0080 - Why ‘I Have Feedback for You’ Feels So Scary—and How to Move Past It ft Jason Rosoff

Ever felt your heart sink when someone says, “I have some feedback for you”? You’re not alone. In this insightful episode, I chat with Jason Rosoff, co-founder of Radical Candor, about the gripping fear and anxiety that often hijack feedback and performance conversations.

Jason has helped organizations of every size—from scrappy startups to Fortune 100 heavyweights—create honest, human-centered cultures. Drawing on both brain science and real-world success stories. Jason offers practical tips on moving from avoidance and dread to candor and collaboration.

We explore:

• Why feedback sparks so much anxiety—and how to keep conversations future-focused
• Intent vs. content: focusing on the relationship outcome, not just the mistake
• How leaders can “lay down their power” and invite genuine, two-way dialogue
• The surprising power of small, frequent check-ins over staged, high-pressure reviews
• Confronting in-group vs. out-group bias so everyone—from underrepresented employees to introverts—gets the feedback they need

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Transcript

Jason Rosoff

There's a researcher, David Rock, and I believe he's from the Neuro Leadership Institute, and he has this quotation that has stuck with me since I heard it many, many years ago, which is for many people, the words I have some feedback for you have the same emotional impact as hearing footsteps behind you in the dark. And so this was a brain science study. He was looking at fmris of people's brains and seeing, like, what areas lit up when we use certain words. So I do think feedback is a loaded word. In fact, in the book, as you might recall, Kim refers to this as guidance, which I also think is not the right word, but she referred to it as guidance. Because the fundamental problem with the word feedback is the back part. The thing that a lot of people get wrong in feedback conversations is they focus entirely on the past. Do not think about the future. And to your point, the reason why feedback, all feedback is positive is because of what it allows to happen in the future. That's how you defined it. It's like it's going to help me be. Become future, become better at what I do. It's going to help me become closer to what I should be. Should be. The thing that people focus on is content. And I think they should be focusing on intent, meaning you should have a goal in mind for that conversation. And that goal should involve not only communicating information, but some sort of intent for what the relationship or what the sort of like, work looks like on the other side of it. And let me describe what I mean. So let's say somebody you're working on a presentation with, somebody, they get up, you get up to give it, and you realize they're using an old version of the slides, and so they present something that isn't the latest work. And as a result, it causes confusion and people are sort of upset by it. And you feel like there's content in that conversation, right? Which is, hey, you presented the wrong deck and it caused all this confusion. And I want to know how we can avoid that in the future. That's the content of the conversation. But my, my intent for the conversation is that you and I, let's say, Ben, you were my partner, that you and I, Ben, can continue to collaborate together. Well, so I want to bring the energy of my goal at the end of this conversation is that we continue to work together really well. Here's what I noticed. How can I be helpful in figuring out how to avoid a mistake like that in the future? It's very different than sort of the dry delivery of like you did this and this was the impact and as a result I'd like you to do something different. So think about that. Think about your intent.

Ben Owden

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Mambo this is Ben Owden. Your leadership Mr. Miyagi. My hope is that this conversation will help you find the clarity and conviction you need to lead a more meaningful and impactful life. I have curated some of the best thinker practitioners from all over the world to help you get to your leadership nirvana. So sit tight and let's go on this journey together. Greetings to you. I hope you are at peace and are having a meaningful and productive day. Welcome to another episode of the WhyLead Podcast. I am your host, Ben Owden. If you're a leader or just an adult at this point in your life, you've already figured out that telling adults what to do simply doesn't work. You've also learned that telling people that they are wrong doesn't usually end well. But life is filled with moments where we believe that we need to give instruction or where we need to point out certain mistakes. In today's conversation, we will be exploring a compass for candid conversations. We will learn how to have kind, clear, specific and sincere conversations with each other. And to have this conversation, I am joined by a co founder of Radical Candor. He has helped all kinds of organizations, from startups to giants in the Fortune 100, realize the power of creating a more radical candid culture. Through his work, he's helped hundreds of companies develop real human relationships between team members and through those relationships, achieve amazing results collaboratively. Ladies and gentlemen, Jason Rossoff. Jason, you're most welcome Ben, thanks for.

Jason Rosoff

Having me on the show. I'm excited to be here with you today.

Ben Owden

Thank you so much. So I'll start by asking you. So it's sort of a game, but I'll ask you two questions where I juxtapose two different things, and then you tell me where you lean more towards and the reason behind that. Right. So avoiding conflict on one end, radical honesty, radical candor. On the other hand.

Jason Rosoff

My natural inclination is to avoid conflict, and I think.

Ben Owden

I like that natural inclination, which means you work your way to a place where you're more radically honest with those around you and that intentionality to say, I will rise above the natural inclination to. When at what point in your life did you say, okay, you know what? Maybe I'll just have to work my way up?

Jason Rosoff

I mean, I think I say that to myself every day. I don't know if there was a watershed moment in my life, meaning there was, like, a particular experience that led me to believe that I needed to do something different. But I will say that the more I was responsible for other people, the more I was confronted with my. How my desire to avoid conflict was leading to negative outcomes, both in the relationship that I had with that person as well as in the work that we were doing together. And so I was feeling the pain of avoiding those conflicts. Right. And so it was, to some degree, I'd love to say that it was. I was inspired by a. Philosophically to, like, pursue this, but I think it was mostly enlightened self interest. Right. I was like, well, this is not working. Conflict does not work. It's not producing the results that I want. And so if I want to feel better about the work that I'm doing and feel better about the relationships that I have, then I think I have. I have to find another way. And for me, radical candor. I was practicing radical candor, or starting to practice radical candor before I ever heard the term. So one of the reasons why I was excited about founding this company with Kim is because I felt like in her book, she did such a good job of distilling in simple terms, something that I have been sort of feeling my way through the dark to find in my approach to my relationships, especially at work.

Ben Owden

Thank you for that response. So the second one, doing what's easy versus doing what's right.

Jason Rosoff

I lean toward doing what's right. I'm suspicious of things that are easy.

Ben Owden

And where do you think that comes from? Because I think I've heard psychologists say this, and I see that in Myself, where there's a tendency, the hedonic tendency to lean more towards what's easy, what's comfortable, what's convenient, what's pleasurable at times versus what's hard. Although I guess that suspicion is probably there, but it's just not as loud as the desire for ease.

Jason Rosoff

Yeah, I think this is in part like rooted in my upbringing. My family had like a very strong work ethic. There was a strong message in my upbringing that like the things that really matter take effort. And I think the dark side of that is that sometimes it's hard to take it easy. So I think the reverse is also true. So maybe you start from a place of seeking ease and then you challenge yourself to do things that are hard, which means that you have the sort of default which is to find an easy path. And maybe sometimes I sometimes regret my skepticism of the easy because I feel like I make things harder than they need to be at times.

Ben Owden

Oh, wow, that is. So you're more risk averse, so to speak, when you this too easy, maybe it's too good to be true. It is probably, oh, interesting. Now when you talk about, you know, radical candor and usually think of and talk about, you know, feedback conversations, and when people think of feedback conversations, especially in the workplace or I think even in relationships, you see this quite a lot, right? When somebody tells somebody we need to talk, this tension, there's anxiety, It's a sit down conversation, it's a serious conversation. And a lot of us actually believe that to have that conversation the right way, we need to plan ahead of time, we need to be more intentional, we need to think through how the conversation is going to play out. And all of that entails actually time. But in this radical candor approach, there's also the impromptu feedback, the impromptu comment, the two minute conversation where there isn't a lot of forethought. Right. So how do we have those quick conversations that are impromptu without risking saying things that, you know, we don't mean or things that we wish we could take back? I recently read this, I think was like a neuroscientist who was saying that we, we talk faster than we think. And so sometimes when someone says, oh, I didn't mean that, it's not that they're taking back what they've said, sometimes it actually does mean simply that, that they said something without having thought through it and put together the right words to convey what they were trying to say. So how do we give the impromptu. How do we say something when it needs to be said in the moment without risking saying things that we wish we could take back.

Jason Rosoff

I wish I could tell you that there was a way to do that, but there isn't. In fact, I think this is one of the. This is one of the misconceptions about radical candor is that radical candor is sort of like an emotional novocaine, meaning, like, if you practice it right, no one's feelings will ever get hurt. And that's actually sort of exactly the wrong way to think about it. The way that I tend to think about those impromptu conversations is you do need to think a little bit. But I think the thing that people focus on is content, and I think they should be focusing on intent, meaning you should have a goal in mind for that conversation. And that goal should involve not only communicating information, but some sort of intent for what the relationship or what the sort of, like, work looks like on the other side of it. And let me describe what I mean. So. So let's say somebody you're working on a presentation with, somebody you get up to give it, and you realize they're using an old version of the slides, and so they present something that isn't the latest work. And as a result, it causes confusion and people are sort of upset by it. And you feel like there's content in that conversation. Right. Which is, hey, you presented the wrong deck and it caused all this confusion. And I want to know how we can avoid that in the future. That's the content of the conversation. But my intent for the conversation is that you and I, let's say, Ben, you were my partner, that you and I, Ben, can continue to collaborate together. Well, so I want to bring the energy of. My goal at the end of this conversation is that we continue to work together really well. Here's what I noticed. How can I be helpful in figuring out how to avoid a mistake like that in the future is very different than sort of the dry delivery of, like, you did this, and this was the impact. And as a result, I'd like you to do something different. Different. So think about that in. Think about your. Your. In your intent. And the reason why that's so important is because sometimes, no matter how you say it, the person is going to get upset. So, Ben, I don't know you for very. For very long, but given the preparation that you put into helping me understand how this conversation was going to go before we started, I suspect that you're quite a thoughtful person and a planful person. Like, you try to see to the future and My guess is that you probably, like, if this was a real situation, you probably would have realized partway through that you had the wrong. You know what I'm saying? That something had gone wrong, and so you probably were already feeling that. So if I went in with the intent of, you know, just telling you like it is, you might have been already beating yourself up. And so no matter how I said it, you might have already been feeling really bad. And so that's why it's so important to have that intent clear. Because if I saw you feeling upset about it, and I was like, my intent is us to continue to work together really well, that would change my approach, right? Because I'd be like, I don't need. I don't need to hit Ben over the head with this feedback. Like, I need to be here for him right now because he's aware that this mistake was made and that it had a negative impact, and I need to be a partner to him to try to figure out a way to avoid it happening in the future.

Ben Owden

I like that. And I think that's the care, personally aspect of radical candor. And when people talk about feedback, which is something that I, whenever it happens in my presence, I would probably make a comment. It's this idea of saying positive and negative feedback. And I am of the opinion, rather, that all feedback is positive if it's something that's going to help you grow or get from point A to point B, regardless of the feelings that erupt in the moment, it's a positive thing because it's helping you transition from where you are to where you would like to be. So not judging the moment based on what I am feeling in the moment, but actually saying, okay, the intent is right. This person wants me to move from where I am to where I'm supposed to be or to where I need to be or to where I can be. And that's a good thing. And so I love generally radical candor because it's risen above the negative positive. It's like, okay, the goal is not to make you feel good and just say all the things, but the point is to get the truth across, to challenge directly, but also make sure that we don't sacrifice the relationship. Because at times, people avoid feedback because they don't want to damage the relationship. They know that if I say this, the relationship will suffer. And I value the relationship. So let me just be quiet.

Jason Rosoff

Yeah. And what I would say to those folks is, what you're doing in that moment is you're doing a cost Benefit analysis, you might not call it that, but that's what you're doing, right? You're like, is the cost of this conversation greater than the potential benefit of the conversation? And I think for any individual discussion it is probably true that the cost often seems to be higher than the potential benefit. But that is because human beings are very, very, very bad at calculating the cost of inaction. We are very good at anticipating the worst case scenario if we act, but we're very bad at anticipating the worst case scenario if we fail to act. And this is proven true over and over and over again, right? Like, it doesn't just apply to feedback, it applies to like how we treat the environment, for example. We're like, we know that there are things that need to be done to make sure the environment remains sustainable for human life for a long period of time, but we're afraid of doing the thing. We're afraid of taking action because of the potential cost of those actions. You know, maybe it's very expensive monetarily, maybe it's, there's a human humanitarian cost or whatever it might be. But we're very bad at calculating the cost of an action. So that's, that's the first thing that I want people to think about is like really think about the cost of an action. And the best way to do that is think back to other times where you failed to act. What has been the cost to you or to the other person? And I think the other thing that was on my mind as you were speaking was this idea that like you, you described your response to feedback in a very self actualized way. Like you, you separated, for example, you did something fairly sophisticated which is like you separated your emotions from yourself. And I think for a lot of people that's hard to do, especially in the moment, especially when the emotions are very strong. Right? Because they're not. Emotions aren't only thoughts. There's like biochemical feedback that's going on. Like there's, we're releasing hormones, there's like are out of our control that might cause us not to be able to separate those things in the moment. But going back to what I said about intent, if you're the one giving the feedback, you are in a much better place to manage your own emotions than the person receiving the feedback. And so when I think about relationship damage, and when does relationship damage occur? It often does not occur at the moment of saying something offensive or wrong. Meaning that's hard. Where relationship damage becomes significant is when the person shows you that you've done something that has hurt them, and you do not respond with compassion. And so that's the other part of intent. I think that the practical application I would describe as maintaining presence in the conversation, like being present for the other person's reaction, managing your own emotions. Like, those are the things that you can do to support someone who maybe can't separate the emotion from the value of the information that they're receiving.

Ben Owden

I really love what you said there. Right. This idea that we're good at underestimating the impact of our inaction. I think that's very true. And that's seen more in our relationships probably outside of work. There was a. I watched a conversation. I think it happened on the Lex Friedman podcast. There's a divorce lawyer called Jim Sexton, and he was, you know, he just shares accounts of different cases that he was a part of as a divorce lawyer. And he said one of the main reasons relationships like marriage don't work is because people aren't honest with each other. So a lot of the stuff could have been avoided if people were honest with each other. But it's also because the symptoms or the signs of failing relationship. It takes time for those signs to show up. They're not as loud. It's usually very quiet. And by the time you start to notice signs, it means the damage has probably already been done. And I think that's also true even in the workplace, in our relationships. And so that's why it's very easy to underestimate the impact, because it's. It's not the loudest thing. Profit and loss, you know, looking at the PL sheet, that's easy to see. We can assess that on a monthly basis, on a quarterly basis. But on the relationship side of things, it's very hard to know how you are doing. You have to be very present. Like you said, you have to be present here and now, and you have to be intentional. There will not be smoke coming out of anything in the present moment. Now, something else that's evolving in the language around these conversations is for a long time, it's been feedback. You guys have added, expanded the language, and now there's radical candor. But now we're seeing things like feedforward. I think I've heard of Feed Future. So all kinds of new language. What do you think has gone wrong and made some people and organizations switch things up a little bit and change the language around these conversations? And is changing the language the right path forward?

Jason Rosoff

Yeah. So I'm. I am of the mind that words do matter. And there, there's a. There's a researcher, David Rock, and I believe he's from the Neuro Leadership Institute. And he has this quotation that has stuck with me since I heard it many, many years ago, which is for many people, the words I have some feedback for you have the same emotional impact as hearing footsteps behind you in the dark. And he. So this was a brain science study. He was looking at fmris of people's brains and seeing what areas lit up when we use certain words. So I do. Feedback is a loaded word. In fact, in the book, as you might recall, Kim refers to this as guidance, which I also think is not the right word, but she referred to it as guidance. Because the fundamental problem with the word feedback is the back part. The thing that a lot of people get wrong in feedback conversations is they focus entirely on the past. They do not think about the future. And to your point, the reason why feedback, all feedback is positive is because of what it allows to happen in the future. That's how you defined it. It's like it's going to help me be. Become future, become better at what I do. It's going to help me become closer to what I should be. Should be doing. And so I. From a. From a conceptual perspective, I think that's the problem with the word feedback. And that's why Marshall Goldsmith, I believe, is the person who coined the term feedforward. That's why that term was important. At the same time, I hear the word or the term feed forward and I sort of throw up in my mouth a little. It just feels like. It feels like corporate doublespeak somehow to me. And I tend to agree with Kim that praise and criticism are better descriptors. So, like, of what we're actually doing. So sometimes we're appraising the thing that a person did well, and sometimes we're criticizing a thing that the person could have done better. But in both cases, the conversation isn't over until you talk about the future, right? Until you talk about, like, what does it mean. So if I told you, Ben, you did a fantastic job at the beginning of the podcast, making me feel really welcome and secure in what we were going to talk about. Like, that might feel good. But, like, what I really mean to say is I think that was very effective and you should do that on all future podcasts. Now, you don't necessarily need that guidance from me. Like, you're fairly secure in the way that you do things. But that would be. That's actually my intent in telling you, that is, like, I think other people would benefit from it, so I would encourage you to do it again, because I know it's not effortless, right? You. It's. You have to put some thought, reserve some time for it, things like that. In the same way that if I offer criticism, like if I said, you know, Jason, you showed up a couple minutes late to the podcast, and, you know, while it's not a huge deal, it would be really helpful to show up on time because we have so much to talk about, and this is going to be such a great conversation. So I hope you at least can consider trying to make it so that you can show up on time in the future. Same thing, right? It's like, it's what to do with that information. You're not just telling me you're mad at me. And this is not something that Ben said to me for his audience, just to be really clear. But the goal is not to end on what went wrong. The goal is to focus on the future and how it could go right or how it could go better. And the reason why I like praise and criticism is because they. They more accurately describe what's going on. Feed Forward is a euphemism. And I think I feel like the business world in particular needs to start fighting more actively against euphemistic terms because it's harder and harder for people to understand what we're talking about. I was someone the other day who is never worked in a corporate environment. I said, we'll circle back on that. And they were like, what does that even mean, circling? What does circle back mean? And I was like, oh, I mean, I'll get back to you in a couple of days to let you know what I think about that. And I realized Feed Forward is another example of that. If I said that to a person who has not worked in a corporate environment, they'd be like, that is nonsense. Like you're saying nonsense. Like you're saying nonsense words to me. And we should be concerned about that. I think as professionals, one of the ways we can make the environments that we create more inclusive is to use language that more clearly and accurately describes what we are doing.

Ben Owden

And I like that. And speaking of being inclusive and making sure that we don't keep certain people outside by using this exclusive language that maybe only people within a particular system are familiar with. Something else that you guys talk about is this idea of in group versus out group, right? And in most organizations, these groups exist. In some, they are much smaller. In others, they are much bigger. In some organizations, there's a meeting after a meeting because a particular group would like to have their own debrief after the meeting and share what they really think about everything. And so how do we, especially now with hybrid way of working, where maybe some people are working partly remotely, and that face to face in person interaction is limited, which is where you can discern sometimes a lot of the relational aspect of how things operate. And so how do we create a workplace culture where that this in group versus out group behavior doesn't flourish and these subcultures don't thrive?

Jason Rosoff

Yeah, I feel like you've asked the hardest question in all of like human social groupings. I don't know if you've heard of the research on minimal group theory, but it's a real mind bender. There is a person who wanted to study the formation of groups and I can't remember the scientist's name. Maybe I'll send it to you after our conversation so you can share it with your audience. Their goal was to study how groups form, and they wanted to start with a control experiment. So the goal of this experiment was to have no groups form. Okay, that was. The goal of this experiment was to create a control condition where no groups formed, no group identity was formed. So the way they constructed this experiment was they showed people a piece of paper with dots on it, and they asked each participant to estimate the number of dots on the paper. Okay. And then they randomly told them. It didn't matter what they said. They randomly told them either they were overestimators or underestimators. Okay? So they were just randomly assigned. It had nothing to do with the actual, their actual skill at estimation. Their assumption was this would not form a group identity. So the follow up task was they said, okay, you have $10, which you get to distribute however you want. And automatically people showed a preference for distributing more of the $10 to either the overestimators. The underestimators, depending on which group they were randomly assigned to. So you're like, okay, I sort of understand that, you know, it's not a very strong affiliation, but like, why wouldn't I give my group more money? Right. Second experiment was they said, okay, you have $10 and you can either split it evenly or your group can get $4 and the other group can get $3. Meaning we've destroyed $3 of value. Right? We've obliterated value. You wind up with actually less as opposed to splitting it evenly. And wouldn't you know it, people chose to prefer their in group Even though it destroyed value over their out group.

Ben Owden

Wow.

Jason Rosoff

This. And so this finding. They were so shocked by this finding because they were like, how is this even possible? Like, how is it possible? They redid the experiment. It has been repeated hundreds of times across cultures, across the entire globe, in different situations and settings. This is one of the strongest findings in psychological research that exists. And so that's why I say your question is fundamentally about one of the hardest things to avoid, which is these sort of group identities forming. And so I think the way I would answer your question, I apologize to your audience, that was a bit of a long road, but context matters.

Ben Owden

Definitely. Thank you for sharing.

Jason Rosoff

Yeah. The way I would answer your question is as opposed to trying to prevent the groups from forming, because I think that's basically impossible based on my own experience. And then the research backs it up. What we have to think about is what are the ways that groups that sort of like subgroups at work harm the ability of a team to collaborate effectively together? And one of the ways is the way that you described, which is that they either hoard information, right? So that meeting after the meeting where they're like talking about how it really is, but they're not telling anybody else, that's an example of information hoarding. Okay. Or they show preference in some way either in like, who gets promoted or what projects get approved for a particular group of people. And so from my perspective, it's like, it's great that you have a group of friends at the organization and it's not everybody. Like, not everybody's friends with everybody. That's fine. But the moment. So there's two things you can do. One is you can say, look, it doesn't matter who you work for or who you work with. We're going to design systems that prevent or at least limit the power of groups from distorting or influencing important processes in the organization. So for the promotion thing, for example, one way to prevent the power of in groups from distorting who gets promoted or who gets interesting work is to have that decision not live with a single person, to have that decision live with a group of people from across disciplines who don't always work together all the time. And so that's a thing that companies, I think are adopting more and more and is, generally speaking an excellent practice, is this idea of cross functional or cross organizational calibration on decisions that affect who gets promoted and what ideas get worked on. The second thing you can do is you can have a policy or approach that says, no information hoarding and if you get win, and the way to stop it is fairly straightforward because usually the information does leak out. So usually what will happen is that in group will talk, and then they'll send a representative to influence somebody else. They'll say, hey, a bunch of people are saying X, Y and Z. And it's at that moment that you have the opportunity to send an interrupt signal into the system. You can say, hey, great. This is really useful information, but I need to hear from the other people. So let's get together, like, whoever's talking about this, let's get together and have a conversation about it. In the same way that if there's feedback that's going through the grapevine, there's a responsibility to say, hey, let's say you and I had a conversation after a meeting about Kim, and we said, you know, I think Kim really could have done that better. One obligation that you can create, sort of a cultural obligation you can create, is to say, hey, if you're talking about someone who isn't in the room, you have an obligation to tell them. And it only takes one person in that conversation to help you do the right thing. So I actually think that things like that can really help. So this sort of idea of like, no backstabbing or behind the back, like talking behind people's backs as a rule, is a really important one for companies to have.

Ben Owden

I like that. There's a book by Frederic Laloux. I think it's called Reinventing Organizations. And he just talks about the history of different ways that we have evolved to organize as human beings. And there's one that he labels teal organizations, where he says, this is the organization of the future. And it's basically about dismantling hierarchy and making sure that people have more autonomy and agency within a particular system. And there are a few organizations who are operating with that. And the one example that he shares is this French company that creates automobile parts for, I think, sports cars. And they basically don't really have a hierarchy and decisions that have to be made, hiring decisions, promotion decisions, whether certain positions just become obsolete, you know, over time. All of those. All those are group decisions. And so if this team that's working on this engine, they need to expand their team, then it has to be a group decision. Do we actually need this? So it's not a manager. The manager doesn't even exist. And he talks. So he shares a lot of stories about how effective that is. And so going back to the point that you were saying here, this idea that I think Sometimes it's not so much about making sure that groups don't exist, but as long as more people are involved in decision making, then the groups might exist, but they won't exist in such a way that's detrimental to the organization. So it could be social groups because we have shared hobbies, because we believe in the same things, because of this and that, but it's not going to be something that's detrimental to the overall organization. So I particularly liked that. Now, speaking of, again, these conversations and radical honesty, sometimes part of the frustration, and I remember in the early days of my marriage, I had the same frustration where you feel like you're receiving feedback over things you have no control about, things that you know, I don't think this aspect of who I am can change. And I know that this happens in all aspects of life, including the workplace, where people are frustrated because they're receiving information about improvements that they need to make over aspects that they believe they have no control over. So someone might, you know, make a comment about something that you didn't know. So you have to learn about something that's fairly easy to do, developing a skill, maybe improving your attitude. All those are easy things. But then what if somebody is making a comment, constructive, you know, criticism over your personality, when you know, I am an introvert or I'm an extrovert, I can't really tone it down. This is, I am high energy most of the time, or I am mostly quiet. I take time, I'm analytical. I have to think about what I'm going to say. I'm not going to just, you know, share all the ideas in a meeting. So all of these different things and aspects of who we are that maybe we can't change or maybe we shouldn't change, right? So when we receive feedback over those aspects of our being, so to speak, how do we reconcile that and how do we communicate that to those around us? Because I think sometimes we tend to overstretch this idea of having a growth mindset to mean you can change everything about who you are. But there are certain things maybe they could have changed at one point in your life, maybe when you were younger, but at the time you're an adult, it becomes very, very hard to make those improvements that, that people are signaling that you should be making.

Jason Rosoff

And who knows if they're really improvements, right? Because I believe that the world needs differences. Like I believe that the world is richer when people aren't all the same. Often when we get feedback about our personality, it has nothing to do with what would be better for us, but what would be more comfortable for the other person. And so I think that. And I don't think we should be optimizing for everyone's comfort all of the time. That doesn't mean everyone should be uncomfortable all the time. But I think that discomfort is an important part of creating an environment and where interesting things are happening. Because if we're comfortable all the time, that means we're never stretching ourselves, right? We're never doing anything that's sort of just outside of our. Of the box that we're used to playing in. And so we tend to say, look, look, you should not give feedback on personality traits, like being an introvert or an extrovert, for example. Instead, you should focus on behavior or work and the reason, the way that you can do that. So in the second edition of the book, we talk about core context, observation, result, and next steps. Like the E is capitalized, the next and steps. And that can be really useful because sometimes it's not about your personality, but about the way your personality plays out in a particular situation. So, for example, I tend to be an introvert, and I have gotten the feedback sometimes that, like, hey, when you're quiet. Well, in fact, my radical candor story is about the fact that when I'm thinking hard about something, I look sort of annoyed or angry. There's a term for that in the zeitgeist that, you know, we don't need to swear. But, yeah, I know exactly what you.

Ben Owden

Mean because I've pointed that out about me a number of times.

Jason Rosoff

Yes. So, like, when I'm thinking about things, I look annoyed. And the problem is when you combine that with sort of either social or organizational power, it can feel like a judgment. Right? Like, if your opinion about something matters, it can feel like a judgment. Now, I cannot control this unconscious thing that my face does, even though I am aware of it and I've worked on it. And like, sometimes I'm like, really tuned in and I can tell when I'm doing the right thing with my face. But sometimes, again, when I'm really engaged, my brain is working overtime and I've lost some of the sort of like, cognitive capacity to control these sort of the expression of my face. And so the feedback that I got was like, hey, when you do that, it makes me think that you really hate the idea that I'm presenting or that I'm doing something wrong. And so. And I'm. The person was checking in. Like, do you hate, like, did you hate that? Like, idea. And I said, no, I didn't hate the idea. And I appreciate you bringing that feedback to me because like, even though I know this is sort of like, like to some extent it's a part of who I am, like this facial expression stuff is part of my being, I said I appreciate the chance to address it. And so what I did was I told my entire team, like, hey, this thing happens. Like, someone brought this up to me and this thing happens. And what I want you to know is that when it is happening, it is not because I have a negative perspective on what you're talking about, but because I'm considering deeply what it is that you're saying. I'm thinking hard about what you're saying. I'm paying close attention. And of course that doesn't eliminate all the bad feelings, but it at least gives us a way to talk about it. So my team started calling it my thinking face and that was actually really helpful. So again, by making it specific, not that, hey, you just need to control your expression. That wasn't the feedback, which is like, because that's really hard to do. To say the improvement is you need to control your expression, but instead to say, when you do this, this is the impact it has on me. That opens up the path for finding a way around it to address the behavior. Maybe it's not about changing who you are, but about giving context to the team. So that's my way out is like don't focus on the sort of deep seated personality trait or attribute. Instead focus on the impact that the behavior has in a specific situation that might open up a way to resolve it.

Ben Owden

That, wow, that's a, that's a very powerful story you've shared because, and, and I liked the language, right, my thinking face because I tend to have the same problem. I remember my book was published a few years ago and during the launch of the book and there was, was a, you know, successful event and one person looked at me and they're like, why aren't you happy? This is a very big deal. I was happy, but I was so focused that my face looked like I was angry at someone or something. But I was like, no, this is nothing to do with my happiness. I am very excited and happy that this is a big deal. But my face didn't show that in the way that people see happiness. And so I like the giving language to some of these things that this is just my thinking face, this is my focused posture, et cetera. Now speaking of the four quadrants with the radical Candor, ruinous empathy. Manipulative insecurity. Obnoxious aggression. Zooming in on manipulative insecurity. What do you think is required on an individual level, right, for the transition to happen from manipulative insecurity to radical candor? Because insecurity is. It's one of the hardest things to overcome and to work on as an individual requires a lot of vulnerability to admit that I am actually being insecure. I am trying to manipulate this. I am not being as honest as I should be in this situation about myself, about my feelings, about what I want. So how do we make that transition from that to radical candor?

Jason Rosoff

Well, two things. One, the term in the book is manipulative insincerity. But I actually like manipulative insecurity better. And the reason why. The reason why I think it's helpful to frame it that way is because in order to figure out how we get out, the question is, how do we get in? Like, how do we wind up in that place? And I think there are a couple of things that cause us to be in that place. One reason we wind up in that place is when we feel disempowered. We feel like if we say something either have no effect or it will have a. It will. It'll backfire, right? It'll have a negative. Like, I'll be punished for speaking up. That causes a lot of people to slide into that quadrant. And the other reason we might wind up there is that we don't really care about the other person. And so we don't feel like we don't want to risk conflict with them because we're like, why? Why am I gonna. Like, what's in it for me? You know what I'm saying? Like, there's this question of what's in it? What's in it for me? And so the way that I think about this is the way I think about getting out is one, the feeling disempowered. Sometimes there are things that we can do, meaning sometimes we are overestimating the potential cost of saying something right? In our mind, we're like, oh, this person's gonna punish me if I say something. And that's not really true. That's just a story we're telling ourselves. And so I always like to say, for people who think that's the. Who are in that quadrant because of that reason, test the waters, right? Like, don't start with the big problem, but have a conversation with that person about a small thing that you might disagree about and see how that goes? Like, you don't have to. I think going back to this idea of a cost benefit analysis, I don't think you have to like sacrifice yourself on the altar of radical Cantor. If someone has shown that they will punish you for speaking your mind or like sharing your perspective candidly, I think it's reasonable to respond with manipulative insincerity. Right? Like, I think that's a self protective action. But at some point you have to look yourself in the eye and say, is this a good environment? Like, am I, can I, can I be productive here? Like, I think that's an important question for us to ask. If we find ourselves there for that reason, if we find instead that we're disempowered, meaning like we're having. Because like the most common version of manipulative insincerity or insecurity is the sort of like talking about people instead of talking to that person directly. That is the most common version of this that I see. And if we were doing that because like it's the CEO and I don't really know how to like, how do I even reach out to them and like, what's the way to do this? So we're just having this sort of like closed door conversation about this person. The thing that I say is like, well, have you tried, have you sought advice? Like, have you, you know, have you sought advice from your manager of like, hey, this thing happened and I want to find a way to give this information. So if you're feeling disempowered, seek advice. That, that, that's like, there might be a channel for, for you that you're unaware of. But seeking advice about how to resolve an issue is very different than just complaining about the issue. Right? Like, I just want to distinguish, like that's the act, the action you take is like, get help. And then if the reason that you're there is because you're like, what's even the point? Like, you know, Ben and I don't get along. So like why, why would I bother, you know, challenging Ben directly? I think that's the place where you have to, you have to be honest with yourself and say like, if you have to collaborate with someone, one, it is essential that you be able to disagree. And that means that you need to respect that person enough to be willing to disagree with them. You have to. So like, you need to move up on, you need to find a way to move up on care personally. It doesn't mean you have to like know the person's hobbies and their kids names and all this other stuff. But you have to like show them enough respect to say, Ben, you and I need to collaborate on this. I see this differently. And it, and what's in it for you is it can be an act of enlightened self interest, is making your job easier going forward. Right. Like the ability to disagree about things is going to make it easier for you to get stuff done. So I remind people that even though in the short term it might cost you something more, in the long term, there's probably a benefit to be gained or you realize that you're in category one and Ben is going to yell at you every time you try to get some feedback. Yeah, go ahead.

Ben Owden

Yeah. Because funny thing is, I've had someone on the podcast who actually worked with the Weinstein brothers at Miramarks and he shares this story, just lots of stories about this culture of yelling. There's a lot of very aggressive yelling, you know, talking and dressing people down and just like a very, not very nice culture in the place. And you know, as you talk about this idea of challenging or saying, maybe I look at it from a different point of view. A lot of this has been associated with this idea of psychological safety. And so there will be individuals. And in the case of this person, his name, Stacy Spikes, is he was one of those people who can get past the toxicity and just speak his mind and say what he wants to say. But a lot of people require the environment to facilitate that level of safety where I can say something, because we all have, you know, different orientations around challenging and share speaking our mind. There are people who've been nurtured in such a way that it doesn't matter the environment, they'll always speak their mind at whatever cost. And there are some of us who we're dealing with fear and just this tension inside. And so the environment has to help open the door for us. And so how can organizations begin to build that culture for people who are not going to be the outspoken individuals? I'll say whatever I have to say. How do they create that sense of safety so that people, even those who are hesitant to speak their mind, can speak their mind?

Jason Rosoff

I have one piece of advice for people who, if you're a leader listening to this and you're worried that this is you that we've just described, your organization, start soliciting feedback and rewarding people for giving it, solicit it publicly. Talk about the feedback that you receive publicly. The best way to change the culture is to make yourself vulnerable publicly. And the reason why that's so important is because if you do this just behind closed doors and you're relying on word of mouth to get out, the problem is that again people, it's really easy for people to sort of imagine the worst case scenario. So if they're not seeing it with their own eyes or hearing it with their own ears or reading it, you know what I'm saying, it's going to be hard for them to believe or at least easy for them to play up the worst case scenario alternative to that. So it has to be public and it has to be real. And I had a, I worked at Khan Academy for many years, which online educational, not for profit. And Sal, who is my boss there and the founder of the organization, he did this thing every year where he would do a 360 review and then up in front of the whole company he would read the summary, he would say here's what I heard in my 360 review and here are the couple of actions that I'm taking based on the feedback that I received. And I thought that that was such a powerful example of this. Right. Like I'm soliciting feedback not from literally everybody in the company but like we've selected a group of people who are going to talk to a person who's gathering this feedback for me. So I've solicited feedback and I'm rewarding the candor by reflecting honestly what I've heard. And he made the document available with the summary feedback so like you could go read it yourself if you wanted to. That I think a lot of leaders are paranoid that like that the people will lose respect for them if they show that they have things that they need to work on or like they're clear about like their, their areas of development. All I can say is that every year that that ritual created a true sense of safety in the organization that not only was Sal willing to listen, but he was willing to do something about it if we were able to give him clear enough feedback.

Ben Owden

Is that the, this concept of laying your power down, is that what that looks like?

Jason Rosoff

It's, it's related to that. I think the. Often it is one version of laying your power down. I think the. You can take this even further like in some organizations where manipulative insincerity has really taken hold. There was an example, I think Kim sells the story in the book, but of a leader that she knew in Silicon Valley that basically made a comment box and would take something out of the. Where People could put their questions or feedback and. And during staff meetings or all hands, this leader would take something out of the comment box at random and read it in front of people. And I do believe that that is an act of humility, which is really what laying your power down is all about. Is sort of humbling yourself in front of the staff. And maybe a more concrete way of saying that is, is you do not rely. You create a situation in which you do not rely on your hierarchical power to protect you. Right. Because anybody could have submitted that comment or question. You don't know who it is. You're choosing it at random. You are fundamentally not relying on your hierarchical power to protect you.

Ben Owden

I think this idea of laying down your power is. It's transformational if applied especially in contexts and places where there's a strong honor culture. And I think, for example, where I'm at, in Tanzania, we have very strong honor culture. And I know in a lot of other countries you find this. In Japan and so many other countries, you'd find that. And something that I read in past couple of days, someone tweeted online and they were basically saying that they were at some engagement and the leader of that particular. The person who was the highest ranking in the particular engagement was not. Was late. And so she made a comment, so. And so is late. And then somebody else corrected her and said, no, no, no, they're not late. They haven't arrived. And the idea was that this person is so high in ranking that they can't be late. They arrive exactly when they need to arrive. Right. So the tendency to avoid criticizing and connecting these ideas, you could see that clearly. There's a culture of hoarding power. There's no laying power down to a degree where people feel like you don't make mistakes. Then there's always a reasonable explanation as to why things didn't play out the way that they did. And you see, in many organizations, leaders have apologists, people who are always making sure that they find some reason as to why they didn't do this or as to why they did that. They must have a reasonable explanation as to why that happened. They are above reproach because they rank at a certain level within the organization. So laying down your power is something that only leaders can do. It's something that they have to demonstrate. And I like this. This intentionality of saying, let's all gather together and here's what you guys have said, and here's my commitment to better myself, or this idea of just selecting random comments, you know, you're not like sifting through the comments and picking the ones you like, but just like, you know, picking at random and saying, okay, this is what, you know, this person has said about how I show up in the workplace. So I love that intentionality.

Jason Rosoff

Yeah, I think, look, look, I, I don't think radical candor is going to address centuries of cultural training, you know? You know what I'm saying? Like, I don't think it's an automatic fix for, for many, many years of. Well, let me say, I think all human beings have the ability to out create their own experiences, their history, their past, whatever you want to call it. I think it's one of the most incredible things about humanity is that we do not have to be defined by the things that have happened to us. And so it's possible, but I think just learning about radical candor is not likely enough to help you out create those experiences. Just because we grow up in an environment that value that, like these strong honor cultures, it doesn't mean we have to accept that. Right. Like, we can change our behavior. And even though it, there might be a very strong pull all the time toward sort of going back to this default behavior, we can be different, we can do something different. And that's incredible. I don't think just learning about radical candor is like going to change, you know what I'm saying? It's not going to like change people. I, I don't think saying lay your power down and you'll get better results is necessarily going to convince people who are bought in for one reason or another to those existing power systems to change their ways. And so I don't think this is, you know, I, it's not a, it's not a miracle cure to, to, to like, to, to different ways to. It's not a, it's not a great equalizer. It's not going to make everybody think the same way about the right way to structure an organization or the way to treat people in power, et cetera. It's not going to do that. Recognize that. And at the same time, I think it is helpful to at least give language to different ways that we might approach things or what we might learn from other cultures. In the same way that I think there, there is often a powerful something that goes along with some honor cultures, like Japanese culture is like a, like an abiding respect for one another. Like there's deference to hierarchical differences, but there's also a deep respect that's expected of people. And I think that's A positive thing. So it's not like all of that, like, you know, all of the honor culture is bad and all of the sort of radical candor culture is good in all situations. I think there's something that we can sort of take from each other or learn from each other.

Ben Owden

Cool. Now, there's a question that we ask all of our guests. I'm just going to throw it to you right now and think through it, and I'll ask you this in a couple of minutes. We call it the 1, 1, 1, where basically the idea is, suppose you could time travel and go back 10, 20 years ago. What book that you've read along your journey that you will take back, a book that you wish you had read earlier in your life. Right. And then the what is the one habit that you've developed over time that you wish you developed earlier as well in your life? And what is the one personal value that you will not compromise, no matter the cost? So 1, 1, 1, 1 book, 1 habit and one personal value. So I'll let you think through it as we continue the conversation. Something else that I think is very important to talk about is this idea of diversity. Now, we live in a world where it looks very different in different cultures, but we're all striving to be more diverse in how we organize our communities, in how we build our organizations, et cetera. And there is a study that I'm sure you're familiar with because I saw this on the radical Candor platform from Textio, which found that most underrepresented people in corporate leadership usually receive inadequate or poor feedback. And it was interesting because there's a researcher, a behavioral scientist from Germany and Austria who's moves back and forth called Matthias Suzuta, who published a book, it's called Behavioral Economics, and he shares this study that took place in France, where they had this organization, I think was managing a bunch of convenience stores across France, and some of their staff were immigrants from other countries, neighboring countries, and I think high conflict nations who had migrated to France. And they realized there was a pattern there, that these immigrants who were working for the organization were not receiving adequate feedback. There was a sense of neglect, not necessarily discrimination. There was nothing outright that showed that I'm discriminating against somebody, but the points of interaction were minimal compared to other colleagues within the system. So this idea of neglect. And so when I saw this as well, I was like, oh, this is very interesting that this, it keeps appearing. And so when we talk about this idea of diversity, clearly there's Some natural tendency for us as humans to maybe unconsciously avoid the others. That could be anything, right? So how do we make sure that as we are striving towards more diversity, we make sure we don't fall victim into this clearly this unconscious tendency to just spend as little time as we can with those outside of whatever we consider the norm?

Jason Rosoff

Well, I think this question is a topic that probably could be an entire additional hour of conversation. But, but I, but I think it's a really important one. And so I'll try to answer briefly to some extent. I think the answer to your question is in the question itself, which is the recognition of the preference for people who are similar to us and the recognition that there is a sort of majority culture that without being intentional about it, is going to exclude people. And I think the textio research, one thing that's interesting is in the United States, you know, historically there is a, there's like a white culture in the, in the United States. There's more racial division. At least I perceive there's more sort of emphasis on race and racial division in the US Than there is in other places in the world. And so there's this tension that gets created of like, there's this historically sort of like white way of doing things, for example. So like a lot of business culture and things like that are rooted not only in what's like, what works, but like what a bunch of white powerful people decided was good for them, like, you know, many, many years ago. And once we acknowledge that, like, it allows us to examine things more closely and to say, is this policy actually good for all the people who work here or is it only good for some of the people who work here? You know what I'm saying? Like, are we. And, and the only way to do that is to look at it honestly. And I think one of the things that textio does that's so important is they actually analyze the words that go into people's performance reviews. And that's one of, that's how they were able to surface these findings of like, there are fewer words in, in reviews for people who are underrepresented in that organization. So like, what that means is let's say the organization is majority white and majority male, that people who are either female or trans or some other race other than white are more likely or are less likely to get high quality feedback. But interestingly, it's also true if you flip it. So like, if you look at a majority female organization where men are underrepresented, there's A similar pattern that can occur where the underrepresented group gets less attention. And so it's not just about, you know, racial like writ large, like who's powerful, who's represented and who's not. It can be very specific to the organization. So that's one thing that's important to understand, which is like, who we surround ourselves with affects the way that we treat these issues. And if there is a group of people that are significantly overrepresented, especially as compared to the population that we live in, there's a chance that unconscious biases are going to creep into our processes that prefer the group of people. What sort of like what most people identify as or look like in that organization. Right. I think there's a. So that's the important understanding and the antidote to it is to understand one, I think to start with why diversity matters. Like, why do we care about this issue in the first place? And from my perspective, especially when it comes to communication, which is fundamentally what radical candor is about, there's no way to give advice about communication without considering cultural differences, identity differences, like, you know, family of origin differences, religious differences, you know what I'm saying? Like, you can't give generalized advice. You have to consider these other things. And I think that's. So that's one reason why diversity matters to us is like those different perspectives make us smarter about how to offer people guidance. And then you need to be honest with yourself about how you are achieving that diversity. Like, what active steps are you taking? Because the default is exclusion. To your point, the default is to like, be around people who are like you, who think like you, who look like you, who believe the same things that you do. That is our default. And so we have to create policies that actively work against that default. And that's what I think. I think a lot of organizations skip to the end result, which is like, what is the racial makeup of our team? And then work backwards from there. Whereas I think you should start with why does the racial makeup of our team matter? So that as you think about those policies, you're doing things that ensure the long term success of any changes that you make to try and in trying to increase the diversity of your team and that you measure what actually matters. Because just representation alone is often not enough to sustain these, these policies in the long term. Like, for example, a common pitfall that people run into is they achieve their representation goals, but then they have high turnover in underrepresented people. Meaning the underrepresented people don't feel like a part of the organization. So they hired them all and then they all leave because they're like, well, you didn't make it comfortable for me to be here. You. It's still the sort of like, you know, majority in group focused culture. I didn't feel like my identity or my ideas were valued in the same way that my colleagues who fit into that the mold of the previous culture, they weren't valued in the same way as theirs.

Ben Owden

Yeah, I totally agree with that because I think, yeah, the idea of diversity and that's why I like the whole die. It's like diversity is one thing, it's probably what it's the appearance, it's the surface level, but inclusion. Inclusion is the individual feeling. It's only I can say whether or not I feel included. No one can say that on my behalf. So I think aiming for that next level where we truly have to actually sit down and now with many organizations rushing to meet their diversity quota and you know, it's well actually the real experience of the people who you're trying to create an environment where they are included, don't really share that experience. It's definitely something that we have to think through as organization. It goes back to intent. Intent is very important. Now, as we're winding down our conversation, there's a question that we ask pretty much all of our guests. The 111. What is the one book that you've read at some point? This could be a book that came out last month that you say, I wish this was available. I wish I had my hands on this book, you know, however many years ago, a habit that you've developed over time that has been very, very useful to you personally that you wish you had started earlier and a personal value that you will say, I will, I will fight to protect this particular value.

Jason Rosoff

Okay, so first the book. Let me see. I. I have this temptation. This is a bit of a recency bias, but I like it's. This book has, has. Has fundamentally has like stuck in my mind. And it's called what's our Problem? A Self Help Book for Societies. It's written by this author, Tim Urban.

Ben Owden

Oh, I love Tim Urban.

Jason Rosoff

Yeah, he writes the Wait, but why Blog. And the, the reason why I think this is so important is because it helps. It's one of those books that helps to interrupt binary thinking. And those are the books that I tend to find most helpful. And by what I mean by binary thinking is good, bad, right, Republican, Democrat, left, right, right, wrong. Yeah, exactly. It interrupts binary thinking. And it gives you a more, a more complete systemic perspective way of, of thinking about what happens in, in societies and cultures and why those things might, might happen. So I, I would take that back with me because I think I was stuck for quite a while in a lot of binary thinking, especially earlier in my life. I was more convinced that there was a right and a wrong and, and that that was, I lost a lot of subtlety as a result of that. That the habit, the habit. Getting up early is the habit that I would take back with me. I, I, I missed a lot of daylight hours when, when I was younger, convincing myself that I was a night owl. Like, like that I worked better at night or like that that I, I preferred staying up late. I am healthier, more productive, happier. It's like by a significant margin since I started to manage my sleep better and get up at, go to bed basically at the same time every day and get up at the same time every day has been a transformative thing in my life.

Ben Owden

Wow. And personal value.

Jason Rosoff

I think the way I would, the, the way I would capture it is, is sort of like part of the Hippocratic oath, which is first do no harm. I think there is a, the, the reason why this is on my mind is not because again, I, it's not, I don't mean it to be Pollyannish like you, you, you can't avoid doing harm. But I think it's important to think about the externalities of our actions. Like how, yes, this action I take, maybe it doesn't seem significant to me, but maybe it seems significant to other people. And that encouragement to pause and think about, like, what are the real implications or consequences of the choices that I make and are they helping me and the people I care about in my community, or are they potentially harming me, the people I care about in my community?

Ben Owden

Wow. Thank you for sharing that and thank you for the conversation. So we've come to the end of our conversation and yeah, just one more time, thank you so much for having this conversation, for saying yes and for exploring all these different ideas and for making me think. And I'll definitely look forward to, I mean, if you be able to send that study, I think when you find it, that would be useful and maybe we can just add the link on the description so that other people can access it as well. So do you have any last thoughts, questions that you would like to leave us with before we wrap up the conversation?

Jason Rosoff

Just a word of gratitude. Thank you. I really enjoyed our discussion. I felt like you I don't know if your audience gets to see these recordings or if they only hear them, but you are such a attentive listener. It made it really enjoyable for me to be a part of. So thank you for doing that. And a word of good luck to your audience. I think we talked about a lot of things today that are difficult. I think the most important piece of advice that I gave is, look, if you want to build stronger relationships and get things done and you're not sure where to start, and you're a leader and you're not sure where to start, like, really start by soliciting feedback, like, doing it publicly and talking to your team about what you hear. We hear this over and over again, from large organizations to small, that that act is the most powerful step that any organization can take to improving the culture of candor.

Ben Owden

I love that. I love how we started because you shared your own story of how your natural tendency is to avoid conflict and the steps that you've taken to get to a point where you're more open to having these conversations and the challenge that you're leaving the leaders with. Right. In terms of trying to take that first step towards creating a space where those conversations can flourish. So thank you so much, Jason, and to our dear listener, this has been the Wylead Podcast. I'm your host, Ben Oden. This podcast is brought to you by y lead consultancy. We are dedicated to helping organizations develop leaders who inspire conviction, commitment, and congruence. If your organization wants to develop leaders worth following, please please email us at yoda@whyleadothers.com or visit our website at www.whyleadothers.com