May I Speak to the Manager? with Melissa Nightingale | Crooked Media
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November 16, 2022
Work Appropriate
May I Speak to the Manager? with Melissa Nightingale

In This Episode

Often, people get promoted into management because they’re good at their jobs– not because they know anything about managing people. In this episode, Melissa Nightingale from Raw Signal Group joins host Anne Helen Petersen to posit that management is a skill that can be learned. From learning to manage a remote workforce, to dealing with generational differences in the workplace, to setting a good work-life-balance example to young reports– we answer listeners’ questions about all things managerial.

If you’ve got a workplace quandary you need help figuring out, head to and let us know.




Anne Helen Petersen:  Hi. I’m Anne Helen Petersen. And this is Work Appropriate. [music break] Management is a skill, but in the vast majority of workplaces it is not treated as one. Instead, it’s something you do because it’s the only way that you can get promoted. It’s an add on to your existing responsibilities with little attention to whether or not you actually have the skills or attributes that make you a good manager. That’s long been the case and it was a problem even when we were primarily doing management in person. But now that many workplaces have moved online or to a hybrid setup, the ability to manage by just, you know, walking around and looking at people that is no longer possible. And if management training before the pandemic was bad, now it’s even worse. A lot of people tell me about their dysfunctional or toxic workplaces, but a lot of people like their workplaces. They even like their managers. They just wish they were better at their jobs. Or if these people are managers themselves, they wish that they actually had the tools to make them better at their jobs. And that’s why I wanted to ask Melissa Nightingale to come and be my co-host today.


Melissa Nightingale: My name is Melissa Nightingale. I’m a co-founder and partner at Raw Signal Group and at RSG we build better bosses.


Anne Helen Petersen: She knows what it’s like to be an untrained manager foisted into the position with little to no training because that’s what happened to her. And now she trains managers in a way that is honestly the least bullshitty time waste that I’ve ever seen. As part of her work with the Raw Signal Group.


Melissa Nightingale: So much of the work that we do day in, day out is with leaders in fast moving organizations. And one of the challenges that we see with leaders in fast moving organizations, is that they’re often moving very, very quickly, but not often given a time to take a moment and take a beat and learn how to do the job that they’re doing day in, day out, really well.


Anne Helen Petersen: I want to be clear that I am very dubious about people, selling management skills or management skill training or any of that sort of thing. I feel the same way about management trainings that I do about like random Instagram ads for jewelry that I know is going to turn my ear lobes green. But Melissa, she is the real deal. And if you, too, are skeptical, I think our conversation and Melissa’s approach to listeners management questions just might begin to change your mind. [music break] So, you know, one of the reasons I wanted to talk to you is that we’ve had conversations before you and I, and I always find your history with management and how you got into even thinking about management really, really interesting. And I also think it’s pretty relatable. So can you trace that trajectory from basically the beginnings of your work history?


Melissa Nightingale: Sure. So in the very early days of the Web, I was hired as the first PR person to work at Mozilla, the folks that make Firefox. And I was hired in when the organization was about 50 people. And that organization grew very quickly. Right. A very, very, very fast rise of the organization. And we went from about 50 people to up over 1200 in the span of about three and a half years. Most of that growth happened and we didn’t have our first full time HR person until we were about 300 people.


Anne Helen Petersen: I feel like anyone who has worked in a startup is going to find all of this very, very relatable.


Melissa Nightingale: So basically everything you can think that would be hard about being in a fast growing organization, being in a global organization, being spread across several different labor markets, trying to figure out the tech tools in terms of being able to manage remotely like we were doing that in 2007. And so a lot of the problems today when folks talk about sort of the things that are challenging are relatively familiar. And so as sort of we got into that role. One of the things that happened was like a thing that happens to a lot of leaders, which is that I was told, you’re smart, you’re really clever, you’re really good at the individual work that you’re doing. You’re running a team of people who are doing that work. And we hope you figure it out. Good luck.


Anne Helen Petersen: Right. So it’s like this style of promotion to management that I sometimes like to call it at on management where you’re very good at your job. So why don’t you manage people even though you have no prior experience or training with managing?


Melissa Nightingale: And at the time we thought that was sort of a reflection of the the weird and wild nature of the Internet in that timeframe. Right. We just said, okay, well, the organization is growing really fast. Who has time to slow down and teach us how to do this next part of the job really well? And what I found sort of the longer I stayed in tech organizations, the longer I stayed in management positions, is that you talk to people and everybody basically everyone comes up with some version of the same story, which is I was good at the thing I was doing. I got tapped to lead a team of people who are doing that thing, and that was the start and end of the training. I got to do that job.


Anne Helen Petersen: Yeah. And I feel like, you know, Charlie and I in our book, we talked a little bit about this history of management and how I’m being somewhat reductive here. But essentially over the course of the seventies, eighties, downsizing, layoffs, we subtracted management as a discrete skill from many organizations. This middle layer of management became very disposable. And now, as we’re building companies back up from a startup into these larger sprawling organizations, kind of like what happened with Mozilla, we’re realizing the importance of good management.


Melissa Nightingale: And so much of the timeframe that you’re pointing to. Anticipated a homogenous workforce. Anticipated a workforce that was either highly local, right? Which is like I’m going into work at the factory in my town and everybody who works there also lives in my town. And we have a lot in common and we share for the same sports team to a workforce that is not only sort of massively global in terms of like I may be signing in to work in a, in a Zoom window and the people sort of across from me are not only not in my time zone, they’re not in my town, I mean, have never met them. And like, it’s just a really different context. And we’re asking leaders to lead in a space where, like many of them are like, I, I have never done this before because almost nobody’s ever done this before.


Anne Helen Petersen: Right. And management oftentimes before was conceived of as like just walking around, walking around, looking to see what people are doing. And so what happens when this primary mode of management is no longer part of your job description? Like what happens when you physically cannot walk around and look at people anymore to see if they’re doing their jobs?


Melissa Nightingale: No. And we hear from leaders a lot. It’s particularly over the last two and a half years that they’re struggling with. How do I know what my people are working on? How do I know how long something should take and when when sort of they flag for me that something’s gotten in the way or something’s taking longer. I really just have no way to contextualize it because I have no visibility into what they’re doing day in, day out.


Anne Helen Petersen: This is a really good tee up for our first question, which is somewhat of a deviation from what we usually do, does not actually come from one listener, but comes from many listeners and many readers of my newsletter who have been asking me this over the course of the last year, year and a half, two years. And it’s essentially I have no idea how to get better at hybrid and remote managing and whatever these like, you know, the webinars or the pointers that we’re getting in terms of like here’s how to be a more empathetic manager. Like all these things they’re not helping. So how can someone [laugh] this is a huge question. How can someone get better at managing a remote or hybrid team?


Melissa Nightingale: This is going to sound like a punt, but I promise I’ll come back to it and make it. Not a punt. [laughter] But the short answer is if you want to get better at remote management, you have to get better at management.


Anne Helen Petersen: Yeah.


Melissa Nightingale: All of the core skills that make you exceptionally good as a manager, all of those foundational skills are harder in a remote context. And so we hear from leaders a lot who are like, I have not. I got promoted into a position of management when half my team got laid off in March of 2020. Right? Like I was stepping into management for the first time as everything shut down. And so I’ve never managed in a way that wasn’t remote management, so I didn’t have an opportunity to establish those skills in a non remote context. I’m trying to learn as fast as I can and it’s really hard and the hard part of the feedback for them is that like it’s hard even if you were all in-person. The things that make management hard in a remote context are like are an exacerbation of some of the things that are really, really challenging. Like it is challenging to give somebody hard and direct feedback even when you’re sitting in the same room. It is challenging to figure out your own workload and figure out how to take pieces of that, hand them off to someone and feel confident. What they’re going to hand back has anything to do with what you handed them in the first place. Like, these pieces are really challenging. And so when we talk to leaders who are saying, How do I get better at the remote pieces if you have a. A strong core foundational management skill set. The remote pieces get easier, in part because the toolsets for remote aren’t the part that people trip over. Like most folks at this point, at this point in 2022, like most people know how Zoom works—


Anne Helen Petersen: Yeah.


Melissa Nightingale: —they know how Slack works, or they know how Microsoft Teams work. So they know how Google Meet, like that’s not the piece that people are getting stuck on. People are getting stuck on like, how do I check in on somebody and see how they’re doing when I can’t see them?


Anne Helen Petersen: Right. Well, and here’s the thing that I think it’s often hard to talk about, and that’s fine if you excel at your job and you have been promoted in this sort of add on situation where it’s like, here’s the way that you get a promotion. Here’s the way that you make more money is by becoming a manager. The skill set that makes you good at your job is oftentimes a different skill set than what makes someone naturally inclined to be a good manager. Right. And so someone might be really accustomed to things coming easily to them in the workplace. Right. So like I catch on to things really quickly. I’m just a quick learner. Like everything is pretty easy for me, whether that’s in school or in my job, and then here I am as a manager and like a why am I not that good at this? Like, it’s it’s very discombobulating. Do you know what I’m talking about here?


Melissa Nightingale: Yes. It’s part of the reason why it’s very disorienting for many managers who are extremely successful individual contributors is that oftentimes the things that the people need to be doing are really clear to them, the really obvious to them. And they’ve got an understanding of sort of the core workings of that of that role or of that job. And so when they’re faced with explaining it to someone for whom it is not obvious, it is not clear. And they’re thinking about the problem in an entirely different way than that individual who’s just been promoted for being exceptionally good at that. It’s very hard to teach them what they need to do or to help them troubleshoot because they’re the mental model for they’re thinking about this in a really different way. The things that I take for granted because of either like my education, my background, my tenure within the organization are not things that this person has at their disposal, are not things that they have available to them. And so you end up with folks who are very frustrated because they’re like, well, why can’t they just do the thing? They’re like, Well, they could just do the thing. They would have done the thing already. [laugh] And so troubleshooting that and untangling that is a really discrete set of skills. But the reason why ends up really hard for a lot of leaders is like we tell people, like you’re you’re either like a natural born leader, right? You’re like the tallest in your class. You have a January birthday. Like we use a bunch of factors to say, like, you just you look like what I think of what I Google the word leader. [laugh] That’s what comes up in my mind. And that’s not particularly helpful because if you find that, like people have told you that for your whole life and you’re still struggling, you’re like, well, I am just a fuck up because like I am, I am both a natural born leader and this is really hard. And then on the flip side, we tell people really unhelpful things like you’re just no good with people.


Anne Helen Petersen: Right. [laugh]


Melissa Nightingale: You’re just not very good with people. And you’re like, well, how do I I’m sorry. Like, I was born a human and I live amongst the humans. How do I then get better at that? And so for us, it’s really important when we’re working with bosses to say, look, let’s let’s break it down. Right. Which skill that the skills that we need to do the job well and how do we get better at those because the natural born and not good with like it’s very hard to get better from there.


Anne Helen Petersen: Yeah. Yeah. And I think that people who are sometimes natural managers just have like the thing that they were naturally good at growing up is oftentimes like they were really empathetic, great. They were really good at putting themselves in other people’s position. But that doesn’t mean that the only people who can be managers are people who have that skill that has come really naturally or easily to them. Like empathy is something that can be cultivated.


Melissa Nightingale: And when you meet really empathetic bosses, when you talk to them, they’re like, I have a very hard time delivering hard feedback. Like, yes, because you can imagine what it would be like to be on the receiving end of that hard feedback. It’s just one of those things where for many folks, the skill set is easier to improve on that I have a proclivity to or I’m inclined in this way. Like, great, that’s a phenomenal starting point, but that’s not usually where it stops.




Anne Helen Petersen: So question two is a real question this time, and it is from Maggie. Let’s hear from her.


Maggie: I recently joined a fully remote nonprofit organization. We’re mid-to large size and we have employees spread out across the country. I joined the org because I heard great things about the work culture, including how the organization protected and promoted work boundaries. And so far, I’ve been really impressed with how true that’s been. One aspect of my new job is supervising a team of people, including somebody who I’m going to call Ellie. Ellie is a young Black woman. This is her very first job. Straight out of undergrad. She just graduated a few months ago. I’ve noticed that Ellie is sending emails really early, sometimes as early as 6 a.m. and working very late. Sometimes I’ve seen documents saved by her as late as like 11 p.m.. Over the summer, she worked during the holidays, despite getting messaging from executive leadership team H.R. and myself that those were holidays that all staff should take off. I’ve talked with her about this every time I’ve noticed it, but every time I’ve brought it up, she’s kind of turned the blame on herself and said things like, I’m really bad at time management. Really bad with figuring out how to juggle multiple deadlines. I need to figure this out for myself. Don’t worry about it. And my response has always been that as her supervisor. Part of my job is helping her figure out how to manage many projects, how to figure out how to support getting her work done within 40 hours, within work days. I know that the transition from undergrad to office work can be difficult, especially if you’re used to being able to work on homework at all hours of the day with no kind of real firm end time. And I’m trying to figure out how to support her and communicate that if she wants to be flexible with her hours, she can. I just am concerned that she’s working more than 40 hours a week and she should not be. I know her other project directors have talked with her about this, too, because as her supervisor, I’ve been in communication with them and we’ve all made an effort to pull back some of her work and align our deadlines and communicate with her better about all of that. I am sure as a young Black woman that she feels a lot of pressure to prove herself, but everybody has been incredibly impressed with the work that she’s given and provided. So my question for you all is twofold. One, how can supervisors support their direct reports for whom this is their first full time office job with creating and sustaining healthy work life boundaries? And then two, how can white supervisors support their BIPOC direct reports with creating and sustaining healthy work life boundaries? Looking forward to hearing what you all have to say. Thank you.


Anne Helen Petersen: So I’m hearing a couple of things in this question. And the first is that there’s a manager who wants to encourage a healthy and sustainable work life balance for her employee, but is also recognizing some of the racial dynamics that may contribute to why this employee feels the need to essentially work twice as hard. Right. So let’s address the first part first. How can a manager actually encourage and I think I’m going to lead us in a direction here, but say model healthy work habits. And when does this become something that the manager can’t control?


Melissa Nightingale: There’s a piece that feels like it’s missing for me in the in the question, which is, what’s Ellie’s experience? Where’s Ellie’s voice? And I understand that Ellie didn’t submit the question. The manager did. But I think the part that I’m most curious about is what’s Ellie’s version of this? Because there’s there’s information like one of the things we say to bosses all the time is, if something doesn’t make sense, get really curious. Right. And so, like, if something doesn’t make sense, like one. One version is that like, you’re just missing information. And so the there’s a piece here which is like Ellie is clearly someone who is going to work every day and wanting to do a good job. Right. This is someone who, like just shown up every day, wanting to succeed, wanting to thrive at work. And so there’s a there’s a piece that feels like it’s missing from the manager in terms of help me understand help me understand what’s going on here. Right. We’ve had a conversation about boundaries. This is and I hear from the manager that this is something that they really to their core value, that it is a piece of why they came to the organization is the thing that they find very important in their own work. But I think, you know, to template and say that’s really important for me and my own work, therefore it needs to be identical for the people on my team. Typically it isn’t right. Like we’re going to work with all all types of folks who come with all types of assumptions, who have all types of family members giving them advice about working extra hard, putting their nose to the grindstone—


Anne Helen Petersen: Totally, totally.


Melissa Nightingale: —like there’s just a bunch of that out there. And so just hearing from Ellie and saying like just opening up that communication a little bit to find out, like, what’s the. What’s actually going on here?


Anne Helen Petersen: Yeah. Well, then I think there’s also, you know, I don’t know if this is a solution to the question so much as like highlighting a problem is that the author of this question is making some assumptions about why Ellie is working the way that she is. And part of it has to do with race. And maybe this author also feels awkward because they are white saying and I actually don’t think they should say, do you feel like you have to work harder because you’re Black? That’s very presumptive, and maybe some of that would be alleviated—


Melissa Nightingale: Also illegal in several labor markets, [laughter] we should just say out loud there are many states where that’s right off the table.


Anne Helen Petersen: Right. So. But maybe that would feel different to Ellie if some of the managers and maybe her direct manager was someone who wasn’t white. Right. Like maybe some of this subtext could become explicit if the racial dynamics were different. And, you know, this goes back to something that I remember someone telling me when I was first in the workplace, which is that if things were different, then things would be different. But that I think it’s just interesting and important to highlight that this is a problem that I think is not unique but also is is difficult to solve sometimes because so many organizations, the the management layer is still so white, even if the organization itself is attempting to diversify.


Melissa Nightingale: And I hear Maggie’s version of it, right. And Maggie’s perspective, which includes quite a bit of guesswork in terms of what’s going on. But I could tell another version of sort of leaving school, starting my first job, being really excited and eager, thriving and getting feedback that I’m thriving within the organization. And every time I submit a new project, being told that some piece of my work is getting taken away.


Anne Helen Petersen: Yeah.


Melissa Nightingale: And how confusing that might be. Right. Again, I haven’t spoken to Ellie, so I don’t know. But how confusing it might be to, on the one hand, be getting really positive feedback and praise for the quality of the work that you’re doing. And again, without necessarily a ton of context or lightness around how work works in the first place, right? Like this is sort of first job and that what should feel like a celebration moment is starting to feel like punishment.


Anne Helen Petersen: Yeah, well, and it’s also counter to what I think many students experience in their education, which is that more is always more.


Melissa Nightingale: Mm hmm.


Anne Helen Petersen: And so when you hit the workplace and suddenly you have someone trying to encourage a more like work hard and then rest style of work, it can be very jarring. It can be very counterintuitive. And it can also feel like I’m just doing the best that I can do. Like you said, I think that it might feel like negative feedback. So how do you situate that in a way that Ellie can understand?


Melissa Nightingale: One thing for bosses is that it’s a superpower to remember what it was like to be new.


Anne Helen Petersen: Yeah.


Melissa Nightingale: And a lot of folks leave that phase and don’t want to spend a bunch of time dwelling on what it felt like to be new there. Like, I worked so hard not to be new anymore that I don’t really want to spend a lot of a lot of mental energy or a lot of mental time on on sort of that reflection. But in terms of sort of things that happen when you’re new. Many times tasks take you ten times as long as they will eventually take you when you learn the shortcuts of the industry. But you don’t have any of those shortcuts in your pocket. And so in terms of like an opportunity for a really heart forward and caring boss to have a profound impact here, mentorship is a thing that is available to you. If you’ve been in the workforce for more than a minute and you’re managing someone who’s been in for basically a minute, any of the things that you learned the hard way, right? Like I remember early parts of my career, like things taking 4 hours a day, really taking like a full half day to get anything done and then six months in those things taking 15 minutes. And so if you can start to think about where those things are that are massively time consuming, when you’re just learning them and accelerate that learning process, you start to to not need evenings and weekends because the workload starts to get easier, because you start to get faster. And so then you can have a more profound conversation around, you know, those boundaries in the Labor Day and the, you know, 4th of July. Those pieces, I think, start to sort of lock into place. But in the early days, like, there’s such a development opportunity for someone who’s just starting out.


Anne Helen Petersen: Yeah. Gosh, that’s such a good point. I mean, this is somewhat different, but I remember in my early days of grad school, there would be some piece of reading, some piece of theory. It would take me a day to read, to go through the assignment. Right. And I would feel like I was working so hard through the entire thing. And by the end of my grad school career, I knew how to parse these sorts of I knew how to read them differently. But it took me time to develop that skill. And I was always hungry for a class, for a teacher, for other older graduate students to tell me how it was done. And I really I think I absorbed some of it through osmosis, but it was pretty painful. And I also had to deal with a lot of older grad students saying, like, don’t work as much. And I’m like, but this is how long it takes me.


Melissa Nightingale: But this is how long it takes me now because I’m doing it for the first time. It will not take that long forever. And that is also a really hopeful message for someone who feels like, you know, it is taking them a long time. And the between the lines is like you don’t nobody wants to be slow. Right? Like even when you’re just starting out, like it’s no it’s no fun to feel like you’re slow at your job, even if you’re doing a great job, even if what you turn in is phenomenal. Like, it’s no fun to feel like, you know, it takes you twice as long as it takes somebody else will. Often when we look at what’s taking twice as long, it’s all the skills you develop along the way when you get really practiced at of thing.


Anne Helen Petersen: So if you were Maggie and you were planning your next Zoom meeting with Ellie, how would you shape that conversation?


Melissa Nightingale: I mean, I start, I think with her help me understand. Let’s talk through a recent project. Right? We’ve got something that we’re trying to gain. Talk me through from like sort of start to finish sometimes for very junior folks. The question teach me about can be really powerful because the the it flips the orientation, right. It flips of me as your boss to you being able to talk me through like teach me about how you’d approach this project. But in the first steps you do second steps. Like often through that conversation you can identify like massive workflow misconceptions of like, well, it’s been like the first 6 hours Googling, you know, these terms like, oh, actually, like there’s a doc on our internet right here. You don’t need to spend 6 hours doing like you can find some of those spots. But I think the straight up conversation of you work too much. This is how this is how much I work in order to do great work and I’m fine with it. Like that dynamic isn’t it’s not productive. If it were productive, they would have again, they would have solved it by now. I think using those tools, I think we got to bring in some dimensionality to it in terms of what is the work that’s happening, how is that work happening? And not from a micromanagement perspective, but just from a like getting more informed about what’s going on. And then the flip side of like talk to me about sort of how work fits into your life because you may find that different people are coming to that with really different assumptions.


Anne Helen Petersen: Yeah, for sure. And I love that. That point that you make about how like probably her parents are like work as hard as you possibly can or someone else in her life. Right? Like that’s just there is a very different, attitude that I think some workers receive from people outside of their bosses, that they’re like, well, this my mom says this is the best way to prove myself on the job. And my mom is, you know, the person that I trust the most right now.


Melissa Nightingale: And cross generationally some of those changes, like the changes in terms of expectations of the workforce. And when many of the folks who are giving that advice provided like when they were coming up to the workforce, there wasn’t there wasn’t the Internet.


Anne Helen Petersen: Yeah.


Melissa Nightingale: You weren’t you didn’t have a mobile phone. You weren’t you left work. And you may have stayed an extra half hour or an extra hour at your desk, but it wasn’t possible for your work to message you at 3:00 in the morning unless they were calling your home phone. And that’s a really different context. And so a lot of the advice was good advice or at least was was well like it served the people who gave that advice. It may have served them well, but it didn’t anticipate a workforce that is constantly digitally connected. [music break]


Anne Helen Petersen: Our last question is from Jane and our producer Melody is going to read it.


Jane: As an employee, how should you handle being stuck in the middle between managing a team of Gen Zers who have a set of expectations and a boss or CEO who are from the Gen X generation and are at odds with the kind of workplace Gen Zers expect. Basically, I felt stuck in the middle understanding the change that Gen Z is asking for and agreeing with many of the things they want, but also understanding the challenge of their more outlandish requests and attitudes and why executive level folks dismissed their asks. It feels like millennials. I’m personally 36, are stuck between two sets of workers who are at odds, and it’s a challenge to manage both up and down to these two cohorts.


Anne Helen Petersen: So I love this question very much, and not just because I am also a millennial, but also because I think it really speaks to one of the most common tensions that I hear about, which is that like older leadership, people who have been in companies for a much longer period of time have different understandings of what work looks like and what is possible, right? Even like how culture and how mentorship can be formed. Then younger generations. I have this idea that I’ve been talking about with other people, even in episodes of this podcast, about how older generations, because they never made friends online as teens and as like people in their early twenties, like they don’t know how possible it is to have a really intimate relationship with people, even when you just meet them online. And so there’s just a break in experience, right? It’s not good or bad. It just is. And that’s hard, too, to bridge that divide. But so for this question, what advice do you have for this particular millennial?


Melissa Nightingale: I feel like they are so lucky to have you and may not feel that way, but to be able to have someone in a middle management position like one. Do you feel like you’re stuck in the middle? Because that’s exactly where you are? You’re exactly in the middle. That’s the role. But to have somebody who understands the concerns of senior leaders in the organization and also can speak credibly and authentically to junior staff members who are just starting out, like what an amazing leader within the organization to have somebody who both understands the challenges, understands what we’re trying to get done from a strategic level and can be the bridge. The opportunity is just a slight reorientation of like, I am tired and this is hard because this person sounds tired and this sounds hard to like. You are one of the only people in the organization who gets to apply bi directional pressure. Middle managers is the only place where you get to manage and apply pressure downward but also upward. Your executives can’t do that. They can only apply pressure downward and your most junior staff members can only apply pressure upward. Real change in organizations often comes from that middle, and they often see it first because they’re talking day in, day out to the people who are either new to the organization or individual contributors within the organization. And they’re also talking to the sort of C-suite or senior leaders within the organization. And so, like with that viewpoint and vantage point, there’s so much power, but it often feels like a really disempowered place and often feels like everyone comes to me to complain about the other part.


Anne Helen Petersen: Right. [laughs]


Melissa Nightingale: And so I think that the opportunity is to sort of get clear on like, how does it actually work within your organization today? Like, if you ask the C-suite, if you ask the folks who like maybe, maybe sort of have a sense that the new folks in the organization have unreasonable expectations. Okay, well, let’s lay out how it works. Just say out loud, like, how does it work? I start tomorrow. What are the things that are really important for me to know? Again, like because many of those folks like haven’t started a new job from a place of non management or non-power in a really long time. And when they were starting out in their careers, careers in general and organizations and offices were a lot more linear in terms of how you progressed within them. I start a job, you’re loyal to the company, you spent 20 years there. You get to a management position, maybe you get to a senior management position, but all of that is pretty laid out for you, and that’s not the workforce today. And so when you find you’ve got like folks coming into the workforce straight out of school and they’re like, how does all this work? They’re right to ask it because the answer with any given organization is really different from one to the next.


Anne Helen Petersen: So I want to rewind slightly here because I think it would might be interesting to think about this. In a paradigm that we don’t always think of as like a managerial situation, but something like, say, a school where you definitely have managers, you have a principal, you have a vice principal, you have these people who are managers. And I don’t think this is what Jane is talking about, but there is probably in these school environments, you have teachers who are one, two, three years into the job and who might be younger. And then you have this millennial who maybe has been teaching for ten years. Right. And then you have people who are nearing retirement. And this millennial feels like they can relate to those younger teachers in a lot of ways, and they can also relate to some of those things that those older teachers are thinking about. And so how did they communicate with both the principal, but then also become a leader themselves within the school? What are these misunderstandings that might be happening.


Melissa Nightingale: In this starting point that that I often find really helpful is that most people want to go to work, they want to do a good job. They want to have relative collegial esteem for their colleagues. They may not necessarily need to be best friends and like go for tacos later, [laughter] but they like want to do sort of have an opportunity to go to work, to do good work, to be respected in the environment that they’re in, to find that they respect their colleagues and to thrive. There’s no age limit on that, right?


Anne Helen Petersen: Yeah.


Melissa Nightingale: That’s true across the board. And so often we get into these sort of divide situations where it’s like, well, I think it should look like this and I think it should look like this. And we lose sight of the fact that like the starting point for most folks is that they really want to be heard and they want to be understood in their work environment. So if you’ve got a work environment that’s spanning, like do we have a place where where across the board people can be heard in terms of like what they bring to the organization, their own lived experience, like do we have a space where the only people who get heard are, you know, 60 plus years old and they’re in the board meeting and everybody else can like sort of like keep quiet and go home and gripe about it on the Internet. [laugh] But like we’re not interested in hearing it. Or do we have an environment where like, you know, we have somebody starting in a role at 22 coming into the organization and saying like, hey, I understand that we’ve always done it this way, but I’ve got an idea here. Those are the organizations that succeed. Like when you look across organizations like hundreds of thousands of organizations and say, what makes successful organizations tick? It’s this idea that, like, we can have those conversations and and in organizations where you can’t have those conversations, you often end up with like monoculture, and you often end up with an organization where we get blindsided or we miss out on some idea or some shift in the market or some movement or some trend in education. And we would have heard it if we’d been listening to our staff across the board. But because we were only listening to our folks with 20 plus years of experience, we only heard the things that you would say if you had 20 plus years of experience.


Anne Helen Petersen: Well, and I can even think about things like the fact that people who are younger in their careers, they’re really thinking about the rest of their careers, like, how am I? Thinking about work and thinking about the future of our industry. Within a paradigm of, you know, 25 years in the future, whereas people who are later in their careers are like, How am I think about my legacy? How am I thinking about the fact that I might retire in three years? Like, it just is a really different mindset. And to be able to understand that is really, I think, unique.


Melissa Nightingale: But if you as an organization can get those folks talking to each other and not past each other, but actually to each other, you get all of the sort of canon of best practices from a long time of doing it, mixed with all of the energy and enthusiasm for what change might look like. It’s so good, but in most organizations like those people are just like are frustrated and that that’s such a mess.


Anne Helen Petersen: Yeah. Are you hearing about this like about this more generational sort of mismatch or difficulty communicating and some of the work that you’re doing?


Melissa Nightingale: I mean, I think like get off my lawn is like it’s in fashion for for as long as it’s been in fashion.


Anne Helen Petersen: Right.


Melissa Nightingale: I think like kids today is like the thing that happens and has happened for a really long time. But I think for for most of the organizations that we’re talking to, it’s really about like how do you take it from the frustration into something constructive?


Anne Helen Petersen: Yeah, right.


Melissa Nightingale: Like how do you reimagine it to say like, well, what would it be if it were great? Because it could be great. It isn’t right now. It doesn’t feel great right now. But like not from a Pollyannish or a pretend perspective of like sort of sunshiny optimism, but from a like actual what could it be if the parts of your organization that right now hate each other and don’t talk to each other and shit, talk to each other on Slack? What if those parts of the organizations got together and made something amazing? It’d be so good.


Anne Helen Petersen: So is your advice to Jane, our question asker, is it to re-imagine her place as like this place of real power and privilege instead of this place of like exhaustion and frustration?


Melissa Nightingale: I think my advice to Jane, like I think that Jane is in a position of power and having an incredible place of transformation and privilege. And if it helps to hear a stranger say that, then I hope that that’s helpful. But in terms of like an actual concrete thing that Jane can go do. I think figuring out what is the roadmap for our organization? What is success look like for us? Like, are we a remote organization? Are we a hybrid organization? Do we have core our, like what are the the core pieces that she needs to know to be able to then go speak credibly to the rest of the workforce and say, like, this is what it is. And can she also, through the process of, let’s say, these things out loud, advocate for some of the changes that she feels like are important to keep the workforce current with what the expectations are, the folks who are coming in.


Anne Helen Petersen: So what is something that you are seeing a lot of? Like a tendency, an inclination, an eagerness, an openness that you are excited about in the future of like how work is going to evolve over the next ten, 20 years.


Melissa Nightingale: I mean, I would say this, but I am excited that bosses are advocating for themselves. People are getting promoted into positions of management, and particularly folks who are in sort of newer to the workforce. Generations are getting promoted into positions of management and at the moment of promotion they’re saying, I need I need to be equipped to do it. I will accept this role I’m willing to accept. And there’s so much smarter than I was, right? Like I got promoted to manager and I was like, cool new business cards. [laughter] Like they’re getting promoted into management and they’re like, oh man, this is a entirely different role than, than the work that I’ve done. And in order to do it well, I need I need some framework for doing it. And so we’re hearing from more organizations where the reason why they’re reaching out about getting their managers trained is not because somebody in HR said you have to do it, not because some CEO says it’s mandatory, but because the leaders within the organization and the people who are getting promoted are like, I need this and yes, I’ll do it. But but not without, not without some of the foundations in place.


Anne Helen Petersen: Yeah, I think that’s a great indication of a self-awareness, like knowing what you don’t know, which is really fantastic.


Melissa Nightingale: Yeah. And sometimes they, they don’t know. They’re like, I can’t I can’t articulate the thing that I’m missing, but I’ve had really shitty bosses. I’ve had really like a string of really shitty bosses. And I know, I know what it is when it goes wrong. And I would just love not to do that to other people. Great. That can be a good starting point. Is just like not to traumatize the rest of the workforce. Awesome. Like more bosses should start there. [laugh]


Anne Helen Petersen: That is a fantastic place to end. [laughter] And Melissa, people want to hear more from you. Where can they find you online?


Melissa Nightingale: This is the funniest thing to have to say to you, but we run a bi weekly newsletter that is free and it is it the URL World’ [laughter] With apologies. [laughter]


Anne Helen Petersen: No, it’s very clever. Clever. And where can they find you on Twitter? Where they find you on Twitter?


Melissa Nightingale: On Twitter I’m @Shappy.


Anne Helen Petersen: Awesome. And thank you again. It has been a real pleasure and I’m just really grateful for your insight today.


Melissa Nightingale: And likewise. Thank you for having me. [music break]


Anne Helen Petersen: Thanks so much to Melissa Nightingale for joining me into the team at Raw Signal Group who made it happen. And as always we’re grateful to those of you who wrote in with your questions. If you’ve got a workplace quandary, you want help figuring out. Get in touch. You can find submission guidelines at Or you can send a voice memo with your question to Work Appropriate at We’re interested in all of your questions, but in particular, we’re working on episodes about unions, about how to really and truly rest and about how to have awkward but necessary conversations at work. 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. You can sign up for my newsletter at Subscribe to Work Appropriate wherever you get your podcasts. And I’ll meet you here next Wednesday as we answer questions about the growing pains of starting a new job and whether it can be easier.