We talk a lot about toxic bosses here. The yellers, the 3 AM emailers, the ones who think "psychological safety" is a helmet you wear on a construction site.
But there is a more subtle, under-the-radar flavor that makes work suck.
The "Nice Guy."
This week's reader is drowning in pleasantries and starving for direction. That combination can contribute to burnout.
Dear Peter,
My boss, let's call him Gary, is the nicest human being on the planet. He remembers my kids' birthdays, he buys the team donuts every Friday, and he never, ever raises his voice.
The problem? He also never gives negative feedback. When I ask how I'm doing, it's always "You're crushing it!" When another department dumps work on us, he smiles and says "We'll figure it out," instead of pushing back. I feel stagnant, overloaded, and weirdly anxious.
I feel guilty for hating working for him. Am I the problem?
—Guilt-Tripped in Gary
Woof.
First, put down the guilt. You aren't the problem. You are suffering from a classic case of Ruinous Empathy.
Gary isn't leading you; he's pleasing you. Or at least appeasing you. And while that feels good in the short term (who doesn't love a glazed donut?), it is absolutely not a way to feel a sense of progress. It's hard to move up when you're already a "rock star."
Being pleasant is only part of the job. Sometimes helping someone means having a conversation neither of you particularly wants to have.
- Nice is keeping your mouth shut about spinach in my teeth because you don't want the awkwardness of telling me.
- Kind is telling me I look like a swamp monster so I don't embarrass myself in the board meeting.
Gary is prioritizing his own comfort (avoiding conflict) over your growth. Here is why that makes work suck:
1. You have no air cover
When Gary's manager lays down a ridiculous deadline, he folds like origami (but not in an artistic way). He wants to be liked by his bosses just as much as he wants to be liked by you. You end up with the workload, and Gary offers you a sympathetic smile and passes you the Krispy Kreme box.
2. You are flying blind
“You're crushing it!” leaves you guessing about what you did well and what needs work. If you don't know where you could use some practice, you can't get better. A manager who refuses to critique your work is setting you up to fail later on. It's like a personal trainer who counts your reps but never tells you your form is going to slip a disc. And let me tell you: hernias are not for horses.
3. Uncertainty breeds anxiety
You mentioned feeling anxious. It's hard to know where you stand when every conversation ends with the same reassurance. If Gary says everything is great, you start waiting for the other shoe to drop. You start scanning the horizon for the threats Gary is too polite to mention. You'd have more reason to trust the praise if you knew he'd also tell you when something needed work.
So, how do we fix it?
You can't transplant a spine into Gary (another reason you don't want a slipped disc!), but you can manage him.
- Change the question: Stop asking him "How am I doing?" Start asking, "What is one thing I could have done better on that last project?" Force him to dig.
- Ask for the "Why": When he accepts a ridiculous project, ask, "Help me understand the priority here compared to X and Y." Sometimes you have to force him to make explicit the tradeoffs he's accepting.
- Diversify your portfolio: Find a mentor outside your team who will give it to you straight. You need a dose of reality to counterbalance Gary's toxic positivity.
Give him something specific to respond to
For example, bring the proposal you just wrote to your next one-on-one. Instead of asking whether you're doing well, try:
“Could we look at the recommendation on page two? I wasn't sure how much detail the client needed. What would you keep, and what would you change before I write the next one?”
If the answer is still “it's great,” ask him to show you the part that worked. Useful feedback can be positive. You need to know what to repeat, and where you'd make a different choice next time.
Then use what he tells you. Bring the next version back and ask whether it addresses the thing you discussed. You're giving the conversation somewhere to go beyond another round of “crushing it.”
If he still won't engage, you've learned something. Here's how to think through your next step when the conversation doesn't change anything.
Don't settle for "Nice." Demand competence. You can buy your own donuts.
—Peter
I no longer offer coaching sessions (here's why). If this one hit close to home, or you'd like me to write about your version of it, send me an email.