🚀 Breathe.



“Early in my management career I found it really uncomfortable to be a boss. It’s a really uncomfortable thing for a lot of people. This shift from we work together and there’s no power dynamic to I’m now in charge of you. There’s an inclination to give that power away as quickly as possible.”

In this episode

In episode 41, Melissa and Johnathan Nightingale emphasize what the manager title exactly entails and how to own the role. 

Melissa and Johnathan are founders of Raw Signal Group, best-selling authors of “How F*cked Up Is Your Management? An Uncomfortable Conversation About Modern Leadership.” and editors of The Co-Pour. 

Before all that, Melissa has been a startup warrior, previously holding executive roles at Wattpad and Edomo … and was also Mozilla’s first Director of Global Public Relations. Johnathan, on the other hand, has built and operated entire organizations, all while helping improve diversity. He was previously VP of Firefox for Mozilla and CPO at Hubba.

In today’s episode, they shared lessons learned from their early management mistakes and why setting expectations is one of the most impactful things we can do as leaders.

Last but not least, Melissa and Johnathan explained how to help your team with burnout and “borrow from your future self”. 

Tune in to hear all about Melissa and Johnathan Nightingale’s management journey and the takeaways they learned along the way!

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Why management?


Dealing with skeptics in leadership programs


Mistakes made early in their careers


Learning from those mistakes and pivoting


Owning the job


Distaste for management


Is it possible to have a manager/peer relationship not fit?


Are you super f*cking clear?


“My expectation is…” & setting boundaries


Every space has rules


Servant leadership


The boss hat does not come off


Perceiving yourself


Trifecta of needs


Borrowing from your future self


Parting advice



Aydin Mirzaee (Fellow.app)

Melissa and Jonathan, welcome to the show. 

Jonathan Nightingale (Raw Signal Group) 03:26

Thank you. It’s great to be here.

Aydin Mirzaee (Fellow.app)  03:28

You know, I’ve been looking forward to this for a long time. You both are very obvious guests for such a podcast that talks about management and leadership. You were I think, to a large extent, pioneers in teaching management through things like social media and newsletters and the blog and your writing. And all of this. And I think like you know, to get started, I’d love for you to tell the audience how you both got very interested in management.

Melissa Nightingale (Raw Signal Group)  04:02

So, Jonathan, I both come from 20 year careers in technology. And when we were first getting rolling, we got promoted at very similar times. We were working at Mozilla in the very early days of Firefox. And we both started as individual contributors. And as the organization grew, our teams grew. And as our teams grew, we were really sort of thrown into the deep end and told, like, you’ll figure it out. This story is so common in technology organizations. But at the time, we sort of thought it was a product of how fast Mozilla was growing, how fast the web was growing. Now, you

Johnathan Nightingale (Raw Signal Group) 04:32

can tell yourself this story that it’s, you know, it’s situational. You know, obviously, other companies would be more intentional and careful about this stuff, right? It’s a big deal. There’s a lot of new skills to learn. Maybe it’s because we were an open source project, maybe it’s because we were growing faster than we expected to. We weren’t a standard startup. We didn’t have VCs that were going to give us that advice. Now, it turns out none of that’s true. Turns out almost every organization that’s growing quickly, is field promoting people are given the management responsibilities based on what based on their individual competence, right? You’re a good engineer, you don’t seem to be a sociopath. So we’re gonna have you manage some engineers like whatever it is, but not giving them the skills necessary to be great at that job. And I

Melissa Nightingale (Raw Signal Group)  05:12

I think for both of us, we sort of came up through the like, you’ll figure it out, like you’re, you’re clever, you’ll sort out the path eventually. And then got to the point where we were running sort of executive roles in fast moving startups and realize like, this is entirely learnable stuff. This is stuff that not only can you learn, but you can skip a lot of the like banging your head against the wall until it’s bloody phase.

Johnathan Nightingale (Raw Signal Group)(Raw Signal Group) 05:33

Yeah, it’s sort of, you know, it was a mix of like, we had energy about it. But also, we were frustrated by it like to watch. To watch, people have to learn this from a blank piece of paper over and over again, there’s one thing was like, Oh, you know, the learning curve, everybody’s got to climb that curve. But, but the people on your team are suffering while you’re climbing that curve, right. And you started to hear more and more stories louder and louder about people really having a bad employment experience. And so much of it to us, without making excuses. So much of it to us was at least partially explained by those, those bosses not knowing what they were doing, or what was expected of them.

Melissa Nightingale (Raw Signal Group)  06:09

And specifically, the frustration when we were getting started was that the loudest voices on this stuff, were either coming from academia, where they were sort of studying organizational design, but not necessarily specific to startup, and would put out research that sort of fell down when you tried to apply it within an organization. Or it was from the venture capital community where a lot of the folks who were who are sitting in had like a bird’s eye view of what was happening with technology startups hadn’t operated in a very long time. And so when they would make assertions about what it was like to manage and lead in a growing startup, it felt really flat, it felt really out of touch and out of date. And for us, we said like that, but isn’t our lived experience, and nobody out there is talking about what it feels like to actually try and lead in a fast growing org.

Aydin Mirzaee (Fellow.app)  06:50

Yeah, that’s amazing. And I think very relevant. And in your right, like, we don’t invest in a lot of leadership training in general, or like, it tends to be like a one and done thing, oh, we need to do leadership training. Let’s, you know, do this one thing. And then now people are trained, like, let’s move on. 

Melissa Nightingale (Raw Signal Group)  07:09

it’s like no dirty or words in startup, right? Then like you’re going to management training, right? A lot of folks find that like the the response internally, when you’re told that you’re rolling out a program like that is like crossed arms, lean back sort of frustrated or skeptical, very skeptical. And we get it, we were also very skeptical. 

Johnathan Nightingale (Raw Signal Group)(Raw Signal Group) 07:26

We see that all the time, like when we start with a new group of bosses, there’s always somebody just sitting back in their chair, right? Even even now that it’s all remote. They’re sitting back. And they’re not sure if this is going to be garbage or not, because because their expectation is not only that, like, I have to learn this as I go, but that anybody trying to teach me is gonna give me a bunch of stuff that isn’t very useful.

Aydin Mirzaee (Fellow.app)  07:47

Yeah, I think that that makes a lot of sense. And so what is it that you tell those people that are kind of leaning back cross their arm in their chair? Like, why should they listen, when you’re up there, and running one of your programs?

Melissa Nightingale (Raw Signal Group)  08:01

I think like you can’t sort of bang your head on the table or a bang, bang your hand on the table and say, Well listen to me, because I’m credible, because I’ve worked with 1000s of leaders, and it doesn’t matter if you don’t think that it’s going to apply to your work. The most valuable thing we can do is teach you something on Tuesday, have you really try and apply it on Wednesday, find that it works and have you come back hungry to learn more like that is the credibility as in the practical application?

Johnathan Nightingale (Raw Signal Group)(Raw Signal Group) 08:22

Yep, that’s it. There’s the nice thing about working mostly, we don’t work exclusively with startups, but it’s a lot of the we work with. The nice thing is that there’s this culture of like, I can just go learn it. Right that if this isn’t useful, I can drop that tool, I can pick up some other tool, right? So they’re, there’s an openness to learning new ideas, what they need to do is figure out like, are we? are we bringing useful tools to the conversation? Or are we bringing like personality tests and horoscopes and a bunch of stuff that they can’t really attach to and that struggle, you can get over really quickly. You just show don’t tell, right? You don’t say like we’re credible? Or you should listen to us because we ran big teams before you just say like, how are you one on ones going? Do they feel awkward and sort of useless? Do you not really know what they’re for? Let’s talk about how to know whether they’re working or not like, what’s some feedback that you’re sitting on right now that you haven’t given other people in your organization? Why is that? Let’s talk about how to structure that in a better way. And they go through the process and they’re like, Oh, crap, that that you would be much more useful. I’m gonna go try that tomorrow. Because it’s solving a real problem they have.

Melissa Nightingale (Raw Signal Group)  09:23

And for a lot of organizations, when like your management and leadership is the thing that’s most on fire, you know it because your team basically likes you double in size, but you have half the output. That’s a management problem, right? Like if you have sort of twice as many resources in terms of like the humans actually typing on keyboards, but half as much work is getting done. That’s usually a time where people know it’s time to call us. Although, you

Johnathan Nightingale (Raw Signal Group) 09:43

know, it’s funny that it’s true. People do call us but they don’t always diagnose it. Right. So they’ll say like, they’ll say something like my team is moving really slowly or my team is inviting, right? Just different people working on different things. They lack a sense of urgency that just sort of in their own little bubbles. And we say, well, how’s your goals process? Like? Well, you know, we tried okrs. And we the first quarter they worked and the second quarter, I think engineering still does them. But we started, let them fall off. I’m like, so let’s walk you through that, right? That often they can, they can name the problem without really understanding what’s underlying it. And when you give them those tools with a framework that says Like, this is how this thing accomplishes this thing for your business. It starts to all click together, that’s it’s the best thing for us to watch those skeptics lean forward because they want, they want there to be something useful here, they don’t want their job as a manager to be like a scam. Right? But they’ve just encountered a bunch of really awful management writing that are contradictory tools, and they just need some clarity.

Aydin Mirzaee (Fellow.app)  10:40

Yeah, I love that. So that’s a good good kind of point to take, which is, if you have increased in size, and your output seems to have slowed down, it’s not because that’s just what happens with scale. And maybe that’s something that’s acceptable. And that’s worthy of note, and probably a management problem. What one thing I wanted to do, though, was just go back to your earlier careers. I mean, you know, today you teach 1000s of leaders, management lessons, you’ve written a book called how fucked up is your management, which is an awesome title. You’ve done all these things. But I’m curious if we were to go back to your early careers. And you know, you talked about it being painful for teams to kind of sit back and be subject to you learning and climbing up this learning curve. What were some of the mistakes that you each made early in your careers that you obviously have now corrected?

Melissa Nightingale (Raw Signal Group)  11:38

Early in my management career, I found it really uncomfortable to be a boss. It’s a really uncomfortable thing. For a lot of people this shift from going from, I’m up here we work together, and there’s no power dynamic to I’m now in charge of you that there’s an inclination to give that power away as quickly as possible. And so the first time I managed somebody who was more senior than me in career experience, and more senior than me, and age as quickly as possible, I want it to be like nothing’s changed. You just do it, you do it, you do, it’s great. But I will just sort of step up and sort of be on the sidelines, and not really manage. And I think anytime you as a leader, or at least for sort of for my own career, anytime I as a leader, specifically put down aspects of management and said, like, those are tools that are management tools, but I’m not going to use them, there’s a there’s a good kick to ask why. And so in terms of things I got wrong really early on, just just pretending that the power dynamic didn’t exist was a big mistake.

Johnathan Nightingale (Raw Signal Group) 12:34

You know, for me, we talked with so many bosses, and some of them have had really horrendous management experiences of their own. But for me coming up, I didn’t, my default experience, I had four or five, maybe six different managers before I got my first management gig. And the word I would use for all of them was just sort of apathetic, right, they just didn’t take management very seriously, they show up to the occasional one on ones like eating your vegetables, they knew they had to do it. But like, I was really the one pushing for any, any change in my role in my work, whatever. And I said to myself, I remember thinking, you know, the first day I become a manager, I’m going to be better than they ever were. Because I’m going to give a shit. That’s it. I’m just going to care. And in the process of caring, I’m going to show up for my people really differently than my own bosses have shown up for me and, and I did, I had long searching one on ones I gave lots of feedback, lots of opportunity for growth. Congratulations, Jonathan, what a great boss you are, I had run to the other side of the boat, I was like, utterly ineffective at giving them feedback when they screwed up. I was utterly ineffective and holding them accountable for missed deadlines for missed commitments to other teams. Because I was so focused on the relationship and then having the experience of a caring and involved boss, that I’d lost the plot on effectiveness for my team and like what we were accountable for and whether I was pushing them. And that was a hard thing for me to unlearn right how to step back into holding those people accountable, and not worry that you’re going to jeopardize the relationships you just spent? So long building, particularly with people who used to be your peers like that was it took me work to undo that one and realize that that doesn’t hurt my working relationship with those people. It just makes the boundaries clearer. But that’s it’s easy for me to spot that as a mistake. Now.

Aydin Mirzaee (Fellow.app)  14:17

I feel like both of what you said have similarities in that, you know, you Melissa wanted to give away control as soon as you got in. And I feel like there’s a lot of relatedness to holding people accountable. And I find that it is also particularly challenging if you do have someone who is senior and yours or an experienced than you. How did you both turn it around? Like how did you realize that you know, Jonathan, you were being too friendly and more so you weren’t taking the control? Like how did you pivot out of that kind of situation if you happen to be in it?

Johnathan Nightingale (Raw Signal Group) 14:54

It took a while. But for me, I started to really internalize like, wait a minute, I’m being paid to do a job. probably wasn’t until I was a director honestly that the penny dropped for me, I’m being paid to do a job, I got a bunch of people on payroll as part of my organization, and we’re here to do something. Right, I started to be involved in directors meetings and be asked by my peers in directorship and above what my team was committed to right and how we were going to deliver that. And the more I started to engage with, like, Oh, crap, like, by 14 people on payroll in a startup fully costed, even back then, that’s a couple million dollars that the organization is spending to get what, right, and as I started to be in conversation with my peers and management, that’s when I realized, like, I have an obligation here to the organization I have, I have things that I’m being paid to get done for us. And then I would turn around to my team and be like, wait a minute, we’re not going to get these things done. And how do I do that? And sort of pulling that into conversation and saying, like, yes, my, my relationship with my team is a superpower, it means I can ask a lot of them because they trust me. But I need to get clear on what I’m actually committed to. That, for me was a real unlock realizing that, that I had an obligation not just to my people not to be a shit umbrella, like you hear people use that language, right? I just got to insulate them, I just got to get everything out of the way so that they can focus on their work. That’s part of it. But also that we’re making a set of commitments, we’re accountable to other parts of the organization to fulfill those commitments. And that once I really let that in and started writing goals that advance the organization’s goals, instead of just writing down what my team was doing, and calling those my goals, it was a real inversion for me and a powerful one, it didn’t hurt my relationships with my people. It gave them some stretch, it gave them a North Star.

Melissa Nightingale (Raw Signal Group)  16:36

Yeah. And I think for me, I think the mistakes that you make that you’re making, because it’s the first time you’re doing something, often having an opportunity to like really just sort of basically screw it up. But then you’re like, Okay, well, I know what that mistake is, I’m not going to make it again. And I think the mistake of that period of boss transition and not making those sorts of roles, and that power differential sort of better defined, you do that once, ideally, you don’t do that every time, right. And so I think for a lot of leaders, the challenge of sort of going from being an appear relationship to being a boss dynamic, once you’ve done it, then the next time you are more clear about it, because you know, the implications, you know, the downside of it. And so for me, when I sort of walked into roles where I was hiring my team, or where I had peers who sort of came into a management relationship with me, just being really clear in the first one on one of like, hey, like saying out loud, like, this is weird. We used to be peers, we’re not peers anymore. And so here’s what the here’s what the expectations are. And here’s what shifted, but I think for me, that pretend that nothing has shifted it, it clearly had,

Johnathan Nightingale (Raw Signal Group) 17:38

Yeah, if I connect those dots, I think the thing that we’re both really saying is that you have to sit in the job, that it’s a real job. And there’s such a temptation. But listen, if there’s such a temptation to pretend it’s a fake one, when I’ve heard so many bosses, I’ve been the boss, saying it’s just any business card, like nothing really changes about the work that we’re doing, like, I got to sit in more meetings than you do. But other than that, like, you’re the one doing the real work, um, just administrative overhead, like all of that stuff, is a way of not owning what the job actually is that like, I have an obligation here, I’ve got work that I’ve got to do. It’s legitimate work. And that work is around communication and coordination of effort, which is, which is important, especially as organization grows.

Melissa Nightingale (Raw Signal Group)  18:17

Yeah, I think so much good stuff falls out of sitting in it. It is a real job. And it’s a real job that I can do well, or poorly. Like we said before, a lot of what we teach leaders how to do is how to assess whether it’s going well, or poorly. And that starting point of like, it’s a real job, it is a set of discrete skills and their skills that you can get better at, you can sort of like I think we work with heavy technical organizations who like to sort of take things apart and put them back together. And making it scriptable is one of the pieces that’s really helpful for a lot of leaders is like, Hi, can I stare it down and say, how is it working? And if it isn’t working? Can we talk through what I do instead?

Aydin Mirzaee (Fellow.app)  18:49

Yeah, one of the things that you said, Jonathan, this management overhead concepts, you know, if I sit in more meetings, you do the actual work, why do you think that people just generally have this almost like distaste for management, especially like I feel, especially in technical organizations? But where does this come from? And why is it that we have this perception of managers in general? Is it just because we have so many bad bosses out there? Like, why is it?

Johnathan Nightingale (Raw Signal Group) 19:22

I think that is half of it? Like, would you want a business card that says like, you know, gives you the label? That is the butt of every joke, and and you know, even if you sort of ignore that, that is often very ineffective, right? Like they’re great engineers and poor engineers that are great marketers and poor marketers, right? But many people have had an experience that involves a lot of really bad management, even if they’ve had a great boss. They remember that person because it’s such a standout right, because the people they report it to before and after that person were really mediocre. Like, it’s a weird thing that we do that with the exception of MBAs, which is not quite the same as first line management anyway, nobody goes to school for management, they go to school for whatever their individual discipline was, and then we elevate them into management. And we don’t equip them. And then we act surprised that their incompetence, I think, I think that’s one piece of it. And I think the other piece is the thing Melissa was talking about, about being really uncomfortable owning that power, that it’s really, you want to do everything you can to not seem like you’re putting yourself above other people, and you’re not above them. But you do have power that is that you got to reckoned with.

Melissa Nightingale (Raw Signal Group)  20:26

I also think like in terms of why specifically tech doesn’t value management or historically has had a hard time valuing management. It’s like so much of how we write our stories around how tech organizations come up how startups are built is like, either like a lone wolf in a dorm room, right. And there’s not a lot of sort of priority on collaboration at that moment, right? Like, if it’s just me in a dorm room hacking on a computer, or me in a basement somewhere hacking on a computer. Like, there’s not a lot of management in that story, honestly. And I think it’s also one of the things where if you think about tech organizations as they grow, there are a bunch of things sort of early on where you’re like four people around a table, right. And in that moment, there isn’t a lot of management present in that moment. But as the organization scales, you hear you hear this sort of more like it got to 150, people got to 200, people got to 1000 people, and the wheel started feeling like they were coming off. And even in those moments, we don’t ascribe that to being a management failure. We talked about that being a sort of byproduct of success, but I think it’s because management is missing from a lot of how we tell our startup stories.

Aydin Mirzaee (Fellow.app)  21:27

Yeah, I think that makes a lot of sense. One question that is kind of related is, you know, you were saying that, you know, sometimes you’re gonna have a boss and, and then and then you do comparing, well, this boss is a lot better, a lot worse than, you know who I had before. And then you may make some judgments based on that. And when you become a manager take on certain qualities. But one of the questions I have is, is it possible that there’s this thing of like a manager and kind of employee fit like, besides like this concept of a cultural fit? Is it possible that like, sometimes there isn’t a fit between like a manager and employee, and it’s not that it’s a bad employee, or it’s not a bad manager, but maybe it’s just like a bad fit for that team or the way that that team happens to operate. Sometimes Sometimes it’s the

Melissa Nightingale (Raw Signal Group)  22:21

sometimes but the broader risk there in terms of like, if I’ve got a boss who says like, it’s just not a fit is that like, what, the reason that it’s not a fit is that I have a bunch of assumptions in my head that I have failed to say out loud, and that person is bad at guessing them. And we see this all the time in organizations that a lot of leaders, they make the first hire, and the first hires in their own image, the first hire somebody who thinks like them, may may look physically like them, but certainly, like came up through a path that is very similar to their own path. And that the more folks sort of deviate from that model, the harder they have time they have being managed by that person. So the shove for the leader in that moment is maybe maybe you’ve got sort of a misfit or misalignment there. But where have you done work to make sure that you’re creating that your management style is one where a lot of different people can thrive within your organization. Because if you only have a leadership style that works for people who are like you, you’ve got some limitations. And I would say you’ve got some bias that you’re bringing to the role.

Johnathan Nightingale (Raw Signal Group) 23:20

That’s it, it’s not that it never occurs, it’s that it’s a really dangerous lens to especially to apply to your own management, because you’re going to use it as a rationalization. Like there’s a, there’s a great bit of danger, in that, that you’re going to that if if I look at 1000 cases of manager, employee misfit, I boldly predict, I’m going to see gender difference, I’m going to see racial difference, I’m going to see ability difference, right that I’m that the people who just naturally I tend to vibe with are people where I share a great deal of life experience. And the people that weirdly just happened to not be a good fit are the ones who come from a really different background, or who are dealing with a different sort of life context right now. And that it’s not that it will never happen that a fully competent manager will just be not really compatible with how someone wants to be managed. But it’s very rare because a fully competent manager knows how to talk to different people and situate things and, and clarify expectations, and not take for granted a bunch of those shared assumptions. And it’s one of the things we say to the bosses we work with, like most people show up wanting to do a good job at work. Sometimes you have someone who’s just really been fried, who was burnt out whatever it is and just wants to sabotage the business. Most people want to do good work to be recognized for good work to collaborate with people that they respect, right. And so in most cases, a boss is doing a clear job of articulating expectations and measures for success and stuff like that is going to find employees thriving that’s the danger. It’s just it becomes a rationalization it becomes a tool for justifying exclusion but a different name.

Melissa Nightingale (Raw Signal Group)  24:55

And we talked to leaders about this idea of super fucking clear, right like are you being super fucking clear? And like not not like, Am I clear in my own mind? But like, specifically like staring it down like did you did you say it in a way that was super fucking clear and for a lot of leaders like just getting getting practiced at maybe that means I have to play a little bit with like I said it this way in this meeting and I’m gonna say it a different way the next time just to make sure that I’m really communicating what I need to hear.

Johnathan Nightingale (Raw Signal Group) 25:20

There’s a it’s you’re allowed to expect your people to show up like grownups at work, you’re allowed to expect that if you hire, you know, a bookkeeper, that they know about bookkeeping, right? But so many bosses have so many things that they consider to be obvious that they’ve never said out loud, right, Melissa wrote a post a chapter in a book called obvious to you is not the same as obvious. And that shove is really important for a lot of bosses that you are going to take things for granted, because of your time with the organization because of your access to the CEO because of whatever it is, and be surprised when other people don’t act on that obvious information. And it’s always worth asking yourself, is that a professional failure on that person’s part? Are they just not competent at the thing we hired them for? Or are they missing context that I have? And that I’ve done a bad job of sharing?

Aydin Mirzaee (Fellow.app)  26:06

I would love an example of super fucking clear means, it you know, if it’s an imaginary one, if it’s an anonymized, one have a situation where like, maybe an expectation wasn’t clear, and how you go about the process of figuring out because this is one of the hardest things, right? Like, it’s not just like a human, like a relationship, like issue. It’s also like a business issue, right? Like you go into business, you have this idea. You may have these assumptions. And maybe you haven’t, like, clearly articulated to yourself or done the deep work of like, what are the assumptions we’re making? You know, in our business plan that we’re not like outright saying, and I think it’s probably the same in I guess, work relationships. So yeah, if there is an example of what would love to hear one. Hey there before moving to the next part of the interview, quick interjection to tell you about one of the internet’s best kept secrets, the manager TLDR newsletter. So every two weeks, we read the best content out there, the greatest articles, the advice, the case studies, whatever the latest and greatest is, we summarize it, and we send it to your inbox, we know you don’t have the time to read everything. But because we’re doing the work will summarize it and send it to your inbox once every two weeks. And the best news is completely free. So go on over to fellow dot app slash newsletter, and sign up today. And with that said, let’s go back to the interview.

Johnathan Nightingale (Raw Signal Group) 27:38

Sometimes they’re really small, right? So a lot of bosses avoid structure because it feels rigid and procedural and stuff. So they don’t do things like, like, have an agenda for a one on one or record often action items coming out of it, right. But if you start doing that, it becomes pretty easy in our next one on one to check in and say, Hey, you said you were going to email marketing about the thing? Did you email marketing about the thing? Like No, I didn’t do that. Once. Okay, fine. like everybody’s, particularly during a pandemic, everybody’s gonna have drop balls from time to time, right? That recording of action items is supposed to be a way that we help each other remember those things. But if it becomes a continuing thing, one of the phrases we have bosses practice is my expectation is right, my expectation is that if we say a thing is gonna happen, that you do whatever you need to do on your side, and let me know if you need other things for me, but that, that you’ve committed to that, and that thing is gonna happen. And once I get it, but on an ongoing basis, there’s a problem, because my expectation is that the commitments we make in this room happen, right? That that is very uncomfortable for some bosses to say, especially bosses like me early in my career that was so focused on the relationship,

Melissa Nightingale (Raw Signal Group)  28:43

we also see it in organizational values, right? We’ll see organizations or we’ll hear from organizations that say, like, people are behaving in a way that is not in keeping with how they should behave within this organization. We’re like, cool, where was that written down? And they’re, they’re yelling at each other, like, full on yelling at each other. They’re screaming in meetings, I’m like, okay, is that do you have it anywhere? That that’s not how you do within your organization, right? That the expectation in your organization is that like, people are maybe you disagree respectfully, or whatever, whatever it is. And for a lot of folks, they feel like Well, that’s, that is obvious, right? Like, clearly, you’re not going to go into a meeting and just like yell at your colleagues, but there are cultures where they do, right. There’s cultures, there are cultures where that’s just how you show that you’re passionate about your perspective, is that you’re willing to go to the mat for it. And I think for a lot of founders in particular, we have a set of things where we just like no that that would be totally out of bounds. If you haven’t written it down. And you’re onboarding people into an organization without saying it. Somebody is going to sort of like trip that wire and it won’t be their fault if you didn’t tell them.

Johnathan Nightingale (Raw Signal Group) 29:48

This is really important too. Because we see this all the time, especially with love in my heart with founders and CEOs, where they discover an expectation they didn’t realize they had where they discovered a value. They didn’t realize they had Write that somebody does something and they’re like, Oh, shit. Like, we never wrote that down. We never, we were never clear about it. And sometimes it’s really minor stuff. Like, if you ask 100 hiring managers, whether they expect to receive thank you notes. 50 of them will go to the mat and be like, if you don’t send me a thank you note, you’re out. I don’t care how great you are. And the other 50? Or like, Is it the 1870s? No, you don’t need to send me a thank you now, like, but that expectation is like as a candidate that’s totally impacting my ability to get a role in your organization. And I don’t, if I was raised with that, then I have that. And if I wasn’t, then I don’t and like, how am I, I will be so happy to write a thank you note. Write that whatever it is being able to articulate that and spot it when somebody pisses you off. Be like, Okay, wait, did we? Did we ever say that that was a thing, right? You can say, Oh, we should take some things as common sense. But we can also just be declarative.

Melissa Nightingale (Raw Signal Group)  30:51

Similarly, during lockdown, we’ve got bosses who are sending emails at 11 o’clock at night, is the expectation that I respond to that email at 11 o’clock at night? Or is the expectation that I wait until tomorrow morning, when I’m sort of clear headed and awake and have had coffee? And either one can be the right answer for your organization, I have a preference about which one I’d like it to be if it’s an organization where I’m working, but either one can be correct. But if you haven’t said it out loud, like how, how am I if I’m new within your, your team, how do I know?

Johnathan Nightingale (Raw Signal Group) 31:17

Please write and I see an email from my boss at 11 o’clock. And I just start this habit of checking my email in the middle of the night just to make sure I didn’t miss anything. And my boss might be mortified to hear that that’s what I’m doing. Because that was not their intent at all.

Melissa Nightingale (Raw Signal Group)  31:30

Just super fucking clear. Is that what you want? Or is that not what you want?

Aydin Mirzaee (Fellow.app)  31:33

That’s so interesting. It reminds me of a situation that, you know, we were discussing this at work, which was, you know, obviously pandemic, people working from home, you have kids coming onto the screen, or a dog comes in and like, or a cat walks over your laptop, or one of these sorts of situations, and someone on our team was saying like, you know, sometimes I feel embarrassed like that, you know, something like this happens. And so maybe we should have make it permissible that people can have their video off or, you know, or go on mute or something. And I was like, Yeah, I mean, I think that makes sense. Yeah. Why don’t you just do that? It’s like, Oh, well, like, I didn’t know that. That was okay. And it’s kind of like, Oh, I just assumed that everybody knew that. Well, yeah, obviously, everyone’s at home. So clearly, like, these things are gonna happen. But it wasn’t super fucking clear. Like he said,

Melissa Nightingale (Raw Signal Group)  32:27

Oh, I mean, I’ll give you an example. Right? We’re working with leaders. And we’re doing like, leadership training, management training with bosses all over the world right now. And one of the things that happens is we get on and they’re like, Is it okay, if I chew? Yeah, like, is it? Is it cool if I eat while we do train? And so we obviously shifted sort of our patter to salad, of course, like, please feed yourselves. We don’t want to teach like hangry managers about sort of delivering hard feedback, like that’s hard, that’s a hard audience. But a lot of folks, I think feel like unless you’ve said it out loud, like my, you know, I’m not sure. And I’m living in this sort of in between space of what’s Okay, and what’s not okay.

Johnathan Nightingale (Raw Signal Group) 33:00

Yeah, you know, every fundamentally, every space has rules. Right. And I don’t mean that in an authoritarian way, I just mean that we have shared expectations. We always do. Zoom rooms are a great example, right? Where we always do, but in a context where new people are coming in, they don’t know the rules. And so a fair question for any corporate culture for any manager anywhere is like, how are they going to learn them? And for that matter, to the five of us on my team, I’ll have the same understanding of what they are, right? So anytime we start work with a new group, for instance, we’ve got a set of things where like, here’s how the conversations go in here. Here’s what we’re asking you all to commit to. And here’s what we’re committing to as well. And there’s even stuff where we say like, here’s how we zoom, right? You have the participant window open in the chat window open, because we know that some people will not put their hand up to ask a question, but they will put it in the chat. And we want everybody to sort of be in the same place. Right? That, that that kind of you know, you own your own mute button, if you need to jump in, just jump in. But we reserve the right to mute you if you go to the bathroom and forget to mute it. Like maybe those things are obvious, but saying them out loud. Just it just lowers everybody’s sort of burnout levels in a time where everybody’s burnout levels are very high. And makes it clear like these are the rules of the space. I understand them. And we all heard Jonathan Melissa say them together. So we’re all working from the same page. I know I’m allowed to unmute if I need to. I know I’m allowed to eat if I need to.

Melissa Nightingale (Raw Signal Group)  34:21

And it’s not about coddling, right. If you’ve got bosses listening, who are like that sounds like coddling. It’s not about coddling. It’s about creating the space for your people to do innovative work, right. And if you want them spending all of their brain cycles on whether it’s okay to face mute or not face mute, they can spend all their brain cycles on that but it probably you’ve got more important challenges that you need them solving. And so the more you can relax the like that just the noise and the shit like that and sort of get that out of the way, the more opportunity for that for folks in organization to do really amazing work.

Aydin Mirzaee (Fellow.app)  34:50

So, there is something that I wanted to ask you because we know, we started off the conversation talking about countability acknowledged Like that this is a different role. And there are powers that you now have. I’m curious because one of the things that is a very popular language today is servant leadership. And I think like when you just say the term servant leadership, it just sounds like you know, it’s a one sided thing. And it almost sounds like you have no power. So I am curious what your if you agree with the concept of servant leadership, or like how you define it, and how it can actually be practiced,

Johnathan Nightingale (Raw Signal Group) 35:31

such a delicious phrase as a servant leader, like if you’re somebody who feels uncomfortable, having power over other people, and you find this sentence, you’re like, that’s what I am. I’m that, right? Because it just, it gives you a smart sounding way to give away all that power and say, Oh, no, they were inverting. You know, you don’t report to me, I report to you, my whole job is just to get obstacles out of your way. It sounds delicious. If you want to dive into it. It comes from an essay from the 70s by Robert Greenleaf that the leader is a servant. And that is fine. I think it’s a good thing. I think Melissa and I would both agree that the leaders should understand their role to be at least partly about helping their people thrive. Right that that’s, that’s a real core element of it. It’s not about lording power over them, it’s really about creating a space where they can be excellent. And so in that, that much I totally I’m here for what we’ve learned is that a lot of the people who use that phrase, sort of like before, when we were talking about, oh, there’s just not a good manager employee fit. A lot of the people who use servant leader as a self describing phrase, or using it as a way to give away power and have not done the work. Right, that servants don’t fire people. Servants don’t say you’re not getting a raise. Servants don’t say you screwed up. And like if you do that, again, I can’t put you in meetings with clients anymore. Right? Those are not those are not things that a servant says. And it’s, it’s worth asking yourself like, is that? Are you doing those things? Because hard feedback is service, right. But a lot of people who take that phrase on for themselves are using it as a way to get out of the awkward parts of management.

Melissa Nightingale (Raw Signal Group)  37:06

Yeah, I think for a lot of leaders, like certainly, like the idea of servant leadership comes from a really beautiful place, sort of the authoritarian, awful job of management, and they are trying to react to a set of things. But when you look at it in practice, when you sort of talk to folks who are doing that work, or folks who are managed by people who self identify as servant leaders, often there’s a massive gap in terms of whether folks are actually managed, like, like capital M managed, are they doing the management? Or have they sort of like, sort of stand on the sidelines and are back to shit umbrella?

Aydin Mirzaee (Fellow.app)  37:35

Yeah, I think that’s a very valuable way to look at it. And it definitely is a spectrum. You didn’t want to have John-Michel, who’s the CTO at Shopify, on the show. And one of the things that he mentioned was, he called it like the 25 50 25 rule. So 25% of the time, you know, I’m your boss, and I’m going to tell you and hold you accountable, and so on, so forth. 25%, you’re my boss. And, you know, I’m gonna unblock you and help you and 50% of time, we’re peers, we’re gonna brainstorm and work together and problem solve. And I just like that, because it wasn’t, it seemed less like a, there’s just like a one size fits all like, this is the model, just do that. It’s, you know, and don’t stray from it. But

Melissa Nightingale (Raw Signal Group)  38:18

It’s total bullshit. Like with respect to John-Michel, like, it’s total bullshit, that you are never not my boss. Even when we’re peers, you can still fire me, even when we’re pretending that I’m your boss. Like, you can still decide whether I get a raise or not like, there’s no point in time, where you as my boss are not my boss.

Johnathan Nightingale (Raw Signal Group) 38:35

And it’s so attractive. And I get what he’s trying to say he’s trying to, he’s trying to describe a workflow scenario about like, how many of my utterances are meant to be command utterances. And how many of my utterances are meant to be consensus utterances. Right. Okay. But framing matters. And, and it’s really hard. I have been on a team with a VPN when I was a director and or a manager, where I wanted, like, where we wanted to be friends, and where he wanted to be friends where he didn’t want to have that sort of title. Right? where we’d go out, we traveled a lot of mazola, where we go out to the hotel bar and just talk about whatever and like, isn’t it nice that were appears? And maybe he felt that way, but I never did. You never forget that. Like, this is a person who can promote you or not, this is a person who’s showing affinity to you. And that generally is a positive forward looking indicator, right? And that, like, if I say, No, I don’t really want to do that. I’m not gonna get fired, probably. But I’ve I’ve missed, right, that might be a career limiting move to do that, and hopefully not, and hopefully, that leader governs themselves in ways that are more equitable than that. But it’s a dangerous signal to send and when somebody self describes that way, I’m like, I don’t know. I don’t know what it’s like to work for you. I don’t know how true that is of the people who work for you. But I know that for me, bosses who wanted to be peers might have believed that and I never did. 

Aydin Mirzaee (Fellow.app)  40:03

That’s definitely a very different way to look at it. I definitely see the point, you’re right, it does never change. And that’s always there. And it was very interesting just to hear the way that you put it, which is like, even if you as a manager think that you’re acting like you appear. The person on the other side definitely is not, it’s easy to miss that.

Melissa Nightingale (Raw Signal Group)  40:26

It matters a lot in in tech, in part because we have such blurry lines between when we’re in a work context and when we’re socializing less so during pandemic, obviously, but but sort of in the before times, when you you leave the office and everybody’s grabbing a drink, like, Are you are you my boss’s boss in that moment? Or are you my peer? And like, if I have like, a third drink, and I say something foolish? Is that okay? Is that not okay? Is that showing up in my performance? Or like there’s just a whole bunch around it? Where, where I would prefer that if you’re in a management role, like you just recognize that the boss hat does not come off?

Johnathan Nightingale (Raw Signal Group) 41:01

Yeah, we had. We worked for a CEO part of our time at Mozilla. When Mozilla was growing very quickly, and he got caught flat footed, because he would say in meetings, yeah, even a designer at Apple before that. And he really liked getting into the product details. And he would say in meetings we’ll have we thought about doing it this other way, right? And just ask the question, and then three months later realized that there was a whole product branch built off the CEOs direction to think about going another way, right? And he’s like, No, I was just asking a question, right? And it’s just, it’s a moment of not understanding the power that you hold in the room and wielding it really carefully, right? That, that it might feel cumbersome. To say, I’m not asking this as the CEO, I’m just asking a design question. Because I’m invested in it. This is not a direction like that might feel like so much work. But obviously, he was not the same as obvious. It was obvious in that moment to him that he was just asking a question to appear on the team. That is not how, you know, employee 136 would only ever experienced Him as their managers, managers, managers manager received that feedback, right. And so it’s just, I guess, I would say to the people listening to the podcast, be careful. If you are tempted to self described that way. I, you can’t read other people’s minds. But there is a high likelihood that your team does not experience that the way you do. And you don’t want to be in a position where you’re self evaluating your management very differently than your team is experiencing your management. That’s,

Aydin Mirzaee (Fellow.app)  42:33

that is fascinating. And I love the framing of that’s not how employee 136, who’s only experienced you, as you know, the managers, managers manager is going to perceive that. So I think it’s very interesting, one of the guests that we had on board was talking about her experience doing stand up comedy, and one of the things that she brought up is like, in order to be a very effective comedian, you have to first understand how the audience is going to perceive you. Like when they look at you just like by looking at you, how do they kind of perceive you and you know, some of the stereotypes that they might associate with you. And then like, you have to understand that first, before you can start to communicate, and I feel like it is the same if your manager, your CEO, your VP, there’s a lot that comes in, and you kind of have to understand that before you start to communicate.

Johnathan Nightingale (Raw Signal Group) 43:23

I love that. I think that makes a ton of sense and and is a much better framing of it to say like, I think any manager at any level of seniority would be better at their job. If they started by saying like that, how do I? What is it when I come into a room? What is it when I ask a question, what is it when I send an email? And from that place? How do I adjust the conversation I’m having to, to acknowledge that.

Melissa Nightingale (Raw Signal Group)  43:48

We also talked to leaders about this idea that there’s like a trifecta of needs that we’re always trying to balance, which is like, Who am I? What does my team need for me as a leader like Who am I as a leader? What does my team need for me as a leader, and then what does the organization as a whole need for me as a leader, and sometimes those things are like, super well aligned. And sometimes they’re way out of step. And for a lot of leaders like just figuring out sort of how to manage that, that triangle of needs. I think it can be really helpful,

Johnathan Nightingale (Raw Signal Group) 44:13

your will not surprise you to hear that. You know, anytime we’re working with bosses, one of the first things we open with is like here are practical skills that you can learn on Tuesday and apply on Wednesday. That’s really important, right? Not just because there are real skills, and we want them to have those skills, but also because seeing that investing in your management can pay off is a really important entry point. But by the end of our programs, more of the work is on Who am I as a leader, and is it working for me, right? Like, I tend to bias all the way towards consensus. And that means my team loves me, but it means we’re very slow to reach decisions. Is that good or bad? And if I don’t, if I don’t think that’s working for me, how can I be intentional about moving it? Right now that self awareness is you know, it’s a good predictor of long term management success, but it’s hard. It is Some work that is different than learning the skills but also really important.

Aydin Mirzaee (Fellow.app)  45:04

Yeah. And it’s also the sort of thing that, you know, I get the sense it’s not a one and done. It’s a constant, I mean, self awareness. I feel like it’s a spectrum. It’s probably like driving and that everybody thinks they’re better than average. But it’s a spectrum and you’re always working on it. One thing I did want to, you know, ask you as, as we’re getting close to time, is you have this, you have this amazing newsletter, and you were just telling me about the the domain name, what is the domain name again?

Melissa Nightingale (Raw Signal Group)  45:37

the domain name is worldsbestnewsletter.com. And I have no idea still, why that was available for purchase.Wasn’t it like one of those like, 399 domains, kicking around? I’m like, how has nobody scooped this up? 

Johnathan Nightingale (Raw Signal Group) 45:50

You can find it on our corporate site, right? It’s on rawsignal.com. But worldsbestnewsletter.com is the one that people remember.

Aydin Mirzaee (Fellow.app)  45:57

And you know, the thing I really love about your newsletter is that we always know what’s on top of your mind, the latest and greatest things that you’ve read and your commentary about. So it feels very current. So it’s not just management, but it’s also like management with a current lens. And there is this one, I guess, like, issue where, where you talked about this, this concept of borrowing from your future self. And I thought it was just like a very clever way to phrase the concept. And I’d love for you to talk about what it means to borrow from your future self for leaders.

Melissa Nightingale (Raw Signal Group)  46:34

And this is something that we were seeing a lot where we’re talking to you in March, right. So it’s about a year into lockdowns and a lot of leaders leading from a pandemic place. And one of the things that we were seeing was that more of the bosses that we were talking to, wanted to talk about burnout, not only for their own teams, but for themselves. And it wasn’t like a little shift, it was like a 400% increase in terms of the number of times we would hear burnout in conversation with bosses.

Johnathan Nightingale (Raw Signal Group) 47:01

Yeah, it’s it. I don’t know, I’m careful about using a word like dire. But like a lot of a lot of the bosses that we were talking to are trying their best. But the questions we’re getting is not just about like, how do I help an employee with burnout? It’s how do I help all my employees with burnout, when I’m also burnt out, right? There, there’s a real depth to it. And there’s so many articles out there that say, well, you need self care, you know, you just need to if you need to take a break for a couple hours, just give yourself a massage and your chair or whatever, you should do that. And it’s, that’s great. That sounds great. But many of the bosses that we talked to can’t, they’re slammed because like they don’t have casual conversations anymore. Everything has to be a zoom call. And so there’s zoom calls getting time slice, you know, 15 minutes, 10 minutes at a time. And they’re, you know, their workday has increased by two or three hours a day. And there’s just, there’s no room for it. And so we said, okay, so maybe present you as screwed. Maybe present you your calendars totally booked up, right? But what we need to start to build systems in place, because you know, it can’t keep going this way, you know, it’s not sustainable. And so that’s when we started talking about future you.

Melissa Nightingale (Raw Signal Group)  48:10

Yeah, and how do you put in the things in place today, like we were talking to leaders who are so underwater that that their HR team would be like, take a vacation, just take, take a couple of days, like, sign off, unplug, turn off Slack, whatever, it’s gonna be okay, they would take the days and they would, they would have like a week of Sunday scaries, right, where they’re just the feeling in their gut was so much stress at what they’d be coming back to, that they didn’t even get any of the the sort of relaxation or any of the benefit of taking a weekend unplugging, these was all dominated by the anxiety of what they’d face when they came back. And so we started saying, like, you can’t, you can’t fix that in that moment. But you can start to build forward. And as you’re thinking about what it’s like to build forward, just looking at your calendar and saying, like, Where are there decisions that I can make right now in service of my future self. So if I am a team lead, and I’m responsible for individual contribution, and responsible for management, and I don’t have any more flow to be able to do my own work, like, if your flow isn’t on the calendar, your flow isn’t happening, or your flow is happening, like after hours at nine o’clock at night, or 11 o’clock at night. And so just talking to leaders about like, Where can you build it back in so that when you go to reach for it, it’s there.

Johnathan Nightingale (Raw Signal Group) 49:15

That’s the you know, the core idea of that newsletter was that if you look forward, maybe it’s next week for you. Maybe it’s a month out. There’s some place on your calendar that still has room, right even with all the recurring meetings, a lot of what’s eating up our days right now, is that the little drive bys, they’re like, Hey, can I just get some time today, right? But the nice thing about those is that those people asking for time will route around the existing blocks in your calendar. And so I think that you can do is you can look a couple weeks ahead to where there is some space and you can start to block that off and say this week sucks. It sucks for the same reason last week sucks right? But three weeks out I’ve actually got some room and I’m way overdue to do some team planning or to think about like, we haven’t even written 2021 corporate goals yet. Whatever the thing is, and say like I’m gonna block time there. And it’s not perfect, right. And I think one of the greatest crimes that Google has ever committed is that when somebody sends you any calendar invite, it automatically gets added to your calendar. And so everybody else gets to control your time. And that’s really hard. But most people will avoid the existing blocks, they’ll try and find the white space on your calendar and put something in there. And so if you’ve got a private block in there, or if it’s going to be suspicious to have a private block, schedule it with the peer and say, This is our two hours synced up and just the two of you are helping each other now, right? Because you’ve both got that. And you can be on zoom together quietly typing or, or not. But finding that protection is the thing that you can do today to help future you because current you has already been screwed by past you.

Aydin Mirzaee (Fellow.app)  50:42

Love that framing, it’s, it’s, it’s so nice to be able to refer to these as different people. It just allows you to think about things in a different way. I love that. Melissa, Jonathan, this has been incredible, so many great insights. And, you know, so many things to kind of reference and I’m excited to share this with everyone. One question that we always leave our speakers and our audience with is what parting advice, resources tips, or just you know, words of wisdom would you have for all the managers and leaders out there looking to get better at their craft?

Melissa Nightingale (Raw Signal Group)  51:22

And I’d say right now, a lot of leader is the part that we tend to be the tool that we tend to sort of overuse or the muscle that tends to be overworked in our own management practice, is though the downward rotation, right is I as a manager, focusing on my team and the people who report to me, and the muscle that’s underdeveloped right now, particularly because we’re not physically seeing those people in person is the across muscle, the across management muscle for most organizations is is essentially the success or failure of that organization. But for a lot of leaders, I don’t see those people they are far from me, I’m not in meetings with them, I’m connected to my own team. But that connection and the link between myself as a leader and the other leaders in the organization. They’ve atrophied now is a great time to go reinvest in building those muscles,

Johnathan Nightingale (Raw Signal Group) 52:07

not just because it’s nice to know what other people are working on. But because it’s very hard to prioritize for your own team, if you don’t know how it connects to other pieces, right, then when everybody’s fried, and you’re like, something’s got to drop, you’re the one we’re paying to have the broader context, you’re the one who’s got to see what’s going on in other parts of the org, so that I know as a person on your team, which things like put down and which things we absolutely have to deliver, because other parts of the organization are counting on us. And we’ve got so much space for how hard it is to do that right now. And but it’s the thing that only you can do, that your team can’t do for you that you can’t delegate off because you’re different meetings than they are.

Melissa Nightingale (Raw Signal Group)  52:45

And for a lot of folks like part of how we help the future you is we stopped doing work twice. And in a lot of organizations right now we’re doing work twice, because we just don’t have the ambient awareness of where the other work is

Johnathan Nightingale (Raw Signal Group) 52:54

happening within the organization. And the last thing I think I’d say on that is that, you know, maybe obviously, because of the work that we do, but if you’re a boss, and you’ve never gotten any training, you’re not alone. 80% of the leaders out there have never had any training. The stat is that between the first time you get management as a job, and the first time you get training, it’s about 12 years. Wow. So most of the people doing it, have never been taught how to do it. You’re not alone on that. But it’s not fair. Right. And so whether you talk to HR, whether you’ve got internal tools, whether you can get mentorship from somebody more senior, finding some way to start building some systems around this stuff is how you get yourself above water, like it’s a learnable set of skills. It’s not just a natural thing that you’re born with or not born with. And so if you’re struggling with it right now, get some help on learning those fundamentals, it’s gonna, it’s gonna unlock some stuff for you.

Melissa Nightingale (Raw Signal Group)  53:43

I say like, nobody comes out of the womb, knowing how to do the work of a group of highly like creative and generative individuals. Like it’s just not a thing that most people like are born knowing how to do. 

Johnathan Nightingale (Raw Signal Group) 53:56

Everybody says we would say that because that’s our job, but it’s the other way around. That’s our job because we know how powerful it is.

Aydin Mirzaee (Fellow.app)  54:02

Yeah, I love that and a great place to end it. Melissa, Jonathan, thank you for doing this. And that’s it for today. Thank you so much for tuning into this episode of the Supermanagers podcast. You can find the show notes and transcripts at www dot Fellow.app/Supermanagers. If you like the content, be sure to rate, review and subscribe so you can get notified when we post the next episode. And please tell your friends and fellow managers about it. It’d be awesome if you can help us spread the word about the show. See you next time.

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