I once found myself in a situation where a temporary employee, reporting to me, was underperforming. There were usually reasons behind why she hadn’t made any progress on a project, but the end result was that everything took much longer than it should or was left unfinished. Rather than invite friction into the relationship, I tempered my expectations and tried to treat each assignment as a learning experience. I offered specific feedback on a project-by-project basis, but I wimped out when it came time to discuss her experience holistically at the close of her contract. The kindest approach was to let her contract run its course. I let her believe that her output had been acceptable, even that I was happy with it.

Was that nice? In hindsight, pen to paper, it doesn’t seem as kind as I intended. And this became hyper clear when, a few months later, she asked about returning full-time. I was shocked—until I realized the disservice I’d done her. She didn’t know that she had underperformed. Everything I hadn’t addressed directly was going to be a problem somewhere else, for someone else—and subsequently for her.

Managing is not about friendship

Perhaps I made a mistake that many newbie managers make, erring on the side of being “too nice”. Our one-on-ones were peppered, after all, with stories about our families. We had what I thought was a good working relationship. But managing isn’t about becoming friends. Leadership requires fortitude and experience. There are business goals to be met and those must be balanced with managing people—and all their quirks, intricacies, needs, and aspirations.

But managing isn’t about becoming friends. Leadership requires fortitude and experience.

According to Kim Scott and Russ Laraway, the founders of Candor, Inc., bosses who are “too nice” care too much about hurting their employees’ feelings, which makes it hard to give criticism. In fact, they may avoid giving negative feedback altogether.

Using their Radical Candor™ framework, leaders who show up high on “caring personally” but low on “challenging directly” exhibit behaviors that fall into a category called “Ruinous Empathy”. The label sounds foreboding, but is less important than the challenge at hand: to offer praise that is specific and sincere, and to provide criticism that is clear and kind.

The value of criticism

As one might imagine, lack of criticism makes it difficult for employees to grow and improve, and even to identify areas for additional development. To the employee, “niceness” can end up being devastating, deeply confusing, and career-limiting if the employee is passed over for opportunities without understanding why. From the outside, thinly-skinned interactions undermine the manager, who may appear “soft-headed” or even completely unaware of the ways their team needs to improve—

In my case, although I cared about my direct report as a person, I had not applied the same care to her career path. For me, that was an important and helpful distinction. “Sometimes the kindest thing you can do for someone is to criticize them,” Russ Laraway advised. “That criticism will help them know what to do better and enable them to have more success. It’s kind of a ‘tough love’ idea.”

“Sometimes the kindest thing you can do for someone is to criticize them.” - Russ Laraway

If you’re a leader who tends to live in the “Ruinous Empathy” quadrant, you have to learn to “just say it”—exactly what you think. Laraway recommends starting by reminding yourself that criticism helps people know what to do better and, in turn, be more successful. “By giving criticism regularly—every week, in short bursts—

The folks at Candor, Inc. recommend thinking about feedback in a 3:1 ratio—3 parts praise, 1 part criticism. “In theory, people are doing a heck of a lot more well than they are doing poorly,” Laraway added. And when you regularly praise someone in a specific and sincere way, you pave the way toward making criticism easier to hear. Just don’t mix praise and criticism in the same conversation, as they dilute each other.

Toughening up


Criticism: How to be more clear

The challenge for bosses who fall prey to niceness is not to be mean. Instead, the challenge is to be more bold. Offer criticism that is direct and clear, and include specific examples. Moreover, this criticism should be offered in person, in private, and in context

Praise: How to be more specific

Chances are, you’ve got the sincere part of radical candor down. When you praise, much of the same holds true: give it immediately, in person, but this time, in public. If, for example, your employee gives a great presentation, it’s okay to lead with, “Great presentation,” but follow that up with substance. What was the best thing about it? Where might they expand next time?

Hard conversations only get harder...when you put them off

Sarah, who has led a team of customer success executives for the past seven years, recalled a situation early in her management career when she consistently received negative feedback about one of her reports. It was feedback that she didn’t always agree with it or think was fair, so her response was to disregard it.

The workplace rumor mill, however, diligently churns. When her report eventually got wind of the bad feedback, they were completely blindsided—and hurt. “It took me too long to level with them and to say, ‘Hey listen, this is the perception out there. I don’t agree with all of it, and here’s my perception, but I want you to understand the full picture,’” Sarah explained. Though her intention had been to protect the employee, she could see in hindsight that she hadn’t.

“Over the years I’ve learned that difficult conversations only get more difficult, and more necessary, if you put them off,”

Take ‘nice’ to the next level: Respect

No one’s saying that being nice is a bad thing. We spend a lot of time with our colleagues, and it’s great to have good working relationships. It’s only our feedback that shouldn’t be too nice or ingratiating.

This is something that Zendesk CFO, Elena Gomez, also learned early in her career. Elena recalled a moment, years ago, when her boss at the time sat her down for some radical candor. On a spectrum between “like” and “respect,” he explained, she was so well-liked that she needed to pivot back the other direction. “It’s more important to be respected than to be liked,” he said.

For Elena, this was eye-opening. She was aware, as a leader and business partner to her colleagues, that she sometimes had to deliver news no one wanted to hear. But her boss’s feedback helped her see that the way she went about handling disagreement, in particular, could be improved.

“I realized that my approach was to profusely apologize for why I took a particular stance,” she said. “I’d try to make sure that we connected, that there was an emotional agreement over a decision, as opposed to being fact-based and saying, ‘Hey, I appreciate and have empathy for your position, but here’s mine and here’s why.’”

This insight became a mantra that Elena has carried with her. Instead of approaching a difficult conversation from a place of worry over whether a colleague will dislike her, she takes a more rational approach: “I need to leave the room with the idea that this person respects me. Therefore, how am I going to approach this conversation?”

For starters, it means offering a lot fewer apologies.

Next week we’ll take a look at the flip side, known as "Obnoxious Aggression" in this four-part series on Radical Candor and how you can be a better boss and colleague by giving better feedback. Missed last week? Learn about the pitfalls of "Manipulative Insincerity".

Suzanne Barnecut is a content marketer for Zendesk and a frequent contributor to Relate. Fascinated by technology, but a diehard reader of paper-made books and sender of snail mail. Find her on Twitter: @elisesuz.

Illustration by Andrea Mongia.