Epic Fail at the Office: How to Recover from a Major Work Blunder 7 | 34

We’ve all been there—that heart-sinking moment when you realize you’ve messed up at work. Kim, Jason, and Amy discuss how to recover from a big mistake without letting self-blame take over. Inspired by a Reddit post about a project that fell months behind, they share lessons from their own experiences, practical ways to take responsibility, and how to follow through with a recovery plan that actually works. 

Watch the episode: 

Episode at a Glance: Mistake at Work

 We’ve all made mistakes at work—but what you do next matters most. Learn why asking for support is a strength, not a weakness, and how managers can identify trouble early, check in effectively, and foster a culture where it’s safe to speak up before problems escalate. Whether you’ve missed a deadline, dropped the ball, or just want to be ready if things go sideways, this episode will help you rebuild trust and turn a setback into an opportunity for growth.

Radical Candor Podcast Tips

When you’ve made a major mistake at work and feel frozen with guilt:
First, forgive yourself—if you don’t, you’ll stay locked in denial. You can’t do right if you don’t know what you did wrong, and being too hard on yourself will keep you from admitting it. Then, go admit what you did wrong, and remember: the cover-up is worse than the crime. A mistake you got away with today doesn’t mean you’ll get away with it tomorrow.

When you notice a peer avoiding conversations about something they’re behind on: Be as generous with them as you would be with yourself when you’ve made a mistake. You might even share, “I’ve made this mistake before—how can I support you so you can avoid the same thing?” Make it clear you want to help without stepping on their toes.

When you’re a manager and realize you haven’t checked in on a long-term project in months: Be direct about what’s happened, even if it feels uncomfortable. In Kim’s “Bob” story, she had to tell him his reputation with the team was shot, and if he wasn’t willing to resign, she’d have to fire him, despite her recognizing she was partially responsible. Acknowledge your role in the situation, but take action to protect the team’s overall health. Don’t wait—address credibility concerns before they become irreversible.

Radical Candor Podcast Resources

• Transcript
• Barings Bank: Its Collapse, Acquisition, and Lessons Learned | Investopedia
• I Fell Behind At Work And Fucked Up: How Do I Move Forward? | Reddit
• Resources For Feedback Training, Coaching & Development | Radical Candor
• How Delivering Bad News Early Strengthens Your Relationships at Work | Radical Candor
• Why Procrastinators Procrastinate | Wait But Why
• 6 Steps for Setting Measurable Goals to Avoid "Productivity Paranoia" | Radical Candor
• The Bob Story, a Tale of Ruinous Empathy | Radical Candor Podcast 4 | 1

The TLDR Radical Candor Podcast Transcript

[00:00:00] Kim Scott: Hello everybody and welcome to the Radical Candor podcast. I'm Kim Scott. 

[00:00:09] Jason Rosoff: I'm Jason Rosoff. 

[00:00:11] Amy Sandler: And I'm Amy Sandler.

[00:00:12] Kim Scott: Quick I'm gonna interrupt you, Amy, sorry. Before we get into the episode, I wanna solicit some feedback from you two.

[00:00:22] Amy Sandler: I'm Amy. Okay, sorry. 

[00:00:26] Kim Scott: I have a random question. I'm soliciting feedback. I'm not giving it. I always say hello everybody, but the notes always suggest that I say everyone, and I have had eye rolls at everybody instead of everyone in other,

[00:00:44] Amy Sandler: What eye rolls?

[00:00:46] Kim Scott: Not from you all. Is there any reason why I shouldn't say everybody instead of everyone? That's my question. 

[00:00:55] Amy Sandler: I don't know, but I feel like that's a good question that we can be asking someone in the background.

[00:01:00] Kim Scott: Or our listeners can write.

[00:01:02] Jason Rosoff: Maybe there's, there's a good reason. 

[00:01:04] Amy Sandler: I think this is just a guess. There may be something that I don't know in terms of the origin of that word, but you sometimes say it like, hello, everybody. Because I was actually just listening to it, like an episode from a few years ago, and then you were like, and everybody has a body, so I don't know if any eye rolls were related to like what was happening. 

[00:01:25] Kim Scott: No. So the reason why I did that on that podcast is I was asking this question and I was gonna come back to it and then, and then I got, I forgot that I wanted to solicit feedback.

[00:01:35] Amy Sandler: Well, I'm so glad that we've picked it back up a few years later. People were on the edge of their seats. 

[00:01:41] Kim Scott: Yes. Alright.

[00:01:42] Jason Rosoff: That's how Kim's brain works.

[00:01:43] Amy Sandler: Everybody.

[00:01:43] Kim Scott: Now you know. Okay, let's go on with the podcast. I have solicited my feedback.

[00:01:49] Amy Sandler: I don't know who I am, I was interrupted.

[00:01:51] Kim Scott: I don't know. And that's okay. 

[00:01:52] Amy Sandler: Okay, so we have a question for you all listening, and please do let us know if there's an issue with the phrase everybody versus everyone. Email us, podcast@RadicalCandor.com. I am Amy Sandler if you are also wondering. Today's episode is about something almost all of us are gonna face at some point in our careers. What to do when you seriously mess up at work. So this is another one we took from Reddit and here's the summarized version. Quote, oh, I'm already feeling anxious just as I read it. I fell months behind on a work project. No one noticed until my boss just found out, and now it's a big deal. I feel awful. It was completely my fault. I deprioritize the work while juggling other responsibilities and it snowballed. I used to be seen as reliable, and now I'm afraid I've tanked my professional reputation. How do I recover from this? Is there a way to move forward without losing credibility? End quote. 

[00:02:53] Kim Scott: I feel the pain for this person.

[00:02:56] Amy Sandler: To everybody.

[00:02:58] Kim Scott: Everybody.

[00:02:59] Jason Rosoff: This is what most of my nightmares are about, is this, right? This thing. Not exactly this version of it. But it's basically this thing, like I've forgotten something important that I was supposed to be doing. 

[00:03:09] Amy Sandler: Jason, I had a nightmare more about like school. Like I had to show up for an exam and I had never actually attended the course. So do you have like a work flavor of that one. Because that one is actually like, also, it's been a minute since I've missed a exam, so. 

[00:03:25] Kim Scott: That's a universal one that will plague you the rest of your life. 

[00:03:29] Jason Rosoff: It's not, that one's not going anywhere. Yeah, I'll, I'll have this, uh, I, because like, I, I think often I will be, there'll be like a work thought that's sort of in my head as I'm falling asleep of like, this is a thing that I wanna do. And then my dream will manifest that as like, you, you were supposed to have done it already. Now it's late. Everybody's expecting it to be done. And so I'll, I'll wake up and I'll realize that it was a dream, but that feeling of like panic and disappointment, like disappointment in myself, like it just, it lingers.

[00:04:03] Kim Scott: It'll stick with you all day long, won't it? 

[00:04:05] Jason Rosoff: It really does. So I have to imagine my dream is, the impact is less than this person's reality. So like I feel so much compassion for the person in this position. And the, I will say, like one of the things that comes to mind, since we've all made big mistakes at work at, at some point in our lives, is you're asking, you're asking a tough question, which is, am I, have I tanked my professional reputation? And the question of like, how other people perceive you after this, that's not really within your control. There's some things you can do to try to adjust that, but what you can do, I think, in these moments is to act in integrity with yourself. I feel like the guidance that we'll give is really about how to approach this situation with integrity, as opposed to how to save your professional reputation. Because unfortunately, once you've made a big mistake, you don't always get to decide that. 

[00:05:01] Kim Scott: But you, there are things you can do. I think, Jason, at the risk of sounding harsh to this questioner, I would like to propose that they rephrase their question and I say, how do I recover from this? That's a good question. The second question is what's flawed. Is there a way to move forward without losing credibility? Unfortunately, my feedback to this listener is you've already lost credibility. And the question you should be asking is, how do I regain it? And yes you can, I wanna reassure this person, you can regain credibility, but it's gonna take some work.

[00:05:33] Jason Rosoff: I think that's a good way to say what was on my mind. 

[00:05:35] Kim Scott: Amy, is that too harsh? 

[00:05:37] Amy Sandler: No, I actually think that's a helpful, like decoupling those two questions, which is what Jason was saying. I'm especially curious for people listening, like maybe we're in the midst of mistake making, like how can we learn, like we can give advice to this person, but I would love to also spend a little bit of time on the, like, we're in the midst of the mistake making and how can we potentially not duplicate this problem? 'Cause one of the things, Kim, you and I were just chatting about a little bit before we started was like, it's human nature that once you make mistake, the tendency may not be to correct for it, but to actually start to hide it. So I just, I wanted to start there first so that we can then talk about what to do once we've made the mistake. 

[00:06:20] Kim Scott: Yeah, and I think it's, the thing that's especially interesting about this question and important because we've all been here, is that this person made a mistake. They were behind, they got behind on a project and they got away with it. Nobody noticed. The thing about a mistake that we make, that we get away with is that it's tempting to make that mistake again. Oh, nobody, maybe I don't have to do that work. This is a random example from dog running, back in the days when I used to run, instead of walk with my dog. I used to run around this open field on the Stanford campus when I lived in Palo Alto, there were some busy roads on a couple of the edges of this field. My dog loved to run, not on the leash. One day I let her off the leash and nothing terrible happened. She didn't run into traffic. The next day I let her off again. The third day I realized I'm making a terrible mistake here because there was a 5% chance the dog was gonna run into traffic and get hit by a car.

[00:07:29] One day you can get away with a 5% odd, but if you do that thing every single day for enough days, your odds are now a hundred percent of a terrible thing happening. I realized I should keep the dog on a leash while I was running her around this field. I got away with it twice and I realized that I should stop trying. Like I had just gotten lucky and I should stop trying to get away with it. And the reason I was able to have that realization and avert my dog getting hit by a car, one of my nightmares, one of my recurring nightmares, is that I had just read a book about this. Now I don't remember what the book was. So I hope that one of the things that was very generous that this person did by writing this question is it gives people an opportunity to understand what's happening. They're behind on something, nobody noticed. Can they just never do it? No. You got lucky. Fix the problem. That's what I have to say for people who maybe haven't gotten caught out yet. 

[00:08:32] Amy Sandler: Well, and I also wanna talk about, kind of, and this, I'm, I'm writing myself into this letter. I'm curious, Jason, I feel like you'll know what I mean. If, if we pause it, there's almost like a freeze frame and, and capturing the mental like story that's happening. If I am making this, like this happens for me, there's like maybe a big project I need to do, or some big ticket item with multiple steps in it, and it just, I, I know I have to do it, and it keeps going into my, you would call it proactive forbearance. I just move it from Monday into Tuesday into Wednesday, and, and it's still weighing on me. Like I know this thing has to happen. So I suspect, I mean, this letter writer said, I feel awful, and it was completely my fault. I don't feel like they just started feeling awful. I feel like they probably were feeling awful, like, the whole time. 

[00:09:19] Jason Rosoff: There was a realization earlier on where you became aware, the writer became aware that something was going wrong, but to Kim's point, it hadn't turned into a problem yet, and there were other things to do. And, and so I think I, I think the, there's a difference between this and like, procrastination is an element of this story, but I think there's a difference between the kind of procrastination where you are avoiding things that don't absolutely have to be done, and the kind of procrastination where you are avoiding a thing that must absolutely be done. And so I don't want people to make the mistake of thinking like just because they're procrastinating on something means that something has gone wrong. Sometimes your procrastination is actually a sign that you should not be doing that thing, but not this case. 

[00:10:09] Kim Scott: Yeah, and usually procrastination is, is not always, but usually it's a sort of a, a coping mechanism that people use to get things done efficiently. Like Andy is a, my husband is a procrastinator. But it's, it's reasonable procrastination because he knows that if he waits till just up before the deadline, he'll work really hard and, and really efficiently and get it done. 

[00:10:35] Amy Sandler: That is my style of like dopamine adjustment program. It works. 

[00:10:39] Kim Scott: But that kind of procrastination happens before the deadline. 

[00:10:44] Jason Rosoff: Right. Correct. 

[00:10:46] Kim Scott: If it's happening after the deadline, it is no longer procrastination. It's denial, I would say. When I was at Google, we used to draw this chart that would help people understand the difference between procrastination and denial. And the chart, we've talked about it before on the podcast, but it's one of my favorite ones, so we'll talk about it again. There's time and there's your deadline. And if you tell people enough, with enough time before the deadline that you're not gonna get the thing done, then you don't do very much damage to your credibility. But if you tell people after the deadline that you're not gonna get it done, you do a lot of damage. And if you don't tell people at all that you haven't got the thing done, then you do almost infinite damage to your credibility. Now, that sounds harsh and extreme and it is harsh and extreme. 'Cause I don't think this person has done infinite damage to their credibility. But the point is, they've done a lot of damage and we call it infinite damage to your credibility to help you prevent. But once you're in this situation, how can this person regain credibility? Does that make sense? 

[00:12:00] Jason Rosoff: Yeah, it makes sense. And I think distinguishing between procrastination and denial, and talking about the difference between minimal damage to credibility versus maximal damage to credibility, is really useful. Amy, going back to your original question, which is if you're in the midst of making a mistake, especially where you are not going to be able to do something that you said you were going to be able to do, you're far better off, as early as possible, owning up to the fact that you are not gonna be able to do the thing that you said you were going to do, both for your short term and long term reputation.

[00:12:31] Kim Scott: It's harder, like it's easier to tell my boss or, you know, my kid, or whoever, that I haven't done the thing I promised to do two weeks before, or I'm not gonna be able to do the thing that I promised to do two weeks before it, they're expecting it. It's much harder two weeks after, when they kind of assume I've done it, but I haven't done it to tell them, actually, I never did that thing. But it's more important. It's harder and more important to say that two weeks after the fact than two weeks before the fact. I wanna acknowledge, this is why I think the person, I mean I'm reading into the question, but is there a way to move forward without losing credibility? The reason I rephrased the question, and I think it's important to rephrase the question, is that I think that the person is still avoiding, acknowledging that they failed to do the thing.

[00:13:27] And I would say the only hope that this person has of regaining credibility is to acknowledge in full how badly they screwed up. And to say, look, I should have told you all months ago that I was running late on this project. And the fact that I didn't means that it's now a catastrophically big deal or extremely big deal or whatever. And just to, you have to explain, right? The thing about explaining is it feels ridiculous 'cause it's so, at some level it's kind of obviously bad. It's an obviously bad mistake. And the thing that I will reassure this person about is by acknowledging, the reason it's obviously bad is that we've all made that mistake. And so this person is, people, people are likely to have some compassion for the mistake, even though it's quote unquote, obviously bad because it's one we've all made.

[00:14:33] Amy Sandler: Kim, as you were talking about the sort of distinction between, you know, the procrastination and the, the mistake making, we'll put this in the show notes. Have either of you heard, this is from a while ago. I was just looking it up. It was from 2013. Tim Urban did a TED talk about why procrastinators procrastinate. One of the things he talks about is the panic monster, which I think Andy and I, your husband, must share, which is like, that is the part of our brain that gets us going. So we'll put it in to the, to the show notes, but there's all these other ways that we're kind of procrastinating or avoiding it. And Kim, I think that's somewhat of what you were talking about, that in retrospect, it's like how do you explain to your colleagues like, oh, I was nervous about saying it, but like in the moment it feels insurmountable. And I'm curious, have either of you worked with someone who made a mistake such as this, where they got behind and did a good job of making an apology? Like the one, Kim, you're talking about? 

[00:15:34] Kim Scott: I'm not sure, Jason, if this is an example of that, but I feel like this is how you and I met, was me writing a blog post. Russ Laraway and I had started this company, Candor Inc. And Candor Inc was building some software that was supposed to help managers put the ideas of Radical Candor into practice. And I, you know, we built an app. It wasn't working. We built another app. It wasn't working. We built a third app. It wasn't working. This is what Russ and I and our team did, and I was, I was getting so stressed. So stressed that in fact, I couldn't sleep and I lost 10% of my body weight. I was like back down to my high school weight, which I had no business being at. And I was not doing well, and I think the reason why I wasn't doing well is that denial is a really heavy burden to carry around. And finally, Shona Brown, who was one of our investors, I showed up for a meeting at her house and she looked at me and she said, you're not okay. You are just not okay.

[00:16:52] It was like the greatest act of kindness she could possibly, it was Radical Candor. And she said, you've got to cancel every meeting you have for the next two weeks. I don't care how important it is, cancel everything and figure out what's going on with you. 'Cause you're literally wasting away before my eyes. And I did what she recommended and I realized that the idea that we had was just flawed. And that I had been in denial about it, and that I thought that my job as a founder was to keep pressing and keep charging and keep pushing, and yet my brain was waking me up every night at 2:00 AM and not letting me go back to sleep because it was like, it was sending me a warning that I was trying to repress, and that was an extreme case of denial. I wound up writing a blog post about that and, Jason, that is how you and I met. So that's an example of me being in this person's shoes in a different kind of way.

[00:17:55] Jason Rosoff: Yeah, and I think for you, like the act of writing the post, at least how you and I have talked about it, was an important therapeutic step. 

[00:18:06] Kim Scott: Yes. 

[00:18:06] Jason Rosoff: And, and I'm, I, I know that it was helpful to other people also to, for you to tell that story, like it didn't just help you, it helped other people understand. Because I'm sure other people on the team were feeling stressed and you know everybody, when things aren't working great, everybody's sort of aware that they're not working great. But it's hard to put a finger on like what is going wrong. And your willingness to take accountability for like, we didn't, this is, A, this is really hard. We don't have it. Like we don't have the idea that's going to like make this happen. And that just has to be okay for now. Like we, 

[00:18:39] Kim Scott: Yeah, we gave back half the money. Like we could have spent it down to zero, but there was a lot of pressure. And I imagine that the person who wrote us this note also is under, I remember one of my investors said to me, at the time, the problem here, Kim, is that you're just not trying hard enough. And this investor went on to invoke this football player who had spoken at some conference and this football player had broken his finger. He was in the Super Bowl and he had broken his finger. And there's a rule in the NFL that if you break a bone, you have to come out of the game. But there was fear that they would lose the game if he came out. And he was like, cut it off. There's no rule about a missing finger. And they cut his finger off and he continued to play the game.

[00:19:35] And I remember looking at this investor and holding up my hand and saying, you're not getting any of my fingers. Like, fuck you. Excuse my French. This investor was angry with me and, I know nothing about football or whether this was a true story, and I looked it up and everything that this player had said, he's very famous, but of course I don't remember his name. But everything this player had said was that he had given too much to the game, like he shouldn't have cut his finger off. But that was not the lesson this investor took from the story. And that is like, I, I, there's a lot of pressure not to admit that you've broken your finger.

[00:20:16] Amy Sandler: Looking it up. It's Ronnie Lott for those of us who are scrambling with, and I did not know that story, Kim, that is,

[00:20:23] Kim Scott: Oh, it was awful. It was like, no wonder I was waking up at three. I was blaming myself. 

[00:20:29] Jason Rosoff: And I think this is the key point, to me, which is taking accountability for the mistake does not mean punishing yourself for the mistake. It does not mean turning this into self-flagellation or, or like,

[00:20:41] Kim Scott: Do not cut, de-digitation. Don't cut your fingers off. Like that's the title of this episode. Like you can say, I screwed up without, you know, like I could have gone to the investors and that is why I wrote the blog post, probably. You're right, Jason. Like, and said, I screwed up. I had a bad idea. The idea's not gonna work out. I know it's not gonna work out now. And we're shutting the company down.

[00:21:03] Amy Sandler: Kim, I wonder because you had the investor, Shona Brown, who practiced Radical Candor, and gave you permission, right? So I wonder if that

[00:21:12] Kim Scott: Keep your fingers. Like, and, and figure out how to sleep again.

[00:21:16] Amy Sandler: It's like the opposite of it. But I wonder like if that had just, if that advice had just been coming from a friend or even your husband, you know, it was like, was it because they were also in, literally invested in your company that it sort of gave you permission to hear it?

[00:21:32] Kim Scott: Probably. Because Andy of course, had already said to me, this is not working. Something's gotta give and it can't be your health, you know?

[00:21:40] Amy Sandler: Or your fingers. So look, what are the lessons from, I mean, I think that is such a powerful story and I didn't know, uh, all of the backstory, but for folks who are listening to this, who are managers who may not be soliciting feedback or who may have someone working for them who's making a mistake, what can they do to start to create the conditions, the psychological safety so that we don't end up in the same situation?

[00:22:06] Kim Scott: Yeah. Well, first of all, make it safe for people to come to you early, make bad news early not only safe, but expected. Like you need to create the conditions, this doesn't help this Redditor, but for the Redditor's boss, what the Redditor's boss could have done that would've made it easier, is first of all, to create a system to hold people accountable for deliverables. And, and to let, to ask people about when their deliverables, are they on track, are they not on track? And to create multiple opportunities early on for people to tell them when they haven't done something that they said they would do. Because I think what happens often, and I've been guilty of this as a manager and also as an employee, is that managers ask people to do five times more than they could possibly do. And when some stuff falls on the floor, they don't say anything until they care about that thing, and that's not a fair way to manage. So don't do that to your people. 

[00:23:17] Jason Rosoff: Yeah. I think if you are, and maybe this person's working like entirely on their own. We don't know what the type of, the nature of the work is, but like even if that system, ideally they create a system for accountability. And I think the other thing that I've seen work is celebrating learning as opposed to only celebrating outcomes. If the only thing that matters is the outcome and the learning doesn't matter, then it's really hard to talk about mistakes, because mistakes become failures as opposed to springboards for future success. The, the world is littered with failed ideas and failed companies and failed projects. 

[00:23:58] Kim Scott: The world is enriched by all these failures because, the world is composted by all these failures.

[00:24:05] Jason Rosoff: We're composting our failures into the loam of success.

[00:24:08] Amy Sandler: I just made a really bad title in my head, which was composting our fingers. Anyway.

[00:24:14] Kim Scott: No, no, no.

[00:24:14] Amy Sandler: That is terrible.

[00:24:14] Jason Rosoff: Yeah, and so like, I think that the story of what not to do right is pretty clear, which is like if people feel threatened, if they feel like they're going to be punished for admitting a mistake, you're just never going to hear about them. It's not that they're not gonna be made, it's that you're not gonna hear about them until it's too late. And so if that's the position you wanna find yourself in, then you know, making it scary to make a mistake or telling people they're just not trying hard enough when they admit that they need help, maybe that's a fine approach for you, but I would argue that for the vast majority of people, that's gonna wind up backfiring spectacularly. 

[00:24:48] Amy Sandler: I have a thought, Kim and Jason, and I will play along too. I was wondering, just Jason, as you were talking, if your boss, like knowing that mistakes are prone to happen and we wanna build safety, what would you want your boss to ask you if you were kind of maybe a month before this letter writer or this Redditor writes it? In other words, what would be a go-to question that would give you the safety you want to share? Like, oh my gosh, I'm so behind and I don't know what to do. And I can certainly start if that's, so, Jason, like for me, this would happen if there was a really big project, but I've got a lot of other short term deliverables. So I would want you to say, hey, you know, I know you've got this big project and I know that you're someone that needs some check-ins.

[00:25:41] And so what would be the most helpful way for me to support you in making sure that you're on track with the deadline? So almost like starting broadly and then having me volunteer how you could be helpful, which would land more as thought partner versus micromanage-y. And then we could have that conversation. So I could say like, okay, well if it's due in October 1st, let's have like a work back plan. And so, I might actually, Jason, need like a weekly almost schedule so that I am staying on track. Like that would help me to know that, like it would give me the safety to know that I'm meeting it. And then in our one-on-ones, I can let you know how that's going. So like I'd almost want you to understand my working style and then let me kind of create it and then you could give me some ideas. 

[00:26:26] Jason Rosoff: Cool. I mean, makes sense to me based on what I know about you, I'm kind of curious. 

[00:26:31] Amy Sandler: Like that doesn't feel like anything remotely what Kim would want.

[00:26:34] Jason Rosoff: As we were talking about this, there's this thing that was coming to mind for me, which is that software projects fail in the open like this on a regular basis. So what I mean by that is like there is a phenomenon in the world of software estimation where people drastically underestimate how long something is going to take them. And then they fail to reach that deadline and they say, well, it's gonna take me another month to finish it. And they get to that deadline, they're like, well, it's gonna take me another month to finish it. And what's interesting about it is, I can't remember what book this was in, but it was described as a death march. Where it's just like this progressive failure.

[00:27:11] Where every month you know that the update is we need another month. And what's interesting about this phenomenon, it, you know, we talk about what we learned, but the psychological effect on the person who's failing to meet that deadline over and over again is actually quite similar to what the person in the post has described. Like, they start to feel terrible about themselves, like they can't possibly do a good job. Like I've seen this happen over and over again to capable people. And so I think your question is a good one, which is at some point, and I've had this conversation with more than one engineer, it's not gonna take another month. If it was gonna take another month, you would've been right about it a month ago.

[00:27:45] Kim Scott: If it's 99% done, it's 10% done.

[00:27:48] Jason Rosoff: The question is, like that I, like if I was the boss, like the question, or if I was the person in the sort of abysmal negative feedback loop of missed deadlines, I would want someone to say, it's not gonna happen. Let's just take the, like take, I know it's important, but let's just pretend that there isn't actually time pressure, for a second, to get this thing done, and let's free our minds from thinking of the next 30 days and actually go back to the drawing board and say, what is it going to take to get this done? What actually needs to happen in order for this thing to get shipped? Because I know, like when I'm in that position, the thing that I struggle with is like I'm trying to balance two things, which is my credibility with my manager and my peers, as a person who can successfully deliver a thing, and the reality of what work is left to do. And often I don't balance those things correctly. Like I try to optimize for maintaining some level of credibility. 'Cause I feel like it's worse to admit it's gonna take me three more months to finish this thing and like I can't even do it myself. I actually need another person for a month to finish this thing. In my mind, that's worse.

[00:28:59] Amy Sandler: Are you saying by taking out the time, you're kind of giving the person permission to actually see if it's even, like that they're not thinking about they, maybe they need additional resources or they just don't have the capacity to do it? 

[00:29:15] Jason Rosoff: Right. I think the thing is, is like the question I want the person to ask me is like, let's remove the constraints. Let's pretend that we haven't missed the deadline three times. Let's pretend we don't need to hit this deadline in a month. Let's remove the constraints and let's talk realistically about what actually is necessary in order to finish this. Because I do feel like when you're in it, you feel like there's pressure to be consistent with the things that you previously said and done, and the problem is, like in this case, consistent with what you previously said and done is gonna lead to more failure.

[00:29:45] Kim Scott: I think what the manager could have done to prevent the situation from, once the situation has arisen, the emotions are so strong that it's really, really hard to deal with. So what can the manager do to prevent the person from having gotten into this situation in the, in the first place? I think OKR is a good goal setting system where the employees set their goals and have to rate their goals every week or month and say, you know, I'm, I'm, I'm ahead of Target. I'm behind Target. And putting those goals in a publicly, in a public place. So that the relevant people, who are depending on that person to deliver the thing, can, can see them, and you as the manager can see them, is really important. It's one of the most important things managers do and managers hate doing it. You wanna create the freedom for people to set really aggressive OKRs and miss them.

[00:30:43] Like that's why I think at Google, the expectation is that you would, if you're hitting more than 80% of your OKRs, you're not setting aggressive enough OKRs. So that kind of worked at Google, but it still, at Google, there was this situation that you described often. Where things were behind and people almost didn't even know they were behind. In fact, when I left Google and went to Apple, I was coaching someone and they called me like at 11:30 one night, late at night, in tears, because they were gonna miss a deadline that was the next day. And I was sort of astounded 'cause I was like, gosh, if people wouldn't have even had a deadline to know that they were missing a deadline.

[00:31:26] And so I got really interested in what was happening that was so different. And I'm not saying Apple's better than Google, just let me be clear. My heart belongs to Google. But at Apple, what had happened is Scott Forstall, who was leading the iOS team, set up a system where everyone who was working on what he called a top level feature, and this was people, often four levels deep. You know, he was SVP, and there were, you know, individual contributors working on important aspects for the next iOS release, would send every week on Thursday night, a report of how things were going with a red, yellow, or green flag on top. And so he could take a look at the green things, the yellow things, the red things, and he would ask these people questions and not just his direct reports, but the reports of the reports of his direct reports, three levels down in the organization.

[00:32:23] And this was a really helpful way to sort of make it expected that every week some people were not gonna have achieved what they were supposed to have achieved. What was a sign that things were going wrong was that this person called me at 11:30 at night in tears because they were gonna set the thing to red. It should have been more okay, less scary to set it to red. And I didn't even quite understand that that was a problem at the time. I think if Scott had realized that were happening, he was a great leader and I think he would've done something about it. He would've changed something. 

[00:32:58] Jason Rosoff: I like that story a lot, Kim. I think we, we've been sort of prescribing vitamins so far, and I wanna make sure that we address the Redditor's pain, which is like,

[00:33:09] Kim Scott: Yeah, we sort of told the Redditor's boss what they should have done, but what should the Redditor do?

[00:33:13] Jason Rosoff: Yeah. So I think closing with this, because what you said early on in our conversation was like, you've done some reputational damage. Unavoidable. It has happened. So the question is, what is available to this person to do?

[00:33:27] Kim Scott: So I think one of the things that this person can do is talk to their boss and say, I screwed up. I've lost credibility. Here are the things that I plan to do to regain credibility. And some of the things I would recommend are, I'm gonna give you a weekly red, yellow, green on all my goals. And also if I get overwhelmed, I mean, the reason this happened, probably, was that this person had too much work to do. If I get overwhelmed, I'm not gonna drop balls silently. I'm gonna drop them explicitly. And just to make that commitment. And then solicit some feedback on that commitment. So here's what I'm gonna do and then say, is this enough for me to earn, regain your credibility? How long will it take for me to regain your credibility. If the boss says, you're done, you're toast. You're never gonna earn, regain my, like believe them the first time, and polish up the resume and get another job. I hate to say it, but that's, that may not feel like a good painkiller, but there it is.

[00:34:37] Jason Rosoff: I do think that, going back to sports injuries, sometimes you need to rebreak the bone to set it properly so that it'll heal. That's what we're talking about. 

[00:34:44] Kim Scott: Yeah. 

[00:34:45] Jason Rosoff: Do not think it is pleasant, and hopefully that's not what's going to happen. I like the idea of sharing a plan with your boss as a way to check in. The other question I have for my boss is, I know other people rely on me and this team to get work done. Do you have any advice for me on how to make it, what, you know, because it may not, it certainly doesn't seem like it's a practice to share status updates. 

[00:35:09] Kim Scott: Yeah. 

[00:35:09] Jason Rosoff: Regularly at this company. But I would love to be able to share transparently with other people who are relying on this work, what I'm doing, and how it's going. Do you think that would be okay? Do you think that would be well received? 

[00:35:21] Kim Scott: Yes, and I think I would offer a tweak to that. I wouldn't say, is it okay? Is it well received? Here's my plan for communicating with my peers. 

[00:35:30] Jason Rosoff: Sure. Great. 

[00:35:31] Kim Scott: Because I think that this person shouldn't ask for permission to make it right with their peers. It's like something they need to do. It's never, in my experience, when my boss is trying to make things right with my peers, it never works. Like I have to make things right with, you can't delegate your relationships to anyone, no matter how good your boss is, they're not talented enough to fix your relationships with your peers.

[00:35:59] Jason Rosoff: Yes, and I, I appreciate that. I, like, my, I was not clear. My intent was to solicit, to encourage this person to solicit feedback on that plan, as opposed to ask for permission.

[00:36:11] Kim Scott: Yes, exactly.

[00:36:11] Amy Sandler: And before we close, I wanna just bring in one idea, and this might be a good follow-up conversation. It recently came up in a workshop I was leading around, I was asking the question, how do people build trust with you? And for a bunch of folks reliability and accountability was kind of job one. And I just wanna name, we've talked about this a bit with some of our other episodes, but there's sort of cognitive trust, like the trust that comes from people being competent, reliable, et cetera. And then effective trust, which is really more about kind of the empathy and the emotional connection.

[00:36:43] Kim Scott: It's also about integrity. Can I rely on this person to do it? Can I rely on this person not to be an asshole? And can I rely on this person to act with integrity to tell me the truth? 

[00:36:57] Amy Sandler: Yeah, and I think that's really, I mean, a good follow up conversation because I do think that some people will weigh, like once you've broken the cognitive trust, like there's no way to get it back if you've demonstrated that you're not reliable on a deadline, et cetera. And so I think also just, Jason, to your point, especially with peers, maybe your boss will be willing to give you a chance, but maybe with your peers, it's really gonna be an impossible task. So wanted to name that and I think that would be a great follow-up conversation, Kim, around, you know, the link between integrity and different types of, different types of trust.

[00:37:31] Kim Scott: Yeah, I love it. I would guess that this person's peers are gonna be more forgiving than their boss. Usually if you go to your peers and say, look, I screwed this one up. Here's what happened. Your peers are gonna have a story about a time when they did the same damn thing, and probably your boss will too. People are usually kind of decent if you give them a chance to be, and so I think this person's job is to create the space for people to forgive them and to allow them to regain credibility.

[00:38:02] Jason Rosoff: I like that. 

[00:38:03] Amy Sandler: All right. Well.

[00:38:04] Jason Rosoff: Shall we check out with our checklist? 

[00:38:07] Amy Sandler: Let's close with our tips for practicing Radical Candor, and one way we could do this, if I just give each of you just a rapid fire situation. So Kim, tip number one. You made a major mistake at work. You feel frozen with guilt. What's your first step?

[00:38:24] Kim Scott: First, I have to forgive myself. 'Cause if I don't forgive myself, then I'm gonna be locked in denial. So again, you can't do right if you don't know what you did wrong. And if you're too hard on yourself, you won't admit. So I try to forgive myself. And then I would push myself to go and admit what I did wrong, and to remember that the coverup is worse than the crime and that a mistake that you got away with today does not mean you'll get away with it tomorrow.

[00:38:58] Amy Sandler: All right, Jason, tip number two, and you were just talking about peers. So you notice a peer of colleague at the same level you're at is avoiding conversations about something they're behind on. 

[00:39:09] Jason Rosoff: I would try to be as generous with them as I tried to be with myself when I was making this mistake, and maybe I would even share with them, I know we've all got a lot going on. I imagine that it's hard to juggle all the things. I've made this mistake before. How can I support you in helping you get this done? I don't wanna step on your toes, but I wanna help you avoid making a mistake that I made. And see if they're open to me helping out. 

[00:39:37] Amy Sandler: All right, Kim, bring it home. You are a manager and you realize that you have not asked about a long-term project in months. 

[00:39:46] Kim Scott: This is kind of the Bob story, isn't it?

[00:39:48] Amy Sandler: It is.

[00:39:48] Kim Scott: Uh, where Bob was making a lot of sloppy mistakes. I wasn't, I noticed that he was making sloppy mistakes and I didn't say anything until I realized that he had totally lost credibility with the team, that his reputation on the team was shot. And I think that my job in that moment, even though I felt bad, and it was partly my fault that he was in the situation he was in, my job in the moment was to be really clear with him that his reputation on the team was just shot. And in fact, if he wasn't willing to resign, to fire him, even though it was partly my fault. And that felt horrible, and yet if I had to continue allowing things to happen, I would've lost the whole team. 

[00:40:34] Amy Sandler: Jason, how about you tell us a little something to end on a, on a more positive note.

[00:40:38] Kim Scott: On a more positive note 

[00:40:40] Jason Rosoff: Well, if you're interested in learning how we help folks build these skills so that they can apply Radical Candor to repairing trust and rebuilding relationships after mistake, we do offer public workshops. You can head on over to RadicalCandor.com/workshop and register for one of our public workshops. Which will give you an opportunity to practice with your peers. Some people sign up, a couple of people at an organization will sign up together, but in many cases, these are just individuals who care a lot about Radical Candor and wanna practice it with their team, so you get the opportunity to learn from people outside your organization.

[00:41:17] Kim Scott: I love these workshops because they help you avoid making the mistake that I made, by reading about it, rather than being in that terrible situation. 

[00:41:29] Jason Rosoff: If you do wanna bring your whole team in for training, keynotes and workshops are available at RadicalCandor.com/services. 

[00:41:37] Amy Sandler: All right, well, if you're wanting to see the show notes for this episode, go to RadicalCandor.com/podcast. If you're a more visual person, you can now watch our podcast on YouTube and Spotify. Kim, what do we always say? 

[00:41:51] Kim Scott: Praise in public, criticize in private. 

[00:41:54] Amy Sandler: And if you like what you see and hear, please do rate and review us wherever you're listening or watching, we would really,

[00:42:01] Kim Scott: That's praise in public, by the way.

[00:42:03] Amy Sandler: Well, we hope. It depends how they're rating us, right? 

[00:42:06] Kim Scott: Well, we also want to, the criticism.

[00:42:08] Amy Sandler: We do want the criticism. Please do share criticism or any questions, any thoughts for a future episode. Email us podcast@RadicalCandor.com. Bye for now, everybody. 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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