Overcoming Bureaucracy: Radical Candor Podcast

From Bottlenecks to Buy-In: Overcoming Bureaucracy 7 | 16

Ever feel like getting anything done at work means running a marathon through molasses? You’re not alone. In this episode, Amy and Jason go full throttle on the soul-sucking systems that slow teams down and wear people out. Sparked by a listener stuck in a tangle of outdated processes, they unpack how well-meaning rules morph into momentum killers—and what to do when speaking up feels like you’re just making it worse.

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Episode at a Glance: Overcoming Bureaucracy

With a blend of straight talk, lived experience, and a whole lot of Radical Candor, they offer a new playbook: lead with curiosity, advocate with clarity, and stop waiting for permission to fix what’s broken. This one’s for anyone who’s tired of navigating systems built to say “no” when the work is begging for a “hell yes.”

Radical Candor Podcast Checklist: Overcoming Bureaucracy

  • Tip number one. The key to the whole approach is starting with curiosity and then framing your observations very clearly. Like we do in feedback, you want to encourage the other person to share the context of what they need, their observations about what’s going on or where the challenges are, and the impact that that has. You’re trying to gather that data in the same way that you express your observations about the situation. When you say, well, here’s what I’m trying to accomplish, and my observation is that we have a way to solve that. But the result of that is, you, my manager, feel frustrated that I haven’t done the process correctly, even though I’ve solved one problem. And I’d really like to understand better how we might accomplish both of those goals. Can we explore that together?
  • Tip number two. If you encounter resistance, remember to stay focused on your shared goal. So from the listener writing in, it’s about team performance and reducing manager burnout. From the role play, it was about this idea of this third way between inventory management and a happy customer. So for the listener, you might say, you know, I understand the importance of oversight, and I want to help find a way to maintain appropriate control as well, allowing our team to work more efficiently. So could we identify a few decisions where we could test a more streamlined approval process?
  • Tip number three. The processes didn’t come into existence in an instant, and they’re probably not going to change in an instant either. Don’t be totally shocked if the initial conversation isn’t a roaring success or totally well received. The important thing is to keep gathering data and information, to look at specific reasons why those bottlenecks are appearing, and offer concrete ideas for how to address them. The general pattern is important, but in order to make a dent in the way things are currently happening, you want to patiently and persistently pick out specific examples. And then keep reinforcing that idea that the goal is not to create chaos and have everything happening willy-nilly, but instead to create a process where oversight and approvals happen in a way that actually makes the outcome better for the company and the process more pleasant for all the team members involved.
  • Tip number four. Ideally you’re in an organization where your manager is soliciting feedback and noticing there’s something in the processes that are frustrating. Make sure that you are in the right mindset to have these conversations. If you are a leader in the organization managing up and advocating on behalf of frontline managers, it’s important to remember that leaders in an organization need to be on the same team, working and pulling in the same direction, in order for people not to be more confused or frustrated than they already are. That instinct of managing up is a good one but if you frame that slightly differently and say, hey, I’m part of the leadership team in this organization and I have two teams. I have the team of people who I’m advocating for, and I also have this team of leaders that I’m trying to help. That can sometimes help get out of the us versus them mentality that can come from the idea of managing up.

Radical Candor Podcast Resources: Overcoming Bureaucracy

Amy and Jason Radical Candor podcast

The TLDR Radical Candor Podcast Transcript

[00:00:00] Jason Rosoff: Hello everybody and welcome to the Radical Candor Podcast. I’m Jason Rosoff. 

[00:00:06] Amy Sandler: I’m Amy Sandler. Today we have got a question from a listener about how to communicate a problem and persuade management to adopt a new process. So this person writes, quote, in a recent podcast episode Kim mentioned that often she would need to ask a manager for approval and Kim would go ahead and ask for forgiveness instead of permission.

[00:00:30] Jason Rosoff: That Rebel, that Rebel, Kim. 

[00:00:32] Amy Sandler: Kim. Yes. Rebel, rebel with a cause. Uh, we will advocate on behalf of Kim, who’s not with us today. The listener continues, quote, I’m in a framework like that where everything needs approval, which leads to bottlenecks. And the frontline managers get burnt out and have to face the problems caused by the bottlenecks. It’s problematic and stunting our growth and even seems to be paralyzing the already unnecessarily complicated standard procedures. When attempting to communicate why this is an issue, it leads to more bottlenecks and often I come off as escalating the situation. So my question is, how can I communicate this to my managers and at the same time persuade them to adopt a new process to eliminate the bottlenecks while staying within the Radical Candor framework. Thank you for that great question. I know Kim would be very grateful for that question, but Jason, um, what’s your kind of blink reaction to what this person is having to face? 

[00:01:36] Jason Rosoff: The first thing is to acknowledge that how frustrating it is. ‘Cause I think there’s two elements. There, there’s the efficiency element to why it’s frustrating and I think when you work in an, since having worked in an environment where there’s a lot of seeking approval type of, um, steps and processes and things like that. The other part of this that wears on people over time, and I think, you know, potentially leads to burnout and things like that, is this feeling, uh, of not being trusted, right? Because even though it’s technically part of the process to seek approvals at various stages, if those approvals don’t add meaningfully to the quality of the work, for example, then it just sort of feels like someone’s constantly looking over your shoulder, you’re being micromanaged. And I think the combination of those two things, which is like, it feels slow and sort of difficult to get things done, and I, I’m not really trusted to make decisions on my own. I do think that those two things combined really do contribute to burnout pretty quickly. So I just wanted to acknowledge that and commiserate a little bit. Like having been in an environment like that, i, I, I can appreciate just how frustrating it is. 

[00:02:46] Amy Sandler: Jason, um, I really appreciate you mentioning about almost the hidden costs. So to your point about the efficiency, but on the trust, do you, have you, you mentioned that you’ve been in a situation like this. I’m curious what kind of sparked for you around how that takes away from trust?

[00:03:05] Jason Rosoff: It’s one thing if you are, let’s say, let’s say you have a company, uh, this will be, I’ll, I’ll modify the example slightly to protect the, the innocent, but let’s say you have a company that has a budget of fifty million dollars, so the total overall company budget, fifty million, fifty million dollars. And you have to purchase a piece of equipment and that piece of equipment is gonna cost you, let’s say, two million dollars. It makes sense to me that something that represents a significant chunk, increase in the overall budget of the company would go through sort of a multi-layered approval process, right? Like you, you wouldn’t want someone to be able to go sign a two million, well, most organizations wouldn’t want someone to be able to go sign a two million dollar check, uh, effectively increasing the budget of the company by five percent without asking anybody else. 

[00:03:57] That, that I think makes sense to people. And so you want both the, the specifics of that decision as well as the rationale for that decision to be examined and approved by other people. Because you’re not the only one, almost, you are almost never the only one who’s gonna bear the cost. Some way that cost is gonna have to be made up in the company. Now, if you also need to get approval to buy a box of pencils, that is where the, the trust starts to break down. And I think this is what I experienced, um, was not so much like it was the tiniest things, uh, although there was scrutiny on, on those. It was that it seemed nearly random and it very rarely felt like the decisions were consistently improved by the approval process.

[00:04:43] And from my perspective, the point of having some kind of approval process, unless you work in like a highly regulated industry or something like that, the point of having an approval process is to bring the perspective and experience of others into the decision making process in some formalized way so that the decision is more likely to be correct. That, that it’s gonna are more likely to succeed, uh, in that decision. That’s the good reason to bring some level of approval process. But that wasn’t my experience. It was just like random things I would have to get approval on. And sometimes it felt like I had to jump through multiple hoops, uh, to get approval on buying a piece of software that I needed, for example, for my, for my team. Uh, you know, we’re talking an expenditure on the order of a thousand to three thousand dollars a year.

[00:05:30] Uh, I, I would have to, you know, get signatures and triplicate, uh, in order to make that kind of decision. That really did slow us down because I, I was not the type of person to spend frivolously, spend other people’s money frivolously. And so by the time I was going to somebody with a decision, uh, or request for funding or something like that, I had really thought this through, I had considered alternatives. And, and in many cases I was the expert in what I was asking for. And so there’s a person having to quote, unquote approve it was really nothing more than an obstacle in, in my way because they didn’t add anything into this, into the decision making process. So that over time, 

[00:06:10] Amy Sandler: And I think one of the things you’re talking about is, you know, certainly in Radical Candor, Kim talks about, you know, move those decisions to the person sort of closest to the facts. So in other words, you are the one that had the best visibility into the reasons for, for doing this. So you, quote, should have been the decision maker on that allocation. 

[00:06:29] Jason Rosoff: Correct. So I share those examples because I think that, um, there’s a spectrum here. I, I don’t want us to come across as saying approvals are bad and you shouldn’t ever have any obstacles to making decisions. I do actually think that it, it, it could be helpful sometimes. I wanted to give an example of when I think it’s actually helpful versus when I, when I, when I think it can be harmful from both an efficiency perspective and, uh, and, and, uh, a sort of like enablement or, or, or sort of trust perspective. Uh, and my guess is that, you know, that they have the set of standard processes, uh, that this person describes in their note.

[00:07:06] And my bureaucracy, and that’s like sort of a bad word. Um, uh, which is like some set of processes or procedures that are pre-agreed on in order to accomplish a set of tasks. That’s effectively what, like bureaucracies are designed to do. Bureaucracy as being described here one of the things I’ve noticed about it is that it’s very often, very rarely rather reexamined. So it’s very rare to go back and say, hey, do we still need all these processes and do we need them to work exactly the way that they’re working now? That I think is quite rare. So I, I would guess that this person is maybe up against a couple of things and one of them may be sort of history or, or, a path that this organization took to get there. 

[00:07:50] Amy Sandler: We had a really great conversation recently with Stanford, uh, professor Bob Sutton, uh, and talking about efficiency and friction. He’s also written a lot about how to work in an environment where you’re surrounded by assholes, uh, and he uses that term. So I encourage you, we’ll put that in the show notes because he does distinguish between, you know, simple challenges, which, you know, there can be quicker results versus more complex situations. And so I think just that idea, Jason, of, of reexamining a little bit of how we got there. So just to go back to our, our letter writer and getting into some, some practical tips for them.

[00:08:29] One is around, thoughts around the actual process, like how you would recommend this organization and this, this letter writer sort of advocate for a new process, but specifically around the communication. Because this person said, how can I communicate this to my managers and at the same time persuade them to adopt a new process? So I’m just curious what guidance you might have at a broad level for this letter writer in terms of communicating upwards. And then maybe we can get into some actual practical tips on what this person specifically could say. 

[00:09:03] Jason Rosoff: Yeah, so I think my preamble was really teeing up my first point here, which is that process often exists for some reason. It’s very rare that there, there are people who are like, you know what would make everybody miserable? I’m gonna come up with a bunch of processes. Uh, that, that’s rarely the place that they start from. Uh, but what I, uh, as I was saying right before you, you teed up, what I, I think is a, a great framing for the rest of the conversation is like, things change. And so the rationale that led you to having a process in this particular spot in the company, maybe that rationale is no longer valid. Um, and it hasn’t, hasn’t been reexamined. But I think it’s important to start with the assumption that think people have done things this way for a reason. 

[00:09:44] And because I think one of the best ways to, um, to make enemies of the, the sort of like people with approval rights is to make them feel silly for doing a thing that, you know, there is a rationale behind, um, that you may not fully understand or appreciate. Uh, and so instead, the, the place that I like to start from is a place, like we say this all the time, a place of curiosity, which is like, hey, we, we do things in this way, but I don’t totally understand why. So the first conversation I might wanna have with somebody is basically like, can you help me understand why this process works in this particular way? And it’s important to say that this is, if you want to make an a difference, if you wanna have an impact in this situation, I, I think this can’t be, this can’t be insincere. Like you actually really need to want to understand, uh, what’s going on. Because I’m sure you are not the first, nor will you be the last person to criticize whatever this process is. 

[00:10:53] Uh, and so my guess is that the people that you’re talking to are likely going to be on edge a little bit if you come in saying like, tell me how this, why decisions are made this way. Because most of the people who have asked them that question were not sincere. They weren’t actually curious about why the decision was made that way. And so you might encounter, even though you’re approaching with curiosity, you’re doing all the things sort of right, you might encounter some resistance because other people in, in an effort to sort of pay lip service to curiosity, have come before you and asked that question and then immediately said, well, you know, uh, another way to do this is blah, blah, blah, blah, blah. Um, so clearly it was like a tee up to give themselves permission to, to share their own idea as opposed to understand. 

[00:11:38] Amy Sandler: It’s kind of like a flavor of the feedback sandwich where it’s like, let me give you this throwaway praise so that I can get to what I, what I really wanna say, and people have such good BS detectors. You know, as you were sharing that, Jason, I was reflecting, and I may have shared this story before, but I have a, a story when I landed in manipulative insincerity about a project that I had been working on for years where I was doing the research. And originally I’d written this really obnoxious email to the project owner and I said how they were wasting millions of dollars and I felt very righteous. Um, and then I was no longer on that project, but the project continued. And so a new project owner came on board and they said, you know, the reason this project failed was because there was no research. And I’d spent several years doing the research. 

[00:12:26] Then I spent several more years like trying to get the people to listen to me about the research, and I sort of gave up at that point, and that’s where I landed in manipulative insincerity. But one of the helpful things from that experience, which was very stressful to kind of be in that spot, was that it gave me a lot of empathy when I was a new employee, the first thing I noticed was kind of, why are we doing it this way and why are they doing it that way? And it just, none of it made sense. But rather than kind of coming in guns blazing, which is probably what I would’ve done before, I realized like, oh, there is probably a reason why this is happening and it might not be obvious. And so, at least for me, I think having been on both sides of that point, and it’s not necessarily just about being new, but sometimes those fresh eyes can point those things out. And we might not realize that, to your point, like, this process started for a reason and now it’s like, well, it’s just the way we’ve been doing things. 

[00:13:22] Jason Rosoff: And, and like, I think the, the sort of second level of, uh, of investigation is not just like, why do we do things the way that we do? ‘Cause that often gets you a sort of historical answer. You also wanna dig one level below that, which is like, and why is that important? Because my guess is that there is actually alignment to be found as to like why it is important to have some level of process or rigor around these types of decisions. And if you can get to that underlying need that these processes were created to, to meet, then I think you’re, you’re building from a much stronger foundation to talk about like how we might be able to approach things differently. Because you’re talking to, you’re speaking to that person’s sort of need, underlying need or the goal, uh, that, that the process exists to meet. And that’s a very different point of departure, I think. So if, if we said like, hey, um, you know, I, I know we, we have these approvals on software purchases, for example. 

[00:14:24] Amy Sandler: Yeah. I love a specific example. That would be great. 

[00:14:26] Jason Rosoff: Yeah. We have these approval processes on software purchases because technically, you know, they’re over, it’s over the thousand dollar, you know, limit that managers that, that have discretion over. And almost every software purchase is going to be over the thousand dollars limit that managers have, um, con control over. Uh, and so I, I’m, I’m wondering like, like why do we have the thousand dollars limit? Was there a problem that we were trying to fix by putting, by putting that limit into place? Um, uh, because I, I imagine that this is also a lot of work for you. Like you, you wind up having to approve a lot of, uh, a lot, a lot of things coming out of like the tech teams and stuff like that. Uh, and so I’m wondering if like, if we can explore that together. Because I want, like, I wanna make sure that, you know, I’m thinking about this as sort of like clearly and holistically as possible when I’m giving guidance to my team. So before I make, suggest that we make changes, like, help me understand, uh, tell me like what problem we were solving when we put this into place so that I can give my team some advice, uh, about how to, to do this. Because you’re gonna hear from us a lot, um, uh, since almost every purchase that we’d make is gonna cross the threshold.

[00:15:45] Amy Sandler: So helpful. Jason, I’m just, to rewind the clock a little. When you were talking about your own example with that software purchase, like, did you actually have this conversation with your manager or are these lessons from things that didn’t quite go as well as you would’ve liked? 

[00:16:00] Jason Rosoff: Yeah. No, I, I, uh, I was really early in my career and I, I, I didn’t really know like what to ask for, and so I was, I just put up with it basically. Uh, and, and over time it did really, it did really sort of wear me down and contribute to burnout. Like not addressing it. And in other instances where I have addressed these things, um, so I’m thinking of a, of another example maybe ten years later where, uh, there I was working at an organization that had like tons of leeway. Uh, and then there was like a very specific issue where, uh, we wanted to invest, uh, some money in some new hardware. Um, we were building, uh, we were building products. This is at a time before AWS and all this other stuff, uh, where you didn’t have, we had to build our own server infrastructure. Um, and we wanted to invest in some hardware that we thought was gonna take a bunch, uh, save us a whole bunch of time. And, and all of a sudden we like ran into this like, pretty big set of roadblocks, uh, and uh, in, in, in the purchasing process. 

[00:17:25] So like that my team wasn’t able to do this and we had to go get approval from somebody else and they had to get approval from somebody else, which is like very unusual. Um, and, and so when I asked the question, I was like, hey, you know, this is like really, this is really different than the experience that I’ve had here so far. I’m not used to getting these kinds of approvals. Can you tell me, uh, why is it that we do this particular thing this way? And they, they were able to make it clear that like, one of the, one of the challenges with this is like another team is, uh, there’s some cross-functional responsibility. So even though we’re purchasing the hardware, we’re reliant on another team to actually go to the data center and install it. And they’re also then responsible for making sure that piece of hardware stays up and, up to date and running smoothly and all this other stuff. 

[00:18:15] So it wasn’t the same kind of decision, uh, because we didn’t operate independently, uh, we couldn’t operate like nearly or completely independently. Uh, it, it feels sort of react, like to me it felt sort of reactive. Um, I wonder if there’s like another way for us to communicate that this type of decision is being considered so that it’s not like all the way at the end of the process that we like run into the roadblocks. Because I said, you know, I think it feels more frustrating because we’re at the, you know what I’m saying? We’ve already made the, we’re like all the way down this path and we made this decision and now all of a sudden we’re have to check with all these other people in order to make sure it’s okay. Like is there some other way for us to approach this so that, you know, the system administration team can be brought along earlier on and give us sort of their approval as we’re going through the decision making process. And we can get their perspective as we’re going through the decision making process, uh, so that we, we don’t, like, it doesn’t feel like we’re throwing up roadblocks at, at the very end. 

[00:19:18] Um, and it feels like it’s helping the decision be stronger or better. Uh, and that was like, you know, it was the right environment. Like I said, there was a lot of trust and, and leeway given to people. That was met with like a really positive response, especially from the head of the system administration team who was sort of like, that would be great. Like we’d love to be brought in on these conversations earlier. Like I kind of hate the fact that I have to, like, it feels like I throw on the brakes in these conversations at the very end. Um, you know, the, the process of approval is there as a sort of backstop, but there was no proactive process to like get the system administration’s team perspective earlier on. Um, and that would be much better, uh, for both for the team making decision and the team responsible for sort of, uh, dealing with the, the work after the decision was made.

[00:20:19] Amy Sandler: Just to kinda reframe or repeat what I heard you say, there was kind of one step, which is the curiosity. Help me understand why this process works this way. Why is that important? Find some alignment of, you know, what’s the problem we’re trying to solve? So that’s kind of one one initial starting point. And then if I hear you correctly, you’re also suggesting what is the timing of when to have this conversation and to have it be more of an ongoing check-in rather than some kind of frustrated, like at the end, uh, coming in and, and dealing more with, let’s try to get a new process rather than potentially almost like a pre-mortem, a post-mortem, just some kind of more frequent communication. So like, just to go back to the listener’s question, they say, when attempting to communicate why this is an issue, it leads to more bottlenecks. And often I come off as escalating the situation. So their question is, how can I communicate this to my managers and at the same time persuade them to adopt a new process? So, is, am I hearing that correctly, that you’re saying this is really almost a process about communicating about the process, that we’re doing it more frequently? 

[00:21:29] Jason Rosoff: I, I don’t know that I would make that specific recommendation. So like, if I was gonna generalize the point I was trying to, to, to make, it was more like, once I understood that the issue was that there was another team involved that needed to, to be aware of and give input on these decisions, essentially, I said, well, I think the, the, that doesn’t frustrate me. I, I, I feel bad, sort of, you know what I’m saying, that I got through this process and I didn’t consult that other, that, that other team. But I think it’s a flaw to, to, to say like, we make, we make a bunch of plans and then once those plans are formulated, we, you know, we present them to the system administration team who then signs off on those plans. I was like, that seems wrong, like. One, we’re not getting their perspective. 

[00:22:18] And so we spend a bunch of time thinking about things in a way that actually isn’t likely to work. Uh, and two, the, like, it’s much harder for them to absorb all that context and figure out like, and, and harder for us to document everything. So like, if they were brought along in the process, were able to give their input earlier, that would just make things easier. And so instead of an approval process that happens at the very end, it’s a collaborative process, uh, collaborative decision making process on what architecture or sort of what, what computer equipment we should be buying as we go along. And, and, and that I, I don’t know, that’s sometimes maybe generalizable. That idea of like, if the issue is sort of like other teams or people are relying on information and they need to be informed about what’s happening and have the ability to give input into the decision, et cetera, then maybe massaging the process so that’s happening on an ongoing basis is, is a generally useful, um, uh, approach to, to getting away from the sort of like approval at the end, um, which I think can often be very inefficient. 

[00:23:23] But I think more generally, like what, what this person is basically saying is, or how I interpret what they’ve written, um, because this may not be what they intend is that they’re trying to address the meta pattern of processes require, like being too overbearing. And I think just like our current, our conversation where you’re like, you know, what a, a really specific example, like instead of focusing on the overall pattern, like focusing on a specific example and coming up with a specific solution, um, is really useful because otherwise it’s sort of hard to understand. ‘Cause I could imagine if I was this person’s manager and they’re like, our processes are so overwrought and it’s really hard to make decisions. I feel like we’re constantly being slowed down. We need to know or need a different process. Um, but that would feel like an, like sort of vague escalation. 

[00:24:12] Like you’re, you’re sort of like, and the intent is to make things better, but it comes across as sort of a complaint, like energetically, it feels like yet another break that we’re sort of trying to put in. As opposed to, uh, saying, you know, Amy and I talked about this and we’d like to, you know, I think I understand that why this process is the way that it is. You know, this is what she and I, uh, discussed and I’d like to try the next time we have to do this, I’d like to try something a little bit different. I’d like to try, you know, bringing Amy in earlier. So if I went to my, like, that’s very different. If I’m your manager, you come to me and say like, hey, you know, I’ve been feeling a little frustrated about this, so I did some digging and here’s what I’ve discovered and here’s a concrete recommendation for how we can make it better. You know, would it be okay if we, uh, if we try, if we tried this new approach, the, the, the next time around? 

[00:25:06] But that’s very different than saying, you know, people are frustrated and, um, we, we need to improve things. Uh, basically like the, the, there’s two theories here, which is like, some people like to, and I, I, I tend, I, I strongly sympathize with this because I tend to be like pattern, big picture thinker. Like that’s the way that my brain likes to work. And so I tend to try to generalize from the, uh, uh, to, to specify from the generalized pattern. Like that, that tends to be my approach is like big to small. Um, but when things are sort of grindy, uh, or, or difficult, like sometimes it helps to try to generalize from the specific, to take a small example, show a different thing that can actually work. Um, and that tends to build a permission structure for trying something bigger.

[00:26:01] Amy Sandler: So would it be helpful just to, you know, for our listener, just to give one specific sort of role play of, if you were coming to me of what you were talking about of a specific, uh, example that you would like to deposit to your, to your manager. Should we give that a shot? 

[00:26:18] Jason Rosoff: Uh, sure. What, what are we, what are we trying to get agreement on?

[00:26:22] Amy Sandler: I don’t know if this is a good example, Jason, but recently we were together for a team offsite and the, this, this came to mind because, uh, I was with Brandi, our, our producer. And we were renting a car and the car was so large that, uh, it was, it was, car isn’t actually the right word. It was, it was basically like the size of a bus. And as we were leaving the rental car place, the woman at the front, she said, you know, you don’t, you don’t look that comfortable driving this truck. And I said, I am not comfortable driving this truck. And she said, let me see what I can do. She also mentioned that she had a manager that was not gonna be very happy about this, but she wanted us to be happy. So she actually enabled us to get into the, the car that I, that we were more comfortable with. And so I was so grateful that she felt empowered to, to make that decision. But like, let’s say maybe she got in trouble from her manager because, oh, at the desk, this customer got this truck, but then they left, and this, like, what happened here? 

[00:27:26] Jason Rosoff: Sure. So I’ll, I’ll, I’ll try to put myself in the position of that person because I think, uh, and, and let’s just for the sake of argument, let’s say that to, to add some spice to the, to, to the role play. Let, let’s just say that ’cause of corporate policy, these changes to a reservation, uh, once a car has sort of been assigned to somebody do require management approval, right? So a manager has to approve these changes. If you imagine that for a second, I could, I think you can imagine why a manager would be frustrated. ‘Cause I’m sure there’s lots of reasons why people wanna change a car after it has been assigned to them. Some of the, many of them not having anything to do with sort of safety or comfort. Um, but you know, like some, some other sort of like unstated preference or, or something like that. Um, and, and let’s imagine there’s like some paperwork or form that the manager ha has to fill out. 

[00:28:22] Amy Sandler: So I, I’m gonna play the role of the person who, who helped me, so I can be closest to it and you’ll be the, the manager.

[00:28:31] Jason Rosoff: I, I’m happy. Which is that, would you like to do it that way the other way? 

[00:28:33] Amy Sandler: Yeah. Yeah. I’ll, ’cause I feel like I have a visible, so I, I’m now coming to you and now have to explain myself. 

[00:28:39] Jason Rosoff: Well, yeah. So, so you’re, you just had, you’ve just seen real Amy struggling with the car. Um, and you, you’ve, you, you’ve given me, 

[00:28:49] Amy Sandler: And by the way, it was not what I had requested at the, to be clear. Like I paid a certain amount. Like, so they were actually, it wasn’t like I, they gave me something more expensive. We actually got something less expensive, but more what I had requested at the front desk. That’s like the validation I would give to my lovely customer service person. 

[00:29:06] Jason Rosoff: Oh, okay. fantastic. But I, I’m not aware of all this. 

[00:29:09] Amy Sandler: Correct. 

[00:29:10] Jason Rosoff: Okay. You’re goal in this scenario, it is to get me to, to understand why it’s important for you to be able to make this change. 

[00:29:19] Amy Sandler: Correct. 

[00:29:20] Jason Rosoff: Okay, great. Let’s do it. 

[00:29:22] Amy Sandler: Okay. So, hey, Jason. Uh, I saw that you wanted me to meet with you. 

[00:29:27] Jason Rosoff: Uh, yeah, we approved another change order at the last minute and I, you know, I feel like we talked about this last week, like these change orders, um, they take a lot of, a lot of effort. Um, and I just don’t understand why they keep, why it keeps happening. 

[00:29:42] Amy Sandler: We did talk about it. I hear you. I didn’t feel like you heard me about why I need to make these changes. This was a customer who was in a vehicle that they had not asked for. They had said at the front they wanted something smaller and they were clearly uncomfortable, didn’t feel safe in the vehicle, and from my perspective, our, our primary role is, is customer satisfaction. And so they were extremely grateful. I got them the vehicle they needed. It was actually a less expensive vehicle. Um, and you know, from my perspective, I wanna feel empowered that I can get the customer happy with what they actually, you know, purchased in their agreement.

[00:30:25] Jason Rosoff: Yeah. And, and I, I did hear you, but the, these processes exist for a reason. Like we, we are not just responsible for the customer’s happiness. That’s one part of it. But, you know, we are also responsible for managing this fleet of cars, and it’s really hard to do inventory management when we’re changing things at the last minute, uh uh, right? We can’t, like, it makes it, we increase the risk that someone else is gonna come in and we won’t have the car that they asked for either. So it’s just that like, you know, it’s important that we, we, we follow the, the process of, you know, giving them the, the, the, the car that, you know, the, the front desk orders for us.

[00:31:06] Amy Sandler: So are you saying the next time this happens and I see a customer who is clearly uncomfortable with the car, I just let them leave? Or what, what can I do to meet my goal of a happy customer? 

[00:31:20] Jason Rosoff: That’s an interesting way, way to frame it. I, I would say like, you have two goals. One of them is a happy customer and the other one is to make sure that we’re, you know, uh, we’re give, we’re, we’re managing the, the car inventory correctly. And so what, what I like, I don’t know what was going on with this particular customer, but maybe there’s a way to, uh, maybe you could sell them on the bigger car. You know, maybe you could say, ah, yes, you seem a little uncomfortable, but wait till you get on the road. It’s so much nicer to be higher up in the car and you can see over everybody. Uh, uh, like maybe we could make them happy. with, uh, 

[00:31:55] Amy Sandler: So are you saying lie to the customer? 

[00:31:56] Jason Rosoff: Well, well, I, it’s not a lie. Like I drive a big car and it’s really like, I enjoy the, 

[00:32:01] Amy Sandler: Do you drive a bus?

[00:32:02] Jason Rosoff: Uh, I, it is a small, it’s a small bus. Um, yeah, I, I guess the, the, the, the thing that’s on my mind is we can’t trade short-term happiness of one customer for sort of like long-term problems of managing this fleet. Because like I said, it doesn’t just affect this customer. Like there might be another customer who reserved that exact car that we just gave away. Um, and, and that’s the thing that, that’s why this process exists. So in this case it was okay, right? Because we actually had that car wasn’t reserved by somebody else. Um, but that’s the risk. And so I think the, 

[00:32:41] Amy Sandler: So, so how, how could we create a process or reevaluate our process so that we could, in that situation, I would feel empowered to do something, but at the same time, not potentially impact another customer. So, because I hear you on the, the inventory thing, but I, I wanna feel empowered that I can kind of do the, do the right thing. And maybe there’s, there’s a, a third way that we haven’t yet thought of. 

[00:33:08] Jason Rosoff: Yeah. I mean, may maybe, you know, uh, things tend to move fast around here, but maybe there’s like a way for us to, uh, you know, when we, when when we start a shift to go through and tag all the cars that are, uh, already reserved. Um, so that you can visually see, maybe they just get a little piece of paper or something underneath the windshield wiper so that you can see like, you know, these cars are reserved. 

[00:33:35] Amy Sandler: Because that’s the problem you’re trying to solve for. You don’t want me to give away a car that’s not available. 

[00:33:43] Jason Rosoff: Right. And so, ’cause like, even though technically we might be able to meet that customer’s need, like there, there’s like another car, like we’ve set one expect, you know, we’ve set an expectation with them that they’re gonna get a particular car. So I don’t want us to be essentially creating, you know, another, another problem that that’s really what I’m trying to solve.

[00:34:03] Amy Sandler: Well the real problem is that the people at the front desk don’t really know what they’re doing when they’re assigning those cars. And then I’m left at the end just before they go out, kind of having to clean that up. You know, that’s, I think that’s probably my bigger frustration. 

[00:34:18] Jason Rosoff: I, I mean, we, that’s certainly something we could ask them about, right? We could bring that up to, to, to the team in the next meeting. Like, I don’t have any direct influence over them. Like I’m, I’m, I, I like manage what’s going on back here. I don’t, I don’t manage what’s going on over there, but we, we could talk to them about it. 

[00:34:33] Amy Sandler: Okay. And scene. 

[00:34:35] Jason Rosoff: And scene. All right. We did it. Role play over. 

[00:34:38] Amy Sandler: All right, Jason, um, how did that go? 

[00:34:41] Jason Rosoff: I mean, I, I think it, I think it went well. I, I think the difference between what, what I had in mind before we went in and what you did, not that it’s necessarily bad, is that you were framing things from the perspective of you getting what you want. Which is to be able to meet these customer’s needs, which I think is really important. Um, uh, and I think that the, the thing that I would say to this person is that if you’re going into the conversation with your boss is like being concerned with and curious about what they are trying to, to accomplish. Um, uh, but I thought the, 

[00:35:23] Amy Sandler: I, can I just like pause on that because I think that’s such a great example and especially if you’re going to your boss, like you as the direct report might have a very legitimate frustration, right? And so I just wanna acknowledge that tension there of, of what you know, for you to be successful in this conversation there is that frustration of like, I’m just trying to do my best possible job. And now I’m having to go into this conversation where I have to worry more about you. And that could potentially be frustrating. 

[00:35:53] Jason Rosoff: Yeah, and what I, what I would say is like, if you want to be able to give someone else the benefit of the doubt, uh, as that there’s a reason why things work the way that they do, I think that means showing a genuine concern or interest in what they are trying to accomplish. 

[00:36:11] Amy Sandler: So are you saying I should have started that conversation based more like rather than what I think could have happened, someone saying, hey, I got another, you know you had another approval and this is a real issue. So then just rather than me saying, I’m so frustrated, I’m just doing it for the customers. Just for start, tell me more about this process. I heard you last time, but I clearly didn’t get why it’s so important. So explain to me why this is so important ’cause I think I’m not getting it. 

[00:36:37] Jason Rosoff: Yeah, I mean that you, you could have done that. I don’t think you have to be quite so self-deprecating. I think you can say like something to the effect of, you know, I just wanna acknowledge that it’s really hard for me ’cause I’m standing there in front of a customer and they’re saying they’re really frustrated and they, they, this isn’t the car that they want or they don’t feel comfortable in it. And I don’t want that to be their experience, uh, leaving the, you know, the, the rental agency ’cause I feel like that’s bad for us. And, uh, I recognize that, you know, this isn’t the first time that we’ve talked about why it’s important for inventory management, but I feel like, right now, I feel like it’s sort of a choice that I’m having to make. Which is like, make the customer happy or like do, you know, follow the, the process. And, uh, you, you said this, uh, in, in the discussion, which I thought was a really, was a good turning point. It was like, maybe there’s another way that I’m not thinking of because maybe I don’t fully understand the goals of the process or what we’re trying to accomplish. 

[00:37:32] Amy Sandler: I think that’s, that sounds really, really helpful. All righty. Shall we, shall we wrap it up? 

[00:37:37] Jason Rosoff: Yeah, let’s wrap it. 

[00:37:38] Amy Sandler: Shall we take this car out for a spin? This bus? 

[00:37:43] Jason Rosoff: Yes, I think that’s right. 

[00:37:45] Amy Sandler: All right, so now it is time for our Radical Candor checklist, tips you can use to put Radical Candor into practice immediately.

[00:37:55] Jason Rosoff: Tip number one, I think the key to this whole, the key to the whole approach is starting with, with curiosity and then framing your, uh, your observations, uh, very clearly. So when we’re discussing a situation, you want to encourage the other person to, just like we do in feedback, to, to share their sort of like, the context of what they need, their observations about like maybe what’s going on or where the challenges are and the impact that that has. So you’re trying to gather that data in the same way that we, you’re gonna express your observations about the situations. So when you say, well, here’s what I’m trying to accomplish, um, you know, the, the customer’s frustrated in front of me, clearly feeling uncomfortable in the car. Um, uh, uh, and my observation is like that, that we have a way to, to solve that, uh, by giving this person another car. But the result of of this is, is like, you, my manager, feel frustrated because I haven’t done the inventory management thing correctly, even though I’ve solved the, the customer problem. And I’d really like to understand better, like how we might accomplish both of those, uh, goals. Can we explore that together?

[00:39:11] Amy Sandler: Tip number two, if you encounter resistance, remember to stay focused on your shared goal. So from the listener writing in, it’s about team performance and reducing manager burnout. From our role play, it was about this idea of sort of this third way between inventory management and a happy customer. So for our listener, you might say, you know, I understand the importance of oversight, and I want to help find a way to maintain appropriate control as well, allowing our team to work more efficiently. So could we identify a few decisions where we could test a more streamlined approval process? And I think, Jason, you gave a really good example of in this way getting really specific, like what is that one next test that we could actually try out? 

[00:40:00] Jason Rosoff: Yep. And then tip number three, the processes didn’t come into existence in an instant, and they’re probably not going to change in an, in, in an instant either. So don’t be totally shocked if this initial conversation isn’t, you know, a, a, a roaring success or like a, a totally well received. I think the important thing is to, to keep gathering data and information. To look at, uh, specific reasons why those bottlenecks, uh, are appearing and offering concrete ideas for how to address them. Uh, I, the general pattern is really important, but I, I think in order, in this case, in order to make a dent in the, the sort of the way things are currently happening, you’re gonna wanna patiently and persistently pick out those specific examples. And then, you know, keep reinforcing that idea that the goal is not to create chaos and have everything happening willy-nilly, but instead to create a process where, uh, oversight and approvals happen in a way that actually makes the outcome, uh, better for the company and the process more, uh, pleasant for all of the team members involved.

[00:41:13] Amy Sandler: And I don’t know if this is a tip number four, Jason, but what’s coming up as we’re talking is putting myself in the shoes of the, of the letter writer, the emailer, that they’re having to do this upwards management. So ideally, we’re in a, in an organization where our manager is soliciting feedback and oh, you know, it seems like there’s something in our processes that are frustrating. So I just wanna acknowledge our listener for writing in and the frustration of, of having to kind of manage upwards around this. And also even in the example that we talked about, um, just a place where they can kind of vent their frustration in a helpful way so that when they can go to this conversation, they’re able to show up with some genuine curiosity. Do you have anything more to say? Just given the, you know, we’re, we’re putting a little bit more onto our, our listener, um, just because of the, the dynamic. 

[00:42:05] Jason Rosoff: I think that, I think that’s, that’s really important is like, is essentially like how I would frame that tip is like make sure that you are in the right mindset to have these conversations like you, because it is frustrating. Um, uh, and I, I think, um, to me it sounds like this person is a leader in the organization, that, you know, they’re advocating on behalf of frontline managers. Uh, and, and what I would say is like sometimes at like, even though there’s hierarchical power, like sometimes it’s important to remember that like leaders in an organization need to be on, on the same team, like working, pulling in the same direction, uh, uh, in order for people not to be even more confused or frustrated than, than they already are, already are. 

[00:42:53] And so I, I do think that that instinct of managing up, um, is, is a good one. But I think if, if you frame that slightly differently and say like, hey, I’m part of the leadership team I’m part of the sort of like leadership, uh, cadre in this organization, that can also be, be helpful to say like my, I have two teams. I have the, the team of people who I’m advocating for, and I also have this team of leaders that I’m trying to, uh, I’m trying to help. Uh, and uh, and, and that can sometimes help us maybe get out of the, the, the us versus them, uh, kind of, uh, mentality that can come from the idea of managing, uh, of managing up.

[00:43:34] Amy Sandler: Well said. Thank you so much, Jason. For those of you listening, head on over to RadicalCandor.com/podcast. You can see the show notes for this episode. Praise in public, criticize in private, like we like to say. So if you do like what you hear, we hope you do, please do rate and review us wherever you’re listening. Send your criticism, send your stories. Thank you again to our listener. And email podcast@radicalcandor.com. Bye for now. 

[00:44:03] Jason Rosoff: Take care everyone. 

[00:44:04] 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, 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.

Radical Candor podcast

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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