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How Empathy Gets in the Way at Work (And What to Do Instead)

Entrepreneurship Habits & Productivity
How Empathy Gets in the Way at Work (And What to Do Instead)


  • How to give and get great feedback
  • Kim Scott’s framework for developing radical candor
  • Why leadership is so much more than just hiring the right people

Kim Scott is the author of the New York Times and Wall Street Journal bestseller Radical Candor: Be a Kickass Boss Without Losing Your Humanity. Kim has led AdSense, YouTube, and Doubleclick Online Sales and Operations at Google, then joined Apple to develop and teach a leadership seminar. She recently sat down with Ryan Hawk on the Learning Leader Show to discuss what it means to be radically candid, and how candor can change our work lives for the better.

This conversation has been edited and condensed. To listen to Ryan and Kim’s full conversation, click here.

Ryan: You have spent time around a number of great leaders who have sustained excellence. What are some of the common themes of the greatest bosses you’ve been around?

Kim: The greatest bosses know how to do two things for their employees. They know how to care about them, not just as employees, but as human beings, at a very deep and personal level. At the same time, they’re not so worried about being liked—they’re willing to piss people off. They’re willing to challenge them very directly.

We spend more time at work than in any other part of our lives. At the very heart of being a good boss is a good relationship with each employee. The problem comes when you start to seek popularity as a leader, as a boss, rather than doing the right thing for your people. There’s a big difference. This is true in any relationship, not just in the boss-employee relationship.

Jony Ive, the chief design officer at Apple, tells a really good story about this. One time, he was doing a design review with Steve Jobs, and the team had not prepared adequately. The work wasn’t good enough, and Steve said so in no uncertain terms. After the meeting, Jony asked, “Why did you have to be so harsh on the team?” Steve said, “Well, did you think the work was good enough?” Jony said, “No.” He said, “Why didn’t you tell them? You are just vain. You wanted to be liked.” It’s a fundamental human desire to be liked. But sometimes that desire gets in the way of doing what’s best for other people in the long term.

“It’s a fundamental human desire to be liked. But sometimes that desire gets in the way of doing what’s best for other people in the long term.”

Ryan: In reality, [employees] need that tough feedback to help them improve. Can you share the story [from your book] about when you made this mistake earlier in your career as a new CEO?

Kim: Absolutely. I had just hired this guy, we’ll call him Bob. I really liked Bob—he was funny and charming, and we liked working with him. The problem was that Bob was doing absolutely terrible work. When he would hand something in to me, there would be shame in his eyes. He knew it wasn’t good enough. I would say, “Bob, you’re so awesome—the whole team loves working with you. This is a great start, but maybe you could make it a little better.”

Of course, he never did. Eventually, the inevitable happened. I realized that if I didn’t fire Bob, I was going to lose half my team. because they were all having to fix his mistakes and redo a lot of what he should’ve been doing. I sat down to have this conversation that I should have begun 10 months prior, and when I had finished, Bob pushed his chair back from the table and asked, “Why didn’t you tell me?”

As that question was going around in my head with no good answer, he looked at me again and said, “Why didn’t anyone tell me? I thought you all cared about me.” That was the worst moment of my career, because I realized that I had failed Bob in a bunch of different ways. I had failed to solicit feedback from him. I also failed to give him praise that would have let him know what was genuinely good. I failed to tell him when his work wasn’t nearly good enough. Worst of all, I had failed to create the kind of environment in which everyone would tell Bob what was truly good, and also tell Bob when he was going off the rails. Because I had made these mistakes, I’m now firing Bob. The worst thing about being a manager is that nobody really teaches you what to do, so you learn your biggest mistakes on the backs of other people. That’s what prompted me to come up with the Radical Candor Framework, to help people avoid making the mistake that I made.

The framework goes for all communication at work—whether you’re talking to your boss, your peer, or your employee. It works up, down, and sideways. When you’re developing a relationship at work, you want to be radically candid. You want to both care and challenge at the same time. That’s really hard.

To make it a little bit easier, let’s think about what happens when you fail on one dimension or another. When you are so worried about somebody’s feelings that you fail to tell them what’s truly good and what’s truly bad, that is “ruinous empathy.” That’s the most common mistake that we make at work, both as employees and as managers. When you fail on both dimensions at the same time, when you neither care nor challenge, that mistake is called “manipulative insincerity.” Then the other mistake that we all make from time to time is when we challenge, but we fail to show we care. I call that “obnoxious aggression.”

“When you’re developing a relationship at work, you want to be radically candid. You want to both care and challenge at the same time.”

Ryan: Radical candor is not about hierarchy or status—you need to have it go up and down, left and right. How do you empower everyone to show radical candor?

Kim: You can create a culture of radical candor from the top down, and you can also do it from the bottom up. A culture of radical candor can start with anyone. Whether you are the boss or the employee or a peer, the steps are basically the same. You want to start by asking for feedback–don’t dish it out until you prove you can take it. Lead by example, whether you’re the leader or the employee.

The simplest way to ask for feedback is to take the following four steps. First of all, come up with a go-to question. If you say to somebody, “Do you have any feedback for me?” their answer will be, “No, everything’s fine.” People hate giving feedback. One question that I like to ask is, “What could I do or stop doing that would make it easier to work with me?”

The next thing you need to do is to figure out how to embrace the discomfort. A simple way to embrace the discomfort is to just shut your mouth and count to six. Almost nobody can endure that much silence, so they will tell you something if you can keep your mouth shut for six seconds.

The third step is to listen with the intent to understand, not to reply. That might mean repeating back what was said to you.

The fourth step, once you’ve solicited feedback, is to reward the candor. You need to fix the problem, and you need to be very verbal about the fact that the reason you’re fixing it is that [your colleague] brought it to your attention. When more people bring problems to your attention, you’re going to help fix them.

When you disagree with feedback that you’ve gotten, it’s hard. I recommend focusing on the 5 or 10% of what was said that you agree with, and ask to think about the rest and talk in a day or two. Sometimes the best reward of candor is a fuller and more open description of why you disagree.

“A culture of radical candor can start with anyone. Lead by example, whether you’re the leader or the employee.”

Ryan: In one of your recent talks, you started with a story, and I had trouble looking away. We’re so attracted to personal stories, especially people who are good at telling them. How do you use stories when you’re coaching, giving speeches, and sharing this message?

Kim: Well, why don’t I answer that question with a story? Think about a moment when somebody gave you feedback that was hard to hear, but was really helpful for the rest of your career. Here’s my moment: I had recently started a job at Google working for Sheryl Sandberg. She had me give a presentation to Google’s founders and the CEO about the online AdSense business that I was leading. Like any normal person in this situation, I felt a little nervous. How in the world was I going to get their attention? Luckily, the business I was leading was on fire, and I was feeling like the meeting went pretty well.

As I was walking out of the room, I passed Sheryl and she said, “Why don’t you walk back to my office with me?” Sheryl started by telling me the good things that had happened, and eventually, she said to me, “You said ‘um’ a lot in there. Were you aware of it?” I made a brush-off gesture with my hand and I said, “Yeah, it’s a verbal tic, no big deal.”

Then Sheryl said, “I know a really good speech coach. Would you like an introduction?” Again, I made this brush-off gesture with my hand. Sheryl stopped. She looked at me right in the eye and she said, “When you say ‘um’ every third word, it makes you sound stupid.” Now, she has my full attention. It was the kindest thing she could possibly have done for me at that moment in my career. She knew that those were the words she had to say to get through to me.

When went to the speech coach, I watched a video of myself presenting, and I learned something important. Sheryl wasn’t exaggerating—I really did say “um” every third word. This was news to me because I had been giving presentations my entire career. I thought I was pretty good at it. This got me to think, “Why has nobody else told me? And what made it so easy for Sheryl to tell me?”

I knew Sheryl cared about me as a human being when I moved from New York to California and didn’t know anybody, and she invited me to join her book group. She did that sort of thing for everyone who worked directly with her. We all knew that she had our backs, and had our growth in mind. And because she had our growth in mind, she wasn’t going to pull her punches when we screwed up—she was going to let us know very clearly, and challenge us very directly. That, to me, is the essence of radical candor, and of good management.

“One of the most important decisions that you make is who you hire. These are the people who are either going to make you successful, or contribute to your failure.”

Ryan: Wow. What a great boss.

Thinking about the hiring process, you talk about personality, drive, and looking at a candidate’s motivations and career aspirations. Can you expand on that aspect of hiring, and [finding] the right people?

Kim: One of the most important decisions that you make is who you hire. These are the people who are either going to make you successful, or contribute to your failure. If you’re not dying to hire that person, if you have reservations, then it’s not going to get better. The same is true of choosing a boss when you’re choosing a job. If you’re not dying to work for that person, don’t take the job.

Another mistake that managers make is thinking that the only thing they have to do is hire great people. and then just get out of their way. It’s like saying, “All I have to do is marry the right person, and then never spend another minute with them.” That’s not how you build a relationship. You’ve got to hire the right people, but you also have to invest the time becoming a thought partner to each of the people you hire. You can’t just ignore them, and you don’t want to micromanage them—you want to listen to them. The best results on a team are achieved collaboratively.

Another word of wisdom from Jony Ive is that new ideas are fragile. Part of your job as a boss is to create a space where people can come to you with new ideas, and flesh them out or clarify them. Then you want to open it up to debate—you want to get the thoughts of the whole team on these new ideas, on these suggestions, on these changes that people are recommending. Then, only after you’ve gone through that listen-clarify-debate process, is it safe to make a decision.

It’s important to remember that your job is not to be the decider. Your job is not to tell people what to do. Your job is to create the conditions where people can achieve results collaboratively.

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