How To Be A Better Boss with Melissa Nightingale | Crooked Media
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March 01, 2023
Work Appropriate
How To Be A Better Boss with Melissa Nightingale

In This Episode

In our episode “May I Speak to the Manager?” host Anne Helen Petersen talked with Melissa Nightingale about why and how formal management training has really gone by the wayside, resulting in a plethora of managers without the skills they need to thrive. In today’s episode, Melissa returns to answer questions from listeners about really specific problems they’re having as managers. Whether it’s figuring out your management style, keeping your cool when your trainee just isn’t getting it, or designing an effective performance review system– Melissa and Anne have advice for bosses in any industry.

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Anne Helen Petersen: Hi, everyone. This is Work Appropriate. And I’m your host, Anne Helen Petersen. [music plays] People who make podcasts listen to podcasts. They have formats that they love and that they try and emulate. And one thing I love in a chat podcast, which is basically what Work Appropriate is, only we’re chatting about work questions is recurring guest stars, familiar voices that become a fixture in, in this case the Work Appropriate extended universe. But this is also someone that you know has given good advice in the past and you’re eager to hear from them in the future. We’re going to have a few recurring guest stars here at Work Appropriate. And if there’s a past host that you’d really like to come around again, just drop us an email. But today, I’m thrilled to welcome back the person who gives some of the best no bullshit management advice in the business, the hero of one of our most popular episodes. 


Melissa Nightingale: My name is Melissa Nightingale. I am a founder and partner at Raw Signal Group, and Raw Signal Group builds better bosses. We’ve worked with thousands of leaders and hundreds of organizations around the world to help level up their leaders. 


Anne Helen Petersen: One of the things we talked about last time is how formal management training has really gone by the wayside. Like there is just very little understanding of how to train people to be better bosses. And so it makes sense that a lot of the follow up questions that we received were about, okay, you talked a lot about how to be a better manager, but how do I be a better manager? [laughs] So we’ll get to these questions in just a minute. But Melissa, in your job, what’s the number one problem that you hear from people who want to be better bosses? 


Melissa Nightingale: The number one thing we hear from bosses is I don’t know what I don’t know. I know that I want to be better at this. And I know that I have like maybe two or three tools that sort of kind of work. But I am terrified of putting those tools down and trying something different. Cause I actually don’t even have any idea what thing I would try and so a lot of the problems that we see in terms of sort of how managers show up in the role is because like there’s one the like I am aware that I am not doing the thing as well as it could be done, but the fear of these are the tools I’ve got until you give me something else I really like. I don’t want to put them down even if they’re not working in service of me or even if they’re not working in service of my team. 


Anne Helen Petersen: Yeah. You know, it actually kind of reminds me of parenting that when people realize they’re like, oh, I, like this isn’t working. But also, if I stop doing this and I don’t know what the better solution is, then everything’s just going to be chaos. 


Melissa Nightingale: Yes, so much of the work that we do is just sort of resolving that fear and saying, okay, like let’s let’s put some other tools in the toolkit first and then go from there. But so many I think folks start with the like, I already know that I don’t know entirely what I’m doing and I would like to feel more confident. But that confidence comes from, you know, from knowing what I’m doing. 


Anne Helen Petersen: So this is a difficult question, but can anyone be a better boss? [laughs]


Melissa Nightingale: Fundamentally, like, we feel like the worst thing that we do for people is we say, like, you either have it or you don’t. You’re good at management or you’re not. You’re a natural born leader or you’re not. And that that sort of context in terms of like how we come up and what messages we receive about whether we’re likely to be good at this or likely to be bad at this is entirely unhelpful. And so fundamentally, like most folks are capable of learning new skills. And once you break management down from the like big blob concept of like, I want to be better at managing too. I want to be better at giving feedback. I want to be better at having like challenging conversations. I want to be better at setting deadlines. I want to be better like actually ensuring that we’re going to hit those deadline. Like once you break it down into pieces, it’s much easier to get better at it. But when it’s that giant blob, it’s really hard to improve because it’s insurmountable. When it’s when it’s 37 skills all rolled into one. 


Anne Helen Petersen: Right? And I think sometimes, too, management is perceived as like the most visible component of management, which is like, I’m good at starting a meeting [laughter] right? Like that. That somehow is like if you have aptitude for like starting a meeting or starting a Zoom call, then somehow you’re perceived as a good manager. Like that is the most like discernible management skill when, as you said, it’s actually 37 other skills that people might have incredible aptitude at, but that is not immediately legible as a as a management skill. 


Melissa Nightingale: The one we get all the time is vacation requests. I’m like, I don’t know bosses who spend their entire day doing vacation requests, but it’s the one that comes up really frequently for folks like, I don’t know if I can be great at management. I’m just like, I don’t know. I don’t want to like sit and review vacation requests all day. I’m like, who? Like what boss does, the, no boss has that as their actual job. But I think there’s this perceived notion of like, I am so far from knowing what the day to day involves that I just imagine it somebody sitting there with a rubber stamp being like, yes, you can go on vacation or no, you can’t. [laughter]


Anne Helen Petersen: It’s like it makes me think of, I don’t know, like a movie that has like a depiction of clerks in a workplace where they have a stamp that’s, like, approved, approved, like, that’s somehow your fundamental management scale. 


Melissa Nightingale: Yeah. And like, if you talk to bosses, like, day in, day out, they’re like, I spend maybe like a half a percent of my year reviewing vacation. Like, it’s just it’s just not that time consuming. 


Anne Helen Petersen: Right, right. So the thing that I love about the questions today is that none of them are industry specific. So wherever you find yourself being a boss, there is going to be something here in these questions that you can use. First up, we’re going to hear a question from Holly. 


Holly: I just graduated my Ph.D. and landed my dream job as a tenure track professor. Now I’m finding myself learning a new set of skills, including how to manage master’s and Ph.D. students. I know how I prefer to be managed and advised, but I also know that that style doesn’t work for everyone. How do I transition from being the one doing the work to being the one managing the work? And how do I match my managing style to the person who is in front of me? 


Anne Helen Petersen: So I’ll say first of all that like I said, that none of these questions are industry specific, as in all of the answers to the questions can be applied broadly, like we have people telling us which industries they’re in. But I also appreciate that this question asker comes from academia and is acknowledging that management is part of the skill set right, because that is something that is often actually not acknowledged within academia, that people are doing management when they are advising or they’re overseeing a group of PhD students. Even acknowledging that overseeing students is is management, that this person is already in AP management. So, Melissa, what do you think about this person’s question about matching management styles to individual employees or advisees? 


Melissa Nightingale: I’d offer a layer of nuance, right? I think that often when we’re managing, we’ve got this idea of like if we just like if I’m a blue and there a blue, then like it’s going to be easy. But if I’m a blue and they’re a purple, it’s going to be hard. And like there’s an entire cottage industry around, like, what color are you? What leadership style? Like, there’s just a bunch of that. In reality, if you’re starting from a strong foundational management set of skills, it feels more like tailoring and less like matching. 


Anne Helen Petersen: Mm. 


Melissa Nightingale: Cause if you think about the great bosses that you’ve had, either like in your own career or like a theoretical great boss out there, those great bosses aren’t limited by hiring a team that looks and acts and thinks just like them. Those great bosses are able to bring the best out of that team and get them working together. And in order to do that, like fundamentally, it’s about bringing sort of different skill sets, different perspectives, different abilities in order to like sort of put those things into practice in the organization without having to to be a clone. Right. Or or manage a team of clones. I think the thing that Holly’s got right there is that you’re starting point for a lot of leaders is like, I already know how to manage myself, right? I was successful. I got my Ph.D. somewhere along the lines—


Anne Helen Petersen: Right. 


Melissa Nightingale: —I have figured out what works for me. I think the the neat part about the way the question is being asked is like, I fundamentally understand that what works for me may not work for everybody else. And that’s a phenomenal jumping off point for managing a team, because once you’ve got that in mind that like, like it may make sense in my head, but even though I’m like it is clear to me, it may not be clear to the person across from me. That’s a really good starting point. 


Anne Helen Petersen: So one thing that I think often happens when someone’s new to management is they understandably think the first step is to ask the people that they’re managing, how do you want to be managed? But I think a lot of times people don’t know how they want to be managed. So how would you approach that question? 


Melissa Nightingale: I think there are universals in terms of things that help bosses and and their employees succeed. Right. Is like, am I clear on what I’m supposed to be doing? Do I understand any of the broader context around it? Right. Like, do I do I sort of have the why of what I’m doing clear? Do I have an idea of what the expectations are from my boss? Am I getting feedback along the way? Do I understand the opportunities for growth? Like those aren’t about whether you’re blue or purple or like you’re a yellow personality. Those are about like fundamental components that we need in order to sort of have satisfaction at work. 


Anne Helen Petersen: So, Holly, let’s say that she herself was someone who benefited from monthly check ins when she was doing her research. Right. She liked to not have a ton of contact because that stressed her out. How does she ascertain the amount of contact that her advisees actually want or need? Even if like their advisees, maybe want, they want to say something that pleases her. Do you know what I’m saying here? Like there’s a mismatch in like how someone perceives being a good employee might be and what they actually need to be their best self at work. 


Melissa Nightingale: Yeah. I mean, here, like, let’s say, like there’s wonderful research that’s on Holly’s side in terms of sort of check ins being a really strong predictor of employee engagement and also thriving in the role that like that. We’re not sort of making it up person by person that we have best practices because we’ve been studying organizations and humans in organizations for a really long time. And one of the things we found is that, like, particularly if you’re in an organization where the context is changing relatively frequently, right? Like I mostly work with startups and tech organizations and the context changes very, very fast in terms of the expectations of the organization, but basically figuring out like. When you’re doing a check in with your employee, like a good gut check is how often are you surprised and how often are they surprised? If you are coming out of a one on one with your direct report and you feel like completely blindsided or like something is is they were working on a project and he’s like way off of where you expected it to be. That’s a good sign that you’re that your monthly check in might need to be biweekly. And similarly, if you’re having biweekly check ins with your person. But every time you come in, they’re like, well. You know, they’re having like a strong change response to some of the things that are coming up where they’re like, I either didn’t know that information. I’ve now spent a week working on this project and like it actually got shit canned at the last meeting and nobody told me like that type of strong change response is also often an indicator that maybe your biweekly check in needs to be weekly. There are some good rules of thumb in terms of like managing managers. Like once you’re managing senior folks or once you’re managing managers, those check ins are often less frequent. So most organizations, like when you when you’re brand new to the workforce, your check ins need to be more frequent because you’re likely to hit a wall much faster than if you’ve been at it for a little while. 


Anne Helen Petersen: So as some sort of practical advice for someone in Holly’s position, whether they’re in academia or not, the first time that they’re meeting with people that they’re managing, do you have like a script that is useful for getting the conversation started, trying to figure out, you know, what kind of management style works best for, for different people? 


Melissa Nightingale: I mean. I think it’s really helpful, particularly if it’s like the first one on one that you’ve ever had, either with a new report because there are new to your team or with like it may be the first time that that person is in the workforce and ever having a one on one with their boss at all. It can be really helpful to say like, here’s what this time is for. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: Right, here’s what this time is for. And like particularly in an environment where it matters that it’s research backed, it’s helpful to say out loud that it’s research backed. Right. That that when we’re sort of pulling from a like the data says like this is important and we’re going to we’re going to sort of pull forward and honor the fact that this is an important component in not only our management relationship specific to the two of us, but also broadly in terms of your success within the organization. And so for many folks, like, it’s really helpful to say like, here’s what this time and space is for, and if you want it, if you want to include some status checks. Great. Like have that conversation upfront. I’m going to check in on your project. We’re going to talk about how it’s going. This is a space for us to talk about any blockers or if it isn’t, say out loud, This is not a space for us to talk about blockers. That’s going to happen in some other meeting at some other time. But I think specifically for folks who are starting out, one of the things that’s awkward is like if we’re just sitting there and we don’t know what that time is for, then I can’t like to your point. It’s very hard for me to say like, here’s here’s what I need from you, boss. The power dynamic, like—


Anne Helen Petersen: Yeah. 


Melissa Nightingale: —really militates against me saying, here’s what I need from you, boss. 


Anne Helen Petersen: Right, right, right. Especially since, like, I don’t know if you’re in a setting like this, or maybe it’s your first job or one of your first jobs or your previous jobs haven’t had a manager situation like this. You feel like any time that you have a one on one that like there’s a weird power dynamic, you’re being held to account in some way. Like if you can establish the terms of like this is a time when it’s actually acceptable and encouraged to talk about what we’re struggling with, what we’re succeeding in, those sorts of things. Setting the terms very clearly would be so useful. 


Melissa Nightingale: And in terms of superpowers, like many bosses and their direct reports find that it like takes the stress level way down when we’ve got a shared agenda, like if we have a shared agenda and we both know the like just the broader context around like what are we here to talk about. 


Anne Helen Petersen: Right. 


Melissa Nightingale: What things are going to come up. I said last week I was going to do this thing like it’s now on the agenda. I can anticipate that we’re going to talk about that or no. Like. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: Just having that structure sort of carries a lot of that awkwardness and sort of like just releases. I think a lot of the tension going into those discussions. 


Anne Helen Petersen: Totally, I have had so many awkward what I now understand as like one on one manager check ins where they’d be like, how’s it going? And I’d be like, great, what are we talking about? You know what I mean? Like, I just. 


Melissa Nightingale: Yes. 


Anne Helen Petersen: I didn’t. I didn’t know that this was actually supposed to be the time when we were talking about these other things. So I would defer or deflect to try to make the conversation end. And that is why it wasn’t a very good one on one. [laughs]


Melissa Nightingale: But I think like a lot of bosses are in that spot and then you end up with employees who are like, I don’t want a one on one. 


Anne Helen Petersen: Yes. 


Melissa Nightingale: Like, it’s it’s been awkward enough in my last job that when I go into my new job— 


Anne Helen Petersen: Yes. 


Melissa Nightingale: —and my boss says we do one on ones be like, I would like to opt out. Is there a way I can just not have them? And we come back to that core element of like how you’re going to succeed in this role is if you’ve got like enough context about what’s going on in order to do it. And like a place that’s a safe space to ask questions if you have them that like sometimes don’t suit a group setting, which is like, I think this project doesn’t matter, is a hard thing to say in front of like all of your colleagues who are working on that project. [laughter] Right like we just we just need some room for those things. But again, like we, we sort of shoot ourselves in the foot when we take a thing that is very useful and we don’t give it enough structure to have it be able to do its job.


Anne Helen Petersen: 100%. [music plays]




Anne Helen Petersen: Our next question is all about the feelings that come with management. 


Melissa Nightingale: Mm hmm. 


Anne Helen Petersen: But maybe we can also get into the reason for those feelings. This is from Christine. 


Christine: I have a direct report who is demonstrating an inability to retain training or job specific information after a few months of training and retraining. I found that I am now resentful and annoyed by the person all of the time because I feel so bogged down by them. How can I stop letting this person get under my skin while I have to continue to coach, delegate to, and support this person? 


Anne Helen Petersen: All right. So, Melissa, I think we have to take as an assumption that firing this person is not in the menu of options. 


Melissa Nightingale: Why? 


Anne Helen Petersen: I mean, maybe maybe it is in the menu. [laughter] But I just feel like if they’re asking, what do I do if I can’t, I’m so resentful and annoyed. I don’t know. What do you think is firing in the menu of options here? 


Melissa Nightingale: I would say, like the thing that’s really clear from outer space, like without knowing this person, their direct report or like the specific nuance of the situation, the thing that’s clear from very far away is that the status quo can’t continue. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: We are not in a good spot right now. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: And how we got to that spot? I can tell 600 stories about how we might have gotten to that spot. But where we are right now is one of the like, this situation can’t hold. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: Something’s got to give here. 


Anne Helen Petersen: This reminds me of something you said in our last episode where you said, if something doesn’t make sense, get really curious. So even though Christine didn’t ask us how to deal with this employees performance, what should we be curious about here? 


Melissa Nightingale: First thing I would say is that, like, it should never feel good as a boss to have an employee on your team who’s failing. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: Like if that starts to feel good, you should hang up the manager hat. [laughter] Do you know what I mean. 


Anne Helen Petersen: Right. 


Melissa Nightingale: Like, there’s, like, a million bad boss stories out there. And, like, if you are actively being someone’s bad boss story, like, stop it, stop. [laughter] Like if someone is failing on your team and you’re like, why does it feel bad that someone’s failing on my team? It’s because fundamentally, like your whole job, the purpose of you being in the organization is to help not only like your team thrive, but your team thrive in the context of the organization thriving. And the way that you accomplish that is you help the individuals on the team be successful. And so like if you’re if you’re outside of that, if you’re out of integrity with that, like it’s going to sound harsh, but it should feel bad. 


Anne Helen Petersen: Yeah, yeah, yeah. 


Melissa Nightingale: Because it’s the opposite of what we’re asking you to do. 


Anne Helen Petersen: Right. And I think probably Christine’s annoyance is in some ways probably annoyance with herself and she doesn’t know where to put it. Does that make sense? 


Melissa Nightingale: Sometimes there’s, sometimes there’s pieces of that. Right. Which is that like I mean, I think the question is like, if the person genuinely can’t succeed in the role, then we have a very bad hiring process for the organization. 


Anne Helen Petersen: Mm right. 


Melissa Nightingale: Like if you hired someone and trained them and onboarded them and put them into the role and like gave them a name tag and gave them a business card, like if we’re if we’re at the end of all of that, and at no point along the way have we discovered that like this, this role cannot be done by this person. And I know, like we’re taking it as face value that okay, like, that’s the way the question came in. And so like, that’s what we’re going to take at face value. But if we’re there at face value, that is a failure of a hiring process. And we should do the work internally as the boss in the organization to learn the lessons of how we got there, so that when we’re hiring again for this role, we’ve got clarity about whether the person coming like, we don’t want to be in like, I’ve seen this movie and I know the ending. Like that’s a bad spot to be in terms of hiring. For a role, particularly after a failed hire. 


Anne Helen Petersen: Yeah. Maybe the better way to think about this is she is annoyed and resentful at the hiring process and the entire structure of how someone like this would have landed in this position. You know, it might be this individual’s fault, but it might also be the fault of the system that placed them here without the skills to do what is necessary. 


Melissa Nightingale: For sure. And, and in both directions. Right. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: We may have an employee who was brought in with an ill defined role just like—


Anne Helen Petersen: Yeah. 


Melissa Nightingale: —it happens, right? Not every organization is phenomenal at writing, really clear and crisp job descriptions. And so sometimes you’ve got someone who’s coming in to a really squishy role, which is like, we need you to be the office manager. And you’re like, what does that entail? They’re like, manage the office, and you’re like, cool. That like [laughs] really doesn’t tell me very much, but okay, let’s give it a go. And then you find that like through the course of it, you’re like, oh, that’s actually a really different job than what I thought I was applying for and thought I was getting myself into. 


Anne Helen Petersen: Right. Or people who conceive of something like office manager as an entry level job, because usually the pay is commiserate with an entry level job when really the skills of an office manager are very sophisticated. And—


Melissa Nightingale: Yes. And you’ve got like 600 people who need things from you at any given moment. 


Anne Helen Petersen: Right. 


Melissa Nightingale: And varied things. It’s not like 600 people all need the same thing. They all need different things. 


Anne Helen Petersen: Yes. And so maybe if you were good at like ordering office supplies, you’re not necessarily good at fielding requests from 12 different people who forgot how to access the Internet. Like those are different skill sets. So that’s probably that’s probably part of what’s at work here. But then I also think about this question that we got a couple of weeks ago in our episode with Lyz Lenz about like, you know, sometimes people are going to be annoying in your office and you kind of have to deal with that. So how do we how do we make sure that this isn’t just a question of like, I’m kind of annoyed by this person that I’m supervising and actually a misfit? I think your initial reaction really indicates that there’s something bigger here than just mild annoyance. 


Melissa Nightingale: I think like we we talk to bosses about firing a lot, right? It’s not a ple— Like it’s a somber topic. And like, one of the things that we say to bosses before we head into conversations about firing is like, you’re going to bring everything to this discussion. And like we need to be able to talk about it and know that for many people it’s very charged, right? It’s a very charged topic. But most bosses at the moment of having someone who’s underperforming in their organization need more support than they’ve got in that moment. 


Anne Helen Petersen: Mm. 


Melissa Nightingale: And the reasons it goes so badly, the reasons why, like we have to basically give folks like a heads up when we’re going to like we’re going to talk about the topic because it’s so hot. The reason it ends up so hot is because, like it goes very badly when you’ve got ill prepared people dealing with underperformance and dealing with underperformance in an organization that doesn’t support dealing with underperformance. And so when you ask the question like it or you sort of said like it’s not possible to fire this person, the reason I said why not is because sometimes we’ve got underperformance and we have resources in the organization, we have H.R. counterparts, we’ve got our own boss, we’ve got folks that we can talk to about it, but we don’t because it feels like I’m managing this person and this person isn’t succeeding. Therefore I’m not succeeding. 


Anne Helen Petersen: Yes. 


Melissa Nightingale: And I don’t want anyone to know. And so I’m mean to sit with it as long as possible and wait until the last possible minute to deal with the fact that, like, I’m underwater, things are going badly. And I like the push that we give bosses is you need to reach out for support. Because even if your H.R. counterpart says, yeah, this isn’t going to work, or your own boss says, like, you know, that was not a good hire. And let’s talk about why it wasn’t a good like whatever whatever those folks have to say, then at least you’re not going through it alone. But I think when people are in that spot and they’re in that spot alone, they can get to a pretty raging and despondent place, which is the thing that I’m responding to, is that question isn’t how do I help someone who’s underperforming succeed in the role? How do I come up with creative solutions around like mentoring them to success? That question is like, I am very frustrated. How do I pretend I’m not? And the answer is you can’t. 


Anne Helen Petersen: Yeah, and the ramifications of trying to push that down, you know, they spread throughout an organization because it’s not just, you know, probably this employee is pretty miserable. Right?


Melissa Nightingale: But I mean, the worst part is that like that employee is working for for a boss who, like, doesn’t believe that they’re going to be able to succeed in the role. 


Anne Helen Petersen: Right. Right. 


Melissa Nightingale: It’s like it’s just a shitty spot. 


Anne Helen Petersen: Yeah. And there’s also like, if they’re not doing well in the role, then there are ramifications on other people in the team, you know, like the tendrils spread out across the organization. So it is not an individual or a manager managee problem. Like this is something that is much more to do with the entire structure. And so you can’t just ignore and pretend like, okay, I just have to figure out how to not be frustrated by this person. And I think your advice here, your specific advice to reach out for support is hard because, like you said, it makes someone feel like, oh, I’m failing as a manager or failing as someone who’s training. But that doesn’t seem to be the case here. 


Melissa Nightingale: I mean, we don’t know, right? And like, I guess I don’t know enough to know like which thing is true. But I would say like the the piece in terms of where we are right now is that like this can’t keep going. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: And it can’t keep going for the boss, it can’t keep going for the employee and it can’t keep going for the organization. And once you’ve checked all of those boxes. Then. Then we need some other ideas. [music plays]


Anne Helen Petersen: Our next question is actually in some ways a callback to a question we had in our last episode where you were on as as our co-host. So that question was about a young employee who seemed to be working at all hours of every day, despite assurances that she wasn’t expected to do so. And this question asker noted that her supervisor was Black and acknowledged that perhaps she felt the need to be twice exceptional. So our next question, again is similar to that one, but it’s from a different listener named Meghan. 


Meghan: Do you have any thoughts, guidance or resources on anti-racism in the workplace for people that manage people of color? I’m white and a brand new manager. My report is a Black lady who is really good at what she does, but who also has room to grow and whose reputation seems to me to have been negatively impacted by implicit racial bias. She wants more recognition and has said she’d like to work with me on that. Our previous working relationship has been my reviewing and providing feedback on her work in a formal but non supervisory capacity and we’ve established a good rapport. She’s about 20 years older than me. I don’t know if this bothers her, but I’m not aware of any issues. And in fact her greater experience in the industry is quite valuable. We work in consulting, so it’s definitely small C conservative, although employees politics skew liberal. I say this because while performance standards are deeply informed by and consistent with capitalist white supremacy, even the white boomers that I report to appreciate and support my concerns about how implicit bias affects this individual. And doing what I can to avoid it and fight against it going forward. 


Anne Helen Petersen: So first, I want to acknowledge that you and I are both white women and two white women advising another white person on managing a Black employee like this is this is tricky. But, Melissa, I feel like this is a common theme that you probably hear from other managers and bosses that work with you. So how how have you advised that and how have you kind of worked around the really, I think, difficult racial politics of trying to advise in terms of power dynamics and implicit and explicit racial biases. 


Melissa Nightingale: So we we get this one a lot in a lot of different forms, right? We work globally and we’re working with a number of organizations where like half the team is on one side of the world and the other half the team is on the other. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: We work like in sort of areas like the U.S. we work in Canada, we work in markets where there’s a lot of sort of overlap of like we’re working together, but we have zero lived experience that overlaps expectations in terms of how we came up and and what we’re facing and all of the assumptions that we’re bringing to bear in the workforce are really different. And what we say to folks is that when you’ve got very limited, overlapping lived experience, that is a place where you need things to be more overt in order to get the clarity that you need so that folks can thrive. And so, like, if you’re like the word implicit came up, I think like at least three times in that question. 


Anne Helen Petersen: Right. 


Melissa Nightingale: And like the the big shove is like when you’re worried about things being implicit, move them to explicit. And like, that sounds really simple. It’s like, well, if we’re in that spot, then like nobody who doesn’t think like your boss or look like your boss is going to be able to succeed. And so if we want to create a different system, if we want to create structures where people can thrive who don’t necessarily look like the CEO or look like the existing founding team, then we need to sort of start to capture some of those things and the why behind them. Right. It’s not enough to just say like, you know, we we yell in meetings. It’s like, okay, well, like fine. Yell in mee— But like, why? Right? Like, what are we actually trying to get at? 


Anne Helen Petersen: Right. And I feel like, okay, so this is consulting and it’s also they’re ostensibly liberal. So I just I can really imagine it’s not anything as overt as like [laughs] we only like a certain type of person we don’t like. We only hire a certain sort of person. It’s more like, here’s the management style or here’s the communication style that we privilege. And no one has said that out loud. Right. It’s just that if you look at the way that promotions have worked over the course of the last ten years, people who communicate, people who are present in the office, people who shoot the shit in the same way as the people in power, those people are the ones who are rising up the ladder. So how does how do we make that explicit and actually do something about it? 


Melissa Nightingale: So, I mean, there are two pieces, right? There’s the there’s the manager and this sort of question’s own journey. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: And I would decouple their own journey of learning and unlearning, separate from their duty and obligation to be a sort of effective manager for their employee. 


Anne Helen Petersen: Mm, yeah. 


Melissa Nightingale: And the reason I think it’s really important to decouple those is because we when they are blurred, we are asking a thing that’s really unfair of that employee, right? If we are asking and not paying for DEI education for that boss to come from that employee, then we are well outside of what is actually within scope for their role. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: Obviously assuming that like the consulting that they’re doing is in DEI consulting. 


Anne Helen Petersen: Yeah. Yeah, hopefully. [laughter] 


Melissa Nightingale: Right. And so when we decouple those and we say, okay, there’s learning and unlearning to do on this piece of things, but the obligation and the duty to the employee is to create those structures and to say like, I may not have clarity in terms of like what the expectations look like within the organization, I may need to go have some hard conversations with my own boss about like I got promoted, but this person who’s been here longer didn’t get promoted. And can you help me understand? Not necessarily fighting place, but like genuine, like without understanding what the next steps are in terms of being considered for promotion, being considered for that visibility that that employee is asking for. You can’t be an effective manager for that person. Do you know what I mean? Like, there’s no way that you can provide that. You can’t turn around and provide that clarity for that employee if you don’t have it for yourself. 


Anne Helen Petersen: Right. I think this person also this manager has to is probably balancing some interesting acknowledgment and awareness that they have benefited from those systems of power and trying to dismantle them. But then also, like this is the hard thing with privilege, is that you’re like, am I actually giving myself willing to give up some of my privilege and position? Right. And and that’s what I think oftentimes white people struggle with the most is they’re like, yeah, I want more people of color in positions of management. But also I don’t I should also be at management, right? You know what I mean? [laughs]


Melissa Nightingale: And the clarity of knowing like it may be less awkward for you to ask those questions. Like, again. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: If you don’t have the clarity around like the person, like through the question is doing good work, right, is valued within the organization. So okay, if they’re doing good work and valued within the organization, then we really need to understand the broader context around like how does visibility happen in terms of like accolades for for that good work that’s happening and all of that value that’s that the organization is accruing like and experiencing, then where where are things falling down along the way? And again, like from a position of relative privilege within the organization and of being that person’s boss, the boss has an obligation to go find out, right? 


Anne Helen Petersen: Yep. Yep. And I do think that this person is really thinking, too, about how can I create structures moving forward that don’t replicate what has happened in the past. And I think that that that is useful in terms of like, I don’t want to perpetuate the way that we have hired and promoted in the past. I want to be an agent of change, and in order to do that, they have to do the hard work. Right. It can’t just be like, I’m going to ask people of color about what we can do better or whatever. Like they have to do that hard work of also talking with their bosses. And that’s a lot. But I think it also like if you are actually committed to anti-racist hiring and managing processes, that is the hard work that’s necessary. 


Melissa Nightingale: Yeah, clarity is an act of inclusion and if you don’t have that clarity, then nobody else is going to either. 


Anne Helen Petersen: So there’s one thing that I want to use as kind of a segue way to a question, and that’s Meghan said in her question performance standards are deeply informed by and consistent with capitalist white supremacy. I think most performance standards are actually very deeply informed by inconsistent with capitalist white supremacy. Just in terms of the way that perfectionism relates to capital white supremacy, the way that constant growth and the privileging of constant productivity, all those things. And we got a handful of questions from listeners about performance evaluations and how to do them well, which I think the implicit part there, I know that we’re saying implicit [laughs] so much in this episode. The implicit part is like, how do we do a performance evaluation that is not that right, that is not deeply informed by and consistent with capitalist white supremacy, while also not being just like, what are your feelings? So [laughs] what do you think the pitfalls of performance evaluations are and what is a better way to do them? 


Melissa Nightingale: Okay, so like great performance reviews start 364 days before you’re sitting across from someone. 


Anne Helen Petersen: [laughs] Yes. 


Melissa Nightingale: And when you think about it, you’re like, okay, like, what does that mean? Right? Like, is it just a calendar invite that goes off and it’s like, all right, start, no great performance review start 364 days before because like, we’re giving feedback the whole way along. We’ve got clarity of expectations the whole way along. We’ve set clear goals within the organization, the whole way along, and we’ve got a conversation happening around what growth looks like in the organization the whole way along. When you look at performance reviews, how they happen in like the vast majority of organizations, they happen an hour before the performance review— 


Anne Helen Petersen: Yes. 


Melissa Nightingale: —the person sitting across from you and your boss is like, I’ve got 27 of these to do and I’m going to like the night before—


Anne Helen Petersen: Yes, yep. 


Melissa Nightingale: —like maybe, maybe the night before. I’m going to just like, work my way through them and like a copy paste the comments and change your name so that you know that like this one’s specific to you and your like, trajectory like the [laughter] the way that we, like, we cram for them, like their exams. And it’s so, it’s such a missed opportunity. Like when they’re great, it should be the culmination of an entire year of management that’s happening when they’re shitty. It’s like 15 minutes before you get into the room. Somebody’s like, good work, like, keep going. [laughter] What do I do with good work, keep going. Like, that’s not helpful. Like even the good ones, right? Like, that should be a good moment. And people have walked out of those reviews and quit because like, it doesn’t tell you anything. 


Anne Helen Petersen: Right, right, and they walk out of the review and they’re like this person. Has no idea what I’m doing or what I’m struggling with. Like, this is my sign to leave. I feel like performance reviews are this weird Band-Aid for people who don’t manage at all, right, or who aren’t doing any sort of consistent management. And they’re like, this is how we’re going to show that we’re doing the work by having I don’t know, it’s essentially like finals, right? Like we’re going to take finals on management and no one’s done any of the studying, so everyone fails, right? Like, that is just a completely meaningless exercise, whereas if it’s done correctly. What it feels like is you stop in in your professors office at the end of the semester and you have a free flowing conversation for an hour. And you don’t realize at the end when they say you’ve passed with flying colors, right? Like you’ve just taken the final exam and you’re on the same page you’ve been learning all year and your professor has also been learning along with you. Like it just it’s a different sort of dynamic. But we use it as this this very weird, totally meaningless performance of performance. Does that make sense? 


Melissa Nightingale: Yes. And sometimes it’s worse than that. Sometimes we use it like as a blunt force tool for people [laughter] where like, you’re like, not doing well in the organization. We want you to know that really clearly and we’re gonna make it as sharp and harsh as possible. The result is, like many people going through performance reviews feel like there’s there’s just tons of stuff that gets delivered like that they didn’t know about. 


Anne Helen Petersen: Mm. 


Melissa Nightingale: And that feeling of being blindsided like so many folks come out of reviews being like, you’re talking about something that happened eight months ago and I could have fixed it like eight months ago had you told me. 


Anne Helen Petersen: Right. 


Melissa Nightingale: That was like a resolvable thing. But like, I’m now working with like conspirators who kept information from me for eight months that I needed in order to do my job well. And when you talk to bosses, like, why did you hold it for eight months? Many of them point to, well, the review was coming. I knew the review was like in December, so I don’t wanna make a big deal about it. 


Anne Helen Petersen: Mm hmm. 


Melissa Nightingale: You’re like, but you did make a big deal about it. It was a big enough deal that you then wanted to talk about it in the review. And so I think for a lot of bosses it’s very helpful backstop to say anything you’re going to talk about in the review you should have talked about outside of the review. 


Anne Helen Petersen: Yes. 


Melissa Nightingale: There shouldn’t be a piece of information that’s coming to your person for the first time when they’re sitting across from you In that review. When I talk about like the 364 days before, that’s a lot of the work that we’re doing ahead of time. Not every organization does them, a lot of bosses have pushed back and a lot of employees have pushed back and said, like, this tool is done, like it’s used so badly in organizations that I just don’t think we should use it anymore. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: I fall on the side of like it can be done well, but I also am a realist, which is like it can be done well and a lot of the time it is not being used well. 


Anne Helen Petersen: When you were talking about like bringing up something in the performance of you that have been eight months ago, I think of like how mad I would be if I was in a fight with a friend or a partner and they brought up something I did eight months ago that they had not brought up at the time. Just rude, right? 


Melissa Nightingale: Yeah. 


Anne Helen Petersen: Like, tell me, give me a chance to, like, deal with it and make our friendship stronger. But instead you just sat on it and let it fester. 


Melissa Nightingale: And like, I’m an adult. Like I’m, unless you’re employing children, which like, you know, labor law, like, don’t. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: But like if you’re like, assuming that your workforce is made up of adults then you have to, like, manage them like they’re adults, right? And managing them like they’re adults means again, like if you’re pissed off about something that happened, tell me that you’re pissed off about something that happened and don’t sit on it for eight months. That’s like, so vile. 


Anne Helen Petersen: How can we package this advice in a way that makes it feel less overwhelming to someone who maybe has only known the style of performance review that’s every six months and it just feels like you mean I have to essentially performance review every two weeks? Like how do we make that something that seems approachable? 


Melissa Nightingale: Oh, so like when I mean, when I say it’s like the culmination of all your bossing tools, right? Like it just performance reviews are bad because, like, if all my bossing tools are nonexistent, then like, I don’t have anything that like, is the sum total. But when you’re bossing, tools are in place. Like it means that I’m having regular one on ones to like the Holly question, right? I’m having regular one on ones with my people the whole way along. I’ve got clarity of the work that we’re trying to get done. Like I understand what the outcomes are that we’re driving toward. And when I’m checking in on those, it’s really easy to say like, you know, at the end of six months, like, how are we doing? Well, I literally have a document I have a shared agenda of like questions and problems we’re trying to solve in January. And now that we’re in June, like I can measure the distance. That should be a cool moment as a boss. 


Anne Helen Petersen: Yeah. 


Melissa Nightingale: Like if that gets you, if that gets you excited, like, good, you’re in the right, you’re in the right line of work, right? Like that. Growth should be a thing that you’re really excited about. And even if there are places in there of like, hey, like we in February, like set out to do a thing and like, it didn’t happen for a whole set or whatever, but like, we knew that, that we were sort of driving toward a thing and it didn’t happen. Like, okay, well then we can have that conversation too about like how we’re rolling that into a change of approach for the rest of the year. But when it’s good, it is a tool for reflection, right? Like at its core, it is a tool for like synthesis and reflection in work that almost never provides you that opportunity. Like, if you think about so many people’s job, it’s like, run to the meeting next, Zoom call. Like this Zoom call ran over like, fuck you, you don’t get to eat lunch. [laughter] Like jump to the next. Like it’s we are jumping between things when it’s good. It is this like just like sit and think about what it’s been and like you either feel really good about what it’s been or make a plan for what it’s going to be. But like it can be good is like my summary is it can be good. 


Anne Helen Petersen: Yeah, yeah, yeah. And also like, do you want to have this incredible moment for synthesis and reflection with each of your managees, or do you want to have a horrible night copy and pasting performance reviews twice a year? Like. Which which sounds better?


Melissa Nightingale: I literally had a boss once where I was doing it was like a self eval. Right. It was like, fill out like your whole year annual performance review. Do this deep self eval, work, submit it, then are going to come together with your boss. They’re going to do their their piece of it, you know, come together and talk it through. And I had like been working my butt off just like was so proud of the work I was doing, but also like really putting in the work. And so I wrote the self eval but like put in time and effort and energy to like, really get it. Showed up into the meeting. My boss handed me his notes and across the top of my self eval was the word agree with an exclamation point. 


Anne Helen Petersen: [laughs] Did you leave that job? 


Melissa Nightingale: I did leave that job. [laughter]


Anne Helen Petersen: I’m glad you left that job. And that would also be my advice to anyone who is in that situation. But also I think that this has given us so much to think about and reflect in terms of like, do you want to put in the work and have the entire experience be better, or do you want to have the entire experience of management feel like crap over and over and over again and sometimes— 


Melissa Nightingale: Like literally what we’re paying you for [laughter] if you’re like, worried about like, oh, I have to like, put together these performance reviews and it’s hard. That’s why we’re paying you. 


Anne Helen Petersen: Right. And I think that, like at its heart gets to a real tension in so many aspects of our culture, which is that sometimes we don’t want to put in that work that yields long term rewards because we there’s just we need to we’re like, if it doesn’t make things better right now, then it’s not worth the time. But all of the advice that we’ve talked about today is about putting in real dedicated work that can actually change the structure of your organization, can change the structure of your relationship with your the people that you’re managing. And all of it will make work feel better. 


Melissa Nightingale: Yeah. 


Anne Helen Petersen: And that’s our hope, right? 


Melissa Nightingale: A lot of my comment to bosses is like, I’m going to make you slower and I refuse to apologize for it at first we’re going to slow you down a little bit, but like slowing you down will speed you up. Right now, you’re going very fast, but you’re tripping every two steps. And so we’re just going to slow it down a little bit and like get some of the structure in place and then you can go back to going as fast as you were going. But stop falling over your feet. 


Anne Helen Petersen: Melissa Nightingale. Once again, this is the best advice and we are so happy that you decided to come back on Work Appropriate. Where can people find you if they want to hear more from you? 


Melissa Nightingale: People can find me at World’s Best Newsletter. We write about management and leadership every two weeks at And then I’m @shappy on Twitter. 


Anne Helen Petersen: I allow you to have World’s Best Newsletter, even though I also write a newsletter because I just love the I love the bombast of World’s Best Newsletter. People don’t forget about it.


Melissa Nightingale: We should change it. We can change it to like worlds-best-newsletter-like-except-HAP’ 


Anne Helen Petersen: [laughter] Like. Please. That’s all I ask for coming on the podcast. Appreciate it. [music plays] Thanks for listening to Work Appropriate. If you’ve got a workplace quandary, you need help figuring out. Get in touch. You can find submission guidelines at or send a voice memo with your question to Work Appropriate at That’s also where you can send an email telling us who you want to be another guest host or to come on the show again. Don’t forget to follow us @CrookedMedia on Instagram and Twitter for more original content, host takeovers and other community events. And if you’re as opinionated as we are, consider dropping us a review. Work Appropriate is a Crooked Media production. I’m Anne Helen Petersen, your host. Our executive producers are Kendra James and Sandy Girard. 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. You can follow me on Twitter @AnneHelen or on Instagram @AnneHelenPetersen. And you can sign up for my newsletter Culture Study Meet us back here next week for advice on getting paid.