Kim Scott on radical candor: the secret to helping your team do its best work

Nothing will drain your startup’s talent pool quicker than poor people management.

As Rich detailed in this post, people leave managers, not companies. So what makes for a good boss, one who will enable a team do its best work? According to Kim Scott, it comes down to a culture of radical candor: giving feedback, receiving feedback and encouraging feedback.

Kim is the author of the New York Times bestseller, Radical Candor: Be a kickass boss without losing your humanity, as well as CEO of Candor Inc, which builds tools to make feedback easier, and co-host of the Radical Candor podcast. She’s been a CEO coach at Dropbox, Twitter, Qualtrics and more, a faculty member at Apple University and a longtime director at Google.

I hosted Kim on our podcast to find out makes feedback both a powerful tool and challenging task, the how and the where of Radical Candor (hint: it’s not Slack) and why managers must prove they can receive feedback from their reports and peers before dishing it out themselves.

Short on time? Below are five key insights from the episode:

  1. The most common mistake managers make with feedback is displaying what Kim calls “ruinous empathy”, where an overwhelming fear of not being kind leads to a failure to challenge your employees.
  2. There is no substitute for in-person feedback. Clarity is often lost via email and Slack, and there’s no way to gauge the recipient’s emotional reaction.
  3. Impromptu conversations always beat pocketing feedback for a regularly scheduled 1:1. The latter brings artificiality into the process, is a time for managers to listen and will make reports dread these important meetings.
  4. Before dishing out feedback themselves, managers need to create a culture of feedback. This begins with soliciting feedback from reports and showing you can embrace the response.
  5. A manager who over-empathizes is a manager who doesn’t know their employees personally. To break that cycle, have three conversations with your reports: one about their past, one about their future goals, and one about how their time at your company can help them reach those goals.

John Collins: Kim, welcome to the show. You’ve got lots of Silicon Valley experience having worked at Google and Apple and been a CEO coach for the likes of Twitter and Dropbox. But before that, you worked at what you’ve described as three failed startups. The common thread between them, you said, was bad management. Where were they failing? What kind of things were you seeing?

Kim Scott: I’ll tell you the things I was doing, because I was making a lot of the mistakes. One of the most painful experiences of my whole career was hiring a guy that we’ll call Bob. I really liked Bob. He was funny, he was charming. We were at one of those management off-sites, where you’re playing some get-to-know-you game that everybody hates but nobody dares be the grouch who says it’s ridiculous. Bob was the one who was brave enough to raise his hand and say, “I’ve got an idea, and it’s going to be much faster. Let’s just go around the table and tell everybody what candy our parents used when potty training us.” Weird, but fast. The weirder thing was, everybody remembered.

For the next 10 months, every time there was a tense moment in a meeting, Bob would whip out just the right piece of candy for the right person at the right moment. Anyway, odd, but I found it charming. We all loved Bob and found him fun to work with. Just one problem – Bob was doing terrible work. It was puzzling because he had such a great resume. I learned later that the problem was he was smoking pot in the bathroom every day, but. I didn’t know that at the time. I couldn’t figure out what was going on.

Because I liked Bob so much and didn’t want to hurt his feelings, I didn’t tell him when his work wasn’t really good enough. I would give him fake praise. I’d say, “Bob, you’re so awesome. You’re so smart. I’m sure that if you focus on this maybe you could make it a little better.” Of course, it never got better. After 10 months of this, the inevitable happened and I realized if I didn’t fire Bob I was going to lose half my team.

I sat down to have the conversation with Bob that I should’ve begun 10 months earlier, and when I finished he pushed the chair back from the table, looked right at me and he says, “Why didn’t you tell me?” As that question is rolling around in my head with no good answer, he says, “Why didn’t anyone tell me?” I realized that I had failed in a bunch of different ways and because I had failed, Bob was getting fired. I had failed to solicit feedback from Bob. I had never asked him what I was doing well, or more importantly, badly from his perspective. Maybe I was doing something that was driving him so crazy he was forced to toke up in the bathroom, but I don’t know. I never will because I didn’t ask him.

I had never given Bob any praise that was meaningful – the kind of praise that I was giving Bob was just a head fake – and I’d never given Bob any criticism. I had never found the courage to tell Bob when his work wasn’t nearly good enough. I had failed to solicit praise and criticism, I had failed to give praise and criticism, and perhaps worst of all, I had failed to encourage it. I had failed to create an environment in which everyone would tell Bob what was truly good and what was truly not good when he was going off the rails. It was a terrible moment in my career, and probably the moment in which I started writing this book in my head, the reason why Russ Laraway and I started Candor, Inc. and the reason why we’re doing the Radical Candor podcast. It’s to help people avoid making the mistake that I made with Bob.

What makes for radical candor?

John: Radical candor: What’s your definition of the term, and why do you think it is so difficult for many managers to grasp?

Kim: It’s surprising that it’s difficult because at its heart radical candor is simply the ability to care personally about the people you’re working with and challenge them directly. Because you care about them, you want to help them get better. It’s a pretty simple idea, but also very rare. That’s why I call it radical candor.

Care personally about the people you’re working with and challenge them directly.

There are two reasons why it’s rare. One has to do with caring personally. The problem here begins when we’re about 18-19 years old. We get our first job and we’re told, “Be professional.” For an awful lot of people, being professional gets translated to leaving your emotions, your humanity and the very best part of yourself at home and coming to work as something that’s less than human. That is a terrible mistake. In order to be a great colleague, a great leader or a great follower, you’ve got to bring your whole self to work and be more than just professional. I’m not saying be unprofessional, but you’ve got to be a human being.

The second reason happens when we’re 18 months old, not 18 years old. We all have parents or somebody who tells us, “If you don’t have anything nice to say, don’t say it at all.” Now, all of a sudden, at work it’s your job to say it. Undoing a lifetime of training, undoing an instinct that’s been pounded into your head since you were 18 months old, is really hard.

One of the things that helps is to think about what happens when you fail on one dimension or another on what I call the radical candor framework. When you do challenge someone directly but you fail to show that you care personally? I call that obnoxious aggression – commonly called the asshole quadrant. The reason why I don’t use that word to describe obnoxious aggression is that I don’t want you to use this framework to judge yourself or to judge other people.

It’s very tempting to draw out this two-by-two vertical axis and start writing names in boxes. I beg of you, do not do that. Use the framework to guide conversations, not to judge yourself or other people. Obnoxious aggression is what happens sometimes in a conversation when we get mad or impatient and we fail to show the person that we’re having a disagreement with, or even the person we’re giving praise to, that we care about them as a human being. It happens to all of us. We all sometimes behave like jerks. I can tell you plenty of times when I have behaved like a jerk. That’s obnoxious aggression.

There’s also a lot of times when we do show that we care personally, when we’re trying to be really nice to somebody, but we fail to challenge them directly, sort of like I did with Bob. That’s called ruinous empathy. Ruinous empathy is responsible for the vast majority of workplace mistakes.

John: The boss who wants to be everyone’s friend, isn’t it?

Kim: Exactly. Ruinous empathy is really the thing to avoid. We like to tell stories about the colleague who’s been a total jerk, but it’s actually pretty rare. Most people are not total jerks.

There’s a third mistake that we all make from time to time, too. It usually happens because we’re busy or focused on getting our own work done and we just need to retreat to our own corner, but these are the times when you neither show that you care personally nor challenge the person directly. When you fail on both dimensions at the same time, that’s manipulative insincerity. Hopefully, naming the mistakes when you screw up on one dimension or another with some colorful language will help you avoid them.

The importance of face-to-face feedback

John: What’s the line between being candid and actually causing damage to the employee or a peer’s morale? That seems to be the thing that most people are afraid of. How do you judge between constructive feedback versus, “Hey, you’re crap at your job”?

Kim: It’s really important question because radical candor gets measured not at your mouth, but at the other person’s ear. The most important thing you can do is to make sure that when you’re delivering feedback, whether it’s praise or criticism, to do it in person because then you can see the person’s reaction. You can understand whether you want to move out on the care personally axis.

In other words, you may not have been clear enough and you may need to challenge a person even more directly. Or, you need to move up on the care personally axis and react with compassion the emotions that you’re seeing. Show the person you care about them, that you’re there to help them but not back off the challenge. Just because somebody’s getting upset about what you said doesn’t mean that you’ve made a mistake. It just means they’re having an emotional reaction and you need to react with compassion.

John: That’s the place where people need to feel empowered that, as you say, because someone getting emotional doesn’t necessarily mean you’ve given the wrong feedback.

Radical candor gets measured not at your mouth, but at the other person’s ear.

Kim: Right. I really want to reassure people that just because somebody is upset about what you’ve told them doesn’t mean you’ve said it in the wrong way. There are no magic words. Most of us pour our heart and soul into our work. We spend more time working than we do doing anything else in our lives. So when you criticize somebody’s work, they’re likely to be upset about it. They wish they hadn’t made a mistake. Your job then is to react with compassion, not to try to find some magic words so that the person won’t get upset, because there are no such magic words.

John: It sounds like you’re not a big fan of things like email or Slack or any of these other tools we all use every day now for feedback. Face-to-face, particularly if it’s a big issue, is the way to go.

Kim: Yes, or even if it’s a small issue that if it piles up might become a big issue. The best feedback I’ve ever gotten in my career happens in impromptu two-minute conversations in the moment. The only way to know how someone is reacting, the only way to know how your feedback is landing, is to be able to see the person when you deliver it. If you send feedback over email, you have no idea if you were clear enough or if the other person is upset.

Hierarchy of feedback delivery

If you try to type it into a tool or type it into some sort of process, you’re failing to communicate because 80-90% of human communication is nonverbal. It’s looking in the person’s eye and seeing if their eyes are getting wide or if they’re scowling at you. It’s noticing if their arms are crossed. Most of us are actually really good at interpreting emotions if we bother to see them, if we’re talking face-to-face with someone. It’s usually pretty unmistakable how someone is feeling about what you’re saying.

The right role of 1:1s

John: I like that you say feel free to grab someone for two minutes face to face, because I think an awful lot of people in the tech industry keep everything for the 1:1. The weekly 1:1 is where everything is going to be solved. Do you think that’s a mistake to store up all the feedback and issues?

Kim: It’s a huge mistake. If you’re a manager and you have an employee, it’s the other person who gets to set the 1:1 agenda. Your job as a manager in a 1:1 is to listen to the other person, so saving up feedback for a 1:1 is going to do a bunch of bad things. First of all, you’re not in listening mode if you have a list of things you need to say. Second, a good use of feedback in a 1:1 is to solicit it, not to give it. Third, if you use your 1:1 time as the only opportunity to give feedback, you introduce such artificiality into the whole feedback process. If you have a friend or a family member and they’ve done something that bothers you, it would be crazy to wait for a regularly scheduled meeting to raise it. It would make it so awkward. It would ruin your relationships. So don’t do that at work either. If you see something, say something, and say it right away. The other problem with saving up feedback for a 1:1 is it’s going to make you start to dread your 1:1s because it’s hard to give feedback and nobody wants to do it, and so if you’re saving it up for a 1:1 you’re going to start canceling your 1:1s.

Creating a culture of feedback

John: How do you, as a manager, convey to your reports that it’s not just okay to give feedback on my performance as a manager but you actually want to encourage them to do it?

Kim: I always say don’t dish it out before you prove that you can take it. You earn the right to give feedback by soliciting it. There are four things that I recommend you do when soliciting feedback. You should do this with your boss, your employees, and your peers. You can even try it with your spouse. The first is to come up with a go-to question. For the same reason that you’re reluctant to give feedback, the other person is reluctant to give you feedback and so it’s really important that you come up with a question that falls trippingly off your tongue, that you’re comfortable asking.

I’ll give you two examples. My go-to question is, “Is there anything that I could do or stop doing that would make it easier to work with me?” I was talking to a friend of mine, Christa Quarles, CEO at OpenTable, and she said, “I could never ask that question. It would feel so artificial for me. The question that I like to ask people is, ‘Here’s what I think. Tell me why I’m smoking crack.’” Whatever question works for you, use it, but come up with something you can ask.

You earn the right to give feedback by soliciting it.

Step number two is to embrace the discomfort. Remember, the person doesn’t want to give you any feedback, so the best way for you to get them to say something is to embrace the discomfort. It’s tempting to feel like, “If I make you comfortable you’ll tell me the truth,” but the thing that’s going to make the other person comfortable is to let them off the hook and say, “Oh, everything’s fine.” You can’t do that.

A simple technique for embracing the discomfort is to shut your mouth and count to six in your head. Six is a long time. If you count to six in your head, the other person will say something just to break the silence because most people can’t endure six seconds of silence. Having shut up for six seconds, which is hard, the person’s going to tell you something. When they say something, it’s really important not to react defensively.

Step number three is to listen with the intent to understand, not to respond to the person. Having done that, your fourth step is then to reward the candor. Now, it’s easy to reward the candor if you agree with the feedback. You fix the problem and you tell the person that you fixed the problem. But it’s hard if you disagree with the feedback.

Feedback is a two-way street. You don’t have to agree with all of it. This is not a, “Thank you, sir. May I have another?” situation. If you disagree with the feedback, the thing that I recommend is to find that 5% of what they said that you can agree with, wait a day or two so you’re sure you’re not in a defensive frame of mind, and then explain to them why you disagree. Sometimes the only reward you have to offer is a fuller explanation of your point of view.

How to deliver praise

John: A lot of people have problems praising people who work with them or for them. Is it that people are afraid to patronize their teammates? Why do you think people struggle there?

Kim: A lot of people struggle with praise because praise can feel arrogant. Like, “Who am I to judge what’s good and bad?” Another common trend is they’re afraid that if they praise somebody they will cause them to rest on their laurels. The thing to keep in mind here is that praise, when it’s really specific, doesn’t cause people to rest on their laurels. It teaches them what to keep doing. It’s guidance. If you think about it not as feedback but as guidance, praise lets them know when they’re going in the right direction; criticism lets them know when they’re going in the wrong direction.

It’s not merely positive reinforcement. It’s letting not just that individual but, if you praise in public, the whole team know what success looks and feels. Sometimes people do something and they don’t know whether it’s good or bad, and they can’t know unless you tell them. It’s important for that reason.

Another reason people are reluctant to praise is that it often feels insincere. So many people have been taught to give the so-called feedback sandwich, which is say something nice, then give the criticism, and then say something nice again. Don’t give the feedback sandwich. Make sure that when you give people praise, it’s sincere, that you really mean it. People commonly think praise is the way to show you care personally and criticism is the way to challenge directly, but that’s exactly wrong. Praise should both challenge and show that you care, and criticism should also both challenge and show that you care. Realizing that both praise and criticism are going to help people achieve better results and find success makes it much easier to give praise that’s radically candid.

Where first-time managers struggle

John: Startups often feature many first-time managers, and we’ve all been a first-time manager. Where do you see them struggling most? What’s the mistake you’ve most often come across?

Kim: This is not what people like to talk about, but the most common mistake is ruinous empathy. They fear looking like a jerk, so they don’t tell people when their work is not nearly good enough. When I was early in my career and starting a company and a first-time CEO of a software company, I got this email from about 10 of my employees. It was an article that said most people would rather have a boss who’s a total asshole than a boss who’s really nice but incompetent.

I started thinking to myself, “Do they think I’m a jerk, or do they think I’m incompetent? Which one is worse? Surely these are not my only two choices. I don’t want to be either one.” A lot of people fall prey to this false dichotomy between feeling like they have to choose between being competent and being a jerk, and you don’t. You can be radically candid. You can both care personally and challenge directly.

Getting to know your employees at a human level

John: You’ve said that to be a great boss it’s important to know your employees at a human level. What does that mean? That may be what people are trying to do when they’re too empathetic.

Kim: Too much empathy is not about knowing people well. Often, it’s about worrying whether or not they like you. There’s a big difference between caring personally and being liked. Too much concern about being liked is actually going to move you towards manipulative insincerity, to an even worse place than ruinous empathy. It’s really important to remember that your job as a manager can sometimes feel like a lonely one-way street. You have to care, but not worry too much about whether or not people care about you. That can be hard.

One of the things that makes it much easier to do this is a simple career conversation technique that Russ Laraway, my co-founder at Candor, Inc., developed when he was at Google and also rolled out when he was at Twitter. Caring personally doesn’t mean you have to blow your family off and have dinner with your employees instead of your family, but it does mean you have to take some time at work to get to know them. Not huge amounts of time, but significant time.

Relationships are at the center of great management. Image credit: Candor, Inc.

This involves three 45-minute conversations with each of your employees. The first one is a get-to-know-you conversation. This one often begins with a question, something like, “Starting with kindergarten, tell me about your life.” If the employee looks horrified and would rather die than tell you about their childhood, you can start in grad school or five years ago in their career. This is not you playing psychiatrist and them lying on the couch. It’s just a get-to-know-you conversation wherever they’re comfortable starting. The reason to start with kindergarten is to imply, “I want to get to know you at a personal level.”

When you have this conversation, notice when somebody has made a change. If somebody was a cheerleader and they became a swimmer or somebody was getting a PhD and then they went to Wall Street, ask why they make that change. Usually, what you’ll learn is what really motivates somebody. Is it hard work? Is it adventure? Is it financial success? Whatever it is that really motivates somebody at work, you want to know what that is. When you understand the person you’re going to more naturally put them on projects that are motivating. You’re going to more naturally help them find meaning in their work if you understand what motivates them at a human level.

The next conversation that you have with people is about the future. It’s a dreams conversation. This conversation is really important because you want to get away from the tedious promotion conversation, which is never satisfying for anybody. The promotion conversation is always about, “Why am I not getting promoted faster?” What you want to understand from somebody is what the height of their career looks like. When everything is going just the way they want it to go, what is it going to look like? Usually people don’t have one dream. They have three or four, because almost nobody knows what they want to be when they grow up and those who do confuse the heck out of the rest of us. I sure don’t know what I want to be when I grow up, and I’m about to turn 50. You want to make sure that you’re giving people the space and the freedom to dream big. You want to understand what they really want out of life and out of their careers in the future. You want to know those dreams. Make sure there’s three or four of them.

The third conversation is more tactical. This is where you come up with a career action plan. Let’s say in my case Dream A is to be a great novelist, Dream B is to be a great entrepreneur and Dream C is to be the angel in the house. What are the skills that I need to develop in order to achieve each of those dreams, and how important are they for each of the dreams? As you begin to talk through this, it becomes clear what you as the manager can do in order to help people take a step in the direction of their dreams.

For example, Russ was managing somebody who was an ad sales person. What she really wanted to do was own and operate a spirulina farm. That was one of her dreams. You pause and think, “What do ad sales have to do with own and operating a spirulina farm?” But as they thought about it, one of the things she really needed to learn how to do was to be a better manager. She was in a great place to learn how to do that. She was working for Russ, who’s one of the greatest leaders of people I’ve ever met in my career. Russ was working in Sheryl Sandberg’s organization, also a great leader. Now all of a sudden her work seemed much more relevant to her dream, which it hadn’t before the conversation. It’s surprising the things that come out when you take a moment to really understand what motivates somebody, what they want, and what the skills are that they need to develop in order to stay motivated and get where they want to go.

Writing the book on feedback

John: Your new book, Radical Candor: Be a Kickass Boss Without Losing Your Humanity, is now a New York Times and Wall Street Journal bestseller, so congratulations on that. What were you able to convey with the book that you hadn’t in your previous advisory and consulting work and lectures to date?

Radical Candor: How to be a kickass boss without losing your humanity

Kim: There’s such a giant human dimension to management. What I wanted to do was write a book that was not going to feel like most management books. It was going to feel like a book of short stories that would help people as leaders feel less alone, because I think management often feels very, very lonely. I was really happy the other day I got an email from somebody who had read the book and listened to our podcast, who was alone in a foreign country struggling with a new and hard management situation. He said he got back to his hotel room and started listening to the podcast and reading the book, and he said, “I felt like I had a good friend in the room with me.” That’s why we’re doing what we’re doing.

John: Kim, you’ve been very generous with your time. Thanks for sharing with our listeners.

Kim: Thank you.