terrible bosses

‘My Boss Is Always Making Racist Jokes!’

Photo-Illustration: Marcus Peabody; Photo: Getty Images

What makes a boss truly terrible — and how should you deal with it? Advice columnist Alison Green addresses the stories of your worst bosses ever, as part of a weeklong series about what makes a bad boss, and why we’re so tortured by them.

Dear Boss,

I was working at a tech agency run by a husband and wife team. I learned very quickly that the male owner said inappropriate things all the time. He was in his early 40s, white, and generally socially awkward. It was like every single conversation I had with him was about race. When he saw me, an African American woman, he would often ask if I was a fan of Bob Marley, Ray Charles, or other black artists. One time at a holiday party he was telling us that his two young sons play football in little league and it’s so unfair because the team they are playing next is an all-black team so you will never win, and it’s not fair that the all-black team gets to play because his kids didn’t get a chance. He just said stuff like that constantly, constantly. For Cinco de Mayo he came in with fake mustaches so we could all pretend to be “Mexican” and he was putting on an accent while passing them out. 

When he got called out, he’d say, “How am I racist? How am I racist, look around you, I hire people of all colors.” But my response to that is that’s diversity, not inclusion. 

If there was an incident at work — say someone complained about him being racist or someone quit — his go-to was to make these passive-aggressive posts on LinkedIn without naming anyone or referring to what actually happened, but you always knew what he was talking about. Like, he’d post about people being too sensitive these days, or that they lacked loyalty.

He vaguebooked his employees on LinkedIn? Good lord.

If this were a larger or more established business, it almost certainly would have HR and you could alert them to what was going on. They’d be able to speak to this guy about the legal liability he was creating for the company and the utterly uncomfortable and hostile environment he was creating for employees.

But one of the problems with working for start-ups is that they often don’t have HR, and they haven’t been around long enough or grown large enough to realize they can’t actually let people say this crap. When you’re working somewhere without HR and the owner is the problem, you don’t have much recourse. Sometimes you can try addressing things directly yourself, but that comes with risk to you — and as with this guy, if the person doesn’t want to hear it, they can shut you down. Another option is to get a group of your coworker to push back with you because there’s strength in numbers and it can be harder to ignore a group than a single person, but this sounds like a situation where you’d be better off getting away from the job entirely. It sucks that that’s the case.

Dear Boss,

I respond to 911 calls. My current manager has been with my agency for a number of years. He micromanages a lot and I think on some level, he almost feels like he’s not doing his job if he doesn’t turn down requests. Like, you go to him and ask to swap shifts with someone, and he says no. Someone recently wanted to swap shifts because his sister was graduating from college and he said, “No that’s your shift, you’re not allowed to swap it.” He’s not hostile but he just comes across as very inflexible and like he does not care — and we have high turnover rates because of it. The staff even created a secret Facebook group to complain about him. 

We have a policy called scheduled on-call. One day a month, your boss can call you and make you work anywhere. I would actually give my boss some respect if he worked an on-call shift. We have some managers who are near his level who actually work on the ambulance. In fact, the chief executive officer of our organization has worked a few shifts on the ambulance to cover for employees who got sick. But this guy, I mean, this guy, not in the last five to ten years has worked on an ambulance. It’s really easy to make policies that don’t apply to you in any form. The mark of a bad manager is either that they make a policy where they’re exempt or they make policies that they ignore.

You know, I do think it’s sometimes okay for managers to ask things of employees that they’re not doing themselves, if the role they’re in means that makes sense. But that bit at the end is the key part — if your boss were juggling a crushing load of higher-level work that only he could do, I wouldn’t tell him he needed to take ambulance shifts just for appearances’ sake. But that falls apart if the manager in question isn’t good at the job and doesn’t operate in a way that engenders respect.

It also sounds like your boss handles authority poorly. He should be looking for ways to say “yes” to people when he can, not making “no” his default. And if you’re right that he sees saying “no” as a good way to emphasize his authority, he’s entirely missed the point of what managing is about. There’s far more power in responding to a request with “this will be tricky but let’s see if we can find a way to make it work” than in just defaulting to a refusal.

The whole picture you painted sounds like he sees himself as at a remove from your team. It’s almost adversarial, and it’s the mark of a manager who doesn’t know how to get good work from people and won’t be successful at keeping good people around in the long-term.

Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email askaboss@nymag.com. Her advice column appears here every Tuesday.

‘My Boss Is Always Making Racist Jokes!’