How to Avoid Miserable Bosses

Years ago I had a friend who always had a nightmare for a boss. She’d move firms but end up with yet another one. The third or fourth time this happened to her, I said, “You do know, the point of an interview is not solely for them to interview you. You also need to interview them to see if it’s going to be a good fit for you too.” Then I used all of my willpower to resist being a grating Classic and repeat one of my favorite sayings, “Fool me once shame on you. Fool me twice shame on me.” Often we’re so grateful for a job opportunity that we forget to interview the interviewer. And no, it’s not simply about finding someone with your personality type.

There isn’t a perfect fit for anybody. Just as in relationships, opposites attract and do great work together just as often as similar personality types. A big idea, logical Smart Freedom (NTP) boss can really appreciate the detailed, get it done yesterday ethos of a Classic Structure (STJ) employee and vice versa. In my hedge fund days I had two very different uber bosses — one a nerdy, nervous nellie who always had a million questions — likely a Classic Freedom (SFJ) like me — the other grounded and confident — likely a Smart Structure (NTJ) — who only asked a few things on any given investment. I figured out how to work with both of them because my main goal was finding a collegial place of employment. I found it at both spots by asking questions during my interview to confirm I’d be in the right place — this is all with the caveat that I worked in finance so “collegial” has an asterisk next to it, which reads “Nice people for hedge fund types.”

Recently, we had a great speaker at the NY Network — my women’s business networking group in NYC — a few weeks back; she was full of great ideas about how to better market your business. Essentially, make sure people know precisely what you do, how well you do it, how this will specifically help them or their business and for goodness sake tell stories so you don’t bore them to death while doing so. Naturally she was also full of anecdotes. One of them was about a client of hers who had an impossibly tall stack of resumes to go through. So he emailed them all random times to call him — 4:13pm, 8:02am, 11:53am — for phone interviews. If they called at any time other than his specific request, there was no interview and he immediately removed from the pile. He did this so that he could weed out anyone who wasn’t as precise and attentive to detail as he wanted. At the end, he was left with a handful of candidates.

At first I thought, “Wow, that is really annoying. Who would want to work for this guy??” Then I thought, “Wait though, maybe he is on to something.” Detailed Classics (SJ) like me would notice this request and call him at the specific time. Other more big picture types like Organics (NF) and Smarts (NT) might not … but then again they might. It doesn’t take a rocket scientist to guess this guy is testing you. A Classic might relish working for this seemingly detail oriented, busy body but a Smart might loathe it. Heck, I’m a Classic and I would probably loathe working for this guy if everyday he clocked in my arrival times even if they were within a 10 minute range on days it didn’t impact my work output.

I hope someone, someday asks this guy during one of his absurdly times phone interviews, “So, is there flexibility with this job or does everything always start at 8:02am on the nose?” If he gets the joke then maybe, you know you could work with him after all. It’s worth the risk because working for a boss who isn’t prepared to answer tough questions from an interviewee will likely be a miserable experience for any personality type.