Stop Trying to Be the “Cool Boss” — Start Being a Good One
Why Kindness Isn’t the Problem — Avoiding Accountability Is
On an upcoming episode of the Radical Candor podcast, Jason Rosoff and I discuss a dilemma from a manager who received feedback that from their boss that they are not respected by their employees because they’re “too nice and worried about being cool.”
I’ve never been considered “cool.” But I’ve definitely been told I’m too nice.
And that’s something I’ve learned to challenge — not by becoming mean or detached, but by understanding the difference between being nice and being kind. Because as a leader, your kindness isn’t your weakness. It’s your strength. The real mistake? Failing to challenge your team directly because you want to be “nice”.
There’s no reason why you can’t be really kind and be respected and get sh*t done. In fact, your kindness is going to help you get more stuff done.
However, to lead well, you must Care Personally and Challenge Directly. Anything less risks falling into what I call Ruinous Empathy — when you’re so concerned about being liked that you let your standards slip, and your team suffers for it.
Accountability Is an Act of Kindness
Let me be clear: holding people accountable is not mean. In fact, it’s one of the kindest things you can do as a leader. When you don’t challenge poor performance, you’re:
- Failing the person who isn’t growing,
- Undermining the teammates who are doing excellent work, and
- Sabotaging yourself and the results you’re responsible for.
If you’re not holding someone accountable, you’re not doing them any favors… So it hurts everyone not to hold someone who’s slacking off accountable.
You’re not going to guilt someone into better work. Saying, “Do this for me,” or “Don’t let me down,” doesn’t work. People have to see what’s in it for them to do great work. And here’s a surprise: most people want to do good work. It’s your job to help them see how — and hold them to it.
Redefining Respect
Let’s talk about respect, because that’s where many new managers get stuck.
There are two definitions:
- Admiration for someone based on their abilities or achievements.
- Unconditional regard for the feelings, rights, or traditions of others.
As a boss, you should offer the second kind to everyone — but don’t expect it back. Especially if you were once a peer or a friend to your team.
People love to hate their boss. It’s tricky… But you have to earn admiration through your team’s achievements — not your own. The job isn’t about seeking respect through control or fear. It’s about creating an environment where great work happens — and where you help others succeed.
Emotional Labor Comes With the Role
Being a boss can be lonely. It requires emotional labor — sometimes a lot of it. You’re expected to give care even when you’re not receiving it. It’s not always fair. But it’s part of the job.
One of my favorite hymns from childhood was called Come Labor On. There’s a line that sticks with me:
“To give and give and give again.” That’s leadership.
One of the things I say in Radical Candor that people object to is: a relationship that a boss has with their employees can feel like a lonely one-way street.
Punishment ≠ Accountability
Another myth I want to bust: being strict doesn’t mean punishing people. There’s a difference between punishment and consequences. Punishment feels arbitrary. Consequences are the natural result of someone not doing their job.
When someone slacks off, it has a ripple effect. Others pick up the slack. The team’s morale drops. Your job is to help your team see those consequences — not to punish, but to inform. People need to understand the impact of their actions.
Your job as a leader is not to punish people for doing wrong, but to paint a picture of possibility.
So, How Do You Shift the Culture?
If you’re trying to change your team dynamic — especially if you’ve been the “cool boss” who’s afraid to confront — here’s where to start:
- Tell your Radical Candor story. What’s a time someone gave you tough feedback that helped your career?
- Tell your Ruinous Empathy story. When did you fail to say something, and what were the consequences?
- Solicit feedback first. Don’t dish it out until you’ve shown you can take it. Start with yourself.
- Give more praise. Make it specific. Make it public. Build people up when they’re doing great work.
- Give clear, private criticism. Quick, two-minute conversations are enough. Don’t let problems linger.
- Pay attention to how it lands. If someone’s upset, show them you care. If they brush you off, say it again — more clearly.
Remember, it’s not about being a jerk. It’s not about dominance. It’s about creating a collaborative work environment. Kindness won’t doom your leadership — but avoiding accountability will. You don’t need to be feared to be respected. You need to Care Personally and Challenge Directly. That’s what Radical Candor is all about.
Radical Respect is a weekly newsletter I am publishing on LinkedIn to highlight some of the things that get in the way of creating a collaborative, respectful working environment. A healthy organization is not merely an absence of unpleasant symptoms. Creating a just working environment is about eliminating bad behavior and reinforcing collaborative, respectful behavior. Each week I’ll offer tips on how to do that so you can create a workplace where everyone feels supported and respected. Learn more in my new book Radical Respect, available wherever books are sold! You can also follow Radical Candor® and the Radical Candor Podcast more tips about building better relationships at work.
