The Power Of Radical Candor At Work (And Beyond) with Jason Rosoff
Jason Rosoff - CEO of Radical Candour
This conversation with Jason Rosoff of Radical Candour illuminates the power in caring personally about those we work with and having the courage to challenge directly. It debunks the myths of brutal honesty and presents a more effective and compassionate way to have hard conversations that drive psychological safety.
It's a lesson that’s important well beyond our worklife.
Jason is the CEO and Co-founder of Radical Candor, working alongside Kim Scott the author and researcher behind the Radical Candour concept. Over the last four years, Jason has helped all kinds of organizations, from tiny startups to the giants in the Fortune 100, realize the power of creating a more Radically Candid culture. Through this work, he’s helped hundreds of companies develop real human relationships between team members and through those relationships, achieve amazing results collaboratively.
You’ll hear more in the podcast about Jason’s self-described career meander and how he’s coming to doing this work.
In his past lives, Jason received undergraduate and graduate degrees in business from New York University. He also worked as a product design team lead at Fog Creek Software, the small-but-mighty New York-based software company that created well-loved products like Trello and Stackoverflow. In 2010, he moved to California and helped launch Khan Academy, the world-renowned educational tech non-profit. Over the next seven years, he helped it grow from three people to a few hundred and reach over 100 million students around the world as both chief people and chief product officer.
Jason lives in a small town on the coast of Connecticut with his partner Jillian and dog Jack.
Learn more about Radical Candour, and find a direct link to the book written by Kim Scott here.
For accessible access, view the podcast with closed captions below and access the full conversation transcript.
Episode Transcript:
Spk0 Alexis Zahner Spk1 Sally Clarke Spk2 Jason Rosoff
[00:00:09] spk_0: Welcome to, We Are Human Leaders. I'm Alexis Zahner and together with my co-host Sally Clarke today, we're exploring the concept of Radical Candor with Jason Rosoff. This conversation illuminates the power in caring personally about those we work with and having the courage to challenge them directly. It debunks the myths of brutal honesty and presents a more effective and compassionate way to have hard conversations that drive psychological safety. It's a lesson that we believe is important. Well beyond our work life, Jason is the CEO and co-founder of Radical Candor over the last four years, he's helped all kinds of organizations from tiny startups to the giants of the Fortune 100 realize the power of creating a more radically candid work culture through this work. He's helped hundreds of companies develop real human relationships between team members and through those relationships, achieve amazing results collaboratively. You'll hear more in the podcast about Jason's self described career meander and how he's come to doing this important work. We hope that you love this conversation as much as we did. Now, let's dive in.
[00:01:34] spk_1: Welcome to the We Are Human Leaders podcast Jason, it is a delight to have you with us and we'd love to start by learning a little bit more about your own personal journey and how you've come to the important work that you're currently
[00:01:47] spk_2: doing. That's a good question. And I'll try my best to be brief, but I don't think my story is not very linear. It's sort of a windy path that I took to get here. So my background, I have two business degrees, one undergrad, graduate, one graduate business degree. I got both of those from N Y U in New York and the United States. And one thing I learned from those degrees that I did not want to go into sort of finance or banking or any of those things. And that was because I didn't really like the people who were in those programs. And I mean, as you can imagine business school in New York, the primary focus is finance, right? Like that's where all the jobs are in New York. So I started as a sort of fish out of water. But the reason I went back for more is what I realized is that there was a lot of things that I could learn or sort of ways of thinking that I could learn from the business world that I wanted to apply, maybe in some different ways than my classmates were likely to apply them. And after I graduated, I went on to a series of sort of similar jobs or maybe sort of somewhat related jobs in very different fields. I started, my first job was as a technology operations manager, which basically meant I wrote software to help a company that was what I call, click and mortar. So essentially they took your scanned photos of your trips. So this is like in 2003, so that people were still scanning photos. This is before everybody had a phone camera and all of that stuff.
[00:03:15] spk_1: I remember those days.
[00:03:17] spk_2: Good. I'm not alone then. And then we turned them into books, hardbound books. So we took those memories that you had, we helped you lay them out and then we printed them and bound them and sent them back to you. And it was an incredible thing to work on because we didn't pay close attention to the content of the books. But we saw enough of it to realize like these are people's first like photos of their Children and like weddings and all of these like incredible moments. And so I really enjoyed working on it, but my job was like pretty mechanical on nature. Like I was basically figuring out like, how do we get this file from over here to over here? And then once we print it, how do we make sure that we can ensure the quality of the finished product all the way through the production process by tracking the order and making sure everything is correct, things like that. And so I worked with these multimillion dollar machines and I wrote a bunch of software but it was there that I realized that writing the stuff for the machines while it was gratifying to, like, save the company money and make things more efficient. It was not actually that interesting to me, me, like, it was nice to do a good job, but it didn't sort of tickle my brain in that way that gets you excited about going to work every day. But what did was working with the folks on the production floor and figuring out how to make their lives better? So like on the order processing side of things, like how can we make the software work better for the people who have to do this every day, who have to work with the software every day to make sure that these memories get bound and sent back to people. And once I realized that I started to look around the world and try to figure out. OK. So, like, where can I learn more about this? And I found an organization that was run by someone named Joel Spools. A company was called Fog Creek Software, which is it no longer exists as of a couple of months ago. And he wrote this blog where he talked about this. He talked about the sort of both the mindset of designing software for human needs. So human centered design, which is again, I'm dating myself. That's like a very popular concept now, but it was not a thing, it hadn't coalesced into a thing at that point in time. And he also did this thing, but he had a philosophy about how to create a business that produced great software that actually helped people. And so I was drawn to like that, the, the combination of thinking, not only how do I do this well, but like how do I create a business around creating great software? So I joined that company. I was there for a few years. I made a lot of tools for software engineers that was our primary product line. But over time, we started to branch out into products for, I wanna say regular folks, people who don't write software for a and one of the products that we worked on was called Treo. Treo is a very popular product nowadays and it has been sold and acquired by Atlassian. So now it's part of the Atlassian suite of products. But my last act at Fox software is to hire the team who built Treo. And then I really doubled down on the software to help human side of things because I transitioned from there to K Academy where I was the chief people and chief product officer and Khan Academy for folks who may not know about it as an online educational, not for profit available globally, focusing mostly on sort of like kindergarten through college or university. But it now goes, it even goes beyond that. Now, it's a completely free resource that covers all of those core things that you're going to learn. And that was a pretty exciting and different type of challenge, building purpose driven tools for software engineers. The sort of surface area of the problem was much smaller than building a tool that can help anyone learn anything that's like the surface area of that problem is pretty enormous. And I was there for seven years, I was the first product person that they hired, I was hired alongside the head of engineering. And when I left, we had grown to about 250 to 300 people somewhere in that range. And I had this feeling which is like the next thing I do, I'm not gonna worry about whether it can scale. I'm just gonna like do something that there's no obvious way to scale it. Because one of the things that I missed when I was doing that work was this feeling of like deep human connection. I was creating things for a somewhat anonymous group of people and I was missing that. Like I got it somewhat from the management side of things. So I was leading teams obviously and those relationships sort of filled that in. But I really wanted to develop the discipline of creating deeper human connection and leveraging that connection to help people grow and achieve their objectives. And I wanted to do it in a way that's like very tangible, which is how I wound up at Radical Candor because I reached out to Kim who was shutting down the original incarnation of Radical Candor, which was a software company that was trying to scale tools to help people be more radically candid with one another. And we had this sort of moment of commiseration where we were like, I don't think this works like, or at least we don't know how to make it work. And maybe we should just, we both arrived at the conclusion that maybe it's time to try some things that don't scale. So we've been focused primarily on coaching, training, like on boots on the ground, like human development work. And that was five years years ago. And over the last five years, I have gotten to really lean into thinking about how I can help people grow, but also how to help other people help people grow.
[00:08:10] spk_1: What an amazing story, Jason, thank you so much for taking us through it. And I love a nonlinear career. So I'm completely here for that trajectory you described,
[00:08:18] spk_2: I felt like I was jumping from flow to like, imagine, you know, you're on an ice flow. And I felt like my career is more like jumping between chunks of ice than it was like walking along a path. But I
[00:08:29] spk_1: don't know if you have this two that, that sometimes it's like one of the great things about getting older is you look back and you start to see the connections and how that particular piece of ice flow is actually really key to where you are now. Even though at the time you had no idea that would maybe be the case. Yes.
[00:08:42] spk_2: The only thing I like to say is I don't like to give myself credit for it. There's no like at least not at the conscious level at the subconscious level that I may have been sort of identifying patterns. But one of the things that I have realized is that it is very it to people. Because most of the time when people talk about their careers, they've come up with a story that makes everything make sense. And a lot of the times when I'm coaching people, they're like, my life doesn't make sense. Like, am I doing something wrong? And I was like, no, that's post hoc analysis. Someone got to the end of it and looked backwards and said, now I'm gonna make, I'm gonna do that thing that humans do, which is I'm gonna make up a story that makes everything make sense. Exactly.
[00:09:21] spk_1: Nice. Coherent narrative to make everything nice bow around it. We're good.
[00:09:25] spk_2: Yeah. Exactly. Thank you for acknowledging that. But if you, it doesn't make sense doesn't mean you've done anything wrong. I just, that's the point I want to make like, if you feel like you have no idea what you're doing, you're in good company.
[00:09:35] spk_0: Yeah, I appreciate that Jason because I'm still at the point where I'm trying to connect some of those dots myself. Now, you mentioned you're at Radical Candor now and you know, we want to dive into this a little bit more and we know that, you know, Radical Candor entails caring personally while challenging directly. This feels like it's a bit of an ethos for the company and perhaps the term radical Candor itself. And can you walk us through what this means and how we actually navigate doing this when it might sometimes feel like a contradiction of terms.
[00:10:10] spk_2: Yeah. One of the reasons why I agreed to have that cup of coffee with Kim was not only because she was doing something that was interesting, but also because when I read the book, Radical Candor, I felt that Kim had done this really amazing thing which has organized a bunch of thoughts that had been jumbled in my head for a long time about the way that I was trying to approach my work and like created a very clear way to both describe and to sort of a course toward making my behavior more consistently in the vein of caring personally and challenging directly at the same time. And I think the reason why it sometimes feels like a contradiction in terms is that a common narrative, especially in business school was that look, you can either be effective or you can be nice like those are your choices. Like you either get shit done or you can be a nice person. And that always felt off to me, it felt wrong. And when Kim wrote the book, it was sort of an aha moment. And the reason why it made sense is because she put those ideas into a framework. So if you see a copy of the book right on the cover, like Kim gives it all the way on the cover of the book, everyone should read the book and should buy the book too, like everyone should do that. But on the cover of the book, she draws there's a picture of a two by two grid with care personally on the vertical axis and challenge directly on the horizontal axis in the upper right hand quadrant is what is radical candor when you were doing both caring, personally challenging directly at the same time. And the reason why Kim does a really good job of illustrating, why that is not a contradiction. Because if we think about the best relationships in our lives, they all combine caring and challenging, right? There have been other sort of similar frameworks. One of them is sort of high challenge, high support is like another way to kind of describe something similar. But I like to think of it as love with alongside high expectations, right? Like that's really like deep care alongside high expectations and the people who I wind up appreciating most in my life are the people who do both of those things for me who like want me to be better than I am today. But the way they express that wanting is through deep care for me as a
[00:12:16] spk_0: human. And I think that's a really important differentiation to make there because I think you mentioned the word nice. And for me, I have a lot of problems with this word. I just don't think there is any depth to the word nice. And I also think that nice can often mean placating people. It is to me it is people pleasing when we're being nice, it means potentially we're not speaking out truth, we're trying to save face, we're behaving in a way that tries to manipulate the situation, in my opinion, to make us be seen in a certain way. And I think that it's often confused with the word kind, which to me is what you're speaking about in radical candor. If I truly care about you, Jason, I'm going to give you honest and direct insight around how I'm doing or how you're doing something because to me that's caring when I'm kind and when I'm caring about someone I'm able to deliver something potentially uncomfortable in a way that shows it's from a place of love and caring. And do you see this sort of confusion in your work, this language kind of muddling that people sort of bring to the work when they're getting started in radical candor.
[00:13:27] spk_2: Absolutely. I think nice and polite are the words that I think tend to fall. Um The not challenge, directly end of the spectrum. Like to be nicer, to be polite, often means to avoid difficult things. Like to not as though the world can be a great place and we can love each other in a world where we never feel discomfort. You know what I'm saying? Like nice and polite to me are more about to your point manipulating the environment so that people never have to experience or very rarely have to experience any sort of like conflict or discomfort. But like, that's just not how things get better. And so unless you're totally satisfied with the way that the world is, I would suggest that I don't know if you all remember this. But one of the original, back, back in the day, the Real World, the MTV program, the Real World had this thing where this tagline, which is like, see what happens when a group of people stop being polite and start getting real. And it was done in a way where the getting real was, you know, being obnoxious to each other. And so I think a lot of people saw that and they're like, yep, that's what it means to get real. But what you described kindness also requires getting real with somebody and not just real from the perspective of this is what you're doing. Wrong but also real from the perspective of like I see you as a whole human being. I care about more than just how your work affects me. Like I actually care about you and in order to be kind to you, I wanna make sure that I'm sharing with you my authentic perspective in part because that's what I would love for you to do for me. Like I don't want you to be nice to me either. I'd much prefer that you are kind to me.
[00:15:05] spk_1: Absolutely. It speaks to that sort of genuine connection that I think we can create through kindness, which means because it entails being present to someone and sort of listening to them as well rather than waiting for an opportunity to come back with a superficial remark to sort of keep everything comfortable. Now, you mentioned Jason that there are four quadrants and that radical Candor sort of sits in the top, right? But if you could just sort of briefly walk us through what the other three quadrants are of the behaviors that we might find ourselves in and how we might recognize when our behavior falls in a non radical Candor quadrant.
[00:15:41] spk_2: Yes, I want to mention one more thing about language, which is that the other word that sometimes gets confused. Like Kim chose the word Candor for a very specific reason, which is from her perspective and definition. Candor is about sharing one's perspective, like speaking from one's own experience versus is truth, right? Or honesty is the other word that people often use. And from my perspective, like truth and honesty are arm's length words. Like we're pushing each other away when we start to talk about truth or honest because we're acting as though those are some objective standard. When in fact, Candor is like, there is no objective standard, there's only my perspective and your perspective and the best thing we can do is like, share those things so we can arrive at some sort of shared understanding. I
[00:16:26] spk_0: think that's so important, Jason and I just want to make one point because one thing that we hear so often is that on the opposite end of kindness is this concept of brutal honesty. And we, I feel like it's often so you have to be totally one way like very kind. And again, people almost mistake that for kindness and it is fluffy and it's a pushover concept versus brutal honesty on the other end where it's this, you know, to deliver a truth. And I say truth in inverted commas because as you've just mentioned, we often mistake our opinion for the truth because we are very attached to it in many ways. But I just wanted to make this point that for me, radical Candor sits somewhere in the middle, it's an opportunity to speak what feels true for us in a way that again is delivered with a genuine caring for the other person versus I have this thing to say and I'm going to deliver it because it's the hard truth that you need to hear and it's often never truth and never needs to be delivered in a brutal way.
[00:17:25] spk_2: Yeah. Absolutely. Down with false dichotomies. I feel like that could be another title for the book, a whole
[00:17:31] spk_0: of the conversation as well.
[00:17:34] spk_2: So the Quadrants of Radical Candor, as I said, if you saw the picture, you'd see there's a vertical axis on the vertical axis says care personally on horizontal axis, it says challenge directly. And that upper right hand quadrant is Radical Candor. And the lower right hand quadrant it, that's where we would put brutal honesty and that's where you're challenging the other person directly, but you are not showing them that you care personally. And I think the problem with brutal honesty or obnoxious aggression as we call it radical Candor is that it is very inefficient, it seems efficient because it's easy to say the thing in a brutally honest way. But if the goal of saying the thing is to influence somebody else's behavior in the hopes that it will help them grow, you are taking a pretty big risk by not showing that you care personally because human beings, we are very, very adept at threat detection. And when someone shares their perspective with us in a way that doesn't demonstrate that we our brains automatically go. Well, many people's brains automatically go into sort of a fight flight, freeze or fawn type of response and fight or flight. I think a lot of people are aware of the freeze response. I think people are becoming more familiar with, which is people sort of shut down in the face of a threat like that. And the fawn response was a new one for me, but I actually have noticed it's been very instructive, which is a lot of the times when people feel really threatened, they'll try to appease you instead of real. You're trying to hear what you're saying. They'll respond with appeasement. Like, please don't be mad at me. I'm gonna say what you want to hear because I don't want you to be mad at me. And that one I think is particularly dangerous in the world of obnoxious aggression because it feels like you've gotten through to the person, right? They're sort of saying the right things when in fact, what they're doing is they're like turtle, right? They're like putting a shell around themselves and they're saying what they think you want to hear, but they are not internalizing what you've shared with them. And so there's a temptation to say like, well, I'm being so like, how bad could it possibly be? Well, fortunately, actually, we're not outgrown the limbic system, right? We have these automatic responses to things and in many cases, they're very protective, but when it comes to social threats, like those generated by someone sharing an perspective in a particularly harsh way that makes you feel bad about yourself, feel guilt or shame about yourself. It's incredibly ineffective and inefficient, but it's not the worst quadrant like that's bad, but it's not the worst thing when, when we shift over to the left hand side of the two by two, to the lower left hand side of the two by two, we wind up in the quadrant, we call manipulative insincerity. And this is where you're neither caring nor challenging. Extreme examples of this are sort of like backstabbing behavior. So this is where you're like, actively undermining or trying to harm somebody else. I think we remember those things that are like sort of fun, maybe the wrong word. It is satisfying, I think to tell stories about that. But that's pretty rare, like with someone like really trying to harm you is pretty rare. Much more common is the sort of venting or talking about someone instead of talking to that person directly. And that it's very tempting to see that as sort of harmless behavior. But what we've observed is that it is clearly not caring because you're potentially damaging that person's reputation with the other person you're talking to about their behavior or their performance. And it's not challenging directly obviously, because the person has no idea that you're doing this. And when we give this example, I'm like, who has done this before? Like everybody raises their hand. Of course, we've done this before. Who thinks other people do this about them? Everybody raises their hand, who likes it when somebody else does this, nobody raises their hand. And so I think like that quadrant winds up being the most destructive or the sort of contributes most to kind of toxic workplace relationships. And I think that it's tempting to give ourselves a pass. I'm just venting. But it actually the moment if we normalize the idea of like we don't deal with issues directly. And instead we talk about each other behind one another's backs, the level of trust, collective level of trust just like keeps going down, right? It's very hard to recover, except if you start to address things directly. Like the only way out is through is toward radical candor that last quadrant in the upper left, which is where we are showing that we care, but we're not challenging the person directly. We call that ruinous empathy. What could be wrong with empathy isn't empathy? Like the source of all that is good about human nature. It is the source like the ability to understand someone else and someone else's emotional state, which is cognitive empathy and the ability to experience someone else's emotional state, which is emotional empathy, those are the sources of human connection. But they can sometimes paralyze us like we get into this place where like I can't possibly tell this person this thing because they're so upset like they can't handle it. And so I'm keeping it to myself as a way to protect this other person. And the problem with that is obvious, which is like, over time it comes out, like, you know what I'm saying? It's like over time comes out. And what I've observed is that you can wind up doing quite a lot, nearly infinite relationship damage, even though you had sort of good intentions. The moment someone who you have a good relationship finds out that you have withheld information from them that could have saved them embarrassment at work or potentially even getting fired that relationship. The relationship damage is nearly infinite. Like it's really hard to recover from that because it's hard to argue that you actually did have their best interests at heart. So like, even though internally it feels ok, and this is one of the things we see the pattern we see is people are like, well, can we just sort of hang out and ruinous empathy as a, like we start our relationships and ruin us empathy and we eventually sort of like, find our way to radical candor. And what I say is like, you don't have a very good relationship if you're living in ruinous empathy, like a good relationship is one in which you care. Yes, but you also challenge one another. You have high expectations, you challenge one another to do better.
[00:23:27] spk_1: Thank you so much for walking us through those, I think each example, I can think of my own lived experience and also clients that we've worked with where it's been sort of, you know, maybe a couple of elements of both. I love also that you spoke to those responses, limbic responses that we have as individuals to different situations and also to the concept of trust because I think that what seems to be missing often is that that little bit of courage sometimes that it takes to step into a space of radical candor. So for example, staying in ruinous empathy might feel kind of comfortable. But eventually, I can imagine it's kind of like walking on eggshells where there's going to be. We know that things aren't communicated, resentments build up and that toxicity does sneak in even if it isn't as immediately apparent as it might be in sort of the lower quadrant. So thank you so much for walking us through those. Jason.
[00:24:15] spk_0: I can't also help up thinking that for radical candor to be present sort of shifting to a workplace setting. Now, there needs to be potentially some environmental factors at play to allow that to be. And you mentioned Jason that, you know, people often feel maybe the inability to challenge directly or perhaps there's this environment where employees chat to one another about issues rather than challenging the individual directly, perhaps it's challenging a power source directly. And I'd love to know, you know, in your experience in a workplace setting themselves a and speaks with radical candor. Can this contribute to an environment of psychological safety in the workplace setting?
[00:24:59] spk_2: Yes. Luckily Kim, who wrote the book, Radical Candor and Amy Edmondson, who wrote the book on Psychological Safety Are Friends and they've had the opportunity to talk quite a lot about this and there are even some published articles that they've collaborated on together. Amy says that candor is a necessary ingredient for psychological safety. The ability to say what is on our mind without feeling like we're going to be punished, shamed or ostracized for sharing a perspective, might be different from other people is an absolutely essential component for psychological safety. And from a leadership perspective, I think I just want to slightly turn what you said on its head, which is, I think the leadership behavior that is most important when it comes to creating an environment in which people are more psychologically safe and more willing to be radically candid with one another. Really starts with listening and soliciting feedback because it's hard. It's tempting to say our problem is that we don't give each other there enough feedback. We're not radically candid enough with each other. And so the clear thing to do is like we should start giving each other radically candid feedback. But the problem is like you're not honoring the trust you've been granted when you do that. Or rather, I should say you're putting at risk the trust you've been granted when you do that. And instead the behavior that we see as most directly correlated with successful organizations who are successful in building environments of psychological safety. And radical candor is really when leaders are not only are open to feedback, but actively seek it from their team members. And not only do they listen to what they have to say, but they actually act on the feedback that they get. And it seems sort of trivial when I lay it out like that, it's like, oh, ask for feedback, listen to what people have to say and then act on the feedback that you get. It's like, of course, everybody would do that, but it's actually requires a real energetic commitment of energy to do that. But what I have learned is that it's a far faster and cheaper way to achieve the goal, which is like more trust, more psychological safety, more candor is making sure that leaders are demonstrating their openness to the feedback of their team members
[00:27:07] spk_0: that does feel like a really important place to start. And I'm glad that you raised that Jason. So from my understanding, listening then is sort of the foundational behavior that leaders can engage in to then show that radical candor is perhaps a safe behavior in their workplace that they're open to actually receiving perhaps challenging or discomforting information. Is that right?
[00:27:28] spk_2: Absolutely. Right. And I would go a step further and say, making our listening tangible. I is the behavior that I think is actually most important. One of the most discouraging things that when, especially when I do this sort of training or coaching for people who are like individual contributor level folks, one of the things they report as being most discouraging is like, I keep giving feedback and then nothing happens. And the really sad part is when I'm coaching, the leaders of the same organization where people are reporting that they're like, what are they talking about? I'm doing. So I'm like, trying so hard to implement all this feedback. And so one of the things that we suggest for people is like, you might think you have communicated that you have really heard feedback and you are acting on it but like be theatric like think theatrical, like how could you make like broadway? Like how, how do you in lights? How do you show that you have actually heard the feedback that someone has given you? And usually that pushes people just far enough that other people will hear it? It doesn't get to the point of theatricality. Like the funny thing is like, the guidance is like, go big, like make it really big and usually that pushes people just far enough that other people actually hear it, like, feel the impact of it, right? So
[00:28:39] spk_1: we're a little afraid of actually using the fireworks, but we need to sort of shift in that direction
[00:28:43] spk_2: Yeah, exactly.
[00:28:45] spk_1: I'm curious. I love that sort of tangibility of the feedback. I think that's such an important missing piece as well because obviously if we're listening and we're hearing what people want, but they're not, then seeing that we've done something with that or hearing that, even if we're working sort of full time to manifest that if they're not actually knowing that we're doing that, that's a really important missing piece of the puzzle just at a personal level. Or Jason, I would be really grateful if you, because I'm thinking of all times in my career where I've experienced moments of radical candor and where and also vast gaps where I really haven't. And it's almost only in retrospect that I see the impact that it's had on me at the time when there's been a moment. If you can identify one in your career where you've experienced, you've received the benefits of radical candor from a leader perhaps and tell us about what the impact was for you.
[00:29:31] spk_2: Yeah. So the story that I tell is actually about the time I received feedback from a peer who I was working with. And the reason is because it's probably one of the most important pieces of feedback that I received in my career. And it came, it didn't follow the pattern of oh great mentor passing down knowledge of the ages to me, it was like, no, I was working, collaborating on a project with somebody we were getting ready to present that project to the board of directors at Khan Academy to try to secure funding for some new features to help teachers use, make better use of Khan Academy's platform. And we had been working quite a long time on this and sort of ironically at that moment in my career, I was very, very nervous, like speaking in front of people to the point where I would like sweat through my shirt when I had to like, go stand up in front of somebody. So I was like, here's a trick for anybody who has that, wear a dark sweater or top the shirt that you were sweating through. So I got to the point where I was so nervous about this that I thought I was actually gonna get in the way, like it's gonna reduce our chances of being successful. So I turned to my partner, Dana and I just said, hey, would you be willing to sort of take the lead on the presentation and I'll follow, I'll, I'll show my support, but I'm feeling so nervous and I care so much about this. I just don't want to sort of screw it up. And she said, you know, no, no problem. And she actually had a background in consulting. So like making presentations to rooms full of strangers was like the bread and butter of her. So I was like, great. Now, my job is simple. Just be super supportive. When I get in there, you walk into the room, I'm sweating, even though I'm not going up in front of people because I'm so nervous. But as soon as she started the presentation, like, it was very clear that it was clicking for people, people were engaged or asking great questions and every comment was like, pretty positive by the time we got to the end of it. So they didn't like give us the green light at the end of this conversation. But all signals were, were moving in the right direction. So I'm sort of on cloud nine, I walk out of there. I'm like six months or at the, it's totally paid off. I'm feeling great. Dana comes, taps me on the shoulder and she says, hey, Jason, I'm, I just wanted to check in. I'm curious how you think the conversation went and I was feeling so good. I was playing superlative ad lib. I was like, you're amazing and it was great and I'm so excited and everything is wonderful and I'm feeling great. And as I'm saying this, I'm like paying attention, I start to tune into Dana's body language and I can see that she's relaxing and I didn't like fully register that she was tense until I saw the body language relax. And as a sort of processing that and starting to ask a question in my head about why that might be. She continued. And she said, well, I'm so glad to hear you say that because I look over at you like a couple of times during the presentation, you look pissed off. Like I thought I was completely blowing it. I thought you were mad at me. I thought this is like a disaster. And I remember most people have had this experience of like on a roller coaster. You know, when you go start to descend that first hill and that sort of like feeling of your stomach floor sort of dropping out. That is how I felt. And she continued and she said, and I noticed like other people were, were also reacting to you looking so annoyed and I'm worried that it might have undermined some of the support that you were trying to show. And at this point, I started feeling like I'm in freefall and Dana very graciously and gracefully caught me. And she said, and I know this wasn't your intent, like I know how much you care about this. And that's why I'm telling you that this happened because one, I wanted to know for myself and two, I wanted to give you an opportunity to correct the record. Like if anybody's confused about this, I want us to have the best chance of success here. And so I remember we were having lunch together because the board was there. And so we had Mediterranean food and put some falafel and hummus and Tabouli and stuff on my plate and I ate not one bite of it, not a single bite. I just sort of like, sat there with the food in front of me and I was like, how did this happen? Like, how did things go so wrong? And over the course of about 15 minutes, I kind of screwed up my courage. And I said, ok, I know what I need to do. I was just like, I need to talk, go back to my team. And I'm like, hey, because I had a really good relationship with them. And I was like, hey, you all ever notice like sometimes my face and my words, like they don't say the same thing and they're like, oh, of course, we've noticed that we call that your thinking face like no hesitation, immediate response. And so as I'm sitting there, kind of like, it started to kind of feel funny at that moment. I was like, OK, so this is a group of people who I know love me. And they've had to come up with like a coping mechanism for the disconnect between my body language and my message. I wandered over to my boss's office sal who founded Khan Academy. I was like, sal just check came in. I wanted to make sure. And he's like, you know, we've worked together long enough that I've learned to read between the lines. But it is kind of confusing. And then I did the thing that we all do when we get feedback they're not comfortable with. And she was like, I went home and I complained about it to, in this case, my partner Jillian and like, I'm recounting the story and she's just laughing. So like she said at the longer the story goes on, the more uproariously she's laughing. She's like, of course, of course, this is a problem every time that you do something that requires your full concentration looks like you're in physical pain. And so at that moment, after some 20 odd people had given me the same feedback in 24 in a 24 hour period, I was like, maybe I should do something about this. And the more I reflected on it, like over the course of the couple of weeks, the more I realized people have been giving me this feedback my entire career. This was not the first time, the second time. This was the 20th time someone had tried to give me this feedback and it got me thinking like, what did a do that helped me? And she did two things from my perspective. One of them was she showed me that she cared about me personally, just the act of checking in to see how I was feeling about. Like that was an act of care personally, the collaboration that we, the work we had done together. She had also demonstrated like that we had a shared goal and that felt like care personally to me. But in the moment she was very careful to say this was what I experienced, but I don't think it was your intention. And that was a sort of a gift that no one else had given me when they were giving this feedback. The other thing that she did was she gave me very specific clear examples of what happened and what the impact of those things were. And that was another thing that people had never really done for me in the past. They sort of said, like you're sort of confusing, you see one way and the you seem to feel another way. And I was like, I don't experience myself like that. But when she said, you look pissed off and I got worried that I was screwing things up. That was like very clear to me. And I was like, OK, so like, that's the thing that I need to worry about. And the reason why I said this is one of the most important pieces of feedback that I've gotten is that as I have grown into leadership roles, one of the most challenging things as a leader is to be clear with other people and being clear is not always about saying the right things often. It is about making sure that what you say, how you say it and how you inhabit your body, as you are saying, those things are congruent with one another because you could say the right thing but say it in a way that makes it seem like you're saying the exact opposite. And again, it seems trivial. But it was this moment that I was like, oh, this is a skill. And if I don't learn this skill, I'm constantly going to run up against confusion that could be avoided. The last thing I wanna say about this story is that I have not fixed it. I've learned to manage it. And one of the biggest gifts that I got from her from Dana was this story because now when I meet new people or I'm collaborating with folks, I'm like, hey, I want to warn you that I have this tendency that I'm not fully in control of or aware of. But when it happens, I am very comfortable with you calling it out and saying like, hey, like Jason, I think you have your thinking face on and that will help me bring attention to it. It will help me manage it. But also hopefully it'll help avoid any extended period of confusion about how I'm really thinking or feeling about something.
[00:37:00] spk_0: Jason. I just want to say that I experienced that story on a visceral level while you were explaining that Sally and I were sitting there, we've obviously got our cameras off um for people to see this conversation, but we were sitting there nodding, laughing, feeling our stomachs drop with you riding the roller coaster with you riding the roller coaster with you. And I think the reason that hit us both so viscerally is because I'm sure that most people, if they have even a shred of self awareness have probably experienced a moment like that in their career. And, you know, it had me reflecting on a moment where I had an extremely similar experience when I was managing a team at, at Patagonia based in Canada, where it was brought to my attention that I consider myself someone who's approachable, who's warm, who's open and one of my team leaders at the time. So one of the staff that I had, that was responsible for our floor staff and things like that came to me and raised an issue that she felt that although I was saying that I needed input for changes, I needed input for inventory control and process changes within the business that the way I was delivering, it felt intimidating. So it felt that people couldn't actually come to me with their changes because it almost was like the language that I used maybe was on point, but the body language and the tone and she delivered it so well. She says it's almost like you're saying, I dare you to come to me. And I was like, oh my goodness, I was rattled. I thought no way I am genuinely seeking your input, knowing that I don't know the challenges you face on a day to day basis. And the point was this structure is in place. I didn't build the structure and I'm happy for us to tear this structure down. But for me to get that feedback from one of my floor staff saying, but it felt like you were saying, I dare you to challenge the structure. My world almost fell apart in that moment because I had that exact same moment where I thought, where else is this showing up in my life? And interestingly, I had a conversation with my partner who also worked for the same company at the time and he had a very similar experience. He laughed and he said, you do this all the time. You do this to me when you say, can you bring the laundry and are you to challenge me? You know, and I thought, oh my goodness, I'm trying to be this warm approachable, loving person, kind person which I know I am, but my intention and my impact is completely misaligned. So thank you so much for sharing that. It was a, you know, slap in the face for me to keep checking in with all those moments where I might not be showing up in the way that I'm intending to as
[00:39:34] spk_2: well. Yeah, and I appreciate you sharing that. I think one of the pieces of feedback that I've got about that story is like, it's very relatable and people are also surprised that that's my radical candor moment. They're like, I was imagining it was gonna be something bigger, like, more dramatic than that, you know, that it changed your career path or like, you know what I'm saying? Like people think like, oh radical candor, it's radical, it's extreme, it's big and it's like this is about a very small thing which is like in the moment the congruence of my body language and my message, but it was having this enormous impact actually on my ability to be effective. And so I think the fact that you were open to it in the book, Kim tells this really funny story where she had this similar issue where she was like, someone came to her and said, you're intimidating. And Kim's like, no, I'm not, you know, she's like a five ft tall person. She's like, how can I, I'm not like, physically, how could I be intimidating? And it was her boss and her boss said, you know what, go in there and tell them to do something that, you know, is impossible and see if anybody challenges you, she walked into that room, she told them to do something impossible and they were said, yep, no problem. We'll get right on it. And at that moment, she was like, ok, I think there's a problem dangerous. Like something I've done is actually intimidating. And so like the note that I wanted to like emphasize that you said is that often our intention, our self perception and our impact are so wildly different that it's hard without that external piece of input to ever see it. And so if you're hearing this and you're feeling worried about it, like, go ask a trusted source, like it was actually really easy for me to get this feedback. Like go ask someone if you're like, I think this is happening to me, but I'm not sure go ask a partner or someone you're close to at work and say, hey, do I do this? You might be interested in what you find out and it might make a big impact on you even though it feels like it's
[00:41:19] spk_0: small. I agree for me, it was just a regular Tuesday. You know, I didn't go to work that day thinking that my perception of myself would be radically different by five PM. Now, Jason, you are the CEO at Radical Candor. And I'd like to know, you know, in your experience of working at a company where Radical Candor is a driving force of your interpersonal communication. What are some of the outcomes that you see as a company that perhaps other companies don't, who don't have this sort of imbued in their culture? Yeah, I
[00:41:46] spk_2: will say that a commitment to Radical Candor is a commitment to becoming comfortable with being uncomfortable. I feel like at Radical Candor, the company, I have had more moments of discomfort than in most of my previous jobs. I also feel like I have better relationships than I had with the people that I work with. I have better relationships than I had in my previous jobs. And I have grown and become better as a leader as a presenter, a facilitator, a coach. I've gotten a lot better at those things and I was pretty good at them. Like I was good enough for Kim to be like, sure come be the CEO of radical Candor, right? So I think like I don't say that to scare people. But I say that because one of the things that practicing radical candor and building an organization that values that holds me and us accountable to being radically candid with one another. One of the things I come to appreciate is that discomfort and growth are sort of two sides of the same coin and the more comfortable we are, if your goal is to grow, you should be worried. If you do not feel discomfort, it should be of concern to you if you are not feeling discomfort on a regular basis. Because there's a lot, I mean, there's like an incredible wealth of information that exists in other people's perception of us, especially if the thing that we want to get better at is like that requires collaboration with other human beings. There's a wealth of information out there and if we don't seek it, we don't honor it when we receive it. Even though it makes us uncomfortable, we are very likely to miss that to slow down our development significantly. So I feel like my rate of development has increased, my relationships have improved and I know where I stand and I feel like I can broach more difficult topics with people on my team much more quickly than I have in the past. So in addition to all those things, I feel like we're more efficient and we deal with issues faster and that does not mean we always get it right. But one of the beautiful things about radical and is sort of self correcting because you were like, well, we didn't get that right or I don't feel like we were radically candid with each other in the way that we dealt with that particular issue. It becomes a tool that helps you act as a yardstick to say like, how close or far away are we from both an ideal outcome and an ideal sort of path to that outcome or way of being that gets us to that outcome?
[00:44:00] spk_1: Fantastic insight, Jason, I think that really resonates, you know, for me and I think for many of our that sense of discomfort being correlated with, you know, better relationships, greater rate of learning and actually, you know, higher efficiency and effectiveness as well because we are showing up with courage. And I think, you know, being able to differentiate between that and sort of actual limbic hijacking situations where we are in under, you know, sort of full stress is really important too. And I'm thrilled that you're at an organization where you're able to embody those things and to have that sense of growth and impact. Now, it's been amazing to speak with you. I'm sure we could go for hours more, but I'd love to finish just with sort of one insight if you will, maybe. And it doesn't have to be limited to radical candor because you a thought leader in the space of leadership. What's one thing that you would like our listeners to take away today as a sort of a next step or a tip that they can take to perhaps build radical candor or to shift towards a more radically candid work environment. I
[00:44:57] spk_2: think there are two things that are competing in my brain. The first thing is like, I think one thing we haven't talked about in order to maintain a commitment to radical candor, there's a subtext here which is like, no thyself. Mm And maybe even love thyself. Like, I think there's a piece here where people feel like, oh, if I'm ex like, criticism is gonna undo me, like it's going to break something down. And so when I think about building a practice of radical candor, I think often people are tempted to sort of like jump into the deep end of the pool. And if we're gonna know ourselves and love ourselves, I think that means be gentle with ourselves. So if you're like, this is great. And I'm so excited. I would not go give sort of radically candid criticism to this person who you've like held off giving criticism to for two years or to solicit feedback from this person who you've been fighting with for the last six months. On some project, I would start pick someone who maybe will help you on your journey by allowing you to make your first few steps a bit gentler so solicit feedback from someone who you have a great relationship with. But you might be interested to know if they have something else that they could offer you and offer criticism on a small thing, like pick a small issue. And if that's the thing, the skill you wanna practice, take a small step in that direction. I worked with a great trainer who worked with our teachers at Khan Academy and she ended every training with start small but start, that's the hardest thing because inertia is do nothing. Inertia is do nothing change nothing. And the problem is entropy. When you have the inertia to do nothing and entropy competing with one another, things will get worse like they will get worse. So start small but start
[00:46:34] spk_1: amazing words for us to close with. Thank you so much for your time. Jason, it's been a real delight to have you with us on. We are human leaders. Thank you.
[00:46:49] spk_0: Thanks for joining us for the episode on Radical Candor with Jason Rosoff. What's important to remember here is Radical Candor is a skill that can be built in yourself and in your team. And if this is something that you would like to imbue in your organizational culture, we encourage you to jump onto our show notes and get all of the information about the Radical Candor book and the exercises that Jason described. Find our show notes at W W W dot We are human leaders dot com. Thanks for being with us.