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Radical Candor: Communication at Work

20 Oct 2026 · 44m · 23 chapters

Episode artwork

How can you confront a bullying boss without losing your job? (with Christina Wing)

In short

How to confront a bullying boss without getting fired, using “radical candor” (direct, respectful challenge) plus emotional intelligence and ongoing human conversation—also extending to difficult workplace, race/religion/politics, and money/financial transparency.

Guest background

Christina Wing is the author of Unspeakable. She previously worked on Wall Street at an investment bank in New York City soon after graduating (from a “tier three” college), later becoming a Harvard Business School teacher.

Key claims

Confront directly “above the line,” not by going around the boss; difficult moments aren’t the same as difficult conversations—successful ones require a shared forward-looking goal; silence endorses harm; people need safe, respectful dialogue (not “colorblind” thinking); and emotional intelligence/eye contact matter more than technical output, especially in an AI era.

Notable examples

Her first Wall Street boss repeatedly called her stupid and refused to teach; she asked for reassignment, then he shifted to teaching after she gave him a chance. She also discusses learning that “colorblind” is offensive and advising families to disclose enough financial reality for strategy and responsibility.

Written by AI. May contain mistakes.

Chapters

0:00

The Importance of Emotional Intelligence

Understand why emotional intelligence is crucial in a tech-driven world.

“What I will die on the mat for is ability to converse with people and have emotional intelligence is what's going to survive and thrive in this AI situation.”
1:00

Bullying Experience on Wall Street

Christina shares her story of encountering a bullying boss at her first job.

“I have been looking forward to it all day long, and I'm so grateful to you for writing this book.”
1:31

Facing the Bully: Christina's Challenge

Learn how Christina confronted her boss's bullying behavior directly.

“So describe what the boss was doing to you, if you don't mind, and then describe your response.”
2:32

The Decision to Speak Up

Explore Christina's thought process as she decided to address her boss.

“and I have this boss who hates me, just fundamentally hates me.”
3:56

A Turning Point in the Relationship

Discover how a direct conversation shifted Christina's relationship with her boss.

“And my fellow analysts were all like, you know, three months out of college.”
4:48

Lessons Learned from the Experience

Reflect on what Christina learned about mentorship and personal growth.

“Like there was one thing you wrote, as I recall, he said, you can't do that because then they'll think I'm not a good mentor.”
7:14

The Reality of Workplace Dynamics

Examine the complexities of workplace interactions and expectations.

“And I noticed something that I didn't write in the book.”
9:11

The Impact of Common Goals

Understand how shared goals can change workplace relationships for the better.

“And he taught me that I can learn from people that I don't have a lot in common with or that I don't like initially.”
12:46

Cultural Curiosity and Communication

Explore the importance of cultural curiosity in fostering better communication.

“He would give me a printout of a model and tell me to build it.”
14:01

Cultural Sensitivity and Curiosity in Conversations

Explore the importance of understanding different cultural holidays and the lack of curiosity in current conversations.

“And we don't talk about why is Diwali really important to the Indian culture?”
Show all 23 chapters
16:49

Understanding Difficult Conversations

Learn about distinguishing between difficult moments and difficult conversations and the importance of empathy.

“You know, it's so interesting because I had a speaker in today to my MBA classroom and he's very accomplished in business, but he was nervous before he was speaking in front of my students.”
19:51

The Necessity of Challenging Beliefs

Discuss the value of challenging beliefs and the importance of understanding opposing perspectives.

“The circumstances that are presented to me are changing daily.”
21:47

Addressing Race and Colorblindness

Examine the implications of colorblindness in conversations about race and the necessity for open dialogue.

“Our dads gave us a lot of great advice, but I think that was really bad advice.”
24:59

Navigating Difficult Conversations with Empathy

Learn how to approach difficult conversations with empathy and the significance of timing and preparation.

“Like, okay, what do you want to be called with all of the changes and how we refer to different sexual orientation?”
27:37

Feedback and Workplace Communication

Discover the importance of feedback in workplace communication and how evaluations could foster better understanding.

“Thanksgiving because I'm building all this up and I'm like okay wait a minute Thursday of Thanksgiving, whether you celebrate it or not, is not the time.”
28:00

Building Real Communication

Explore the need for better communication in workplaces and the impact of social media on communication skills.

“We're not trying to burn our way out of the jungle here.”
29:06

Changing Expectations of Communication

Discuss how modern communication expectations have shifted with technology and the need for real human interaction.

“I mean, the truth is I'm as addicted to my phone as my children are to their phone.”
30:48

The Importance of Human Interaction

Highlight the significance of emotional intelligence and human interaction in the age of AI.

“And by the way, if we stick to a culture of turnaround time in an hour, you're getting a lot of false positives.”
33:29

Family Businesses and Financial Literacy

Discuss the importance of financial transparency within family businesses and the need for financial literacy education.

“You have this incredible anecdote about this family business and nobody knew what the family net worth was.”
38:08

The Cost of Silence in Conversations

Examine the risks of not discussing difficult topics and the societal impact of silence.

“They know way more about how to access information.”
40:04

The Journey to Authentic Connections

Encourage openness for deeper connections and self-awareness in personal relationships.

“That does not mean it's going to be easy.”
42:08

The Importance of Authenticity in Relationships

Learn how being open and authentic can lead to better relationships.

“and you want to have a broader perspective, you have to let other people know who you are.”
43:10

Inspiration and Collaboration

Discover the power of collaboration and confronting discomfort to foster change.

“I hope that everybody listening will read your book, Unspeakable, and then they'll go out and speak it.”
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Transcript

Automatic transcript. May contain errors.

0:00What I will die on the mat for is ability to converse with people and have emotional intelligence is what's going to survive and thrive in this AI situation. And so the student or the worker that is really good at doing everything but can't look anyone in the eye, they might get misplaced. But the person that actually understands to take this great information AI can put together for them, explain it, execute it, understand how it's going to work with humans, they're going to win.

0:41Hello, everybody, and welcome to the Radical Sabbatical. I, Kim Scott, am here talking to the authors of books I love, and today I'm thrilled to be with Christina Wing, who wrote Unspeakable. Christina, welcome. Thank you so much for having me. I'm excited to talk to you. I have been looking forward to it all day long, and I'm so grateful to you for writing this book. I think it's going to help so many people in so many different aspects of life. I could talk to you about every page of the book, but I want to zero in on one story that especially spoke to me. So you tell a story about, was it your first job experience on Wall Street where you had a boss who was bullying you?

1:30Yes, it was my first job on Wall Street post-graduating from college. Okay. So describe what the boss was doing to you, if you don't mind, and then describe your response. Listeners ask all the time, what do I do if my boss is a bully? And my new answer is do what Christina did. So, I mean, to give a little bit of context, I was working at an investment bank in New York City, and I graduated from what was probably considered a tier three college. Texas and so I already had imposter syndrome. I bet you probably weren't treated super respectfully. It's hard to move to New York City and have a southern accent.

2:16It is hard for that and also when you know I'm old now when I moved there women had to wear skirts and pantyhose so we already had a dress code for the women and we go through training and I have this boss who hates me, just fundamentally hates me. And I did not know how to do the modeling that he wanted me to do, financial modeling, but that's not why I was hired. You're hired to go through a training program and learn and use everything. You're supposed to teach you to model. And he told me repeatedly for a while how stupid I was. How could I not get this? And I would stay up all night. This is before Claude and all these things.

3:04You have a usual brain. And try to figure it out. And I finally came to the conclusion that either I had to quit or I had to make a change. And I really didn't know how do you complain about your boss. The interesting thing is the man, because they were all men, the man on top of the man that I was working for was the world's nicest person. Yes. But I didn't want to go around my boss because I had been told, don't go around. And so finally, when I hit which end, I basically went to him and told him. So you went to your boss, not your boss's boss. I went to my boss, not my boss's boss. And I said, you don't want to teach me.

3:48I'm not getting better, and we're both losing, and so I'm going to ask to be reassigned tomorrow. And I genuinely meant it. Yeah. And my fellow analysts were all like, you know, three months out of college. We were like trying to pay our rent. They were like, you're going to get fired. And I was like, I'm going to get fired no matter what because I'm not going to ever get better. Right. And it gave him the awakening he needed. I don't know why. So you said this to him. What was the first thing he said back to you? You said, I'm going to ask to be reassigned tomorrow. What was his, like, what was the initial?

4:28His initial reaction was basically like, F you. You're entitled, you're this, you know, you didn't walk to school and snow both ways, like all those things. Yeah. And I just said to him, listen, I need a teacher. I have skills, but I don't have these skills. and I need a teacher and I'm moving forward with it. Yeah. Like there was one thing you wrote, as I recall, he said, you can't do that because then they'll think I'm not a good mentor. Right. He said something along those lines. What was your response to that? He didn't say that until I was out of his. So I was down in a cubicle. He was in a elevated cubicle, an office, but kind of.

5:11And as I was already gone, he was like, you just can't do that because they're going to think I'm not a good mentor. And I remember looking at him and thinking, you suck as a mentor. That would be right. Like, I got the booby prize being assigned to you. Yeah. And I, you know, went about, finished my day, which was probably midnight back in those days, and went home and thought to myself, I'm going to get fired because I am a woman from the South that really doesn't know what she's doing in comparison. My analyst class was in the 30s. Everyone was Ivy League or close to. And we didn't have email even yet.

5:57And the next morning when I came in, he left a note on my chair that said, I want to teach you. What I don't know is how he got there from, let's call it 7 o 'clock at night. I don't know if he went home and talked to somebody else and said, you're a bully. Yeah, how he went from F you to I want to teach you. That was a big, in 12 hours he got there. And I also don't know if, I'll never know, if 10 other people had complained about him. Yeah. What I do know is he changed his behavior and he rolled up his sleeves. And ironically, you know, he was in Harvard Business School alum. It's ironic because I teach there now and went there.

6:43But he was so proud of that. And I remember I thought when I was going through this, I'm never freaking going to Harvard. They're assholes. Excuse my language. Yes, yes. But he changed his behavior and it didn't seem fake. He actually sat down. He worked with me. He taught me. He stopped calling me stupid. He'd still roll his eyes at me. And I think he was a little offended. I didn't get up to speed faster. But as I got better, he got better. And I noticed something that I didn't write in the book. I've always been aware of likability. Yeah. He wasn't very well liked in general. His likability went up with his peers of his associate group.

7:31And it sounds so trite, but I think that's part of managing up. And the consequences of me being fired would have been really severe in that moment. But the consequences of me working there for two years with somebody that didn't want to work with me and didn't want to teach me would be more severe. Because I probably would have left thinking I could never understand finance. Instead, I got up to speed on finance. He was really good. It was like the worst mismatch. Proficient in finance, no nothing. And he couldn't bridge it. Once he bridged it, he bridged it with others. I saw it the next year.

8:13He was like, had a new mentor. He like was creating models and teaching. He found his way to work within the system. And so it's a happy ending. Do I want to hang out with him now? No. No. I mean, I'm sure it's not like you love him now. No. It's not like I'm writing him a love letter. But he did change. And I'm not saying I changed him. I'm saying maybe fear changed him of something else happening, a repercussion. But I got through to him. Yes. And I think the key to this is I went to him first. I gave him an opportunity. I frankly thought he wouldn't do anything except for sabotage me. And instead he leaned in.

8:57And I was a 23-year-old hothead at the time. And when I saw his note, part of me was like, forget this. I'm still doing it. But I leaned in and I worked with him. And he taught me a lot. Yeah. And he taught me that I can learn from people that I don't have a lot in common with or that I don't like initially. But when I left, I liked him. Yeah, yeah. There's so many things that I love about this story. One of the many things I love about the story, we sort of tend to, as individuals and maybe as society, do this toggle between what in Radical Canter I call obnoxious aggression and ruinous empathy.

9:38when I talk about ruinous empathy in the book radical candor I often talk about telling people who aren't doing a good job like there's the Bob story the guy who was smoking pot and doing messy work and I didn't tell him and that was ruinous empathy but I think one of the most dangerous forms of ruinous empathy right now is not confronting directly someone who's acting like a jerk. And it's hard to think of, like what you did was radical candor. And you maybe weren't at the tippy top of care personally with this guy, but you were above the line. You were going to give him the respect of telling him directly rather than going above his head, right?

10:17And you were going to challenge him directly. So excellent radical candor. I think I thought he deserved that respect based on what he had done to get to the position he was in. And so I wanted to give it one more chance. And I think the thing that's interesting is we sometimes think these actions are going to sabotage us for life. And when I was writing this story, I was thinking, how bad could it have been if I'd been fired? It would have been awful in the moment. But if my choice was to work with an a-hole or this, I might have been better off. But at the time, it felt huge. Yes. Where did you get the courage?

11:04If you had been fired, what would have happened? Would you have had to leave New York and go back to Texas? Did you not even have money for the airplane back to Texas? Where were you? did you have some some you know some money to fall back on so that you would have been okay if you got fired like like to what extent does financial security play into this i think that i think that people that um might google me might think i had financial security because my father was successful i had no financial security i was living you know month to month with two other roommates in a three bedroom where we put up a wall.

11:47If I was fired, I would have owed a month, I mean, a year of rent. I would have been humbled to my core because nobody else from my school was in New York City. And I don't know how I would have gotten another job right away. So it was a, it was a big risk, but I, I can't explain to you how sad I was for consecutive days thinking, am I stupid? Yes. I actually thought, am I, like, why am I not getting this? And as soon as he became better, I was like, I'm getting this fast. Yeah. This is cool. Yeah. If we both hadn't met, and I often wonder if I'd been transferred to another group, if I ever would have thought I had such a good educational experience at this place, because they, he, he, he was so tough, but he taught me finance in a way nobody's learned it.

12:45None of my peers were learning it that way. He would give me a printout of a model and tell me to build it. Everybody else is getting an Excel spreadsheet. Yeah, yeah. You had to build it from me. But he taught me. And once he invested in me, it was great. Yeah. So, you know, this was over 30 years ago now. I still remember his name vividly. And I can probably remember 10 people's name at that firm. And so, you know, what my young 23-year-old self didn't realize in the banking situation is we actually had a common goal. And the common goal was a good work product. Yes. I thought he wanted to destroy me and he thought probably she's stupid.

13:34I'll get someone else. But if you actually step back and said, let's have a good work goal of getting me up to speed so you can go do something bigger than watch me model. We couldn't move forward. But I didn't know that yet. But in today's day, you know, these students are studying wars. Almost every war has a religious component. Yet we don't talk about religion. Yeah. And, you know, we're in this cycle. We just had some Jewish holidays. We have a big Indian holiday coming up. We don't talk about it. And we don't talk about why is Diwali really important to the Indian culture? Why, you know, I think if you ask most non-Jewish people in the United States, what's the most important holiday to a Jewish person, they'd say Hanukkah.

14:24That's not the most important. we don't take the time to ask and learn and once you learn you're like oh my gosh happy new year that makes sense or whatever but we just don't do it because we're like oh that's religion i can't ask that all i know is it's rosh hashan and they all go home that's so wrong and you know i think in this culture of not talking about things we've lost our curiosity today because we've basically limited our safe conversations now are about food, Netflix, and sports teams. Basically, that's it. Even the weather is not safe to talk about. Even the weather isn't safe to talk about.

15:10And so how are we going to do things like in the United States, go through midterm elections? What are we going to evaluate these candidates on? food, Netflix, sports teams? No. We have to be able to talk. And most importantly, we have to listen. And, you know, I don't believe that difficult conversations should all be top-down. And I don't believe that having them bottom-up is easy, but I think they're sometimes the most effective. But what I will say is that we, as a society, have confused difficult moments with difficult conversations. Breaking up with a girlfriend, difficult moment. Firing somebody, difficult moment.

15:53We do not have a common goal. Sending your food. But you do have a common, even when you fire someone, you have a common goal. You want to treat that person with dignity and help them find their next job. But that is a, you don't have a common goal of how to work together going forward. Yes. You might have a common goal of empathy in that, but it's a difficult moment. Yes. It is not a difficult conversation where we have a common goal of a go forward. So like what I'm trying to distinguish is some are the ending of something and some are the go forward. Yes. And the ones that are go forward are the ones that should fit into your matrix because that empathy and love and everything is all part of something continuing.

16:39It's not ending. And I think we put them all in one bucket and we avoid them all. Yes. Yeah. And then we'll never get intimacy. We'll never collaborate if we don't. I mean, embrace the discomfort. We learn in discomfort. That is where we learn and grow. You know, it's so interesting because I had a speaker in today to my MBA classroom and he's very accomplished in business, but he was nervous before he was speaking in front of my students. And I said, that's great because you care. Yes. You care. Yes. Like, like caring about things like great. Be nervous. Yeah. And I think also being nervous, I think this is part of, part of the problem with part of the reason why we avoid taboo topics and maybe all topics.

17:35We but part of the reason why we why we avoid talking is that people want to get it right and i think i wish people could go into these conversations like being prepared to get it wrong in fact you're going to get it wrong if you go in thinking you're right you're you're now now you've handicapped yourself now now you're not going to i think that's the wrong no it's exactly the right word if you go into it thinking you want to win yes and you're wrong you're going in looking for a win-win and by the way if the first conversation that you have about this feels like a win you've already lost yes because the other person's just agreeing i mean these are not moments these are continuation of conversations it's unearthing something with a goal for changed behavior that doesn't mean like a coffee at starbucks is going to end with that yeah you know like my husband and i argue about how to do the dishwasher forks up or forks down right and you know these are in my house difficult moments and difficult conversations you have to come to a common thing and then agree and then move forward we both have the same goal we want clean dishes you have to listen and be like you know what you're right yeah or i think you're wrong but i'll do it your way because i love you exactly and like enough so i mean i think when you go into anything with a litigator's position and this is why when i'm asked about the book they're like oh you put role-playing in this i'm like don't over role-play yeah because when you over role-play you get pre-pissed you're like I know what Kim's gonna say and I'm gonna say this and you you start to do that thing where you like are forming your sentence before they're done talking you role play for yourself so that you choose better words but don't role play to assume you know all the answers on the other side because then you just fail and I mean let me tell you I fail at this all the time I'm trying to get better.

19:51I think we all are. The circumstances that are presented to me are changing daily. And so we all have to engage in leaning in and realizing sometimes the best thing that you can do is change your mind. Yes. How powerful is that? Yes. Or even if you don't change your mind, you understand, and even if you disagree, you understand why the person thinks what they want. Like John Stuart Mill said that a belief that never gets challenged turns into a prejudice. So I can believe X, you can believe Y. We can have a very fruitful conversation, even if you don't change your mind and I don't change my mind.

20:35because now I understand what I think and why I think what now I'm maybe I'm dug in even deeper but I understand my own beliefs more deeply than I did before our disagreement and that has real value but you also understand the other perspective yes and and you know the person you're having this conversation with isn't the only person with that perspective and so understanding that perspective Even if you didn't change your mind, you might change your approach a little bit or like start to understand how to incorporate the other. And, you know, we're not running dictatorships as leaders. Leaders are people that others want to follow.

21:21Right. And for me, I want to follow leaders that admit they're wrong, that change their perspective sometimes, stick to their core values, but understand how their values are implemented can vary. Yes. Yes. So let's go back to race, religion, and politics. The easy ones. The easy ones. during I think it was during it was 2020 it was during the pandemic and I remember somebody reached out to me a black woman who was who was working on a number of initiatives at her law firm and sort of helping people understand this moment and and she and I had this great conversation about how both of our fathers raised us in very different circumstances very different fathers to never talk about race, religion, or politics at work.

22:16And I think that that was bad. I love my father. She loves her father. Our dads gave us a lot of great advice, but I think that was really bad advice. I think that's part of how we've gotten to this moment where we can't talk to each other almost about anything. And so I think going into these conversations, being willing and interested in, And I'm going to show you this unconditional respect for our shared humanity, even though we have all these differences. And we're going to talk about these differences so that I know where your raw nerves are. You know where my raw nerves are. And maybe we can avoid those.

22:58But if we can't talk about these things, then we're not even aware when we're saying something that's incredibly offensive or upsetting to someone. So I learned saying that you're colorblind is incredibly offensive. Yes. And I learned that the hard way in the sense that it was something I emulated from my father and others where, you know, I'm colorblind. I like see everybody the same. And a very elegant black man in my 30s said, that is so offensive that you said that. Because I don't want you to be colorblind. I want you to understand we have different colors of skin, but then move forward. And I thought of this like so many times over the years.

23:50But about eight years ago, we had a little bit of a racial issue that happened on campus where a nasty email went around. And a bunch of my students of color wanted to come over to my house and talk about it. And my first instinct was to call on a great friend of mine of color. And then I thought to myself, what am I doing? They want to come see me. I shouldn't bring in a person of color to address them. And that was when I was, so I learned this lesson at 30 about not saying colorblind. I learned at 42, like, okay, they're asking to come see me. Like, why would I bring a person of color to my home thinking that would give comfort?

24:35yes they want to talk to you they want to talk to me what they really wanted is a safe space and they wanted me to listen and my husband and i provided that and it was great but i think i put my foot in it you know multiple times a year um not with bad intentions but with new heightened emotion that is growing for all these categories because nobody talks about anything and so then then something that is said becomes attacked and so as leaders or people in a position you just retract my view is i'm trying to talk about it more i you know if somebody has a issue or something going on i'm like explain that to me what does it mean like okay so let's go back to the horrible thing we did with blacks they're all african americans they're not african americans yeah they're black.

25:34Like, okay, what do you want to be called with all of the changes and how we refer to different sexual orientation? I might screw up. Tell me how not to teach me. And you know, I've never met anyone that has a difference that they want to explain or even not want to explain. If you ask them a question, shies away from it. Yeah. Yeah. And I think that both like your students and also this black man who educated you about the problem with colorblind they were doing for you what you were doing for that boss who and you were open to it but that's learning he easily could have looked at me and been like her intention is good and so we leave it yeah no no and so i think you know things like you do kim with your books i i think radical candor the name made people in some ways think be mean yes and that's not what you meant what you meant was get in the arena and like show your love and your protection of an organization at least that's how I read it yeah your yeah your protection of your shared results yeah you know your protection of the shared relationship but you got to get away from it being mean yes yes I could have called it compassionate candor but but i also read it from a perspective of never thinking it was mean but i think some people like the fear i have with my book and i say this frequently is i don't want everybody jumping out of their car and having difficult conversations about everything yeah for no good reason it's about timing it's about empathy it's about awareness on both sides and it's about this common goal that you're not going to give up because those people you initiate this conversation with are going to be like no and you stick with it and so you know I'm like this is not like a license to talk about everything and I get very nervous when my students go home for Thanksgiving because I'm building all this up and I'm like okay wait a minute Thursday of Thanksgiving, whether you celebrate it or not, is not the time.

27:50Nor is Sunday before you run to the plane. If you're going to have one of these conversations, you have to give advance notice. You have to do this. And they're like, I'm getting in there. I'm like, no, no, no, no. We're not trying to burn our way out of the jungle here. We're trying to build real communication. But I think we can get better. Yes, we must get better. And listen. yes with radical canter it's about soliciting feedback before giving it and giving more praise than criticism you know that's another part of the message that tends to get lost i i love that because i think your book should have been adopted into hr evaluations in a way that was because right now in hr evaluations evaluate your manager evaluate your team evaluate yourself i think there should be like the evaluation of the manager as it affects you as well yes and um like what is good that she or he does and and how it could be i think that if we could get there we could even bridge some of this i do think actually a lot of what happens in the workplace a lot of what managers do is unfinished business from childhood and education.

29:09Absolutely. And I think this, the past 10 years of social media and all, you know, sort of now AI and Zoom school during the pandemic, I think that there's a whole generation of kids who have not learned to talk to each other and or who didn't build the same levels of skills that were built before. And it's really not just kids. I mean, the truth is I'm as addicted to my phone as my children are to their phone. We're all addicted. We're all equally guilty of being addicted to these things. You know what's so interesting, Kim? I started teaching at HBS 12 years ago. and since I had a phone I don't think I had ever gone 80 minutes without looking at it and that's the length of my class so I can't look at my phone yeah everywhere else like board meetings whatever I'd always glance and what happened is my mother wrote me like three months into my first semester did I do something to offend you and that's because I wasn't getting back to her within minutes of her texting me.

30:23And I thought to myself, I have to change how people interact with me and how they think my behavior is going to be. And it's been so freeing because now I don't get any messages like that from anyone that are saying, I wrote you 10 minutes ago, but I got those before. And so I think one of the things is not only do we have to kind of change this culture of convenience and silence, we have to change the expectations of our loved ones that just because you don't write back and give a thumbs up doesn't mean you don't agree. You might be at a movie. You might be getting an MRI. You might be doing something.

31:09But we instantly, as the sender, think something's wrong because we haven't gotten a response and so we have to change yes i agree i agree you know my first job at google was basically managing uh an email it wasn't a call center it was an email center and so there was you know there was an expectation of turnaround times right and and our expectation was 24 hours like like you should not be expected to have a turnaround time in your personal life of anything faster than 72 hours, in my opinion. And by the way, if we stick to a culture of turnaround time in an hour, you're getting a lot of false positives.

31:51Yes, I'd love to go to that. And then in like two days, I'm like, I can't go to that. Let's be more conscious of how we communicate to each other. Let's be more thoughtful of what we put out there. Listen, I'm all still for, like, I have three dogs, forward a dog picture, do whatever. But anything that requires like an actual real answer, let the person you sent it to digest it on their side and give you a real answer. Yes. The whole point of Radical Candor is to put your phone away, shut your computer, go look someone in the eye and have a real human conversation. So that really, I mean, is what your book is about, I think, is having these real human conversations about these difficult topics.

32:36And, you know, with AI and all the other changes, and it's funny because I have kids that are starting their careers and they're like, there's never been anything like this. And I'm like, well, you know, your parents graduated from business school and dot-com started. And, you know, this happened in finance. Like, we have to continue to understand the values and the characteristics that are going to make us stand out. What I will die on the mat for is ability to converse with people and have emotional intelligence is what's going to survive and thrive in this AI situation. And so the student or the worker that is really good at doing everything but can't look anyone in the eye, they might get misplaced.

33:29misplaced but the person that actually understands to take this great information ai can put together for them explain it execute it understand how it's going to work with humans they're going to win now's the time though yeah to like reinvest in human interaction yes so you have such good advice let's talk about money so how do you help in particular family businesses. We're talking about money. You have this incredible anecdote about this family business and nobody knew what the family net worth was. Kim, that story was so crazy because in this family, for your listeners, they had the fortitude to have a family meeting, to bring in outside advisors and to talk about the strategy that the family was going to pursue.

34:23Would they stay in the industry they're in? Would they go into other industries? Would they do startup where they were they gonna invest yeah and when we started the meeting i just had a feeling that people didn't have the same level of transparency and i was like everybody write down on the index card anonymously what you think the net worth was and it ranged so big that i couldn't like 10x 10x that they would fly us across the pond to do this i'm like how are we going to set strategy for anything when no one knows what's possible. Yeah. So one person in the family thinks it's a billion dollar business and the other thinks it's a hundred million or 25 million.

35:06And it's like, how are we even talking about some of these initiatives? And it led me to this, um, like feeling that sometimes disclosing wealth fears, you know, people say, I don't want my kids you know, because they'll lack motivation. I'm like, screw that. You don't have to tell them they're getting the money, but tell them what's there and what their responsibility is. So, you know, if you go join Apple and it's worth X billion dollars, doesn't mean you, Kim, are getting that money. You know what the company's net worth is, their sales, the possibility to invest in R &D. And so people have gotten so bizarrely shy about economics that children now, we have many families we work with that have children getting married.

35:58They don't know how to get a mortgage for their house. They don't understand house payments. They don't understand compounding. They don't understand the 18 % on their credit cards. It is criminal that we don't talk about money more. We have to decouple, not talking about money from a perspective of what are you getting, from basic education. Yeah, financial literacy. Financial literacy is like nowhere. And then on top of it to double down, at least in some of the family businesses, everybody else knows, but you don't know. And that's akin to like, you know, being an owner of a sports team and finding your star was traded, you know, in the press.

36:48Bad, bad. Like, I'm an owner. Tell me before the press knows. So my perspective on money, and listen, I have three kids and I could get better as well. Explain to them what there is. explain to them how they can help with the responsibility and possibly access it that doesn't mean explaining to them what they might get if you're worried about that who knows plus you can change your mind a hundred times but if you you know the best is when families are like well i want everybody to work with me well i don't want them to know what we have and i'm like okay great so yeah your kid goes to a great college how would you feel if they call you up and say dad I got a job at McKinsey.

37:37Where are you going to work? They won't tell me. What are you going to get paid? They won't tell me. Okay, take it. Like, no. Like, there are basic things. Like, you get paid for a job. So, I'm a big believer in talking about money. I'm not a big believer in declaring inheritance early. I think that's silly. Talking about it. And if we think these kids aren't zillowing every house, every everything. Oh, yeah. They know way more than we do. They know way less. They know way more about how to access information. At least give them the transparency. Yes. It's mine. Yes. And I think also acknowledge, I mean, part of it is that our economy right now is just, it's profoundly unfair.

38:25I'd say it in a slightly different way in that we don't want to acknowledge the power of money to access opportunity and other things. And that is a huge disservice. Yes. We don't understand causal effects. And we start to think that the people with this money actually might be smart in what they're saying, like the microphone. Right. Right. We have to acknowledge we believe in capitalism and we want people to make money. That doesn't mean that they should have a societal voice based on how much they have. Yes. People are good at certain things, but not everything. And we've assigned, I think, between social media and reality TV and all these things, we've assigned responsibility to wealthy people being really smart about everything.

39:22Absolutely not. Absolutely not. And so that assigned responsibility has to go away. I think capitalism has to come back in as a good word, not a bad word. Capitalism has become a bad word because we think of it as negative social influence instead of creating value. And so, you know, we need all what's, but we need to talk about it. Yes, yes, exactly. so so profoundly agree and i think that there's this feeling this false feeling that being silent about all these things is safer and i think audra lords your silence will not protect you there's a real cost of not there it does i mean there's a risk of talking about these things but there's also often a much bigger risk in not talking about them you know silence is a decision yes and it's an endorsement of what's happening yes and that's really hard for people to hear because i know sometimes people are silent about horrible things that happen to them and they would never want to feel like they're endorsing that behavior but they are and so it's it's very complicated and it's very personal however if you want a better society for you and those that come behind you, you have to talk about it.

40:49Yes. That does not mean it's going to be easy. I actually think none of it's easy. And the reward is because it's not easy. Yes. And so we have to strive for that. And, you know, I love when I meet a new group of people and I feel an instant connection and we like have some kind of like learning together. That's so rare. Yes. So infrequently, am I going to show my full self to a new group of people? When I do, I get a reward from that said dinner. Yes. When I go in an obligatory way, I go home like I cannot believe I allocated two hours to that. I'm exhausted already. Yes. And so my hope is for people to read Radical Candor, to read Amy Edmondson's book, many books around psychological safety, but to read Unspeakable and realize if you want to grow out of the friend group that you might have inherited or kept, the work group that you inherited or kept, the religious group that you hang out with within your religion, and you want to have a broader perspective, you have to let other people know who you are.

42:13Yes. And you have to talk about it. And it's, you know, I really mean it from the bottom of my heart. And I wish the, you know, 10-year-old me, the 15-year-old me, the 20-year-old me had realized that I would have made better friends by letting them know who I am. Yes. And being included doesn't mean being happy. being included doesn't mean being fulfilled and now I'm happy and fulfilled and most people know who I am by the way I change my mind a lot because I don't know I don't know everything about every topic right I love learning new things but I have an opinion and it's based in love and hope, my opinion can be very wrong, but I'm willing to say I'm wrong and learn.

43:08I love that. I think that's the perfect note to end on. I hope that everybody listening will read your book, Unspeakable, and then they'll go out and speak it. Thank you so much, Christina. Thank you for writing the book. Thank you for inspiring people to get outside of their comfort zones and look each other in the eye and have real conversations about topics that are uncomfortable. It's in the discomfort that we build intimacy and we grow. Thank you, Kim. So we loved this. And I think collaboration is the best force of change. So I hope we can collaborate. Others can collaborate. Your readers, like if they want to collaborate, listeners.

43:52Let's go. Let's make it happen. Thank you so much. Thank you.

44:02This podcast is based on the book Radical Candor. Be a kick-ass boss without losing your humanity by Kim Scott. The Radical Candor podcast theme music was composed by Cliff Goldmarker. Follow us on LinkedIn, Radical Candor the Company, and visit us on RadicalCandor.com.

From the publisher

While the podcast team takes a Radical Sabbatical, Kim interviews authors of books that have had a big impact on her over the past two years. 

We live in a world where the list of off-limits topics keeps growing. Age, failure, succession, failure, death, work-family conflict, money, fear, layoffs, governance, race, religion, and politics: these subjects often feel too hot to touch. So we avoid them and stick to small talk. But avoidance comes at an enormous cost. When we can't address the realities shaping our lives and careers, trust and relationships suffer, making it impossible to achieve results together. There IS a better way!

In this episode, Kim Scott speaks with Christina Wing about her latest book, Unspeakable: The Taboo Topics We Avoid and How to Talk About Them.  

They start their conversation by talking about explained how and why Christina decided to take the risk to confront an abusive boss, and why staying silent would have been more risky in the end. Her Radical Candor paid off for both of them. He hadn't realized how his behavior was affecting others, and ultimately his career. When she explained the consequences, he changed his behavior. 

Christina and Kim explore the costs of avoiding uncomfortable conversations, and some tactics for how and why to embrace the discomfort. Christina shares a story about a family business where people were arguing about where to invest–but nobody knew how much was available to invest. Next, Christina explains how she’s learned to be more open about race, religion, and politics.   

Guest Background: Christina Wing is a Senior Lecturer in the Technology and Operations Management Unit at Harvard Business School. Her research focuses on families in business, and she is the creator of Demystifying the Family Enterprise, a course that explores family dynamics, operating companies, family offices, and legacy opportunities. In recognition of her contributions to the field, she was named a Top 25 Family Enterprise Academic by Family Capital. 

CHAPTERS

(00:40) Introduction to Radical Sabbatical and Christina Wing

(01:30) Facing Bullying in the Workplace

(03:58) Confronting a Difficult Boss

(06:54) The Transformation of a Bully

(09:21) The Importance of Direct Communication

(10:41) Ruinous Empathy vs. Radical Candor

(13:14) The Consequences of Avoiding Difficult Conversations

(13:14) The Role of Respect in Communication

(13:14) The Need for Open Conversations

(14:11) Curiosity and Understanding in Conversations

(17:20) Navigating Difficult Moments vs. Difficult Conversations

(19:07) The Art of Role-Playing in Conversations

(21:21) Understanding Different Perspectives

(23:40) Navigating Difficult Conversations

(27:43) The Importance of Timing in Discussions

(29:49) The Impact of Technology on Communication

(33:50) Addressing Money Matters in Family Dynamics

(38:25) The Power of Money and Its Societal Impact

(41:00) The Necessity of Open Dialogue

Connect with the Radical Candor team:

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⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠

Keywords

Christina Wing, Unspeakable, workplace bullying, direct communication, radical candor, empathy, difficult conversations, respect, curiosity role-playing, perspectives, timing, technology, money matters, family dynamics, societal impact, open dialogue, emotional intelligence
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