Lead with Empathy, Speak with Candor | Kim Scott | 608

And welcome, welcome, welcome. This is Peter Winick. I'm the founder and CEO at Thought Leadership Leverage, and you're joining us on the podcast today, which is Leveraging Thought Leadership. Today I'm really excited. I get to speak to Kim Scott. She's the author of Radical Candor and Radical Respect. She and Jason Rosseff co-founded a company to help leaders build more radically candid organizations. Kim was a CEO coach at companies like Dropbox, Baltrix, Twitter, and other tech companies. She was a member of the faculty at Apple University and before that led AdSense, YouTube, and DoubleClick teams at Google. And obviously she's also managed— and I love this one— a pediatric clinic in Kosovo, started a diamond cutting factory in Moscow. And in addition to her work on the radical side, she's the author of 3 novels: Virtual Love, The Measurement Problem, and the House Husband, which we will not necessarily get into today. So, and I'm a, you know, I feel like back in the days of Larry King, longtime listener, first-time caller. So I'm a big fan for a long time. So it's a pleasure to have you on, Kim.

Well, thank you so much. I've been looking forward to our conversation.

So obviously everybody wants to know how to start a pediatric clinic in Kosovo. So that's not what we're going to talk about today. That's another show somewhere, I'm sure.

Yeah.

So tell me about your journey because, you know, radical candor has become such a thing. It's part of the lexicon. It's, I don't know if it's quite emotional intelligence, but we talk, I, you just hear it all the time. And how did it happen? Like, how did this, how did it come to be? What's the origin story and what's the business model?

Yeah. Well, you know, I had a strange motivation for my career as an operating executive. I went to business. Okay. I went to business school as a way to subsidize my novel writing habit. So my first love is writing novels, but I did not think that I could, that I could make a living writing.

So is this the— well, the irony is that this is the antidote to the vow of poverty for fiction writing.

Yeah.

The only thing that might be a close second place to a vow of poverty as fiction writing is nonfiction writing.

Yeah, yeah, yeah. Exactly. Exactly. Well, so, so it's interesting. I read a lot of books that, that great writers have written. And one— now I can't even remember who it was. It was some, uh, it was a, a writer who's a man, and he said the most important thing you could do to become a writer is marry someone who can support you. But which is, which is cool advice from a man, but like, from a woman in 1980, like, I just wasn't gonna— I wasn't gonna take that advice. And so I decided I would earn as much money as quickly as possible so that I could then quit and write. And so I went through some of my career sort of feeling like my job was about 100% external validation. And then I would write on the side, which got no external validation because not only, you know, did I not get— I didn't get any money. I got— I had a stack of rejection letters for all the novels that I wrote.

Right.

And so it was 100% internal validation, 0% external validation. And then when I had this great coach when I was working at Google and he described being on an airplane with his— this is a long-winded answer to your question, but he described being on an airplane with his 4 sons under the age of 10.

Yeah, that sounds like fun.

Yeah. And it was stuck on the tarmac. And so he was miserable. And he said, in order to be present, it didn't mean wishing I was somewhere else. It was like, how can I express the best part of who I am, where I am, what's going on? And so I decided that I needed to bring all of the, you know, all of the intrinsic motivation that I brought to my writing to my work. And then I started enjoying my work a lot more.

Funny how that happens.

Yeah, funny how that works. It was good advice. And then I got some advice from another mentor. Once I left Google, I went to Apple. I was designing this class called Managing at Apple, and I was— one of the people who helped me design that class was Andy Grove, who, who had been the CEO of Intel for a long time. And he said he too started out his career wanting to be a writer when he was young. He wrote short stories and then obviously went on to do other things.

Right.

But he said, why don't you write a book about management? Because management is very much— it's got all the elements of the drama of the novel.

Yeah. And, uh, there's an audience. Yeah, there's a market.

Yeah, yeah. And so I wrote the book, but I didn't even think I would sell Radical Candor. I started writing it as I was coaching. I wound up, okay, leaving Apple, and I became the the coach for the CEO of Twitter. And then, and then once that happened, a lot of people wanted me to be their coach. And so I wound up writing Radical Candor really in the context of helping them. But also a lot of people were asking me to be their coach and I'm a human being. I don't scale. And so I was writing the book to share what I knew with other people. And then a friend of mine convinced me to try to get it published and the rest is history. Yeah. So there you go.

So you wrote it, but you didn't have this grandiose vision of then it will become training, consulting, you know, all the other derivatives.

No, no, no.

How did that—

how did that—

again, yeah. So, so, so you write it, you, you— well, one is you hit a nerve, right? Yeah. Like there's lots of books on management that sit in the, the pile of mediocrity.

Yes.

In the bookstore and sell 70 copies over their lifespan.

Yeah.

But why do you think Radical Candor took off the way it did and, and how it did?

Yeah, so I think most people who write, most people who have been operating executives are not interested in writing. Like, the, like, the, the overlap in that Venn diagram is very small.

And while that— well, I would, I would, I would push on that slightly, saying at the point when they are operating executives, many of them after the fact want to write to, you know, encapsulate their stories and their vision and all that sort of stuff. But when you're running a multi-billion dollar company, you probably don't, you know, aren't looking for other things to do to fill in the time that you don't have anyway.

Yes. And I think more importantly than that, if you ask most operating executives how much time they spend reading novels and writing novels, it's zero. And I think, I think actually the fiction aspect of it was really important. The fiction reading and writing that I've done. In the past. So, so I think part of it is— part of the reason why the book worked is that I really love writing for its own sake, not just to like share my legacy as the, you know, but I actually like the writing part, uh, and was actually interested in the, the thing that really motivated me. Like, the reason I left Google and went to Apple was that I realized I really didn't care at all about cost per click. The thing that interested me in my job—

by the way, if you're at Google and you don't care about that, you probably shouldn't be at Google.

Yeah, yeah, yeah. I don't know. I mean, I think cost per click was taking care of itself, really.

Yeah, right, right.

It was doing really well. But the thing that motivated me and I think the reason why I was effective at Google was thinking about how do you build teams, how do you set up structures so that people can do the best work of their lives and build good relationships. So that was the thing that really interested me. And what Apple offered that Google didn't was an opportunity to spend full-time thinking about, you know, how are we gonna— how do you manage people? So I think it also, the experience spending 2.5 years at Apple just thinking about teaching people how to manage was also really helpful. Like, I think most people— Yeah, most people don't spend— go from leading a team of 7.

But go back to why do you think that? Why did it take off? Because it wasn't like you went after this with a billion-dollar marketing budget and—

No, no, no, no.

I had whatever, like what was going on either at that moment in time in the business universe or why did it— why did it hit?

Yeah.

Why do you think it hit?

So that was a long-winded way of saying— I think part of the reason why it hit is that it's well-written. It's a good book.

Okay, good. No, but okay, but that— but I think that's important because there's so many books out for so many reasons that just aren't—

they're not especially well-written. Yeah. Yeah.

Okay.

I think also I was genuinely interested from the time I started my first management role in, in 1991. I was generally genuinely interested in the management part of, of building a business.

Okay.

And, and most people aren't. Like, I went to business school, and how many classes did I take about managing people? Zero. Not right. Nothing. The thing I did learn at business school is that a good 2x2 framework can solve all the world's problems. And I think the 2x2 framework in Radical Candor is part of what struck a nerve. Uh, and the 2x2 framework is sort of vertical line is care personally, horizontal line is challenge And when you can do both, it's radical candor. And that's really important because I think we so often feel like we have to choose between being effective and being nice. And you don't. You can do both, you know. And I think that's part of why it struck a nerve. It kind of dispelled the nice, nice people finish last myth. That is, that is really out there. I think a lot of people hate the idea of becoming a manager because it's like if you think about all the relationships in our lives, most of them have a positive valence, you know, family relationships, parent-child, like, I mean, obviously there are bad relationships between parents and children, but mostly they're positive valence. But if you think about the relationship between a boss and their direct report, It's a very negative— even the word boss, manager, leader, all of those words have negative connotations. And yet all of us have managers and a lot of us become managers. And that was one of the things I really set out to fix. So I think it hit a nerve also because we've come to a moment in our economy where people are unwilling to pay the asshole tax. You know, they're not willing to work for someone who treats them miserably.

Yeah.

And, uh, yeah.

So no, and I think that's important because I think, you know, you and I are probably similar age. When we were coming up, it wasn't really an option. Like, if you got stuck in the killer job and the boss was a jackass, it just—

that was your—

sometimes actually they were synonymous. Like, yeah, the best, the best opportunities came working for toxic people, which now the culture has changed. If you're enjoying this episode of Leveraging Thought Leadership, please make sure to subscribe. If you'd like to help spread the word about our podcast, please leave a 5-star review at ratethispodcast.com/LTL and share it with your friends. We're available on Apple Podcasts and on all major listening apps, as well as at thoughtleadershipleverage.com. Forward slash podcast. So I, I wanna segue into, okay, so now it resonates, it's meeting a need, there's an issue, like, okay, the culture's changing, it's well written. Let's get to the business models because, okay, now we're adding, this is like 3D chess, right? Yeah.

Okay.

So first write a really good business book. So now we've just eliminated 85%, 90%, right? Then have it resonate.

You have to like intrinsically love writing to write a great book. If you don't love writing, don't do it because it's probably not gonna be worth your time.

But, but the next piece, but where I was going is, okay, so now there are, there are a smaller subset of the population of business books that are well-written, good business books.

Yeah.

And then click again, there's a smaller, smaller, I would argue, pick a number, 50, 100, 200, whatever, that have actually been the basis for launching really nice businesses.

Yeah.

You're in that special place.

Yeah.

Right. So how, what was the strategy? How did that happen? How did you figure out, wait, I can take the same ideas in this book and turn it into training or coaching or consulting or what, what was that? 'Cause the business side of it has taken off, obviously.

Yes, it has. And, and I, here's a true confession. I had no strategy. I had no idea this was even a thing. In fact, There was one day when I was— I had been asked to give 3 talks in San Francisco, and by the end of that day, 3 talks is probably too, too many in one day for me. And so after the third one, I was sort of— I literally went back into the green room and I was lying on the floor. I was just exhausted. And this other guy who was also speaking, Mike Robbins.

Oh, yeah.

I love Mike.

Yeah.

So Mike was really— he did what a good upstander does. He said, well, how much are you charging? This must have been a good day for you. And I then I sat up, I was like, charging? What do you mean? Oh, I didn't even know you could charge to give a talk. You know, I had no idea that that was a thing.

Okay, so two things that, that deflate me is, okay, there's no strategy and I didn't know you can charge for speaking. So we're going to call you the accidental, commercially successful thought leader.

Yes, it was. It was absolutely. And frankly, I like I don't even like the word thought leader. Like, that's not how I think of myself. So, but, but I do really care about these ideas and I do want people— I do. I think bad bosses create so much misery in the world. And, and if my— if the thing that I can contribute to the world is to decrease that misery a little bit by helping bosses be better, because I think most bad bosses are not actually bad people. They just don't know how to be a boss because we're not teaching them. So that's the problem I'm hoping to, to solve with the business. So anyway, then I started charging and this is a true story. So and then I asked him how much he charged. I was like, oh my gosh, this is a racket.

Yeah.

And I kept increasing my rate until I— until people stopped asking me to talk. And but then there were— then even then I was overwhelmed. I was asked to do more talks than I could possibly do.

But this guy— but this goes back to the coaching issue of it doesn't scale, right?

So No, it doesn't.

If you're going to be exhausted lying at the end, you know, on the floor of a green room for doing 3 talks, it's better to make 50 or 100 grand that day doing it than making nothing.

Yeah, exactly. Exactly. But, but I wanted— it wasn't really about making money. I wanted to spread the ideas. And so a couple of people reached out to me and they said, we really like Radical Candor. And these were people who had been serious operating executives. And at this time it was all kind of happening in Silicon Valley. Yeah. And, and they, they said, I'd love to give some of these talks. And I was like, oh, okay. So I was sitting at breakfast with my children who at the time were like, like in third grade or so. They were really young. And, and I said, well, I'm going to start letting other people do that. I'm going to teach a few other people to do these talks. How much should I— how much of the money should I give them?

And wait, so your board of advisors is, is 7-year-olds?

Yeah. And my husband. I mean, we're just sort of chatting and. Okay. And my daughter says, well, why would you give them any of the money? I'm like, well, they won't do it. And also, I want to spend more time with you all. You know, I don't want to travel all the time. And they— and then they were like, oh, we'll give them all the money. And I said, well, if I give them all the money, then I can't buy you all toys. And then my daughter thought about it, my son thought about it, and they sort of talked between themselves and they said, give them 70% and we'll keep 30%.

So is that how you came to that?

That's how we started. That was how we started. Yes. So I know.

So that's, that's like strike 4. No. So strike 4. So, so what was it? You're not into strategy. Your board of advisors is 7 and probably still drinking juice boxes.

Yeah. You're giving away 70% of the revenue and you're you're not charging for speaking.

So yeah, yeah.

So, well, now I'm charging for speaking.

Yeah.

So, and then I wound up starting, uh, starting a software company, not speaking. I wasn't thinking of like speaking as the main thing. And the software, we built one app, we built another app, we built a third app. They all failed, uh, to try to help people be more radically candid because I wanted to scale this thing, right?

And oh, I thought because your programmers might have been the classmates of your board of advisors, they might not— other— okay, I just Double-checking that.

No, because— no, I had lunch.

Child labor laws.

Yeah. The problem here was I had lunch with a colleague of mine and I was talking to him about the idea of starting this business, this software business. And by the end of lunch, he was like begging to invest $2 million in the idea, which was a lot.

Well, other than the— in Silicon Valley, right?

Yeah, yeah, yeah. Anyway, I should not have moved so fast on that one. Sheryl Sandberg, when she was my My boss at Google said, your biggest problem is you move too fast. And that was definitely a problem on that idea. So anyway, we started this company, the company failed, and finally I accepted, okay, what we have is a— is a— what does work are the talks and the workshops. And, uh, and I wrote a blog post about that because what, what Radical Candor and also Radical Respect, the next book I wrote, are really about. Yeah, they're really about putting your phone away, putting your devices away, shutting down all your apps, and having real human conversations with people. And so, so the talks and the workshops are really important for that. And, uh, and I wrote a blog post about that, and Jason Rosoff read it and reached out to me, and he said, let's start a company that's doing what you should have been doing all along. So that's how it came to happen. Uh, I love Following—

this is great. So I, I love getting under the hood with you and understanding the story and, and, uh, how it came to be. And, uh, this has been great, really. Not what I would have guessed any of the answers to any of the questions were. So that's kind of cool because they're, they're, you know, there are certain things that are manufactured content, I call it. Like, oh, it's designed to— oh, like, we're in a work-from-home environment, let me be the work-from-home specialist.

Yeah, that's not what this is.

Yeah, this was, was, but, but I think that, you know, the, you can't underestimate the good writing. And, and I think also that you were really good at listening to how it landed.

Mm-hmm.

Right. And, and, and where it could go next and what folks could do with it. Um, and I, and I like the idea of, of realizing you can get paid to do, a, a lot of thought leaders don't realize that there's lots of things that they do, uh, before they do this professionally. That someone will pay them a ridiculous amount of money. Like, wait, keynote speaking? You paid that much to do that for 45 minutes? Like, yeah, like, yeah, what?

But, but I had to have had a lifetime of writing and a lifetime of being the operating executive before, you know, on something to write, right?

And something to draw from, right? Yeah, that's, that's exactly right. Yeah. Well, it's been great. Appreciate your time. It's been a pleasure to talk to you. And, uh, A, thank you for all the work you've put out into the world. That's cool. And thanks for spending some time with me today. Appreciate it.

Thank you. Really enjoyed the conversation.

To learn more about Thought Leadership Leverage, please visit our website at thoughtleadershipleverage.com. To reach me directly, feel free to email me at peter@thoughtleadershipleverage.com. And please subscribe to Leveraging Thought Leadership on iTunes or your favorite podcast app to get your weekly episode automatically.