There are many types of toxic bosses out there.

There are the Bullies who only care about themselves, lie to cover up their mistakes, and berate employees to build their own egos.

There are the Micromanagers who don’t trust their team, get up in everyone’s grill, and impede productivity by questioning every single detail on projects.

There are the Incompetent bosses whose skills, despite a robust resume, are nothing more than smoke and mirrors, and they literally can’t do their job.

And yes, all of these bosses are awful.

But there’s another kind of boss who lurks quietly behind the office doors—often with bright smiles and fresh cupcakes in hand.

The People Pleaser.

People pleasers 101

People pleasers are individuals who are averse to saying “no,” desperately need others to like them in order to feel good about themselves, avoid conflict at all costs, and have no concept of boundaries. People pleasers are also often tremendously insecure. They constantly question their own decisions because they fear both being criticized and letting others down.

At first, the people-pleaser boss seems nice, generous, and considerate. They often have a super-friendly vibe that makes you think, “We are so going to get along!” One soon discovers, however, that there is a dark side to working for someone who is so accommodating.

I was working as a manager in a cosmetics company when I learned just how toxic this kind of management style can be.

For the first two years of my job, I only had one major people pleaser to contend with: the company manager. While not ideal, it was manageable because I didn’t have to work with her daily. I almost felt sympathy for the hoop-jumping she constantly engaged in to impress her own boss at the head office. And while her indecisiveness and seriously whacky last-minute requests created extra work for me and my own team, we were able to handle it with a certain level of grace.

One day, however, I got a new direct boss and I knew it was game over.

Overnight, my job went from tolerable to toxic. I was now working under a tower of people pleasers, feeling crushed at every turn.

My new boss, a director, was a classic people pleaser with unrealistic expectations of her staff. She had no “off switch” and bragged about working fourteen hours a day. People pleasers make excellent workaholics, and this woman was going to be the best workaholic her boss (the company manager) had ever seen. She was going to go, go, go and never say no.

With no regard for anyone’s mental or physical health, she demanded productivity 24/7. She also dumped most of her responsibilities on other team members, knowing they could do it better and make her star shine brighter.

The result? Every day was exhausting, draining, and painful.

So, how can you tell if you are working for a people pleaser?

1. Check for work boundaries

Think about the top executives of the company and determine what boundaries (if any) they have in place.

Do they put their foot down when necessary, work reasonable hours, and use all their vacation days? Or do they say “yes” to everyone and everything, work weekends, and send emails at two a.m.? (Have they not discovered the ‘Send Later’ feature in Outlook?)

If it’s the latter situation, you’re likely screwed.

2. Look at the company’s language

While actions often speak louder than words, there’s a lot you can learn about a company culture from their mottos, manifestos, and buzzwords.

When I had my first phone interview for my manager position, I asked for more details on their company culture, which from an outsider position looked super fun and progressive. Without missing a beat, the HR manager said, “We live by the motto, ‘Work hard, play hard.’”

My initial reaction was, “Cool! I’m on board!” As someone who loves to both work hard and play hard (reading on my Kindle for six hours straight counts, right?), I could easily resonate with this work philosophy. Sign. Me. Up.

Little did I know that three years later, after working myself to the bone and no longer sleeping at night because of work anxiety, I would come to loathe that phrase.

According to Adam Grant, organization psychologist and best-selling author, the phrase, ‘Work hard, play hard’ translates to: ‘We work 90+ hour weeks, but occasionally we party instead of sleeping.”

I tried to make it work

Although I’m a certified career coach and I knew much, much better, I was in the position so many of us have been in—I still liked elements of my job. I had a good paycheck with company perks, and I was simply not mentally ready to leave. It almost felt I was letting the bad guys win if I quit. It’s amazing how corporate culture can make you believe that self-preservation is giving up. Yikes.

In a last-ditch effort to make my job work, I started setting some clear boundaries. This included pushing back on deadlines and questioning “make work” projects that I believed were unnecessary. Not surprisingly, my boundaries were not met with enthusiasm. I was immediately labelled “difficult” and “not a team player.”

While Brené Brown would have been so frickin’ proud of me—heck, I was proud of me!—I was not going to win this battle. It was time to exit the ring.

The irony is that I’m a recovering people pleaser. I used to be that person who ran myself ragged, not only to help others but to prove my worth. And now here I was, trying to maintain my sanity in a people-pleasing circus.

I believe things happen to us so we can face what we most need to learn. And the lesson here was clear—I needed to truly disconnect from all the old patterns and behaviours that were no longer serving me. Was I finally ready to put my needs first? Was I done being sucked into the toxic orbit of the people-pleaser?

The answer was a resounding yes!

Once I made that decision, the desire for personal peace far outweighed the fear of leaving the job. I left. It wasn’t about giving up or giving in. It was about doing what was best for my mental and physical health.

I decided I was no longer available to participate in anything that brought out my worst self and left me feeling like garbage. Not only is life too short for that, but there are thousands of other job options out there that will serve you better. It’s your job to find the one that works best for you. Don’t sit and suffer. Don’t try to wait it out. Hold your head high and move on.

Was it scary to leave my job? Yes. But the thought of staying where I was, overworked, undervalued, and never feeling like I could do “enough,” was much more frightening. Opting out of the toxic chaos was a crucial decision in my career—and life. At that moment I fully stepped into my best self—strong, empowered, and certain that the only person I would be pleasing was my own damn self.

To your brave success, Alana