephant in the room!?

What other red flags can you think of? Leave comments in the comments below!