Managing Managers: How to Navigate the Jump from Manager to Director 7 | 32

What do you do when you suddenly have to manage managers? Kim, Jason, and Amy respond to a real-life leadership curveball: what happens when you accept a new role—only to find out mid-interview that it’s actually a director position? Inspired by a question from Reddit, they share practical advice for anyone navigating the leap from managing individuals to managing managers. 

Listen to the episode: 

Episode at a Glance: Managing Managers

 Learn how to build trust early, create a strong feedback culture, and recognize when to listen and when to take action. Whether you’re new to leadership or just feeling a little unprepared, remember: you don’t have to have all the answers. Leading with Radical Candor means you care personally, challenge directly, and stay curious. Your job isn’t to fix everything—it’s to help your team grow.

Radical Candor Podcast Tips

Scenario 1: One of your managers seems overwhelmed and is starting to disengage.
First, check in with care. Ask them how they’re doing and whether there’s anything they might be able to stop doing—or delegate—to lighten the load. Don’t assume they’re just overloaded; sometimes burnout comes from boredom, not busyness. Try asking, “Is there something you'd be excited to take on that would help you feel more energized?” Whether it’s simplifying responsibilities or adding the right kind of challenge, your goal is to support them in finding clarity and balance—without judgment, just curiosity and care.

Scenario 2: A manager on your team is avoiding giving feedback.
Start by asking how that’s working out for them and the team. Then, offer to help. You can say something like, “Let’s practice together—I’ll be the team member, and you try saying what’s on your mind.” Let them know you’ll support them no matter the outcome, as long as they approach the conversation with care and respect. And if they’re still feeling hesitant, try sharing your own “Bob story”—a moment when you didn’t give someone helpful feedback and later regretted it. Ask them if they have a story like that too. You’ll be reminding them that giving feedback isn’t about being harsh—it’s about helping people succeed.

Scenario 3: Your managers feel siloed and aren’t sharing information with each other.
Think about pulling together a cross-functional project—something collaborative and even fun—that brings your managers together in a new way. Encourage them to set up regular one-on-ones with each other, not just with you. And take a step back to look at the system: could there be unintentional incentives that are rewarding people for staying in their own lane? Also, you can try changing how decisions are made—don’t always default to the functional lead. Instead, try giving someone the chance to lead a project that affects multiple teams. That small shift can nudge people out of silos and into collaboration, where they’re more likely to share, support, and succeed—together.

Radical Candor Podcast Resources

• Transcript
• Accidentally Landed A Director Role | Reddit
• What Do Managers of Managers Do? (The Crank Call From Kim) 4 | 16
• Five Principles For Successfully Managing Managers
• Are You a Manager of Managers? Here's How Speak-Truth-To-Power Meetings Can Make Your Workplace More Equitable
• Leading Large Teams: How to Manage 50+ Direct Reports In an Open Office or Factory Setting
• Context Matters — Share Your Radical Candor Stories 3 | 2

The TLDR Radical Candor Podcast Transcript

[00:00:00] Kim Scott: Hello everybody. Welcome to the Radical Candor Podcast. I'm Kim Scott. 

[00:00:08] Jason Rosoff: I'm Jason Rosoff. 

[00:00:10] Amy Sandler: And I'm Amy Sandler. Today we are diving into a real world leadership curve ball. Some of you may recognize, this was a question we came across on Reddit. I'll give an edited version of it. So this person writes, I recently accepted what I thought was a senior manager role at a large company I previously worked for, only to find out mid interview was actually a director level position. The hiring process was rushed due to an outgoing director, and I didn't get to ask many questions. I've got seven years of experience managing individual contributors, but no experience managing managers. Turns out, I'll be responsible for an org of about 30 people. I'm not worried about the technical side, but I am anxious about the people management side. I wanna do right by my team and avoid becoming the kind of unprepared leader. Any advice on how to prepare?

[00:01:12] Kim Scott: So all kinds of advice. I think that at the core of being a manager, you do the same things whether you are a brand new manager or the CEO of a 500,000 person company. You solicit feedback, you give feedback, you gauge how it lands, you've gotta build a great team, and you gotta get stuff done. In fact, when I first started doing Radical Candor talks, even before the book came out, I had a talk that I had prepared for first time managers, and then I got invited to speak to the CEOs of software companies that were about to go public, so relatively senior leaders, and I was super busy and I didn't have time to adapt the talk for senior leaders.

[00:02:09] I walked in to do this talk. I was really nervous. I was like, oh my gosh, these people are gonna think I, and the first question that got asked is, well, we understand that you prepared this talk for us, these CEOs, but how do we teach this to our junior people? And I was not radically candid. I did not tell them, actually, this is the talk I did for junior managers and it worked just as well for you. But I will now be radically candid and tell this listener that the good news, I mean, there's a lot of specifics and we can get into that, but I think the good news is that you're ready.

[00:02:49] Jason Rosoff: Yeah. I'm like,

[00:02:52] Kim Scott: You sound less sure, Jason.

[00:02:54] Jason Rosoff: I'm stuck on the fact that not only was the job different than they expected it to be, but they got it. 

[00:03:02] Kim Scott: Yeah. 

[00:03:03] Jason Rosoff: Like that.

[00:03:03] Amy Sandler: Like, portend for some other potential roadblocks down the road. 

[00:03:07] Jason Rosoff: I think what's on my mind, it, this might be an organization where clear communication and expectations is not their strong suit.

[00:03:15] Kim Scott: Oh. I think that's the case. 

[00:03:18] Jason Rosoff: I do think that in addition to what you said, I actually think what you said is the most important thing, which is, they're, the fundamental activities are the same. I think that what I've noticed as I've had to scale, adjust my leadership to people at different levels is that at each transition from individual contributor to manager, from manager to senior manager, to sort of director, manager of managers there are new bad habits that you have to break. Well, old habits that you had that actually probably contributed to your success that you have to now break.

[00:03:53] Amy Sandler: What got you to the next level.

[00:03:55] Jason Rosoff: Yes. I think it's probably useful to talk about at least some of those. Because I think one of the mistakes that I made when I first became a manager of managers was essentially thinking I had to solve management problems on my team myself, because I had to do that when I was a frontline manager managing individual contributors. Essentially, what I did not realize was how to make a team of the managers that reported to me. To think of my team as two teams. One was the team of managers that were reporting to me and the other one was the full team. Like all the people who reported into all of those managers. 

[00:04:37] Kim Scott: Yeah. 

[00:04:37] Jason Rosoff: I do think that that, that does, not every organization operates that way, so maybe this isn't, you know, totally appropriate for what, what they're doing. But I do think that that made it the, the mindset shift from management problems are my problems and like team, like work problems are my team's problems, that, to management problems are my manager team, my manager team's problems. Like we work on those together.

[00:05:05] Kim Scott: Yeah. So now your job is not to solve management problems. Your job is to help the people who work for you become better managers.

[00:05:12] Jason Rosoff: That's right.

[00:05:13] Kim Scott: You're more of a teacher or coach than solver of management problems. 

[00:05:18] Jason Rosoff: Yeah. So like the same way that a good manager is trying to be a multiplier for their team's ability to get their work done by removing obstacles and making sure they have the resources available to them, you're just applying that same set of skills to sometimes the same problems, but to a new set of problems as well.

[00:05:35] Kim Scott: Yeah, I think the, I'm gonna get super tactical about how to do that for a moment. I think one of the best ways to do that is, and this is something that is different between managing managers and managing individual contributors, is that what you wanna do is you wanna create these speak truth to power meetings. And we've talked about this before, but this is something that managers really need to do because you want to know what's happening in your organization a few levels deep, and you want to create a culture of Radical Candor where people are speaking truth to power, where people are offering each of your direct reports criticism.

[00:06:23] So what you wanna do is you want to say at first, maybe twice a year, instead of your one-on-one with each of your direct reports, you wanna have a group meeting with all their direct reports without them in the room. And this feels very awkward. It feels like it's a violation of challenge directly. You're asking your people's direct reports to tell you how they could be a better boss. First of all, you wanna explain it to each of your direct reports that you're gonna do this and you want them to explain it to their team so it doesn't feel like some kind of punishment.

[00:06:58] And then when you sit down in the room with all of the direct reports or one of your direct reports, you wanna say, look, the reason why we're doing this is because we're having to fight against the gravitational pull of hierarchy to silence us. And so it's my job to help Jane become a better manager. So I want you all to tell me what Jane could do or stop doing that would make her a better boss. And then I'm gonna help Jane respond to the feedback. So that's, that's kind of the idea of the skip level meeting. And we've done this on our team. Jason did it for me. I did it for Jason because we're co-founders. 

[00:07:39] Amy Sandler: Yeah. Kim, I was actually thinking of that when you were sharing the advice and while we, you are getting practical, and we can certainly use our example, but I was thinking for the letter writer or the email or the post writer and Reddit, how long in their sort of new tenure as director, what are the things that they maybe should have done before the speak truth to power meeting? Are you suggesting that's actually like the first thing out the gate? Like is there some sort of sequencing to build trust that they need to do?

[00:08:10] Kim Scott: Yeah, it's a great question. First thing outta the gate for sure.

[00:08:14] Amy Sandler: That was my gut, but I wanted to make sure we were on the same page. And the reason I was actually thinking of our own experience was that we did this, and I've lost control of the years, but I think it was just last summer, is that right?

[00:08:25] Kim Scott: Yeah.

[00:08:25] Amy Sandler: 2024? So obviously there was a lot of institutional knowledge and trust and care that was built up when you started this, and it was still kind of uncomfortable, right? Like it was like, well, do they, like I've already said this stuff to you. Do I now need to say this in front of everyone else? And is it gonna sound weird? 'Cause now I'm like complaining about Kim to Jason and vice versa. So even with all this sort of trust and care it still felt slightly like we had to have some courage in those conversations.

[00:08:55] Kim Scott: Yeah. And we're a tiny little team. 

[00:08:59] Jason Rosoff: Yeah. In some ways it's easier knowing the team is bigger to do this than it is when it's really small. I wanna reinforce what you were saying, Amy. I do think it requires courage and trust that, we're assuming that the person who wrote the note is gonna do the right set of things when you inherit an entirely new, fully formed team, which is to spend a lot of time soliciting feedback. 

[00:09:26] Kim Scott: Yes. From your direct reports before you, um, do speak truth to power meetings. 

[00:09:32] Jason Rosoff: We've had, this has come up in several other podcast episodes, but I think one of the most damaging things, from a trust perspective, that people do, though very well intentioned, when they get a new team like this is they're like, I have lots of new ideas and great ways that we can do things, and here's the plan. Here's how we're gonna change everything. But the purpose of the speak truth to power meetings is like, as you understand, in my mind anyway, Kim, I'd love, if you disagree with this, I'd love to know what you think, but in my mind, the purpose of the speak truth to power meeting relatively early on, it is to help you make sure that as you make plans for the future, that you've really heard from each of the people on your team, regardless of whether they report directly to you or report to one of your managers.

[00:10:18] It, it's really hard, I think, to like, one of the things that is likely to happen as you take on this new role is that you're gonna spend much more of your time with the managers who report directly to you and much less of your time with the people who report into those managers. And as you think about, my guess is that you're going, you will want to make some changes. And as you think about implementing those changes, it's gonna be very valuable for you to have heard the perspective of those, the, the direct reports directly. So in addition to helping you help the manager get better, it also helps you understand each of those people a little bit better, which is gonna help you communicate any changes that you wanna make.

[00:11:00] Kim Scott: Yeah. Yeah, absolutely. So let's back up per what both, Jason, what you said and what Amy said. Step number one is to make sure you're doing the most important things that you need to do to create this culture of Radical Candor, this culture of feedback. And that's, make sure you have one-on-ones with each of your direct reports once a week. Try not to have more than 5 or 6 direct reports, that's not always feasible. If you have 10, have it every other week or 30 minutes a week. But you, really get to know people in those one-on-ones. And at the end of each of those one-on-ones, you wanna be soliciting feedback about what you can do. And then you wanna reward the candor so that people know that you really want to hear what they really think. Like that's kind of step number one is get your one-on-one squared away and make sure you're soliciting feedback in them. 

[00:11:52] Amy Sandler: Yeah. There was interesting conversation in the Reddit thread and very much around one-on-one soliciting feedback, listening, not kind of rushing in and making huge changes, on the assumption that you've inherited a functional team and things are going well. So I'm curious if you would give different advice if you are brought in to shake things up or make a lot of changes versus sort of steady as she goes. Does that influence your decision making? 

[00:12:20] Kim Scott: I think even if you inherit a dysfunctional team, if you go in and start making a bunch of changes before you understand the reasons for the dysfunction, you're likely to do more harm than good. I think you really need to spend at least the first month, if you can afford to spend the first three months, getting to know people, understanding what's happening. What's going well, what's going badly, what people would like to change, what people would like to do more of, what people would like to do, less of, really seeking to understand. And I think that's true, like if things are going well, you know, your first job is to do no harm, but if things are going badly, your first job is not to make it even worse, which you can easily do. So I think you don't want to leap into action. You wanna make sure that you're listening. You're helping people clarify. They're thinking about what's going wrong. You're really spending the time understanding what's going on. 

[00:13:19] Amy Sandler: What do you do if that's how you wanna proceed, but you're getting a lot of pushback from your boss or whoever hired you, and I need to see results. And why are you just listening? You know, sometimes there can be a bias, you know, let me see action. And not necessarily seeing the value of building those relationships. Do you have any guidance for someone in that situation? 

[00:13:40] Kim Scott: I mean, what I would be inclined to say is, if you want me to get things done quickly, you need to let me get things done the right way. Leaping into action is just gonna slow me down. You wanna make sure when you're inheriting a new team, that you're getting the foundation right. You don't wanna build a skyscraper on a shaky foundation. 

[00:14:03] Jason Rosoff: Yeah, I think I would add to that, what is more important that the team is very quickly. 'cause sometimes there might be a reason to jump into action. But my question is, what's more important, that the team does this thing this week or that three months from now, the team is delivering exceptional results week over week? And I think most of the time people are willing to say, no, the most important thing is that you set the team up to deliver exceptional results continuously.

[00:14:31] Kim Scott: I think that's exactly right. I think that the exception to leaping into action is if you see one person really being abusive towards another person, you don't wanna just watch that for three months.

[00:14:45] Jason Rosoff: Yes. 

[00:14:46] Amy Sandler: Did either of you ever get into a situation where you were plopped into a new role and you did have to jump in pretty quickly?

[00:14:56] Jason Rosoff: I was put in that situation, but failed to jump in as quickly as I should have.

[00:15:01] Kim Scott: What was happening? 

[00:15:03] Jason Rosoff: This was a situation where these were a team of technical people, but not software engineers. They worked on complex machines and there was a particular person who was pretty, pretty much just like a bully. I was still quite young. I was in my late twenties. And I was looking at this situation and I was trying to figure out how to approach this person. Because at first I couldn't tell, they seemed to have good humor about it, you know what I'm saying? Like, it wasn't like the team was like performing poorly or everyone was like, you know, unhappy all the time. But like, it took me quite a while, I would say probably two months to notice like the subtle winces of, of like when the, the person was, was like behaving in this way. And so some of the good natured like banter was more self-defense that, you know than, than it was like a coping mechanism more than it was like genuine humor. And people didn't want, like I was soliciting feedback. I was soliciting input from people. But people don't necessarily wanna tell on their bully. 

[00:16:09] Kim Scott: Yeah. Because that's dangerous. 

[00:16:11] Jason Rosoff: Right. So, it took me quite a while to figure out something's wrong. There's something not right about this relationship, and I did start to address it. Part of it was the bully not being entirely aware of the effect he was having. 'Cause one of the things about being a bully is that you're not looking for the subtle winces. 

[00:16:29] Kim Scott: Yeah.

[00:16:30] Jason Rosoff: He thought he was funny. He thought these jokes were really landing. I, I do feel like I was much more sensitive to that later. Having had that experience, I became much more sensitive to it later in my career when I was put into teams, like watch for those subtle dynamics between people, like the jokes that weren't really landing and things like that. But at that moment I really did feel, and as I started to address it, I even got some pushback from the people who were the victims of the bullying. 'Cause they were basically telling me, if you mess with this guy, he's gonna make our lives worse. He's not gonna appreciate it. He's gonna think that we told, they didn't say it exactly that way, but they were like, look, leave well enough, things are like, things are fine. Leave well enough alone was sort of like the feedback that I was getting. I was like, no, it doesn't have to be this way. And it took me quite a long time to actually resolve that situation. Part of it was changing the team. Two of the people couldn't work together. It just was not going to work, and so I had to separate them. 

[00:17:30] Amy Sandler: Jason, I think this is such a good example. Was this an in-person team or was this?

[00:17:34] Jason Rosoff: In person. 

[00:17:35] Amy Sandler: I'm just wondering.

[00:17:36] Jason Rosoff: It was like verbal bullying.

[00:17:37] Amy Sandler: But like how would you guide someone now trying to pick up on those things? You know, one of the things we talk a lot about is to try as the manager, to put yourself kind of in the room to see what's happening. But how do you recommend, whether it's Slack or in Zoom, how can managers now, managers of managers especially, try to pick up on those things if the people that it's impacting don't feel safe to share with you?

[00:18:02] Jason Rosoff: I think I've become much more conscious of and sensitive to the way things are communicated, especially in writing. And I've been much more comfortable going to people and saying, do you realize how that might have come across? I don't think you intended it this way, but this is how it came across. Since I'm more attuned to it and I'm looking not necessarily for everything to be sunshine and rainbows, but to be respectful. The communication should always feel respectful. I feel like my sensitivity has increased, even if I don't feel offended, I am more sensitive to how things are communicated. And it's not to say that I don't make mistakes, like I will screw this up also, but that's one thing that I've done is over time I've become more sensitized to how communication might be misinterpreted. And I think that if you are reading something as a boss and you're like, this could be interpreted in a negative way, it's almost always useful to say, well, I read it in your voice and I know you didn't mean it this way, but this person may not have read it with your intention. 

[00:19:03] Kim Scott: Yeah. Yeah. I think, you know, in terms of moving fast, moving slow, when you come in as a manager of managers, you wanna make sure that you're not changing, like you're not doing a reorg right off the bat, you know? That, that you're not changing the way that people do the work. Usually my mistake is to move too fast. The times when the mistake I've made have, have been to move too slow is when I noticed one of my direct reports doing something that was, uh, not in service of their team, and they didn't even realize it. So, for example, one time I had just, I had inherited a team and one of my direct reports wanted me to attend his OKR meeting, the objective and key results, the goal setting meeting.

[00:19:56] And he sat there and he told his team what their goals were and you could tell that they were not bought in. That, that the team had not participated, you know, the boss was trying, telling people what to do, doesn't work. And this boss was trying to tell his people what to do and when, he picked up on the fact that, and he started getting more enthusiastic and like practically yelling like, this is such a great goal, and it was not working. I pulled him aside after the meeting. I think you need to let your team set their own goals. You're not the author, you're the editor of the goals. He didn't agree and I should have pushed him harder, faster. I was 100% sure I was right, and I just didn't argue with him as much as I should have, in retrospect. 

[00:20:46] Jason Rosoff: If you see someone dropping a brick on their toe over and over again, don't wait 3 months to get them some steel toed shoes or take the brick away and replace it with a yoga block. 

[00:20:57] Kim Scott: Yeah, exactly. There was another time when I had just hired Russ Laraway, who, if you are a podcast listener, you've heard Russ, and he referred to the women on his team as girl. He had just come out of the military and wasn't used to working with a bunch of women. I felt kind of awkward saying something to him and I, I kept telling my, I mean, this is the lie that we tell ourselves. And I was saying, I'm gonna wait to get to know Russ better, and then I'm gonna tell him not to. And then he went to meet with my boss who was Sheryl Sandberg and he sat down and he said something about the girls on his team. And let me tell you, Sheryl did not hold back. He came into my office later, and there were two other people in my office who had worked with me previously, whom I had said, don't refer to women.

[00:21:49] Russ came in kind of pale. He was like, I just, you know, why didn't you tell me? It was one of those moments. And these other guys, Hal and Jared, kind of were sitting there and I was like, you all can thank me now. You know what I should have done is apologize to Russ. I did not do my job as your manager to give you a heads up that this is a problem. Instead, I tried to make a joke of it and I was like, you all can thank me now. And Russ sort of said, why didn't you tell me? You know, it was your job. And so it was like one of those moments where not only had I been unfair to Russ, I'd been unfair to his team. The women on his team did not appreciate being referred to as girls. You know, I just, I hadn't done my job. It's like hard to know when you should wait and listen and when you need to leap into action.

[00:22:46] Jason Rosoff: As I'm listening to this, what I would say is optimization can almost always wait because one of the most evil things in the world is premature optimization. You start talking,

[00:22:54] Kim Scott: What do you mean by optimization? 

[00:22:57] Jason Rosoff: Like optimization is like, I think a lot of the ideas that,

[00:23:01] Kim Scott: Like changing workflows?

[00:23:03] Jason Rosoff: That a new manager gets is like, this thing isn't totally broken, but we could be way better. We could go so much faster if we did this other thing, but like it probably doesn't need to be changed immediately. But someone tripping over cultural norms or doing harmful behavior to somebody else, those things do deserve quick correction. And often I think about like the situation, like these sort of technical, mechanical folks on my team, one of the things that they didn't have a problem with was safety. But if I walked into that situation and I'm like, there's, on the wall is all the safety regulations and you're not following half of them. I would've addressed that immediately. Because there are few worse things that can happen than creating an environment where people are unsafe physically or psychologically.

[00:23:52] Amy Sandler: Kim, your story is, I think on the one hand, one of the things I love about you is that you always kind of take responsibility and look at how you could have done something better. And as I hear that story, there's also, you're holding a few different identities there, like you are, and you've said this, like I'm the man, but I'm not the man. Like you are the boss. But you are now, there was sort of the additional emotional labor of having to advocate for something that's your own identity. And I'm just, you know, I don't know the identity of the person writing this in, but as a new director, I might not feel as confident.

[00:24:27] I might feel like there's certain things that are gonna be hard for me to say or to do, or I don't have as much experience. I'm always having to be the one to advocate for it. So I did just wanna name that, that it can be a bit harder if you're in that role. And Jason, you were a younger manager. Like there's, there's people in these roles that are having to learn and sometimes the examples are, are painful. So just naming that we, we are a manager, but we're still trying to figure things out as human beings as well.

[00:24:54] Kim Scott: Yes, yes. And I, because I thought a lot about this when I was writing Radical Respect. It is harder to be a manager who's underrepresented a lot. You know, maybe you're younger, maybe you're older, maybe you're a woman, maybe you're a man, maybe you, whatever. So I think the thing is that when you are the person who is experiencing some kind of disrespect, you get to choose your response. But when you are the leader it is your job to prevent that from happening to other people. No matter what your identity is. Like when you're the leader, you better act like the leader. And so it's not that I have no compassion for myself, you know, I was sick of having the conversation about woman or girl, like, why do I have to have this damn conversation one more time? Well, the answer to that question is because you're this guy's director and that's your job, no matter what. I think, on the one hand I have compassion for myself. On the other hand, it was my job to do it and I failed to do the job. 

[00:25:57] Jason Rosoff: And I feel very similarly about my, like I was young. No one told me what I was supposed to be doing, like another 3 months of really uncomfortable sit, I allowed a very uncomfortable situation to continue for 2 and a half or 3 months before addressing it. I could have asked for help. I could have gone to somebody, like another more experienced manager and said, I feel like this thing's going on, but I'm not a hundred percent sure. But I didn't do that in part because I was trying to build relationships with each of these people. I was also in the position of saying, maybe I'm misunderstanding it. Maybe I'm not totally getting it right. I don't wanna piss people off right away. But I started to get uncomfortable. Instead of listening to that and taking action, I was sort of like, well, let's wait and see. And that allowed harm to continue on the team.

[00:26:39] Kim Scott: If you notice that you have someone who's working for you, who is hurting the people under them, it is your job to fix that problem and to fix it quickly. Not because, you know, you're new doesn't mean that you get to watch someone who is working for you hurt the people who are working for them. Part of the reason why hierarchy exists, when hierarchy is working well, is that it, it should prevent people who have a little bit of power from abusing that power. 

[00:27:16] Jason Rosoff: That's right. Yeah.

[00:27:16] Amy Sandler: And just to give a specific example, do either of you have a good example of someone who was relatively new and it could be you, but who did do that? Sort of to show what good looks like.

[00:27:33] Jason Rosoff: That's a great question.

[00:27:38] Kim Scott: I, when I first started, it was early in my career and I was working for someone who, and on the team, you know, I forgot. Somebody was using a term that was offensive to someone else on the team. I don't remember what it was, and if I did, I probably don't wanna repeat it. But anyway, it was like one of those, oh, they're too sensitive kind of moments. And my boss sat everybody down and said, everyone has a red word. There's a word that I can use with each and every one of you, and if I use that word, you're not gonna hear another thing I say for the next 15 minutes. And it is easier for me to avoid using those words than it is to ask you to change a lifetime of emotion you've built up around this word. And so in order to get along reasonably, we're gonna avoid each other's red words. Like that's just what we're gonna do as a team. And so I thought that that was very well said. And it just took the air out of the argument that, oh, they're too sensitive. 

[00:28:46] Jason Rosoff: Yeah. I was thinking of, not that long after I joined like the second or third company in my career, I was like a product manager, kinda a product manager type of role. And the, the organization was like very engineering focused, like they were solving hard technical problems. And I, I had, I had basically put together a proposal that in my effort to try to be complete, I had tried to anticipate all the objections and do all this work on my own and tried to define a bunch of the solution. Similar to the situation that you were describing with the goals, I was met with a sort of stony response to this proposal.

[00:29:34] Kim Scott: So uncomfortable. 

[00:29:36] Jason Rosoff: And people were nice to me about it. They were like really interesting, blah, blah, blah. But I could tell I wasn't getting any traction. And my boss at the time pulled me aside and said, like, they're used to making these decisions. Like you are disempower, like I know you're trying to help them by putting the answers down on paper, but it feels to them like you're taking away one of the most interesting parts of their job. And it was so, it was really helpful because I remember going home at the end of that week when I, 'cause I was so freaking proud of the stupid document. I was so impressed with myself and I remembered the reception and just like that feeling of like unease that you get when you're like, this did not turn out in any way like I had expected. Yeah, exactly. And it was really nice when my boss pulled me aside, the beginning of the next week, and was like, let me just, let me tell you what, what you did wrong.

[00:30:28] Kim Scott: Yeah, yeah. It's a relief to know. 

[00:30:30] Amy Sandler: Before we wrap, one of the things I hear you saying, like, Jason, I think that's a great example and Kim, even with this idea of like asking for help or soliciting feedback, I want to encourage this letter writer, you know, advice seeker, if they had some kind of mentor, someone there that they actually could go to for help or say, I have this weird feeling, I don't know, quite, something is off. Jason, you had the benefit that that person was radically candid with you, but you know, how do you, how can you find some of those pockets of support? Especially if you're new in a role and you feel like, oh, but they gave me this director role, they assume I should know how to do it.

[00:31:10] Jason Rosoff: I think knowing what I know now, I would've been soliciting feedback from my, I would've been using my one-on-ones very differently with my manager, going back to the first story with the bully, right? Like I would've been going to him 'cause I, I was making a bunch of things wrong, but I was also like, it's my job to figure this out. So I didn't solicit enough feedback from the team. I didn't solicit feedback from my boss and I didn't ask for help. If I had done any of those things, I probably would've been sort of steered toward the right track much, much faster than I got there. 

[00:31:44] Kim Scott: I think also at this point, this person has the job and so the person, that when they hired this person, they knew that they hadn't been a manager manager before, so there's no shame, in fact, there's a good deal of strength and going to your manager and saying, I've never been a manager of managers before. Here's how I'm approaching it. Does this seem right to you? And I think going to your manager, not saying, I don't know what I'm doing, tell me what, how to do it. Like that's that, that's gonna make your manager feel, oh my god, what have I done? So going in saying, here's my plan. Does this sound okay? What would you change about it? Is a much better approach. So then the, and given what I know about the situation, my prediction is that this person's manager's gonna say, yeah, yeah, yeah, that seems fine. You know that, that this organization hasn't given this tons of thought, but you might learn something. So it's good, it certainly is a good idea to ask. 

[00:32:51] Jason Rosoff: And then I, as you start to develop those plans and become more certain of them, I would go to your direct reports and it solicit the same feedback. Say, this is what I'm thinking of doing. Like, is this approach gonna work well here, for you?

[00:33:04] Amy Sandler: Get the trombones as soon as you can.

[00:33:06] Kim Scott: Yeah. 

[00:33:07] Jason Rosoff: I, I think that you have a source of, of truth, which is like a person, you know, a group of people who can tell you how, at least how they feel about your ideas. And since they're gonna directly affect them, that's pretty good data. 

[00:33:22] Kim Scott: And you can also like do, if you wanna do early skip level meetings, meet with the direct reports of your direct reports with them the first time, and ask them, you know, like, ask a couple levels deep in the organization. I'm not coming in with a bunch of plans. What I wanna know are what are your expectations of me? You know, what, what do you need from me? That's very disarming. People sometimes won't answer the question, but often they will. 

[00:33:50] Amy Sandler: All right, well, let's wrap with some rapid fire Radical Candor tips for managing managers. I'm gonna read a, a scenario and I'm gonna ask, Kim, you and Jason to respond with a Radical Candor move. So here's the first scenario. A manager on your team seems overwhelmed and is starting to disengage. 

[00:34:09] Kim Scott: First thing I would do is sit down and ask what they would like to quit doing. Is there anything that you're doing that you think you could stop doing? Are there things that we could outsource, potentially? I'm not promising that I can get budget for outsourcing, but maybe I can, like, let's look at what we can take off your plate. I'd probably talk about proactive forbearance when I talk about what can you quit doing. 

[00:34:38] Amy Sandler: Jason, anything different? 

[00:34:41] Jason Rosoff: No, I think Kim nailed it. I think I might ask them like, do you want to talk about what's going on? Is there some way that I can be direct, like that I can be helpful to you? But I wouldn't push very hard on that, especially early on. Like if they're like, no, then I would say, okay, then let's talk about what we can take off your plate so that you can get out of this.

[00:35:02] Amy Sandler: All right.

[00:35:03] Kim Scott: Maybe there's something also that you could add to their plate. Like sometimes people are burnt out because they're bored. And a new challenge, I think that we often assume like what people always want is less work, and that's not always the truth. Sometimes people want more work that is gonna take them where they want go in their careers.

[00:35:22] Amy Sandler: I love that. I mean, I can definitely relate to that. If I've been doing something for a long time, I wanna be doing new things and keep learning and growing, so I love that. All right, scenario two, a manager resists giving feedback to their own team. Jason, you wanna start?

[00:35:36] Jason Rosoff: Sure. So I think I would probably start by asking them how that is going. Like what are the results of not giving feedback to your team? Then I, I would offer them a, a lifeline. One of the things that I think a lot of managers are fearful of, about giving feedback, is that they're gonna somehow get in trouble if they actually give the feedback that needs to be given, like, the person's gonna get so mad at them that, and that they're gonna get in trouble with HR. They're gonna get in trouble with me, as their manager that the, this person got upset. And what I would say is like, the thing that is gonna make me upset is that a person is allowed to continue making a mistake over and over again, hurting them and hurting the rest of the team, that makes me upset, like emotions are unavoidable.

[00:36:31] And so here's my offer, which is, I'd like you to, we're, we're gonna let's work on framing the feedback together. We can practice the conversation right now. I'm, I'm gonna pretend to be this person and you are going to, to gimme the feedback. Then we're gonna refine it, and then you're gonna go have this conversation. And I promise you, as long as you deliver the feedback in the spirit that we practiced it and you don't violate any of our company policies in delivering this feedback, I'm not going to be mad. I will work with you to resolve whatever comes up, but I also want you to be open to the possibility that it goes really well. And I want you to go into the conversation thinking that the outcome could be really positive. 

[00:37:10] Kim Scott: I think I would also tell them my Bob story and ask them to tell me their Bob story. I mean, for me, that's the thing that has helped me get over the hump. 'Cause I do really believe that it's the right thing to do, but it is still uncomfortable for me.

[00:37:25] Jason Rosoff: Yeah. 

[00:37:26] Amy Sandler: And if you are one of the few people listening to this podcast who doesn't know Kim's Bob story, we'll put that in the show notes. Kim's ruinous empathy with her employee Bob. 

[00:37:36] Kim Scott: Empathy with a healthy dose of manipulative insincerity. 

[00:37:40] Amy Sandler: Manipulative insincerity. Yes. And then finally, scenario three, Jason, this actually goes back to when you were talking at the top about you've got your team of managers and then the broader team. This scenario, you feel like your team of managers is siloed and they're actually not sharing information with each other. Kim, you wanna take that? 

[00:38:00] Kim Scott: Yeah, I think when, when people are siloed and not sharing information with each other, one of the things that can be helpful is to create a sort of cross-functional project. The, the example of this in the automotive industry, often car companies build Formula One cars or some kind of, I don't know if it's Formula, some kind of race car, you know? Super cool. And part of the reason that they invest in doing that is not just for marketing, because it's a forcing function, it gets the people from one division working with people on another division, on something. And so creating some kind of fun project that cuts across the silos can begin to break those, break those boundaries down. I think also setting expectations about cross-functional communication and encouraging peers to have one-on-ones with peers, it shouldn't just be a hierarchical thing. It should also be, uh, cross, cross-cutting thing.

[00:39:09] Jason Rosoff: The other thing that I found to be really helpful is to not automatically assign decisions to the person who's functionally responsible. Like one of the best ways to get people operating like a team is to say, you know, decision making is not the same thing as implementation, which means that this project, which is cross-functional, needs a holistic vision. And so you know, Bob is going to lead this decision even though it's gonna impact marketing and sales and operations. And that gets people wanting to share information pretty quick because they wanna make sure that their perspective is considered. But the temptation is like to allow the functions to make all the decisions for their function. And I think that that further leads to the feeling of silos, like that you can operate somehow magically, independently. 

[00:40:02] Kim Scott: Yeah. I think also taking a look at what the, if people are behaving this way, it's not necessarily because they're information hoarders. It's because there's an incentive for them to behave this way. And so take a look at how the system that, you know, maybe it's something about the way that people are rated, maybe you take a look at your management systems and see if they're, 'cause often they create perverse incentives. Unintended perverse incentives. 

[00:40:34] Jason Rosoff: Yeah. I think like. What you were saying, like the fun part, Kim, I was just thinking of like this idea of like withholding information or seeing information as like a useful tool, it's definitely a learned behavior. If you watch young children play a game together, they're not withholding information. 

[00:40:54] Kim Scott: Yeah. 

[00:40:55] Jason Rosoff: They're like helping each other figure it out so they can, they can enjoy the game together. And I feel like since it is learned, right, that that means that there's something in the environment that is encouraging that, that behavior and you might be able to address it. 

[00:41:10] Kim Scott: Collaboration should give a person the ability to get ahead. 

[00:41:13] Jason Rosoff: Yeah. Alright.

[00:41:18] Amy Sandler: Speaking of collaboration. 

[00:41:20] Jason Rosoff: Yeah. I feel like if you've made it to this point and you still feel like there's more to know, we agree. Or if you find yourself suddenly in charge of a new team and wanna level up your leadership skills, head on over to RadicalCandor.com/workshop and register for one of our public workshops so you can practice with your peers. If you want training for your entire team or organization, we have keynotes and workshops for that too. Learn more at RadicalCandor.com/services. The public workshops started a couple of months ago and they have been absolutely fantastic, both to the facilitator and for the participants. We've been getting rave reviews, so I'm sure you'll love one. 

[00:41:58] Kim Scott: And we're learning. 

[00:41:59] Jason Rosoff: Always.

[00:42:00] Amy Sandler: Absolutely. Well head on over to RadicalCandor.com/podcast. You can see the show notes for this episode there. If you are a visual person, you can also watch our podcast on YouTube and Spotify. Praise in public, criticize in private. If you like what you see and hear, we hope you do, please do rate and review us wherever you're listening or watching and share the episode. And if you've got feedback or a question for us, we love hearing from you, go ahead and email us podcast@RadicalCandor.com.

[00:42:32] Kim Scott: Thanks everyone.

[00:42:33] Jason Rosoff: I got my hair cut just for this episode.

[00:42:39] Amy Sandler: Bye for now. The Radical Candor Podcast is based on the book, Radical Candor Be a Kick Ass Boss Without Losing Your Humanity, by Kim Scott. Episodes are written and produced by Brandi Neal, with script editing by me, Amy Sandler. The show features Radical Candor co-founders Kim Scott and Jason Rosoff, and is hosted by me still, Amy Sandler. Nick Carissimi is our audio engineer. The Radical Candor podcasting music was composed by Cliff Goldmacher. Follow us on LinkedIn, Radical Candor the company, and visit us at RadicalCandor.com.

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The Radical Candor Podcast is based on the book Radical Candor: Be A Kickass Boss Without Losing Your Humanity by Kim Scott.

Episodes are written and produced by Brandi Neal with script editing by Amy Sandler. The show features Radical Candor co-founders Kim Scott and Jason Rosoff and is hosted by Amy Sandler. Nick Carissimi is our audio engineer.

The Radical Candor Podcast theme music was composed by Cliff Goldmacher. Order his book: The Reason For The Rhymes: Mastering the Seven Essential Skills of Innovation by Learning to Write Songs.

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