Why Being a “Cool Boss” Backfires — And What to Do Instead

Edited By Brandi Neal, Radical Candor podcast writer and producer, and director of content creation for Radical Candor. When leaders prioritize likability over accountability, team performance suffers. Kim Scott, co-founder of Radical Candor and author of the best-selling book by the same name, explains why kindness is not the enemy of leadership—and how managers can earn real respect without becoming authoritarian. Alongside CEO Jason Rosoff, Scott outlines a better way forward: lead with care, challenge with clarity, and stop avoiding the hard conversations.

Kim Scott and Jason Rosoff on accountability, emotional labor, and the real meaning of respect.

When a self-described “nice and cool boss (in a bad way)” posted to Reddit asking how to shift from being too lenient to more respected, it sparked a discussion between Kim Scott, co-founder of Radical Candor and author of the best-selling book by the same name, and Jason Rosoff, Radical Candor co-founder and CEO.

They unpack the myth that kindness and accountability are at odds, and offer a roadmap for leaders who want to be liked—but also want to lead well.

The question:

So I’m a production supervisor and I have recently gotten into hot water because my boss says I am not respected by the employees because I’m too nice and worried about being cool.

I’m not saying they are wrong, they are right. But I went into the position with the mindset that if I’m relatable the employees would like me and go to bat for me. They do occasionally but they also slack off nonstop and all seem unconcerned about me getting in trouble

How can I break this mindset, for both myself and the employees? I really struggle with being stricter/meaner but I feel like if I can just break the cycle I’d be able to continue it. It’s that first step that’s hard for me.

Table of Contents

Nice Isn’t the Problem. Avoiding Accountability Is.

“There’s no reason why you can’t be really kind and be respected and get sh*t done,” Scott said. “In fact, your kindness is going to help you get more stuff done.” — Kim Scott

The key, Scott emphasized, is not about abandoning kindness—but about pairing it with what she calls “challenging directly.” That’s where many well-intentioned managers fall short.

Scott drew a firm line between being nice and being kind. The former can lead managers into what she calls “ruinous empathy”—withholding constructive feedback in order to avoid discomfort or protect feelings.

“Holding people accountable—remembering that that is actually an act of kindness—is crucial,” Scott said. “If you’re not holding someone accountable, you’re not doing them any favors.”

When managers avoid difficult conversations, she added, they don’t just fail the underperforming employee—they also demoralize the rest of the team.

“They feel like a chump,” Scott said. “Why am I busting my butt if so-and-so is slacking off?”

Rosoff echoed the consequences of that dynamic: “When someone is getting away with doing less than great work, it diminishes the motivation of everybody on the team to do great work.”

Two Kinds of Respect — and Why Only One Is Earned

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Respect was another major theme. Many new managers expect it to come automatically with the title, but as Scott explained, that expectation is likely to be “dashed.”

“People love to hate their boss—especially if their boss used to be their peer or their friend,” she said.

To make matters more complex, the word “respect” has dual meanings. One is admiration for someone’s abilities or achievements. The other is an unconditional regard for the feelings or rights of others. Leaders, Scott said, should offer the latter to everyone—but shouldn’t assume they’ll receive it in return.

And when it comes to earning that first kind of respect?

“In the case of being a manager, the achievement is actually not your achievement,” she said. “It’s their achievement. So the question becomes: How can you help your team do their best work?”

Leadership as Emotional Labor

Scott acknowledged that leadership often feels like a “lonely one-way street.”

“One of the things about becoming a manager that is hard,” she said, “is that you have to give a lot of care, but you don’t necessarily get to expect that you’re going to get it in return.”

It’s emotional labor—and most new managers aren’t prepared for how much of it they’re signing up for. But it’s part of the deal.

“You’re agreeing to do more than your fair share of emotional labor to help the team,” Rosoff said. “That’s why you get more institutional authority. That’s why there’s often more compensation. And ideally, there’s a satisfaction that comes from helping others succeed.”

For Scott, the role of a leader is best captured by a refrain from a hymn she sang daily at her Episcopalian school: “To give and give and give again.”

Ditch Punishment. Explain Consequences.

Another misstep managers make when they try to correct course? Confusing accountability with punishment.

“There’s a difference,” Scott said. “Punishment feels arbitrary—like, ‘I’m going to punish you because I can.’ Holding people accountable and explaining consequences means you’re doing your job.”

The goal, she added, is not to make people afraid. It’s to paint a picture of what’s possible. “Your job as a leader is not to punish people for doing wrong, but to paint a picture of possibility,” Scott said. “Show people what great looks like.”

Rosoff warned that fear-based management is both ineffective and demoralizing. “You might get short-term compliance,” he said, “but when people are operating from a place of fear, they’re often in fight-or-flight mode. There’s no way you’re getting their best work.”

How to Shift Your Leadership Style Today

For managers looking to reset their culture—especially those who’ve leaned too far into being liked—Scott and Rosoff laid out five practical steps:

Share your Radical Candor story.
Open up about a time someone gave you feedback that stung but helped you grow.
Share your Ruinous Empathy story.
Reflect on a moment when avoiding hard truth led to worse outcomes.
Solicit feedback first.
Show you can take it before giving it. “Don’t dish it out before you prove you can take it,” Scott said.
Give specific, public praise.
Focus on the positive. Reinforce the behaviors you want to see more of.
Give brief, private criticism.
Don’t save it for formal reviews. Use two-minute, impromptu conversations to address issues quickly and clearly.

And always, she emphasized, pay attention to how your words land.

“If the person is sad or mad, show them you care,” Scott said. “If they’re brushing you off, you have to say it again—even more clearly.”

The Radical Candor Mindset

For Scott, leadership isn’t about dominance or control. It’s about balance—combining care and clarity to create a culture where everyone can do their best work.

“It’s not about being a jerk,” she said. “You’re not trying to establish dominance. You’re trying to create a collaborative work environment.”

And for those who’ve fallen into the “cool boss” trap?

There’s a way forward. Start by being honest with yourself—and with your team. Need helping getting started? join the Radical Candor Community — free forever.

Join the Radical Candor Community

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