Follow These Steps to Scale Your Business Without Burnout w/ Jason Rosoff

0:00Welcome to the Big Success Podcast. Cutting-edge conversations on business and personal success, as well as how to level up. Here's your host, number one business coach in the world, Brad Shoghers. Radical Candor. Jason is my guest today, Jason Rossoff, CEO of Radical Candor. With Kim Scott, they've built an amazing organization that teaches companies how to grow through actual great conversations. Now, background, he's been tech industry, helped scale Khan Academy. You've probably heard of that one. And then went over to building great companies through great conversations. His definition of success, I think, is going to make you really, really think.

0:46And specifically, how he goes back to his college years and how success was defined for him. Follow me with this. Jason Rassoff is going to blow your mind. Radical candor, radical leadership and ways to do things differently. Let's get on with your success. Here's Jason. So Jason, let me get your definition of success.

1:12I think my definition of success is something that I think about every year because it's not exactly the same for me year to year. When I start the year out, I often set an intention that helps me define what success is going to look like for that year. And I think that this year, the word that has come to mind most often when I think of success is growth. And so I I think that it seems trite, except for the fact that people often get to the end of the year and they think of growth unidimensionally, like just in terms of revenue. But one of the ways that I'm most interested in growing this year and acknowledging growth as success is to look back and say, I am smarter and faster at doing the things that I do every day at the end of this year than I was at the start of this year.

2:05Yeah. So how has it shifted over time then? If you go back to as a young man, how you define success through the tech stuff and building all the big tech companies. How has it shifted, do you think? Well, I think in some years, success was, especially in years where survival was at stake, I feel like success, the definition of success is like, can we pay the bills at the end of the month? So Khan Academy was a not for profit, which meant we had to fundraise every year. And that was a stressful thing. And I wasn't directly involved in the pitches to potential donors, but I was building the products that Sal was going out and selling folks and saying, we want you to invest in the future of this company.

2:55And so So even though we always kept our eye on the ball of making sure that students achieve their goals, that was like our number one definition of success. Like, can we help students achieve their academic goals? There were other forms of success, which were like, can we fundraise enough to actually grow the company in the way that we wanted? Yeah, I mean, if you go back and look at success, somewhere in life, most people had success chosen for them or they chose success. Where do you think it happened for you? Was it as a young boy? Was it in your later years? Where did you choose to be successful in life?

3:34Well, I think one of the, as a young person, I think my definition of success was very much predicated on other people's judgment or evaluation of me and my performance. Yeah, we see that a lot, huh? Um, and yeah. And so like, in terms of like success being chosen for you, I think maybe more damning was success being defined for me. Like someone else was, was defining success, uh, uh, for a lot of my life. And I, and I really bought into that. Like I was competitive academically, like I really wanted to do well. Um, and then I got to undergrad and I had this really eyeopening experience. So I went to, uh, to business school, to the Stern Business School at NYU for undergrad.

4:19It was very prestigious. It was great. I hated it. I absolutely, I absolutely hated it. I mean, I loved a lot about my time there, but in particular, the environment there. So there's this thing that existed when I went called the Stern curve, which basically meant that they graded on a curve and only 5 % of students could get A's. 25 or 35 % of students would get B's and everybody else would get below that. And I was like, that seems kind of stupid because like, is, is it really that relative or are there is like, is excellence that easy to, to, to, to distinguish between that? You can say like, here's the exact cutoff point below which no one else would be considered doing excellent work.

5:00And so the game was sort of exposed to me in that moment, but worse than the game was how other people responded to the game. What I, I've had, I've told the story before, but like I had this experience where I was in a like an accounting 101 class and one of my classmates uh started having a grand mal seizure so like one of those really scary like uh uh like you know twitching shaking etc and the teacher you know immediately went out and called 911 and was like getting the campus uh uh security there and all this other stuff and the students around me started to cheat on that quiz that we were taking

5:44and i was like wow i was like this this it's all bs like this is it is like the the definition of success that i've sort of dedicated my life to it was exposed in that moment as completely false and so i i really do feel like that there was a pivotal moment there where i was like i need to define what i want out of life like what i'm looking for out of this experience because if I let other people define it, the path is clear. You know what I'm saying? Like, I'm going to have to live in a world dominated by a bunch of people who can see another human being suffering and decide like, that's an opportune moment to get ahead on their quiz score.

6:23It was a terrible and life-changing experience. It's those people that film the car crash instead of helping the person in the crash. It was like, that's just insanity. Uh, so over the years, you've obviously worked out your methodology of how to make success happen or how to make your goals a reality. What's your formula or what's your methodology or what do you think it takes to be successful in your world? Brad, I don't know if this is going to be a disappointment to your audience, but I'm a, I'm a grinder. Like I'm the type of person who just like gets up every day and works at it. Um, and, and one thing that I feel like has propelled my success is not being afraid of doing things that I'm not already great at.

7:09Got it. Uh, the, the, the important thing that I realized was that for me, I feel most fulfilled when I'm doing a variety of things as opposed to like just being great at one thing. So I'm like a fantastic generalist. That's why CEO is a pretty good role for me because that can mean anything. Yeah, I get to choose which part I do. Yeah, yeah, exactly. And so that's the way I've started to think about my environment, the environment that best supports sort of my fulfillment is having variety. But that means doing things that I'm not great at, right? That means picking up new skills. The benefit of it is that I've often found that my desire to pick up new skills introduces me to what I would call adjacent areas of excellence.

8:02And some of the best sort of problem solves that I've made over the course of my career is not, we're not driven by functional knowledge or functional excellence. They were driven by the knowledge of the sort of intersection between functions or sort of disciplines in business. So I know enough about finance to understand, to evaluate whether we should raise debt or explore capital. I know enough about accounting to make decisions about how we should, how to make sure that we're preparing for taxes at the end of the year, not just managing the money in the bank account and cash flow, but thinking ahead to the implications for taxes and things like that.

8:51That sort of generalist approach has been really, really helpful for helping me scale a business in a bootstrapped way as opposed to a funded way, which is how we scale to Khan Academy. Yeah. So what's your theory on the relationship between failure and success? How do you see them going together? Or do they go together? I mean, to some extent, if you look at the external measures of success, so like financial success, for example, I feel like the relationship between failure and success is that people just did not give up. They were not dissuaded by failure. They basically said, I'm going to keep I'm going to keep trying.

9:37And so I think failure can be a great teacher, but the most important thing about failing is not giving up. I think, and again, it seems trite, but so many people, for example, they try to do something they're not great at. They fail at doing the thing that they're not great at. And instead of saying, I can learn a lot from this and I can do better next time, they say, well, that's just evidence I shouldn't do that thing again. And I feel like that winds up narrowing the avenues that people have for success, their desire to avoid things that they failed at in the past. And from my perspective, I want to keep every avenue of success open to me.

10:19So not seeing failure as an impediment to trying again. You're on the Big Success Podcast. We're going to take a break. Make sure you click that subscribe button. I'm going to be back with Jason Rossoff, and we're going to talk about candor, radical candor, not just candor, radical. Without the proper methodologies and strategies, building a wealthy life can be difficult. If you're struggling with building wealth yourself, this is the time to join Brad Sugar's 30X Wealth Program. The 30 videos in this program will help you learn how to make your money work for you rather than you working for it.

10:50Create the life of your dreams. You're back, big success. Jason, radical candor, how did it come about? What's the term mean and why should we care about it? Yeah, so Radical Candor, the term was coined by Kim Scott. She's my partner in Radical Candor, the company. And she coined the term over more than a decade of trying to describe and teach what management, what successful management actually looked like. And in part, what she was trying to do when she coined the term was to put words to dispel a myth. And the myth is that in order to be successful, you have to be willing to be a jerk. That was the myth.

11:44She felt like people, she was constantly over the course of her career presented with this choice of like, if you want to be successful, you have to be willing to be a jerk to your team members. And she didn't like that choice. And she looked around at the other people who were inspiring her and were being successful as leaders. And she noticed a pattern, which was that there was a type of successful leader that didn't have to make that choice, that was able to be kind and clear with their team at the same time, right? that didn't avoid discomfort, but also didn't descend into obnoxious behavior in order to overcome a problem or a challenge.

12:28They focused on both the person in front of them and the problem, the business problem that they were trying to solve. And the reason I got involved with it was I read Radical Candor. Actually, technically, I saw a talk that Kim gave first before I read the book. And what I felt is what I think a lot of people feel when they read the book for the first time, which is that Kim put into words a concept that is really difficult to describe and is not necessarily sort of widely understood or accepted. And so this idea of like, this is the way that I've been trying to manage my team with heart and mind and hands at the same time, like it's all those things in unison.

13:08To me, that's what radical candor is all about. So I reached out to Kim when I was on my way out of Khan Academy. And I just said, you know, hey, I don't know what's happening in your world, but maybe there's something we can do together. And I was coming off seven years scaling Khan. So there was a, for me, I was like, you know, I'm not really looking to jump into anything else. This is very exploratory. But for Kim, she was like, I feel like there's this big opportunity and we should get going right away. Anyway, we compromised. Six months later, we started Radical Candor, the company, which still exists today.

13:46And our goal is to help people put the ideas and principles and behaviors of Radical Candor into practice in their own lives and in their own work so that they can do the best work of their lives and build the strongest relationships in their careers. Now, when Kim spoke at our BizX event, it's one of the reasons I wanted to get you guys on here. We'll dive into the management styles in just a little bit, but how do you care personally and still challenge at the same time? Well, I think a good example of that is that my mindset and something that can be useful to say to somebody else is that the way I think of it is I have very high standards and I believe that you can achieve the standards that I've set for you.

14:45that that to me is care personally and challenge directly at the same time right that uh it it draws on a fundamental belief and human in the uh in another human being's ability to impress you to to to grow and adapt uh and perform at a higher level one of the things we love to say around here is that there's no such thing as a b player everybody has the capability of doing great work. Maybe not in their current role. Maybe they're not matched. They're not capable of doing great work in their current role, but they have the capability of doing great work somewhere. And part of it, the job of being an effective leader is figuring out how to put that person in a position where they can do great work.

15:29So let's then take a look at the management styles. And Kim and yourself, you break it down into six management styles you should understand and one you should definitely avoid. Where do you want to start? The avoid one or start with the ones we should do? Yeah, so I think the simplest way to think about radical candor is a kind of two by two grid. Like all great management problems, it sort of boils down to a two by two. And the upper right-hand quadrant, with care personally on the vertical axis and challenge directly on the horizontal axis, and that upper right-hand quadrant is radical candor where you're doing both at the same time.

16:07uh and i think let's come back to radical candor and talk about the mistakes that people make because you know in this framework the there's three ways to get it wrong and only one and only one way to get it right well that that maybe is uh overstating it there are many ways to get it right but there are even more ways to get it wrong yeah uh is a better way to say it so when we challenge but we don't care the uh so that's that lower right hand quadrant kim uh and i refer to that as obnoxious aggression. And that is being a jerk, right? That is, you know, maybe what you're saying is useful, is like informationally useful, but it's delivered in such a way that it is completely demotivating to the other person to hear it.

16:50And if the goal in our relationships is to see the sort of potential in one another, a goal in any conversation is to help that person take a step in the direction of the potential that they have, of the growth that they're capable of. And demotivating them is a really great way to turn them off the path of growth and development. Yeah, I was training one of our new dogs yesterday, and the dog trainers, they learn much better when they're happy. It's the same with humans. If they're feeling good, they're going to learn faster, learn better, achieve more. Yeah, well, and there's all kinds of research that actually backs this up.

17:32And the research is actually quite compelling, which is when you're talking to someone who is an expert in what they do, criticizing them, however you criticize them, is more likely to lead to a positive outcome. And it makes sense why, which is if you understand what it is that you're trying to do, and someone's offering you a correction of like, here's a way to do what you're trying to do better. It's easy for an expert to figure out how to integrate that knowledge into what they are doing. But it is very hard for a novice because it and the one of the examples that I love, there's two studies that I love.

18:06One of them is they took novice bowlers, and they videotaped them, and they had an expert bowler review the videotape with them. And in one of the conditions, the expert bowler said, Oh, you made a mistake here. You need to avoid turning your foot out the next time that you go up to the line. And in the other condition, the expert bowler pointed out something they did correctly. And the improvement that they measured in those two conditions was shocking. The people in the repeat a thing you did well group did improve twice as fast as the people in the criticism group. And it makes sense because our bodies and our minds, we have these pathways, these sort of sense memories.

18:54And if you don't know what good looks like, it's really hard to correct. So the most important thing you can do when you're first starting out is help people understand what is working well, especially if you're dealing with people who are more junior or more novice. So let's go to the top quadrant and the top left. What's the word for that one? So that's where you care personally, but you fail to challenge directly. And we call that one ruinous empathy. Ruinous empathy is such a great pair of words. Yeah. Yeah. Well, there's a fantastic book. One of the things that inspired Kim, there's a book called Against Empathy.

19:32And the problem, there's two problems with ruinous empathy. So one of the biggest problems with ruinous empathy is you care so much that it causes you to sort of avoid challenging the other person. Like I care so deeply that I'm not going to say something that might upset you. There's this great book called Against Empathy. And one of the problems with empathy is that it can paralyze us. We start out with the best of intentions, which I want to show this other person that I care about them. But then we get afraid that if we challenge them, that's going to upset them and therefore derail them. But the problem with that is it's a very paternalistic way of looking at another adult human being, which is like, if I have information that would be useful to you, and I don't share it with you, that is not caring, that is abdication.

20:22You know what I'm saying? In my mind, it's abdication of care. And so we often say that what you really want is compassion, not empathy. Because compassion propels us to act on behalf of the other person, whereas empathy is an internal feeling that might cause us to freeze in the moment and avoid the situation altogether. Yeah, we don't want to see them fail long term. And otherwise, if we don't give them the feedback, they are going to. So let's go to the ruinous corner, the bottom, bottom corner. Tell me more about that one and how we get people out of it. The worst of the worst. So that's where we fail on both dimensions.

20:58We fail to challenge directly or to care personally. And we call that manipulative insincerity. and those are hard those are sort of harsh harsh words what i want people to think about because and we often do a survey so we say which mistake do you make the most often and almost no one puts themselves in the in this quadrant even though it is incredibly common the most common example of manipulative insincerity that i see in the workplace is talking about someone instead of talking to that person directly so if you've ever engaged in sort of water cooler chatter you have behaved in a manipulatively insincere way.

21:34If you've ever had a meeting after a meeting where you say, what a disaster that was, and can you believe Jason said this? And can you believe Jason said that? You have engaged in manipulative insincerity. So it's actually quite common, but it's also very corrosive. In any environment where it's okay to talk about someone behind their back, which is the most, as I said, the most common example, it deteriorates trust so rapidly, And it normalizes this idea of not addressing issues directly. And that really gets in the way of building any sort of sense of team cohesion or collective culture, because so much is happening behind closed doors and is not being addressed in a way that allows people to grow and develop from the observations that people have of what could be better, that it stunts the growth of the organization and really dissuades them from becoming Okay, so how do we move forward?

22:30How do we move to that culture or that environment where it is safe to be candid as well as the high performance that we get from it? Yeah, so for the people who I imagine in the audience who are leaders, what I would say is that it really starts with you and not your willingness to give other people criticism, but your willingness to accept criticism from other people. The fastest way out of all of the mistake quadrants is for leaders to demonstrate that they value the corrective feedback that their team has for them. And part of the reason why that's so important is we kind of need to, feedback is sort of scary.

23:15It feels like the cost is potentially much higher than the benefit. it. Even though we know we can sort of see when we take a when we zoom out, we take a sort of wide angle view of our lives, that failing to give feedback led to significant train crashes, you know, I'm saying, down the road, like we created the conditions for disasters to happen by not doing this. It's feels very expensive in the moment. So what you're trying to do is raise the market value of feedback. And one of the best ways to do that is to make sure that people feel comfortable criticizing their leader. Then it becomes much easier for people to accept criticism as part of a natural, one of the natural interactions that you have with your peers and your coworkers.

24:01So that's thing number one is leaders accepting criticism. A step further is not only accepting it, but seeking it. So we call this soliciting feedback. Uh, the, the, the most, uh, the most common signal of success in any organization that we work with, with, uh, on Radical Candor is the leaders operationalizing soliciting feedback. So they add to their one-on-one agendas or to some process they have internally a specific time and place each week to solicit feedback from their team members. Got it. So, and most of the time, Is that done face-to-face or is it done through 360s? What's the – I mean I sit there and you say this and I'm like, do I really want to ask my team how I – yeah.

24:50Like you said, it's courageous to step into that. It is and what I would say is like – as we started this conversation, we were talking about what makes for success. And one of the biggest things that, from my perspective, is not being turned off by failure. I do think that being a leader means, and being ready to be a leader means having enough ego strength that you can absorb the sort of input or correct, the corrective input of the people around you. Because the hard part about being a leader is your organizational positional authority often just like makes it very scary for other people to tell you what might be wrong.

25:33uh and that is one of those things you know what i'm saying like that we're laying the tracks for a collision when people observe things that are going wrong but they're afraid to say what's going wrong like those two trains are headed for each other at some point but it may be years from now before you get a they they crash into each other but they're destined to crash into each other so if i was thinking about you know moving my organization forward because i want you know obviously a better professional growth, personal growth, that sort of thing. Asking for the feedback for myself, step one, how do I then transition that to the entire organization?

26:13Yeah, so to answer the practical part of your previous question, I ask for feedback in my one-on-one conversations with my team members. I also ask for feedback as part of our standing team meetings. Um, we, we, and we, we do have a, uh, a monthly pulse survey that asks just a couple of questions is sort of about like how people are feeling about various aspects of the organization. So I have three ways that I do it. I spend five minutes in a one-on-one, 10 minutes, maybe once a month talking about, uh, like broad feedback at the organizational level. So in my sort of standing meetings and 10 more minutes reviewing the results of that survey.

26:57So I'm probably collectively spending two hours a month soliciting feedback. And it has helped me catch a lot of small things before they become big things. And I would say that the number one thing that it has done, it is I don't I often don't have to wait for that. Like people will often come to my to one on ones with me with like a, hey, I want to talk to you about this thing that I think could have gone better. Got it. Fantastic. You're on the Big Success Podcast. We're going to come back and Jason's going to take us through scaling up. Make sure you click that subscribe button. Jason Rosoff is the CEO and co-founder of Radical Candor.

27:30Over the last four years, he's 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. To learn more about Jason Rosoff, please visit RadicalCandor.com. We're back. Radical Candor. Jason, you've used Radical Candor now to help organizations. What's the difference in your mind between an organization that grows versus one that really scales? How do you see the difference in the two? Yeah, I think growth, again, it depends on how you define it. But growth is often defined by purely numeric things, like the number of people who work for an organization, the amount of revenue that you make.

28:25In our goal setting this year, I have put together a definition for the team and set an objective around sustainable growth. And from my perspective, this is really sustainable growth is scaling. And the reason why sustainable growth is scaling is because sustainable growth is repeatable, whereas growth without scaling the other things that support people is destined to lead to burnout, which in turn leads to degraded experiences for clients or customers. That is the biggest problem that I've seen. Hyperscaling organizations, one of the ways that a lot of the financial success of the last two decades was achieved in Silicon Valley was by people working 20 plus hours a day.