Promotions gone wrong? Yeah, it’s a thing. On this episode, Kim and former Twitter CEO Dick Costolo tackle a listener’s tale of missed opportunities, broken promises, and a management team that just can’t get it together. From the cringe-worthy red flags to the frustrating aftermath, they explore how leadership missteps can wreak havoc on trust and motivation. Tune in for sharp insights, practical advice, and a whole lot of “what NOT to do” when navigating messy workplace dynamics. If you’ve ever felt stuck in a system that doesn’t seem to work, this episode will help you find your way forward.
Listen to the episode:
Episode at a Glance: Promotions Gone Wrong
Promotions aren’t just milestones—they’re moments that can make or break trust in leadership.But what happens when a promotion is promised and never delivered?
On this episode, Kim Scott and Dick Costolo unpack the fallout of broken promises and vague feedback that leave employees disheartened and leaders scrambling to rebuild.
From recognizing red flags to addressing tough conversations with clarity, we’re exploring the real impact of leadership missteps and how to turn setbacks into opportunities for growth.
If you’ve ever felt let down by a boss or struggled to manage disappointment on your team, this conversation is for you.
The TLDR Radical Candor Podcast Transcript: Promotions Gone Wrong
[00:00:00] Amy Sandler: Hi, Amy here. It’s Thanksgiving week in the United States. So we don’t have a new episode for you, but we do have a very special vintage episode we think you’re going to love. This is Kim and former Twitter CEO, Dick Costolo, who is also a standup comedian, answer some listener questions. We’ll be back next week with a new episode. Until then, enjoy the banter.
[00:00:27] Kim Scott: Hello everybody. Welcome to the Radical Candor podcast. Today we have a bonus episode about management dilemmas. To discuss a management dilemma with me is Dick Costello. Dick is the managing partner and co founder at O1 Advisors. He was the CEO at Twitter from 2009 to 2015. Before that, he worked at Google, where I met him. And before that, he was the CEO of FeedBurner. Dick is also a comic, a stand up comic. So we’re going to have a lot of fun talking today. Welcome, Dick.
[00:01:02] Dick Costolo: Wow, that’s a, I love that introduction. I’ll take it.
[00:01:07] Kim Scott: So one of the things that inspired me to write Radical Candor was working with you at Twitter, Dick. And you said something to me that has always stuck with me, which is it’s fun to talk with you about management. So I thought we would maybe give other people the opportunity to join in our fun. Uh, and you get a bunch of questions from your portfolio companies about, sort of, leadership dilemmas, and we get a bunch. So I wanted to start with one about promotions. And, uh, and
[00:01:42] Dick Costolo: We could talk promotions for four hours probably, but,
[00:01:45] Kim Scott: Yeah, we could, but we’re going to just keep it to twenty minutes. So what I thought we would do, I’m going to read this and we’ll take it from the person, from the point of view, giving some advice to the person who did not get promoted, and then maybe we’ll give some unsolicited advice to this person’s boss. All right, here we go.
[00:02:07] This person writes in, I’m in a bit of a predicament at work that I’d love to get your advice on. Background, I am a senior manager at a large company. For the past year and a half or so, I had been working with my manager on getting promoted. She told me that I was doing well, and at one point she said that she was quote, sitting on her hands, unquote, waiting to promote me once she had the money in her budget. Uh, I would say the first red flag was sitting on her hands.
[00:02:36] Dick Costolo: There’s already multiple red flags, but keep going.
[00:02:42] Kim Scott: Then my manager left the company, another red flag, and a promotion was made available. Given the conversations I’d had with my manager, I figured that I would be the obvious choice. Instead, I was passed over for someone else. I began working with my new manager to understand opportunities for advancement and shared that I had been working with my old boss on getting promoted to a director level position. This was news to her, so she said she would talk to her boss in order to see what was possible. There we go.
[00:03:13] Dick Costolo: Yeah.
[00:03:13] Kim Scott: Off the chain. It gets better. Get ready. This resulted in me meeting one on one with my boss’s boss. Dialogue. Her: I did not know that you were up for promotion, so that wasn’t even on my radar when I was planning these changes. Me: That’s disappointing. I’m not sure what happened. That said, I understand that what’s done is done. I’m more interested in what I can do moving forward. Her: Honestly, even if I had known, I still think I would have made the same decision. I’ve been hearing that you’ve been saying things like, this company owes me and that your trust is broken. Me, internally: What? I did not say that. Me, out loud: I’m not sure where that’s coming from because that’s not how I feel.
[00:04:00] Her: Well, it’s important that leaders in this company are all on the same page and are supportive of the changes that are being made. I know that you, I know that you and I don’t work very closely together and we’re not in a lot of the same meetings, but when we have been in meetings together, I’ve seen you be very positive and collaborative. So I haven’t seen it, but it’s important that the rest of the organization sees that side of you. I think you’re a very valuable employee and I’d be devastated if you left.
[00:04:31] Okay. So yes, this person says for personal reasons, finding another job is, so this person is already predicting what we were going to say. Finding another job is not an option for at least another year. So I’m very curious to hear your thoughts and advice on this. Is there anything I can do to make the situation better?
[00:04:50] Dick Costolo: Well, I mean, my, the first sets of things I would say are to the various people in management at her company.
[00:04:58] Kim Scott: Okay, let’s start, let’s start with that.
[00:05:00] Dick Costolo: Let’s start there. I mean, let’s start with her first manager. The worst thing, the thing that I always would see, let me back up. One of the challenges managers have is they hate having hard conversations for some reason. I don’t know why people want to be managers and then also hate having hard conversations since it’s a lot of what managers are supposed to be doing.
[00:05:26] Kim Scott: Yeah, that is the job, isn’t it?
[00:05:28] Dick Costolo: I always used to say, the example I used to use in the managing at Twitter class was, the manager saying to the employee, hey, nobody wants you to have a pay, you know, just make an absurd, an absurd subject so that it made the point. Instead of a promotion or a, you know, I want to work on this project. I would make the manager, you know, hey, nobody wants you to have a pancake more than me. You know, I know that this time Bill was offered the pancake, but, trust me, I wanted you to have the pancake. But, um, you know, point to someone else, which happens later on in this story, they decided, you know, already creating misery because, A, you’re now telling the employee, you’re, you know, like you don’t have the power to make decisions.
[00:06:17] You’re pointing at other people who are barely are making all the decisions that are, seem arbitrary and capricious to the employee. And B, this, these future promises that managers make, which inevitably causes the employees to quit. This person would obviously quit right now if they could and can’t for whatever reason. But this constant, I’m going to try to make this person feel better because this is a hard conversation. At the expense of this person’s, you know, delight in working at the company four months from now, it happens all the time. It’s just horrible. People do it with like, hey, I really want to work on this project. You know, and then of course, promotions, they do it with, I want to transfer this other group. And managers are constantly saying things like, I’ve been sitting on my hands waiting to transfer you to this better group.
[00:07:10] I’ve been, no one wants you to be promoted more than me. It’s like horrible. You can’t do that. You just can’t say that kind of stuff. I mean, at the, you know, the, the first manager should have at least said, look, you know, you’re already senior management at the company. And when we’re thinking about promotions to, let’s call it director or vice president, those are no longer promotions that are based on, you know, checking some boxes and meeting some set of qualification. You know, it’s not like getting a driver’s license, where if you can parallel park and know when to turn your brights on and off, you get a driver’s license. That’s not what makes you a VP or director.
[00:07:49] We’re in a dynamic organization. The needs of the senior management team are constantly changing, so there’s no like checklist or to do list of, do these things and you get to be a director or vice president. It’s constantly in flux, but I can tell you is we’re going to evaluate your performance based on X, Y and Z and you should, you know, you should be thinking about your performance based on these KPIs. And let’s constantly be checking in on those and how you’re doing against those. And that’s kind of the discussion and maybe the end of the discussion from the first person.
[00:08:20] Kim Scott: Yeah. And what do you think was going on with the boss’s boss? I mean, it seems like this was rolling down the hill. The boss’s boss.
[00:08:28] Dick Costolo: The boss’s boss and it’s truly an insane conversation. Yeah. Even worse. A, like to first of all to say, I had no idea that you were interested in being promoted. Like, that’s just a stupid thing to say. Obviously everyone, in theory, everyone in the company who’s not in some job where they never want to leave it, um, which is perfectly fine sometimes. In theory, managers in a company who have been progressing are interested in progressing in their careers, and one of the jobs of their managers is to help them understand how to be successful in progressing their careers.
[00:09:03] So to say, I had no idea this is something you were interested in, is kind of stupid. To then say, I’ve heard you’re being pejorative, although I’ve never seen it. I’ve heard you’re being, you know, demeaning the company, although I’ve never seen it. It’s like a Trump, you know, people say, lots of people say, you’re say bad things about the company. Personally, I’ve never seen it. I mean, that’s like, I don’t know how you could say anything more demotivating to this person than that.
[00:09:30] Kim Scott: Yeah, and therefore I wouldn’t have promoted you even if I had known you wanted to a promotion.
[00:09:36] Dick Costolo: Yeah, I forgot about that part. Therefore I wouldn’t have promoted you anyway. It’s truly insane. This company suffers from a management structure that doesn’t understand management and leadership, seemingly at multiple levels. So it’s, um, it’s just, you know, the advice that I would give to the person, because they’re now, they’re clearly in an environment where, uh, management and leadership skills are challenged. The advice I would give to this person is go into your new manager and say, look, you know, um, let’s just be clear about the metrics and outcomes against which I’m going to be evaluated and which are the highest priority for, for us. And let’s have a discussion about that. And I’m going to go, you know, I’m going to go crush these metrics.
[00:10:28] And, um, and I would like to know over the long run, it doesn’t have to be by a specific date, but I would like to know over the, maybe over the medium term and long run, what that means for, you know, both the company and me personally in my career. And at least start there. It doesn’t even sound, it sounds like there’s just a, as always, this subjective, nobody wants to be promoted more than me. I didn’t know you wanted to be promoted. Let me go ask my boss. He says, she says, you should talk to her. I mean, it’s, it’s craziness, but I would just at least get square on how this person would, at least if I were this person, gets square on how I’m being evaluated so I can prove my value, both myself, uh, my smaller organization and the company at large.
[00:11:15] Kim Scott: I’ve been thinking a lot about this, I wonder what you think. That I feel like there are times in everyone’s career where they’re working with someone or for someone who doesn’t use words to communicate, they, they use words to sort of push you away. Or maybe even bully you or obfuscate, you know, it’s, it’s words is, and I think that when people, when you recognize that people are using words that way, like spending a bunch of brain cells trying to parse their logic and is like, don’t waste your breath. Don’t waste your energy. Don’t waste your emotions.
[00:12:01] Dick Costolo: I was, I was, we’re, we’re on audio, but I was nodding vigorously while you were saying that. Like, yeah, the conversation with the boss’s boss is, uh, not a conversation worth continuing once they’ve said, also, also I’ve heard your, you know, I’ve heard you, I heard your trip to Bill in the hallway and you, you know, you were wanted by the campus police. It’s just kind of ridiculous.
[00:12:25] Kim Scott: Yeah, yeah, yeah. Well, I think we, we can, we can,
[00:12:29] Dick Costolo: Let me say one more thing. It is a, for really motivated employees who want to get ahead and are super ambitious, they do tend, I mean, I remember vividly a couple, more than a couple, I remember the first couple that came to me when I was CEO of Twitter. People would come to my office and say like, hey, I’m doing a great job as director of, you know, function X, and I just got a, you know, exceeds expectations on my last review. What do I need to do to become a VP? And I would tell them just what I said earlier. There’s no like, check these four boxes and you get to be a vice president. It’s, we’re in a, we’re like, I’ve never been a part of a company that’s grown as fast as one right now. It’s super dynamic. The senior management needs of the organization are changing constantly.
[00:13:21] It’s, you know, I may, there may be more VPs next year. There may be fewer VPs next year, let alone in this specific function. So I can tell you, you know, that you should have a conversation with your direct, you know, boss about what it takes to be successful in your role and how you’re going to be measured in that role. I can’t tell you that it’s going to lead to a promotion or not. Um, and I don’t think, I don’t think, you know, senior managers should let themselves get, you know, bullied into a to do list of once, because of course the person is going to come back three months later and go, okay, did all those things. Am I a vice president? Like, it’s just, you know,
[00:14:00] Kim Scott: I totally agree. At Google I remember people were always asking me, it was like, they wanted the, uh, the, let the, you know, very complicated Lego set of instructions, how to build their career. And I said, this is, that’s not the environment where, I know you don’t want to hear this, but if I can tell you exactly what it took to, uh, to, to get promoted to the next level, then we wouldn’t be in the kind of dynamic, fast growing situation that we’re in. But what I can tell you is, you know, here, here are the OKRs that you’ve set for yourself, and I think they’re great. And I can tell you, you know, I can promise you that if I see you making a mistake, I’ll always tell you. And your boss will always tell you. Your boss will be held accountable for telling you about mistakes and about opportunities for growth.
[00:14:54] Dick Costolo: The funny thing is, and it’s a sort of a core tenet of Radical Candor. So often the employee, the boss, the person with status in the work relationship, the boss or the boss’s boss, they just are like, what can I do to get out of this conversation? So they blame somebody else or they tell you you’re going to get to have the next pancake or they go, well, I heard your, I hear you’re mean. So I wouldn’t have done it anyway. Like what else do you want to talk about? And it’s just, if you were just forthright, and you don’t have to be mean when you’re being forthright. You don’t have to say, you know, you didn’t get promoted this time and you probably won’t ever, you can just say, look, you know, I don’t really know why you didn’t get promoted this time.
[00:15:37] Or, here’s why, here’s what I, here’s my sense of what happened. I may be wrong. Let me go figure it out and I’ll come back and tell you. You don’t have to say like, go ask Janet, go figure it out yourself if you’re the person, if the person’s reporting to you. Um, just being forthright about it now and having the hard conversation now, even if the person doesn’t like it, is a hundred times better than, you know, getting them out of the room now and making them feel good about themselves and creating misery for them six months from now and then they quit. It’s the same thing with, I want to work on, same thing with, I don’t want to, I want to transfer to this organization. I don’t want to work on this project anymore. Managers do this stuff all the time.
[00:16:16] Kim Scott: Yeah, yeah. And you know, I think that, I think that the really important thing that you were saying is that, it is really hard to say there’s not specific criteria, like there is some judgment in this. And there’s some unpredictability in this. Like that’s the really hard message that this, that both the boss and the boss’s boss needed to tell this person and they were reluctant to say that. Because it’s hard to say that, it feels unfair. Like I remember at one point, I had a big team and they were complaining about the, about ratings, you know, about the quarterly ratings and they weren’t perfectly fair.
[00:16:53] And I stood up and I said, you know what? They’re not perfectly fair. I’m not perfect. Your boss is not perfect. Like we’re going to get it wrong sometimes. And what I can promise you is that we’re open to hearing about it when we get it wrong. But even in that case, like we’re going to try to make this come out as, as reasonably fair in the wash as we can over time. But like, this is a give and take, this is a back and forth. And we are not perfect. It’s like, you’re right, this is not perfect, justice is not perfect in, in ratings, and demanding false precision, and like, I remember there was, you could have heard a pin drop in the room, this was not a popular message.
[00:17:29] Dick Costolo: Yeah, of course.
[00:17:31] Kim Scott: To deliver.
[00:17:32] Dick Costolo: Of course, and then, let’s like, look at the, you know, call it the corollary to this story. Let’s say the first manager, you know, turns around and does the, like, nobody wants you to get promoted more than me, turns around and promotes this person next time. Word gets around the organization. Hey, if you go in and complain to Janet, you know, uh, she’ll get you promoted because she hates having hard conversations. So pretty soon everyone wants to work for Janet and Janet’s going to have nineteen more of these people banging on her door and complaining to her. Instead of, you know, it’s like, and then, you know, the person who is sitting there and crushing it and quietly, you know, delivering for the organization and not going in and asking what it takes to be, you know, promoted is the one who’s sidelined. So, I mean, it’s all horrible.
[00:18:20] Kim Scott: Yeah. Yeah. This is why I think when I’m, when, when, when I’m coaching CEOs of startups, I really strongly recommend that they set up a promotion process, that is, that is transparent and that can happen once a year. I mean, that’s often enough at a startup. And that you can’t offer people off cycle promotions because they’re unhappy. And you’re trying, like, promotions are something that you, you do on a regular basis and that, and, and where there’s process. Because it can’t be sort of unilateral management judgment because that, that’s not going to work very well.
[00:18:59] Dick Costolo: Yeah. And yeah, and people should, as much as possible understand where they stand. And, you know, your team, as a manager your team has to understand what you understand. And everyone by the way, you know, you know, of course that this person who said I’ve been sitting on my hands waiting for you to get promoted or, has also, you know, they tell this person A, and then they tell the next employee A prime.
[00:19:22] Nobody’s, everybody’s not getting the same story. And then of course these people go out and talk to each other. And are like, oh really? Because she told me this, you know, and then they realize like, oh, I’m just, this person’s just telling everybody on their team what they want to hear. And now everybody on the team’s miserable, not just this one person.
[00:19:41] Kim Scott: Yeah. And then the managers are like, don’t talk to each other about promotions, like lots of luck telling people don’t talk to each other.
[00:19:48] Dick Costolo: Don’t talk to each other about compensation.
[00:19:50] Kim Scott: Yeah.
[00:19:50] Dick Costolo: Great. Good luck with that.
[00:19:53] Kim Scott: All right. Well, I think we’ve solved a lot of the world’s problems in a short amount of time. Uh, I want to thank you. It’s always fun talking with you about this stuff.
[00:20:03] Dick Costolo: Yeah, that was a blast. Thanks for having me.
[00:20:04] Kim Scott: Thank you so much. If you have a management dilemma, either you have a boss who you’re having trouble dealing with, or you are a boss and you’re not sure how to manage your team and you want some advice, send us an email to advice@RadicalCandor.com. And we will, we may not have good advice, but it is free. We will send it to you.
[00:20:30] Amy Sandler: 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 podcast theme music was composed by Cliff Goldmacher. Follow us on LinkedIn, Radical Candor, the company and visit us at RadicalCandor.com.
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