Is A Good Boss Too Much To Ask For? with Melissa & Johnathan Nightingale | Crooked Media
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October 04, 2023
Work Appropriate
Is A Good Boss Too Much To Ask For? with Melissa & Johnathan Nightingale

In This Episode

We wanted to tackle some of the most complicated management questions that listeners sent in, so host Anne Helen Petersen turned to our favorite management experts, Melissa & Johnathan Nightingale of the Raw Signal Group. Whether you’re suffering from micromanaging, a boss who loves to hear himself talk, or way too much work in too few hours– we’ve got some suggestions.

  • Listen to Melissa’s fantastic advice on our previous episodes, “May I Speak to the Manager?” and “How to Be A Better Boss
  • Need advice about a sticky situation at work? Head to and tell us about it– we may use your question in a future episode!
  • Follow @CrookedMedia on Instagram and Twitter for more original content, host takeovers and other community events






Anne Helen Petersen: Hi, everyone. I’m Anne Helen Petersen, and this is Work Appropriate. [music plays] It’s not surprising that the most common question we receive here on the show is about management, bad management, non-existent management, overbearing management, micromanagement. It’s the root cause of so many of our work problems, even in episodes that are ostensibly about other topics. We so often come back to the problem of management, like that’s a problem with DEI, but it’s also a problem with management. That’s a problem with your PTO policy, but it’s also a problem with management. That’s a remote work problem. That’s absolutely a problem with your management. Today, we’ve collected some of the most complex management questions to take to the best, no bullshit management pros I know. [music plays]


Melissa Nightingale: My name is Melissa Nightingale. I am a founder and partner at  Raw Signal Group and at  Raw Signal Group we build better bosses. We help leaders in fast growing organizations to get the skills that they need in order to be successful. 


Anne Helen Petersen: All right, so this is your third time on Work Appropriate. We have two, three-peat. You are one of them. And I’m so excited to have you back. But you also because our questions are so hard or I guess complicated. You brought backup. 


Melissa Nightingale: I did. I saw in the email you were like, let’s try and stump Melissa. And I was like, well, that’s not very kind. [laughter]


Anne Helen Petersen: Yes. 


Melissa Nightingale: And so I did. I brought back up this time. 


Johnathan Nightingale: Oh, hello, I’m Jonathan Nightingale. I’m the other co-founder and partner at  Raw Signal Group. It’s lovely to be here. 


Melissa Nightingale: And like, we’re married, not siblings. Sometimes people ask. [laughs] 


Anne Helen Petersen: No. We’ve never had two guests on an episode before, and like I said, it’s because these these questions are really complicated. You know, when we were selecting for this, Melody, our producer sent me the list of all of the really difficult management questions that we got. It was literally like, I don’t know, 60 questions long, 70 questions long. So I tried to pick some really  ones that were a little bit on a theme, as we’ll see, but also pretty difficult. So we’ve heard a little bit about Melissa’s experiences in toxic workplaces and how she came to be passionate about training leaders, making better bosses. Jonathan, what is your story? 


Johnathan Nightingale: So I’ve been working in tech for about 20 years. I actually met Melissa in one of my I think my second tech job, maybe my third. I started in a Super Corp. I was at IBM and and I would say the management culture at IBM, you know, has been carefully honed over 100 years to mostly ignore people. [laughter] And that’s that’s certainly what I experienced. Like, I think if you’re in the sales organization, I think it’s pretty hands on. But but I was in R&D and and yeah, I think I met with my manager once every quarter or something and and he always he always he said, great job. And that was the management I got. And, you know, after five years of that, I sort of plateaued and moved to Mozilla, which is where I met Melissa in the very early days of building Firefox. And we’ve been working together in one or another way ever since. 


Anne Helen Petersen: And at Mozilla, neither of you had much experience in terms of like management training, right. This is kind of the origin story of like an add on management style where they’re like, oh, you’re good at what you do. Why don’t you manage? 


Johnathan Nightingale: Ha ha ha. Right. It’s purely additive. You’re still you’re an engineer. We still want you to write code. We just also want you to manage six other people. Right? Oh, you’ve been doing that for a while. I guess we’ll make you a director because we need one of those. And at every step and just. Okay, that feels nice. It’s nice to be recognized. It’s nice to be trusted. But what is that job? Like, it sounds cool. It sounds like. Does director mean I’m on the board? No, it doesn’t mean. Does director mean I’m executive? No, it doesn’t really mean sort of. But really doesn’t mean that. 


Anne Helen Petersen: [laughs] I still don’t understand always I have to be like. What does that mean when my friends tell me about, like, organizational schemas, I’m like, so is that good? Like, VP, good right? 


Johnathan Nightingale: It sounds nice. 


Melissa Nightingale: I think it’s good. 


Johnathan Nightingale: Has a lot of syllables, but that was about it. Everything else was just pay attention to the leaders you like and the leaders you don’t read books figure it out and you’re doing all that figuring out on human beings, right? 


Anne Helen Petersen: Mm hmm. 


Johnathan Nightingale: Like there’s a bunch of people who are looking to you like you’re in the seat. Tell me, like, make the decision. Which thing are we doing? Am I doing a good job? When do I get promoted into your seat? Like, and just with no equipment on how to do that and screwing up plenty along the way? 


Melissa Nightingale: I think we talked about a bit though. Mozilla was sort of fully like fully distributed in terms of sort of where we were like, I was in California and Jonathan was in Toronto, but we were working and managing teams of people who are all over the world and it’s now really common. But at the time like this is, I don’t know, like 20 years, this is a long time ago, maybe 15 years ago, it was a lot less common to be managing people where you had never actually been in person with each other. 


Anne Helen Petersen: Yeah, and a lot easier to mess things up. Or not just just like, not manage at all. Just kind of be like, Hey, you’re here. I’m your boss and also your peer. You know, the common theme that we have with these questions is people who are struggling with pretty crappy managers. And I think I like where this is kind of a leading question, especially given what we were just talking about. But why is this such a universal experience? 


Johnathan Nightingale: Because nobody knows what they’re doing. [laughter] We have these stickers, so like because you came up in tech, right? You end up with this weird swag culture and at Raw Signal Group, it’s turned into a sticker culture where [laughter] like every time something happens, we’re like, we need to make that a sticker that’s important. But like, maybe my favorite sticker is like an old, like 1950s style pen that just has competent management on it. [laughs] Just we’re not we’re not reaching for the stars here. We want some basic competence and like. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: In the absence of that, you really feel it. 


Melissa Nightingale: But so many that like so many of the questions that we get on an ongoing basis around management, like when you sort of peel it back, when you peel the layers back in terms of why people have those questions or where like you’re like, because nobody ever told you, right? Because we keep promoting people and saying like, you’re going to be in charge of this team. But like, well, what does that mean? And like, we’ll be in charge like, well, okay, but like, are there are there specific things I ought to be doing? Are there specific meetings I’m supposed to be having? Are there specific conversations I should have or not have? But like most folks are sort of just thrown into the deep end and told like, well, good luck. Like, let us know how it goes. 


Johnathan Nightingale: And then you get into the stress position, right where your own boss, who also may or may not have any real skill here, says to you, Hey, a person on your team is screwing up. You got to go fix that. 


Anne Helen Petersen: Mm hmm. 


Johnathan Nightingale: And you’re like, okay. [laughter] And you act out whatever movie boss you’re imagining, but you don’t actually have any skills in terms of like structuring hard feedback in a way that they can hear or building accountability or being clear about priorities or expectations, like you have none of that. And so you just sort of you shout if you’re a shouter or you hug if you’re a hugger, and you just sort of hope that it’s going to resolve itself and eventually the person quits and you hire someone else and you hope it works better next time. 


Melissa Nightingale: No, like, the state of work can be explained like almost entirely in terms of like we are where we are, not because of cackling like malicious sort of intent, but because our bosses really don’t know what they’re doing. And like, if you’re working for someone who’s sort of cackling malicious intent, I’m sorry, like there are people like that, but the vast majority of folks that we come into contact with who are leading teams of people are like, I literally just don’t know what I’m doing. 


Anne Helen Petersen: So this is actually a great way to talk about the format of this episode, which is going to be slightly different than what we usually do. So usually we read the question, we give some advice to the question asker on how they can handle it, and we’re going to do that. But we are also going to try to offer advice to the bad boss if they’re listening, right? So clearly the bad boss is probably the specific bad boss. Probably not going to be listening, but there might be people who are managing who recognize some characteristics in their own behavior. Right. Like they’re like, oh, this is something that I know I struggle with and I’m super self-conscious about it. I have no idea how to act on this. So hopefully we will be giving advice to to both ends of the equation here. So does that sound good? 


Melissa Nightingale: That sounds great. 


Johnathan Nightingale: Yeah. We’ll talk fast. [laughter]


Anne Helen Petersen: First question is from Sally, who’s boss is taking micromanaging to the next level. Our producer Melody is going to read her question for us. 


Sally: I work for a corporate company that owns various hospitals throughout the country, and I’m pretty much the assistant to our leave of absence team that takes care of our company staff. My manager has been overloading me with tasks and has been inconsistent with his expectations. Plus, there are numerous meetings throughout the week that interfere with me completing my job duties. He recently started making me submit a daily tracker to monitor the duration and frequency of completing each task he has given me. Every day he seems to pick apart my tracker and question why I’m not completing my tasks and questions why it’s taking so long to complete certain tasks. I’ve notified him our department is being pulled for too many meetings, plus I flat out told him that I am working diligently to meet his expectations, but I feel as if he’s constantly making me feel like I’m a horrible employee. I enjoy helping our employees, but I don’t know how to tell my manager his expectations are unrealistic and to please stop micromanaging. How can I verbalize this to him in a professional way without worrying about being fired? And also, what do I do if this continues to worsen without my resume looking bad? 


Anne Helen Petersen: So I think this question gets at a pretty basic dynamic, which is that an employee’s boss is making their life really hard. But they worry that any attempt to try to deal with the situation is going to lead to them getting fired or just like a super toxic situation, even more toxic than it already is. So let’s zoom out a little and Melissa and Jonathan, what do you think is going on in the background that this manager is micromanaging? And I would not even call this micromanaging. I would call this surveillance in this way.


Melissa Nightingale: For Sally. This is a boss who thinks you’re slow. Like the boss has some sense in their head and whether it’s fair or unfair, grounded or ungrounded, whether they’ve got familiarity with the work or not. Like this is a boss who has some idea of how long things should take and feels like they’re taking way longer than they should take and maybe has not said that out loud in so many words, but like the the obsession them like myopic obsession with where is your time going is another form of the question. Like, I think this should take a lot less time than it’s taking. So like, something something is amiss here. And we have some theories about what exactly is amiss.


Johnathan Nightingale: Yeah. One thing I’ll say, though, is that it won’t work to address it directly in the way that that Sally’s asking. Right. So, like, once you once you’re filling out this time tracker, you’re sort of trapped. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: Because I guarantee no matter what you write down on that list, your boss is going to look at the list, find the thing that takes the longest, and say this should take less time because they’ve already internalized this thing of like, Sally’s slow, I’m going to force Sally to prove to me that Sally’s slow. Then I’m going to say that Sally’s slow. It’s not fair. It’s a crappy position to be in. And day over, day over day. It’s just self-fulfilling prophecy and it’s going to like it’s going to cause all the wrong behaviors for Sally, too. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: The first piece in terms of slowness is like there. There are things that sometimes take a long time, and then there are other things where like it takes a long time until you learn the one weird trick. And so like if the boss is holding on to a one weird trick, right? Like in the process of going through the daily tracker, sometimes it’s helpful to say like, Can you talk to me through how you would approach this, right? Like, I just got assigned this thing. I expect that is going to take me an hour, but like I hear you, that that feels like it’s taking too long. Like, can you talk me through like, how would you approach it if you are my shoes? Because you may find that like there is there’s an unlock hiding there that you just didn’t know. It’s a best practice. Everybody else learned it on their way in and you just missed it. Like, that’s possible. 


Anne Helen Petersen: So this makes me think of something that isn’t explicit in the question, which is do you think the boss has done this job before or aspects of this job before? 


Johnathan Nightingale: There it is. Right? So we’re in one of two spots. If we’re in a spot where the boss used to do this work, then this is great. Right. It’s just. Okay, champ, Show me how it’s done by a professional. Right. And like, I’m going to level up so fast in this and I’m going to be asking you for advice. I’m not going to be telling you I’m not slow. I’m going to be saying like, show me how to be fast. And that’s going to be great. But my hunch is that Sally’s not in that spot because otherwise the boss would have said, This takes 5 minutes, here’s how you do it. What’s taking the other 25? Right. And the fact that the boss hasn’t offered that makes me suspect that the boss is responsible for Sally, but has never actually done this work before. 


Melissa Nightingale: But the sort of advice still holds, right? So if Sally’s boss hasn’t done the role before, then then there’s some idea of how long things should take, maybe based on other people who have done the role within the organization. And so there like, even if your own boss can’t provide mentorship on here’s how I would approach this. Maybe you’ve got a peer within the organization. Maybe there’s someone you trust and go to lunch with on a regular basis, or at least are in sort of regular communication with who’s a who, sort of a peer or a colleague. And you can say like, I just like this thing just got thrown over the fence at me and I’m getting ready to start it. But I have this sense that like there’s probably some like something that I’m missing here. Can you talk me through it? There’s another piece that like we have as a theory in terms of Sally’s description, which is that like admin roles are famous for like being catch all of everything. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: And the colleagues who are like passing things off to admin support where it’s generalized admin support are often like feeling like the best way to get good support is to give you a ton of context. And so when Sally is talking about like I’m getting dragged into every meeting, our sense is like, maybe you’re getting dragged into every meeting because like literally people are like, I need to give you all of the information before you can get started, and that that’s slowing things down too. 


Anne Helen Petersen: So how do you address that? Like if that’s something that’s happening?


Melissa Nightingale: If you’ve got somebody who’s like in every meeting, it’s like in there, right. The boss is like, What are you doing with all your time? And if you’re like, well, like I’m I’m getting up to speed on the things that like the billing department needs for me. And in order to do that, they’re spending two hours with me, like teach me how to use their system. And then the next day I’m going in like, I’ve got some other system that I’m trying to learn like and if I don’t need to be doing that, let’s get me out of those meetings. 


Johnathan Nightingale: Yeah, it’s a there’s a pathology here too, where bosses who don’t know what they’re doing are often very bad at communicating what the real problem is. So one possibility is that Sally’s boss is not annoyed that everything is slow. Sally’s boss is annoyed that the most important things are slow and has done a piss poor job of articulating what those are. And so when, when when I see your daily record, I’m like another day where you didn’t get to the thing that actually matters because this stupid thing took 90 minutes. Like, explain to me why that took 90 minutes when actually what would be much more helpful is like these things have to be done by 10 a.m. every morning. After that. I care a lot less about where your day is, but any time one of those things slips, I’m going to come right back on to what made that thing slip. And ideally, the manager could engage with Sally and say like, here’s what this role is for. Here’s how we measure success, right? Everybody in the company loves you. It’s not actually about that. It’s that like when this stuff slips, it causes a huge downstream cost for us. And when this stuff slips, Bill gets annoyed and like, we’re just going to make different choices in terms of which thing is the most important. But if nobody’s had that conversation with Sally, then she’s just going to try to do everything faster and she’s going to make more mistakes and she’s going to be more stressed. And it’s it’s a spiral at that point. 


Anne Helen Petersen: Yeah. You know, the surveillance technology like this seems to me to be such like a. A poor tool for trying to exact results when there’s a problem, right? It’s like instead of having clear communication about priorities or instead of having excellent training or instead of thinking about priorities in terms of time spent in meetings, we just put out this surveillance stuff on the computer and then like, bitch about it. It’s just it’s so shitty. 


Melissa Nightingale: Yeah. And the surveillance stuff is easy to game. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: Right. Like, if you really have an employee who doesn’t give a shit, like they’re going to figure out how not to give a shit with surveillance stuff in play. Like, basically, like the the reason why people use it is they’re like, oh, I could like, train my managers. I could have like a management core that knows what their job is and knows how to do that job. But that’s that’s hard. That feels complicated. But like, spyware is like, okay, that’s sort of easier, but like, it doesn’t get you what you want. 


Johnathan Nightingale: Yeah, and there’s a weird set of incentives, too, because, like, if this thing’s going slow in Sally’s boss’s department, Sally’s boss always has the ability to blame Sally. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: Sort of stress position Sally for a while. And then replace Sally. And the next person maybe is better at reading their bosses mind. Maybe, like, just skips on some. Maybe does not make good relationships with people. And so, you know, she’s got cold or they’ve got a cold a relationship with other parts of the organization, but stuff goes faster. Okay. But like, at some point, there should have been accountability for Sally’s boss and that might not show up ever. And it might not show up until three people have been in Sally’s job and flamed out. 


Anne Helen Petersen: So if you recognize if listeners recognize some of their behaviors or some of this tendency that we’re seeing in Sally’s boss, what would your advice be to them? I think we’ve gotten a little bit of it, but I would love some explicit advice. 


Johnathan Nightingale: If you’re not in a billable context, there are places where time tracking makes sense if you’re a lawyer, if you’re in an agency or whatever. We’re not talking to you. If you’re not in a context where that time is billable and you feel a need to impose time tracking like this on a person because you think something about their work is not where you want it to be. I want you to stop for a second and do one more lap. And what is that? Is it speed? Is it quality is it prioritization? What is actually driving that sense that you have or that sense that you’re getting from your own VP or wherever it’s coming from, and then have a conversation with the grown up that you employ about that and see where that conversation takes you. 


Melissa Nightingale: I really like the like prompt teach me about, particularly when you’re working with folks who are either in the generalist phase of their career or early in their career, like teach me about is a really useful way to gauge understanding. Like do you actually understand what the task is in front of you? Like, talk me through what are the first three steps that you would like a new project, right? Like, what do you do first? Just talk me through it. Right. And for many bosses like that flip of of teaching to listening, right? Like, just puts us in a different orientation and we can spot really quickly if we’ve got a misalignment on how to like, how to approach something. It’s often very visible and it’s not combat. It’s not like you’re fucking up and you’re a terrible employee and like you should be fir— Like it’s not any of that. It’s just like I’m coming at it with curiosity, like, tell me what’s going on. Tell me how you would approach it. And you can often spot like there’s just something that we’re like or misaligned on here. 


Johnathan Nightingale: That’s really good. Yeah. That if Sally’s boss had said on the first day, like, why is this thing taking 90 minutes and then said, oh, we should get that roadblock out of your way. That’s not your fault. Like, let me let me go take care of that. I’m going to sign some forms and give you $250 signing authority so you don’t have to wait for my signature every time you’re making it. And then, like, we’d be in a magically different place, right? But it requires that boss to have curiosity instead of sort of accountability passing. 


Melissa Nightingale: The last thing I’ll say is like, Sally is in a hospital context, like you don’t want people who are okay with like, sloppiness. 


Anne Helen Petersen: Right. 


Melissa Nightingale: You know what I mean? Like, like it is entirely like another read, like a really generous read for Sally in terms of like just bringing it to the bosses. You’ve got somebody who doesn’t want to make mistakes. And like in a hospital, you should want to employ those people, right? There may be things that that help them go faster, but like at a starting point, like they’re assuming that that’s that sort of like laziness or inefficiency or like reading the worst read on it. But like, if you’re working in a job where like it is life or death, maybe it’s okay that you slow down a little bit. [music plays]


Anne Helen Petersen: Our next question is about time management or work life balance, depending on who you ask. This is from Liz and our colleague Ashley is going to read it for us. 


Liz: Is it fair for me to resent my leadership for telling me not to work weekends or nights? I’m in legal and both a lawyer and a manager on the team. So I have people work and knowledge work. We’ve had layoffs and we’re a lean corporate team. Management takes pride in the leanness. I feel like them telling me not to work these times without coming prepared with solutions is really insensitive. I have expectations and deliverables when else am I supposed to get this done. Yes, I can cut down meetings, but one. Sometimes things need to be verbal for confidentiality or privilege purposes, and two, volume is volume. 


Anne Helen Petersen: All right. So I feel like this is an organization that is trying to solve a burnout problem without actually changing the way that their business works. Right. So they’re just saying, like, you don’t need to work on nights or weekends, right? Like they’re trying to do this sort of like lip service towards like, we don’t want you working overtime, but the work demands some overtime. Right. Is that what you see? 


Johnathan Nightingale: Yeah. A lot of bosses have ego riding on. I mean, we don’t know this person’s boss, but, like, a lot of bosses have ego riding on being the kind of boss who says you don’t need to work evenings and weekends is very comforting to me to be like, you know, I’m in it and I’m in a field like law where everybody’s burning everybody out all the time, but not here. 


Anne Helen Petersen: Right. 


Johnathan Nightingale: Right. Like I tell all my people, I tell them every Friday, you better get out of here at 5:00. And like, okay, but you people aren’t idiots. And they figured out what constitutes success. And this person’s gotten promoted into management, right? They figured out what constitutes success in your firm. And if it were checking out at 5:00 and not checking back in until Monday at nine, they know it already and we wouldn’t be in this position. 


Melissa Nightingale: There is a truth tucked in here. There’s like a tiny niceness tucked in here, right between the like. I’m very frustrated, like the the organization that says, like, we don’t want to burn people out and then has leaders regularly burning the midnight oil where their team see it. Like this person says, I’m a manager. And so if we have a situation where, like you’re reporting into somebody who’s sending you emails at 11:00 at night and 3:00 in the morning and then again at six, like you, anybody on that team reporting to that person not only sees it but will model that behavior. And so like as the starting point, like it does to some degree make sense for this person to get that feedback if they’re in an organization that doesn’t want 3 a.m. emails flying around, like once one person’s doing that, everybody is like particularly a person in power, then everybody else is doing it. There’s just like stuff that’s falling down in terms of the implementation. 


Anne Helen Petersen: Yeah, that’s the thing, is that I think like if this question were slightly different and with someone like new to her job and the organization was really trying to keep boundaries and like she was slightly disciplined or like chided for sending emails because she doesn’t know any other way to work. But here it seems like that is the only way to do the work, at least according to this description. And and especially since it’s in law and you have like the you know, the volume is volume part of the question where it’s like we are dealing with billables and they have it doesn’t seem like this is a legal organization that has adopted a new and an innovative way of like profit model. You know, like they’re still wedded to billable hours. So can Liz just, like, ignore her bosses and do what needs to be done? What’s the what’s the more constructive move here? 


Johnathan Nightingale: A thing that I really like in conversations like this is even overs. 


Anne Helen Petersen: Hmm. 


Johnathan Nightingale: So somebody says, like, you know, you don’t need to work weekends. You can you can go home at five every day. That’s the kind of culture we have. And just to come back and say, I can go at five every day, even over missing my billable targets. I can go home like I can I can clock out all weekend, even over people on my team waiting for my review on stuff that’s got to go to a client. Like, is that what we’re saying? And not—


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: Not from a combat place but from a let’s test trade offs because when you say it in the abstract, nobody wants to burn out their people. Nobody would self-disclose, other than demons, nobody would describe as like, I want to harm the knowledge workers that I pay a lot of money to do creative work—


Anne Helen Petersen: I don’t know finance makers they are like—


Johnathan Nightingale: Yeah. Sometimes it’s like it’s a crucible. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: But like, but like normal managers, even incompetent ones, wouldn’t say that. What they’re not doing is confronting the trade off and saying, well, if I’m saying that, am I willing to accept the other thing and it’s not okay, then at least we’ve drawn that into conversation now, particularly as a member of the management team, at least we’ve drawn into conversation like how do we want to approach that trade off? 


Melissa Nightingale: The other thing we’d offer to Liz is that like billability targets go down as management responsibilities go up in professional services organizations as like an industry standard. They don’t go down by very much, but they do go down slightly. And if nobody’s adjusted the billability target for Liz, even though we’ve got management responsibilities that just showed up, then like we are out of step with like really established norms across professional service organizations. Sometimes it’s like in this moment, like I feel very frustrated and like I feel like I’m in an impossible, no win situation. It’s sometimes helpful to look around and just say, like in our industry, what happens? Like other people who are sort of in my position, like what are their availability targets look like? And not because I necessarily need to go work at that other organization just because I’m trying to get a read on is this normal? 


Anne Helen Petersen: That is such a good point. And I do think that all of this is pointing to the fact that, like there needs to be another conversation. She says, like, is it wrong for me to resent them? Like, I mean, resentment is it just breeds and explodes and is not going to lead anywhere good. So I think instead of like an actual conversation, bringing up some of these points would be worthwhile. But then if you are a boss [laughs] who maybe sees some of this in your own communication, in your own organization, what’s the advice you’d give to the bosses here? 


Melissa Nightingale: Just name three things that could fall on the floor. 


Anne Helen Petersen: Mm. 


Melissa Nightingale: Like any time you got somebody who’s overwhelmed, like, and you feel like they oughtn’t be right, okay, like, you’re overwhelmed, but, like, I feel like your. Your workload doesn’t mandate that, or we don’t mandate that as an employer, then, okay, like, what are we what are we putting down? And if you can’t name anything, then like, okay, well, we’re back to the same situation we were in before, which is—


Anne Helen Petersen: This is who we are. Right, yeah.


Johnathan Nightingale: When Liz says the management team is very proud of being lean. 


Melissa Nightingale: Mm. 


Johnathan Nightingale: I think if I were part of that management team, I would, I would sit for a little bit with. What do we mean by that? I think what we’re getting at is we’re not going to spend a bunch on management that’s administrative overhead. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: And we’re lean. We. Lean is sort of the opposite of overhead, right? And so, you know, for Liz to say I’m in management, but I still have, you know, my billi— Billability she didn’t say it, but like, I still have to do that. Like what is lean doing for us and what’s the what’s the real alternative, not the caricature of like a, an organization that’s unhealthy with with way too much overhead, but like, what trade are we making? Can we say out loud when we say lean, we mean are people are going to be under managed because people in management roles do not have the time allotted to do that job well? And like, are we still are we still proud of it when we say that? And if not, how do we articulate that a little more crisply? Because people are just sort of hoping that we’ll intuit that lean is a good thing, overhead is a bad thing, and all overhead is implicitly evil. When what Liz is talking about is the tradeoff between doing individual work and the overhead of supporting the other brilliant people in her organization. 


Anne Helen Petersen: Yeah, I just see like a lean organization and an anti burnout organization is fundamentally at odds, right? Like being proud of being lean is like we have no administrators staff. [laughs] Like you have to do seven jobs in one. Like that is a lean organization instead of we’re trying to make a sustainable organization where people have a sustainable workload is doing something very different. 


Johnathan Nightingale: Healthy would be a great word. 


Anne Helen Petersen: Healthy would be a great word. Yeah. Okay. So our next two questions are about communication breakdowns. And we’re first going to hear from Tamara. And our colleague Amelia is going to read her question. 


Tamara: What do I do about a manager whose Achilles heel is hearing himself talk? He’s a genuinely decent man. He implements strict work life boundaries and expects the same of people who report to him. He cares. In my nonprofit job, which is rare of men and nonprofit sometimes, but he dominates meetings with discursive, winding preambles that don’t go anywhere. So half hour meetings have maybe 5 minutes of substantive work at the end. Politely, how do I tell a manager to shut up and listen to the other people around him?


Melissa Nightingale: I love this question so much. [laughs] Politely. 


Anne Helen Petersen: Politely. So we really we all know this guy. And there’s a fear, too, of upsetting someone with power over you. So what would you tell Tamara to do here? 


Melissa Nightingale: One of the things that is really clear here is that like this, this boss seems sort of unaware that they’re having this impact. And so, like, how do we get a little bit closer to that awareness without saying, like, I need you to stop talking so much in meetings? Because like, that’s a hard thing to say to somebody who decides whether you get promoted or whether you get a bonus like that’s that like from a power perspective. But it is totally fair game to say to this boss, like, I am finding that I get the most value out of our meeting in the last 5 minutes, that that’s where it all comes together. And so sometimes I wonder whether we can like experiment with flipping the format where we make that the first 5 minutes of the meeting and then we can go a little bit deeper on it. But I find like I’m really having my aha moment and like the first 20 minutes, like I’m not there and I don’t know whether anybody else is having that too. But like it just you can personalize it a little bit in terms of like it does sound like he gets there eventually. [laughs]


Anne Helen Petersen: Mm hmm. 


Melissa Nightingale: It’s just a winding path to get there. 


Johnathan Nightingale: Yeah, there’s this sort of truism that gets trotted out all the time, which is that you can teach people lots of things, but you can’t teach them self-awareness. Right? And it’s false. [laughter] There’s good research on it. You can totally improve self awareness. 


Melissa Nightingale: Yeah. 


Johnathan Nightingale: And the way you do this with reflection exercises that like the thing to do is to cause the person to reflect so that they can start to pay attention to what is it about that meeting? And so, like Melissa, I love the idea of just like, can we play with this format? We’ve been having this meeting the same way for a long time and like the context setting is an important part of it, but we get to substantive work as well, and I just feel like it’s time to shake it up. And often that can lead to a conversation about like, well, what would we shake up and how should we balance the time and stuff like that? And you can let the person ease into it. I want to say though, yeah, it is scary to give feedback to someone with power over you for sure. And maybe I’m sort of stating a theoretical, but like it should be possible. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: To give feedback to a person that says one of the things that I struggle with in this meeting is that nobody wants to talk while you’re talking because it’s your meeting, it’s your team. But like that, that’s taking a lot of the air out of the room. And like you really, you really don’t want to have to insulate an adult with power in the organization that much from their own impacts. But I understand that tomorrow feels like maybe that has to happen here. 


Melissa Nightingale: One of the things that happens for a lot of bosses is that they get used to being in rooms that their people aren’t in. And so in terms of like just an empathy moment for this, this long winded boss, like they get used to being in these meetings and being like, okay, well, how do I look? I have this amazing team. I need to get them caught up on the meeting that they weren’t in. So I’ll just play back like, you know, I was in a half hour meeting, so I’ll just like basically be a tape recorder and press play and do the entire half hour meeting that I was just in that they missed so that they’re caught up on the context and like, it comes from a lovely place, but it is like most of the work that you you need to do is to just do some of that like synthesis before you go into that conversation. And so anyway, I had a sort of like question in my head for this boss is like, what’s the meeting before this one. 


Anne Helen Petersen: Right. [laughs]


Melissa Nightingale: Because if he’s coming straight from like, I just had this and they told me to tell my team this thing, then like, I understand exactly what’s happening. That man just needs like 10 minutes to go walk around the block before going into the next conversation. 


Anne Helen Petersen: And, you know, this is a great way, I think, to kind of address the question of like, if you recognize yourself in this and this question is to think a little bit empathetically. And my first thought was like, maybe this boss is just like really nervous and doesn’t know how to fill the time and like he’s the only guy in a group of women and feels kind of awkward sometimes. And so it might be self-awareness, but it might also just be awkwardness. And maybe the suggestion from one of the people that he manages would be very welcome. Maybe they would be like, Thank God. [laughs] Another way to start this meeting. 


Johnathan Nightingale: I will take a step back. 


Anne Helen Petersen: That maybe and that I think also maybe might make the employee feel like, well, what if this person wants an idea? Like maybe it could be really helpful for all of us, right? 


Melissa Nightingale: We hear from bosses all the time that it’s so hard to get feedback from their teams. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: They really like meeting bosses are like, it’s so hard. Like my team never tells me what to think. 


Johnathan Nightingale: You just sit there quietly. 


Melissa Nightingale: Just sit there and you’re like, well, like it’s it’s hard. Like it is a it’s a big hill to climb before they can say like, Hey, boss, that meeting is not going well. 


Johnathan Nightingale: And to your point, like, I have been a consensus driven leader who really felt like so much esteem for the people on my team that I really didn’t want to autocratically sort of say, Here’s what we’re doing. You’re on this piece, you’re on this piece that felt really gross to me. And so I have definitely been guilty of being like context, context, context, context. Here’s all the framing. Do we all unimpeachable agree that this is the only choice we can make? Please, somebody tell me if you disagree, like in an attempt to not insult them, to not seem like I was an egotistical leader who was just coming in and calling shots and didn’t care what anybody thought and like way, way off. Like I was wrong. I was framing 90% more than my team needed in order to be confident about the decision. Now, you’re exactly right. That was my own insecurity that was driving that. And still I ought to have I don’t know if I would have like to Tamara’s point. I don’t know if I would have, but I ought to have been receptive if someone said, you’re over framing and like you need to let the rest of us in because there’s we got it. 


Anne Helen Petersen: All right. So our advice is, if you are the employee in the situation, reframe, offer ways to reframe. And if you’re a boss in this situation, be receptive to others offering ways to reframe. [music plays] So our next question is also about communication, and it’s from Astrid and our executive producer Kendra is going to read it. 


Astrid: I’m a millennial and I supervise a Gen Xer who’s also a manager. About once or twice a week, he texts or emails on an unrelated thread to see if we could talk on the phone for, quote, “Just five minutes or less.” It always takes longer plus for like chit chat and it’s never urgent. I hate playing phone tag and I have a busy schedule, even if it only takes him a minute to share something with me. It takes me time to process and generate a response. I often need to write it down anyway, so he might as well send it over with a date stamp. I respond promptly online when I’m in between meetings and we also have a weekly one on one where we can discuss things. During his onboarding, I explained that my preferred method of contact was email or online chat, but he was welcome to phone or text me if it was something urgent. In response to those requests, I’ve started waiting to discuss those things in our one on one, or ask if he can send me an email if it’s a quick thing. I treat my boss’s time as precious and would only ask for a phone call outside of our normal meeting schedule if it was something that couldn’t wait. What’s going on? Should I address it more directly? Am I being stubborn or rude because I don’t like phone calls? 


Anne Helen Petersen: All right, so on a stereotypical level. This is a classic generational divide of like a lot of Gen Xers and boomers who think that millennials just need to get over and get on the phone. Millennials stereotypically like, avoid the phone that used to be me. Now I love the phone I like. I have totally come around on the phone, which is actually a reversion to my 13 year old love of the phone, right? Like a lot of older millennials have a very close relationship with talking on the phone at some point in their lives. But to me, this seems like a kind of classic, like miscommunication about here’s how I communicate best. How can you deal with that? 


Melissa Nightingale: We think this question isn’t about this question at all. [laughter]


Anne Helen Petersen: Okay, tell me more. 


Melissa Nightingale: We think this guy is lonely. 


Johnathan Nightingale: This is an extrovert working from home. 


Melissa Nightingale: He sounds lonely. 


Johnathan Nightingale: I guarantee they’re not in an office. 


Melissa Nightingale: He doesn’t have anybody to talk to. And he’s like, I miss colleagues. And like, I, I need somebody to talk to. And like, my boss is like the person that I’m in contact with most within the organization. But like, it doesn’t say that this is a remote context, but like, if you gave me $10, I would put $10 down that this is the person who’s working remote without any colleagues nearby. 


Anne Helen Petersen: Right. Because otherwise they would just walk down. This is a guy who in office, he’s a walker. Right. [laughter] Like, he’s like, hey, I’m just stopping by. What’s going on? I got a quick question for you. Right. 


Johnathan Nightingale: I put some cookies in the kitchen. 


Anne Helen Petersen: Depending on your work style, that can be annoying. But it also maybe, like, feels slightly less disruptive because it doesn’t require you to pick up the phone or whatever. So. Okay yeah Jonathan, what were you going to say here? 


Johnathan Nightingale: Yeah, well, you can you can feel it in Astrid’s question. You can like feel the whatever context she had for whatever work she was doing, like crumbling, like, like you’re trying to remember a dream. Like, just every time the phone call comes in, it’s like, well, that goes half an hour of my life for your five minute nothing update, right? And like, on the one hand, it’s totally fair to say if this can wait till our one on one, let’s talk about it in our one on one. That’s actually a really good time management strategy that a bunch of managers fail at is that they like, you know, if you open business as a free answer store where people can just message you and get a free answer, that’s likely to be right most of the time you will be very popular. Like that is a very popular service to offer. And so it’s good first line defense to say we’re talking tomorrow at 11 a.m. Can it wait till then? If it can, let’s talk about it there. But the other thing is, like when Astrid talks about it, she says, you know, during onboarding, I was really clear about my communication preferences and she doesn’t say so we don’t know if he got a chance to be clear about his. 


Anne Helen Petersen: Mm. 


Johnathan Nightingale: Right. And in the next sentence of her question, she says, you know, I would never do this to my boss with this sort of implication that ergo no one ought to do that to me. But like, that’s, that’s a choice around power and communication styles and stuff that, that we should not expect anybody to just magically know. 


Melissa Nightingale: I will also just offer the layer that like I am somebody for whom, like when I am in flow, I like I just like I love to be in flow. And the idea that someone would call me and sort of break that flow and like have the middle of it just like start to fall apart feels really intense, but like, this is somebody like it. From the way that the question is worded, it doesn’t sound like it matters whether the human to human connection is with Astrid or with someone else within the organization. 


Anne Helen Petersen: Yeah, yeah. 


Melissa Nightingale: And so, like, bosses are often like, especially bosses who are like deep flow focus bosses often like undervalue team, team coffee or a team stand up or like an opportunity once a week for everybody to like, even if we’re remote, to like, eat lunch together or eat whatever meal it is, you know, based on whatever time zone you’re in like but that the this there’s like a very deep connection longing here. And like the the good news answer for Astrid is that you don’t have to be the like you don’t have to be the sole guardian of connection for this person at work. You are a primary guardian of it. But like. You’re not the only one. And so, like, you do need to have your one on ones. But if this person, like, wants to have a regular coffee date with someone or you want to organize for your team, a regular opportunity for them all to have coffee even without you so that you can stay in flow. Like that’s okay. That that tends to be all right. 


Anne Helen Petersen: Yeah. So what I’m hearing is. There are some things that, like you can deflect to the weekly meetings as you do have that time for connection, and then you somehow need to funnel this energy somewhere else. 


Melissa Nightingale: And like he can organize it. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: When you find a person on your team who is like, really oriented around like connection, a team building, you think, like if that’s not you like, it actually doesn’t need to be the boss 100% of the time. Like you can have a person on the team who who sort of identifies that way. 


Johnathan Nightingale: Peter we’re putting you in charge. Like once a week. We need the whole team to get together. And you’re just. You’re the guy for that Pete like you really are. And so like—


Melissa Nightingale: Yeah. 


Johnathan Nightingale: Let us know. 


Anne Helen Petersen: This is a job for an extrovert. 


Johnathan Nightingale: And. And Astrid will know when it is. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: She won’t have something else going on because the team call is when it is right. Like, you know, when I used to run engineering teams in a start up, we had daily stand up. It’s a really sort of standard thing to do for engineering teams. And my hunch is that if Peter or whatever this person’s name is, had, one of those calls would go down because you’d already be getting fed in that way right now, that is not a reason to totally change how your team works because you’ve got somebody working preference that’s different. But like. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: Spotting the opportunity there and being like, there’s a sink up call that I hate that somebody on my team has to go to and I’ve been shielding everybody else from it. But like Pete, that’s you take notes send it around to the team afterwards. Like if you’ve got someone who wants to be connecting, lean on that instead of sort of building up shields because you don’t want to connect in that way. 


Anne Helen Petersen: So what do you think if you’re the if you recognize yourself in this person who’s like, hey, let’s get on the phone or like, can we have a little Zoom chat? Right? And I think I know in my scenario I’m constantly sometimes I’m like, let’s just get on the phone and let me talk to you about it. But if someone’s like, Can we hop on a 15 minute zoom? I say, Send me four questions like, I don’t want to deal with this, right? So if you see yourself as the person who is oftentimes reaching out for that sort of connection, what sort of advice do you have for that person?


Melissa Nightingale: If there’s a non hateful way to do it? Right? Like if if Astrid’s like, I really just don’t like, I’m in flow, I don’t like it. Whatever. Okay. But like, if there is a moment where, like, it would be welcome, right? Sometimes some people are like, I’m I’ve got like 5 minutes in the car after I dropped my kid at school before I’m on my way back to my home office or whatever it is, right? Like if there’s a time there where it’s like, okay, I understand that this is a thing that Pete needs, but like, it’s not my favorite thing. But I can, I can hand over 5 minutes of solitude every morning to make sure that, like, that person is plugged in and has some connection to the organization. Just think like it doesn’t sound like Astrid wants that. [laughter]


Anne Helen Petersen: No, no.


Johnathan Nightingale: And if you’re Pete—


Anne Helen Petersen: About. So what about Pete, though? Like, what if you’re a Pete? What if you’re what if you’re a guy who, like, you just really feel like you need that and then you have all these Astrid’s in your life? [laughter] I want to process this in writing and you’re like, No, let’s talk on the phone. Like, what do you what’s our Pete advice? 


Johnathan Nightingale: I mean, one that not everybody is you, right? 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: But you can you can say like a thing that I’ve learned about myself is. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: I do my best work. If I have these touch points, you can say that in a one on one. You can say at an onboarding. I think what I’ve learned about myself is, but you need to have some empathy for the fact that there are Astrid’s out there in the world who find like that thing that you get energy from is energy draining for them. And that’s weirdly counterintuitive, but it’s true. And like and so you’re going to need some creativity about like what? What would fill your bucket in that way. And it doesn’t have to be always from the same source. And can you find people for whom that’s that’s a really natural fit and you two can go for coffee every morning. That’s great. But the awareness is one piece, the labeling. It’s not, can I talk to you for 5 minutes? It’s I am somebody who enjoys that as part of work. Right? And then. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: Try to get more intentional about how do I design that and how am I sensitive to the fact that not everybody works that way? 


Melissa Nightingale: We’ve also met. I mean, we work with a lot of bosses, right? We’ve met bosses over the last couple of years who’ve said, like, I learn like Jonathan’s point, like a thing I’ve learned about myself is that like I do not do well in a remote context and like that, that can be okay, right? Like I am a person who thrives when I can go in to the kitchen and there are donuts and like I can stand for 15 minutes and shoot the shit and talk about TV shows. Like there’s just. 


Anne Helen Petersen: Yep. 


Melissa Nightingale: There’s nothing wrong with that. But I think the the thing where you pretend that you can work from your basement by yourself with a weekly one on one is your only work touchpoint. And it’s not working like it’s not working to pretend that it is. 


Anne Helen Petersen: Totally. So. Our last question, I think is like a great capstone question because it’s about who is responsible for making a boss better. This is from Anya and our colleague Emma is going to read it. 


Emma: I’m consistently the top performer on my team. This isn’t me bragging. It’s something I’ve been told repeatedly in performance reviews and by work leadership. My boss is a first time manager with less professional experience than me, and I struggle to get any kind of meaningful feedback or support from her. She’s there, but she’s not really providing anything to me as a manager. I recently brought this up to my skip level, who seemed receptive to my feedback, but also told my immediate manager how I feel about her job performance. Now my manager wants me to coach her how to be a better manager to me, it’s been suggested to me that if I’m not open to teaching my manager how to do her job, I should look to transfer to a different team. I like everything about my role except my boss. But I feel like transferring is the only option at this point. Right? How on earth do I handle this? 


Anne Helen Petersen: So to me, this seems like Anya is maybe misinterpreting how this is going down. Does that. Do you see that at all? Like, I can absolutely see how she would read this as my skip level went to my boss. And then now my boss says, You need to teach me how to manage. Like this is your responsibility. When maybe the reality is that, like this manager is now aware that she has not been doing a great job of managing and is maybe trying to say what kind of management would work best for you. Right, is trying to be really like trying to be a good manager by asking how to manage her. What do you see? 


Johnathan Nightingale: Yeah, there’s a couple of things going on at once here. So one, I agree. I mean, none of us is ever a perfectly reliable narrator, so I’m not putting this just on Anya, but, like. 


Anne Helen Petersen: No. 


Johnathan Nightingale: This idea of I’m being told that I have to teach my manager how to do her job. Not really. You went to your skip level and said, My manager failing me and your skip level, told your manager, which is not is a party foul. That’s not a perfect way to do that. But like now you both know. Okay, so that conversation has happened. And the question is, can you work together or not? It’s not teach her how to be a manager. It’s what do you need? Have you articulated that clearly? Does she understand that and is she performing her job in terms of bringing you those supports? Like that’s that’s different than teach my manager how to be a manager? 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: The other thing that I would say is Anya, like welcome to the big leagues. If you’re a top performer on your team, congratulations. That’s excellent. But like, there’s only two ways that goes. Either you will constantly report to people who know more than you do. That’s neat, but you really top out at some point you’re going to plateau. Because if you’re if you’re a world class, there’s a limited number of people now, regardless of what your discipline is. Right? Or you’re going to have to figure out how to grow and thrive even when your manager doesn’t know as much as you do about the thing that you’re a top performer at. 


Anne Helen Petersen: Mm. 


Johnathan Nightingale: That is most people, when they get to senior roles, most people who report to a CEO know more about that thing than the CEO knows about their thing. And that’s okay. It just means that you need a different orientation towards how growth happens and your manager can still be a partner in that. 


Melissa Nightingale: We get bosses sometimes in program who ask like quietly, I found out how much somebody on my team makes and it’s more than me. Is that okay? Right? [both speaking] Should I be upset? How should I feel about that? I think I’m outraged. Am I outraged? [laughter] Like how like how outraged should I be? Like. And what we say is like, is some variation of what Jonathan just said, which is like, welcome like that. That not only happens, it’s really normal in the course of working, particularly in management, that you will manage people who are who like you’re like, I am certain that you are cleverer than I am. I am certain that you have more like you have earned more sort of post-graduate degrees that I have. I am certain that like you are 20 years older, like there’s there’s just a lot of those sort of like situations where like you’re, you’re sort of first kick at it is should I be outraged? Should I be outraged that I’m working for somebody with less professional experience than I have? Should I be outraged that, like, I’m working for somebody where it’s their first time managing, but I’ve managed before? Like there’s these things happen across the workforce. And to Jonathan’s point, like, if your thing is that you’re going to be individually excellent in your craft and that’s your path, then like it’s going to happen again. 


Anne Helen Petersen: Yeah. Do you think that there’s a little bit of a sense that this like she is someone who is really good at a lot of things? And seeing like incompetency in some capacity in  someone who is above her in an organizational chart is like, Well, why can’t she also do this thing like this? There is an expectation of excellence instead of, well, sometimes the person who manages me might not be good at every single thing. If I was in that position, maybe I wouldn’t be good at all of those things either. And maybe someone would need to teach me how to be good at those things. 


Johnathan Nightingale: And like, you know, if we speak Anya’s manager for a second, like Anya does need mentorship does need. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: People like helping her break through to the next level, make new connections, build a sort of executive, whatever it is, like a more senior and more expert and more integrated version of what she can bring to the organization. It doesn’t have to be you, but that doesn’t mean you’re off the hook. Like then. Then you’ve got to be a partner in finding that, like, where is your network within the organization or outside of it? How are you looking at like the things that the organization needs from Anya that she still needs to build his skills and going and doing that work together to say like, let’s be partners in finding you the right ways to excel at that, but like not from a place of and I’m going to learn right alongside you that so that one day I’m smart. 


Anne Helen Petersen: Right. 


Johnathan Nightingale: Like that’s not actually your job. The reason it’s okay to have people on your team will get paid more than you is that manager’s a different job than engineer or manager is a different job than marketer or manager. Like, that’s okay. You’re paid to do your job. Anya’s paid to do her job. It is fair for her to hold you accountable for doing your job well. It is not fair to hold you accountable for doing Anya’s job. That’s not actually what we’re paying you for. 


Melissa Nightingale: And and I think you’ve got it exactly right. Like everything about this question, like the the frustration, like you can hear the frustration in it, but the structural but sound like a supportive organization. They did not say to Anya, like, get your shit together or you’re fired. They said, like, let’s see if we can make it work. And if we can’t make it work, we will find another place for you to thrive within this organization is not every organization, right? Like it is not every every boss’s boss or every boss who’s, like, trying to figure out a solution to it. It does feel like the facts on the ground and what was asked in the question, it does feel like she’s got folks who are willing to work with her on it. 


Johnathan Nightingale: And only she knows if it’s cooked already. Like maybe it’s done. Maybe like the relationships too damaged and transferring within the org is is the only way that orgs are going to save Anya, right? Maybe. 


Anne Helen Petersen: Yeah. 


Johnathan Nightingale: But but when you transfer, there’s no guarantee your next boss is going to be smarter at your job than you are, even. [laughter]


Anne Helen Petersen: That’s always the thing. So are you ready to make this a collaborative relationship that she can be better at managing you, that you can have some mentorship, that you can figure out horizontal mentorship, too, and, you know, like those sorts of relationships as well that will make you better at your job. It’s all there. The point that you make that this organization is on board with trying to make this better. That is the good news. So we can go forward from there. All right. So I don’t think we stumped you. I think we had—


Melissa Nightingale: I brought the big guns like I brought back up for a reason. [laughter]


Anne Helen Petersen: But, you know, this is an invitation for all listeners. To try and stump us again. We’ll have you back on so that we can try to grapple this. We still have all that backlog of like 100 more questions about management, because as we talk about here, like it is so foundational, like everything is in some ways a management question or sometimes it’s a loneliness question, or sometimes it’s an awkwardness question. [laughter] Sometimes it’s a power differential question. But management is kind of the hub of the wheel. So thank you so much for coming on the show today. If people want to find more from you, where can they find you on the Internet? 


Johnathan Nightingale: Best way to find us is our newsletter. It’s a It’s it’s both of us. It comes out every couple of weeks. We’d love to see you there. 


Anne Helen Petersen: It is, the world’s best newsletter. That isn’t my newsletter. 


Johnathan Nightingale: Right, right. World’s Second Best Newsletter wasn’t available as a domain. [laughter]


Anne Helen Petersen: Melissa, what were you going to say? 


Melissa Nightingale: I was just going to thank you. It’s like it’s always fun and I love that the questions are real questions, right? Like, I mean, I think there’s this idea that, like, it’s all easy, right? You just do these three things and it’s simple. And like, the reality is like, is humans, right? It’s humans that work, like it’s humans and stuff we care about. Like, it’s it’s not simple. 


Johnathan Nightingale: Yeah. Thank you to you, but also thank you to the question answers. It’s it’s uncomfortable like you can want an answer and it’s still uncomfortable to have your you’re like deep and rich and nuanced like picked apart well on the basis of a few sentences of question. 


Anne Helen Petersen: Yeah. So I hope all but as always, I hope all of the people who wrote in with questions that they feel like we have seen them like that their questions are real and valuable and and this is hard. And also that there’s some kernel of advice in here that you can take forward. So. Thank you again. 


Melissa Nightingale: Thank you. 


Johnathan Nightingale: Thank you. [music plays]


Anne Helen Petersen: Thanks for listening to Work Appropriate. If you need advice about a sticky situation at work, we’re here for you. Submit your questions at or send a voice memo with your question to Work Appropriate at We love building episodes around your questions and you can stay as anonymous as you like. Don’t forget to follow us @CrookedMedia on Instagram and Twitter for more original content hosts takeovers and other community events. You can also follow me on Instagram @AnneHelenPetersen or you can sign up for my newsletter Culture Study And if you like the show, leave us a review on your podcast app of choice it really helps. Work Appropriate is a Crooked Media production. I’m Anne Helen Petersen, your host. Our executive producer is Kendra James. Melody Rowell is our producer and editor. Alison Falzetta is our development producer. Music is composed by Chanell Crichlow. Additional production support from Ari Schwartz and a special thanks to Katie Long and Sarah Geismer. [music plays]