Dear Peter: My boss is a "Nice Guy," so why am I miserable?

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 - yet another ripe context for 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".

Here is the hard truth that "Nice Guy" managers don't understand: Nice is selfish. Kind is selfless.

• 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 the 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. The result? You get crushed by the workload, and Gary just offers you a sympathetic smile and passes you the Krispy Kreme box.

2. You Are Flying Blind

"You're crushing it!" is not feedback. It’s cheerleading. 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. That’s because your brain knows that nothing is ever 100% perfect. 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. The only way you can trust when Gary says you did a good job, is if he also tells you when you didn't.

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.

Don’t settle for "Nice." Demand competence. You can buy your own donuts.

—Peter