Jonathan and Melissa Nightingale

Being a good boss is more than intuition

31 Dec 2018   |   Leadership

Jonathan and Melissa Nightingale

Being a good boss is more than intuition

31 Dec 2018   |   Leadership

Think your management could use some work? Take a page from early tech veterans Jonathan and Melissa Nightingale’s new book on how messed up it might be, and how to improve it.

Welcome back to Work Minus, where we talk about what we need to drop from how we work today, and quick pivots you can make to get closer to a better future of work. Today our guests are Jonathan and Melissa Nightingale, founders at Raw Signal Group, and this episode is Work Minus Mind Reading.

Hello, how are you guys today?

Melissa: Hi Neil, how’s it going?

Jonathan: Great, thanks.


I’m also doing well. It’s good to have you guys on. You are extremely well-known in a lot of tech circles, specifically around Toronto. But why don’t you tell us a little bit about you guys, your history, and the companies you come from.

M: We are both twenty-year tech veterans. Both Jonathan and I started our careers – basically we started going to school in the late 90s for technology, and started our careers right around the time of the first internet bubble – for those of your listeners that are old enough to remember it. And we kept saying that tech organizations make the same mistakes over and over again. One of the things that we got really lit up about was the idea that people in tech organizations and scaling organizations in particular, rarely got the training that they needed in order to manage teams of people.

J: Yeah, one of our touchstones for the writing we do, but also the work we do at Raw Signal group, is the assumption that most of what goes wrong in organizations in terms how people are treated comes from ignorance, not malice. These aren’t people who aspire to management roles so they can make other people suffer – even though sometimes that’s what happens. It’s mostly that nobody ever taught them how to do this better. You’re a good engineer, you don’t seem to be a sociopath, so we’re going to put you  in charge of bunch of engineers. You’re a good marketer, you’ve been around longer than the other marketers, whatever the rubric is – suddenly you’re running a team. And that’s a totally different skill set. And a lot of the people that we were talking to and working with, were getting no training on how to do that.

M: Including ourselves.

J: Yeah, yeah. People ask me: why is the book so angry? Why are you so disappointed? We’re not angry at you – we’re angry at us. These are the mistakes we made 10 years ago. We wish we had learned the fast way, instead of the slow way.


Let’s talk just briefly about your book – How F*cked Up Is Your Management? is the title. And an apt title, at that. I loved it, it that you had a lot of great points in it. I think it really…the way it starts off as just talking about how a lot of the classic management principles that are out there are still relevant, but a lot of the specific operational practices need to be updated, and haven’t been updated specifically for the tech world, right?

J: Yeah, I think that’s actually a really good summary.


There’s a few points about the book I want to talk about, before we get into our our topic of ‘Mind Reading.’ One, is that I really liked is when you said that your job as a manager is to build the best team, not hire the best candidate. Can you unpack that a little bit more?

J: Yeah. In a sense it says it right on the face – your job as a manager it to run a really highly effective team, right? And in a growing organization, that’s going to need a lot of hiring. We meet a lot of managers who say they just want to hire the best person for the job. They often say the best “guy” for the job, but let’s give him credit and assume they’re trying harder than that. They want to hire the best person for the job, and then they end up with this team that’s really homogenous. It’s them, and the eight people they went to college with. Or, it’s them and the four people they worked in their last start-up with. And we know that the diverse teams outperform. We know that you need to make some junior and senior skill sets. We know that diverse backgrounds bring different perspectives to the table. So if you end up with this team of photocopies, your strategy is not working. The thing about ‘I’m just going to hire the best candidate for the job’ – that’s an approach that you can take, but if it leads to a sub-standard team, you’ve got to look into why you continue to do that and expect different results, right? There’s lots of ways to build a team thoughtfully, that have a lot of inputs in terms of: what’s this team missing? Where do we need a different perspective? Where do we need a different level of seniority? It’s not just about the best LinkedIn resume. It’s about where the gaps in your organization are.


That’s fantastic. And also, another point that you make in the book is that: a manager’s job is to maximize the investment the organization makes in that team. How does this change a manager’s perspective versus how they might have operated before?

M: I think it’s a great question. One of the things that we really see managers in growing organization struggle with, is the identity shift from: I used to draw a lot of identity from being an individual contributor, I used to draw a lot of identity from being the smartest person in the role, or the best person in that job function. And now, it’s really about leading a team of people to great outcomes. And so the the orientation shifts from: I used to draw a lot of my identity from my individual work, from the things I was doing day in, day out, to: now I’m helping enable a team of people to do those things. And that can be really a strange shift for many folks, because they were good at a set of things and liked doing that work. And now they’re job is something completely different. And the way that they’re going to get excited about that work is a little bit different than it was before. What I say to managers who are starting out often though, is that the impact that you can have as manager should outweigh the impact that you can have an individual. If you are leading a team of people, you’re leading a team of six, you should be able to do bigger projects and enable bigger work to happen within the organization than you were ever able to do on your own.

J: We joke with managers sometimes. I used to run a lot of engineering organizations. I ran the engineering organization at Mozilla for a while, and at other places too. And I joke when I’m talking to engineering managers that never in the history of engineering as a discipline, have eight engineers spontaneously self-organized to produce eight engineers-worth of well-aligned strategic output. It doesn’t happen. We’re creative people, just like everybody else. We hear about the problems the business is facing. We see an email from a customer, we think about how to solve that thing, and we will run in 17 different directions to try and fix it. And a lot of early organizations struggle with this. They’re like: Yeah, our engineers are great. They’re very smart. But sometimes the things that go out the door aren’t the things that we need. Or we do stuff that sales doesn’t know how to sell. Or marketing asks for something, but the thing that actually shows up looks different. And a lot of your role as a leader in that organization is to say, Not: I’m smarter than those eight engineers…Not: I can do their job better. Maybe that’s a place to get some leadership legitimacy from, but it’s sort of the less interesting place. It’s much more about: How do I actually get six, seven, eight engineers-worth of work out of eight engineers of payroll. Because that’s actually hard to do. And when you do it, what a lift for your organization.


Yeah, wow. It’s amazing. Everyone should go out and check this book out. It’s got a lot of insights in it. I want to turn the conversation a little bit over to our topic of ‘Mind Reading,’ which is something you all suggested we talk about. Tell us what that means, how do you interpret that in terms of mind reading and management, and where you’re going to find that most likely going on.

M: One of the things that we see in scaling organizations is that so much of the start of a scaling organization starts from a place of ambiguity. It starts in place of a lack of clarity around exactly how to get there. The vision is clear but the path to get there isn’t. And so, what ends up happening in many of the organizations that we work with is that they get comfortable with that level of ambiguity. And they attract that level of ambiguity in their hires. They look for folks who are comfortable with that. And as they grow and scale, as the organization gets bigger, as the targets get bigger, as the things that they’re trying to achieve get bigger, they need to attract folks who aren’t necessarily comfortable at that level of ambiguity. And if they haven’t been writing things down along the way, if they haven’t been getting clear in their own minds about how to get there, that tends to be where a lot of the confusion and frustration shows up. They hire later-stage startup people, and those folks don’t necessarily want to live in the space of guesswork.

J: We had a founder we were talking to a little while ago, and the organization that he had co-founded – one of their corporate values was: think like an owner. And when we asked him, what does that mean to him, he said well look: it’s like we’re in this shop and there’s parts all over the shop, and we’re trying to build a car. And ‘think like an owner,’ means: if you see a part that’s got to go onto the frame in order to make this car, don’t wait for someone to tell you. We’re all building the car as fast as we can, we all have our hands full with five hundred things. Pick up the part and put it where it needs to go. And what was interesting is that to him, that was really obvious. That’s what ‘think like an owner’ meant. And it should be something that anybody can internalize. You don’t have to be the founder of this company to understand that we’re building a car, and you should grab the part nearest you and put it where it goes. And the funny thing is, that doesn’t work. Employee #50, employee #500, coming into your organization doesn’t see 28 parts around a shop, and be like: well, that’s a bumper, that obviously goes on the car. Person #50 coming into your organization, and certainly person #500 might not know we’re building a car. And might be a specialist on some sub-element of that thing. Which is great, if you want to build millions of these cars. But it’s not realistic to assume they can just hold the whole plan for what we’re building in their head, and look around and see all the moving parts, and figure out which one is the most important. That’s mind reading. That’s assuming that the person coming in sees everything that the founder sees. Sees everything that their boss sees. And it’s an example, but it’s an example that’s just not true – as much as we wish it were.

M: One of the things that we see a lot, is that the the founders and the owners of the business, the CEO, the folks who’ve been there since the very beginning, since it was just an idea and a kitchen table – they hold it all in their heads really naturally. Because there wasn’t a business before they started running that business. And the folks who are coming in to do the day-to-day work, are much more focused on the details in the space of that work. And it’s not a bad thing, it just means that the way that they’re looking at problems is really different. And they’re often talking right past each other. Because the folks who are holding the business vision are speaking from the 50,000 foot view, and the folks are doing the detail work are speaking from what’s right in front of them. And that can be frustrating, not only for founders but it can also be incredibly frustrating for the folks who are doing the day-to-day work.


Yeah. I know it must be impossible to say, Okay this is the moment when you cross from being just a small group of people who are sharing all this collective vision and intelligence, into more of an organization or a company. But can you share with us some early signals or early indicators that people can be looking for to say, Hey maybe things have changed around here. What are some signals to see?

M: One of those first signals that we see…and often when folks pick up the phone to call the two of us, is that they go for about 20 to 40 people. So, the organization doubles in size, and often there’s a sense that we’ve doubled in size but we haven’t doubled the output of the organization. More people doing more things, but we’re somehow going slower than we did before. That for us is always an interesting moment. It tends to be around the 40-person mark.

J: Yeah. Those doublings keep getting in your way. At 40 people, you do start to hire specialists instead of generalists. You start to have someone who is just in charge of social media, and you  used to have one person who ran all of marketing and probably half of sales as well. We see it again at 40 to 80 people. You start to have people who want to know what their career paths looks like in your organization. And that was not something that you ever heard when there were just 14 people just grabbing parts from around the shop and building the car as quickly as possible. And managers don’t know what to do. You start having managers. Somewhere between 20 and 80, in one of those doublings – this is the first time you realize that the CTO probably can’t manage 27 engineers, no matter how great a manager she is. That the head of sales is now running a big department, and is going to need some people to help. Those moments where you feel the lack of structure, they tend to be the places where it breaks if you deny it for too long. If you still count on the way it was when you were tiny, you’ll find that the problems are getting worse and worse. And they don’t get worse in a linear way. They get worse in a geometric, in an exponential way. They start getting really hard, really fast. And leaders in those organizations often come to us a little dazed. Like, it was all going so well last year, we secured a new round of funding that let us hire a bunch more people, and we’re excited about that. And now, I don’t know what happened to my company. Because, people have stupid problems. They’re bringing me stuff that they should figure out for themselves. And I’ve got people quitting, and people angry with me and I don’t know why, because I’m doing the same stuff that I used to do. Most of the founders that we sit across from…you generally don’t call us when things are going great. So, let’s talk about what’s actually going on.

M: It’s also often the unpleasant surprise. To bring it back to the topic of mind reading, it’s often: my teams is off building something, and what they bring back to me is not anywhere close to what I thought it was going to be. So that frustration of mind reading works in both directions.


What do you tell someone who’s going through this transition of leaving a small…where everyone’s together and tight, and who really feels upset about how things are. You’re talking about: we used to be better, we used to all know what was going on. Is the advice you give them just to accept the fact that, you are now an organization of 80 people and you need to start acting like it? Or are there tools where you can bring back some of that collective consciousness, and that you do re-introduce some element of mind reading?

J: There’s layers to that question. Let me unpack it a little bit. So one, there’s a lot of tools that are really straightforward. Tools that, in fact, a lot of organizations stumble onto, without really realizing their full power. So, having a set of corporate values is an exercise in getting stuff out of people’s brains and onto a poster somewhere. Into the room somewhere, into the Slack channel somewhere. It takes a thing that we all took for granted. Obviously, we’re respectful when we disagree. Or, obviously we do anything to make the customer happy. Those moments where you think it should be obvious, that’s a signal. The first time you feel like one of your employees did something, and it’s weird that they did it, because it was obviously the wrong choice…Melissa has got a chapter in the book where she says, ‘obvious to you’ is not the same as ‘obvious.’ And that lesson just keeps repeating until you learn it. Values are an example. There’s a ton of them. Most organizations at some point in their maturity end up adopting some kind of goals framework, and saying here are the things that are most important. Maybe use OKRs, maybe just have a dashboard in the lobby with the five numbers you care most about. Whatever it is, that moment where you say: Oh, was it unclear that this is the focus of the organization? Let me make that clear. Here are the things that we care most about, here’s what I’d like your work to align around. That’s important, right? That’s a sign post, that’s a north star for people who did not see that as obvious, and who somehow managed to miss it in orientation. It’s a moment where you were counting on mind reading, and then you bring it out. There’s still creativity that happens. There’s still generativity. You still want those people to be thoughtful and entrepreneurial, and have initiatives. But they’re doing it was in a context where they understand anything at all about the expectations of the place. The rules by which we operate, the things that we care about, the things that we don’t.


You mentioned something at the start, that kind of relates back to this about how there’s often not a lot of documentation that happens in those early stages. What are some of the things that a a smaller team – even a small team inside a large organization – should be documenting along the way that can help in this transition?

M: I think Jon touched on values, and I’d also say, if you have a loose encapsulation of your vision, it’s really useful to get that out of your head as much as possible and onto paper. Why does the organization exist? What’s the purpose of the organization? Where are you headed? That capturing of it, especially in the early stage where everybody feels like: yes, that’s what’s in my head, is really helpful for the 50th, 51st and 151st person.

J: We’re talking right now in sort of grand language because a lot of the people we interact with are founders and CEOs. But if you bring it down to the individual manager, I’d say there’s there’s two things they can write down today that make a huge difference. The first one is: any kind of job description at all for the people on the team. What did we hire you to do? And in the very early stages, you interview people, and get a good vibe, there’s not a lot of structure. You bring person in, and you’re indexing a lot off their versatility and their high tolerance for ambiguity. And so you don’t write down a job description, because the the job description for everybody in the company is: do whatever needs doing. Grab the part and put it on the car. But as you start to grow, that moment where you sit down with a person and say: We’re big enough now that we should be clear about what your gig looks like, and what growth looks like. It doesn’t have to be a book; it can fit on a page. Say: here are the main expectations of a senior engineer in our organization, in my organization. And here’s what I expect you to do in terms of mentorship, and here’s what I expect you to do in terms of initiative. Just articulating that can be the start of a really useful conversation. And it gets you to the other side of a bunch of mind reading that person had to do – who was maybe a senior engineer for the first time, and doesn’t actually know what’s different about it versus the job they had before or the job they had before that. You can set aside four hours and do it for every member of your team and call it done. But – bring a lot of clarity in.

The other one I’d say is: you’re doing one-on-ones with your team. Writing those down. Having any kind of agenda at all. I don’t actually care which system you use. I don’t care if you’re using an app for it –  it’s not about that. But having some kind of formalism that says: Hey, this is a space where we talk about important stuff, where I give you feedback, where we commit to actions, and we write that down. And next week, we’re going to write that down too. This means that as you grow, where you’re six months, a year, eighteen months into this practice – you now have some backlog. By the time somebody wants to talk about their career growth, you’ve got a thing you can look at and say: Hey here’s the progress we’ve made over the last year, and here are the next areas I think we should be investing in – does not make sense to you? And that again, is work you can start doing tomorrow, to just get stuff out of your head and down in a consistent way.


Yeah, that’s fantastic. It’s always great to hear about those easy things you can do, even right now, to start this process of getting away from something like mind reading. Let’s bring it into the context of somebody who’s in more of a middle management position, or are brought into an organization – how would you describe the mind reading process going up and down the management cycle? And how can it really cause problems in organizations?

M: One of the things we hear a lot from middle managers who have been brought into organizations where there was high ambiguity before – and they’re starting to professionalize and specialize – is that there’s a high level of frustration of not necessarily understanding why things are the way that they are. And so people walk in, and they feel like everybody around them is an idiot. There’s this frustration of, everyone here is just sort of running around like chickens with their heads cut off. They’re all picking up whatever part but nobody seems to own anything clearly, and there’s no specificity in how people showing up and doing the job. And I think one of the things that we see, is that for those middle managers are coming in, it can be really helpful to just start sentences with: Help me understand…help me understand why this is the work that we’re doing, or why this is a priority –  before you necessarily turn everything upside down, and get people even more confused.

J: Yeah, I just echo that. I think that in middle management, especially when it’s your first time doing it, there’s this feeling that your job is to take care of your team. Your team has got a set of work that they’re doing – and mostly your job is to provide continuity for them. And it results in managers getting themselves trapped a lot. Because when they get harsh feedback about how their team is performing or not performing, they feel like their job is to shelter their team from that. And that’s not helping. Now you’re sort of hoping that your team will read your mind, and figure out that they need to be better of a set of things. Because, your boss is telling you that but you don’t know how to communicate that to them. And then when they continue to fail at it, your boss gets more and more frustrated and eventually starts pressuring you fire these people, who have never gotten that feedback because you didn’t know how to articulate it. That sort of telephone game feedback thing is is a big piece of it.

The other thing I’d say there is, sometimes the mind reading is about the state of the business. I won’t blame anyone else – I’ve been in the spot where I’ve been a manager running team as hard as I could, and whenever it came to goals-time, I would figure out what my team cared about and I would write those goals and I would just go to the max to defend those. And I would never let me in the insights from above that that was the wrong stuff. That the business needed might seem to be doing really different stuff. I would fight it because I thought continuity was my job. Giving stability to my engineers, so that they can keep working, was my job. But also, I had managers who weren’t very clear about it, who we’re hoping that I would figure it out. That I would have the same business sense that they would. That it would be obvious to me that my team was working on the wrong stuff. And as a result, I think my team was much less effective at getting stuff done in the organization than it could have been, in those early days – because I failed at mind reading.

M: One of the things that we see a lot of – that most folks are showing up to work and wanting to do a good job. And so if they’re failing in the role, is it because they’re showing up and hoping to fail in the role? No. It’s often that they’re showing up and trying as hard as they can, but they’re missing some piece of context or some information that would unlock what they’re there to be doing, what they’re meant to be focused on. So one of the things that I think we both pretty hard on is, if you’ve got somebody who’s on your team – if you’re managing ‘down’ in that sense – and you’ve got somebody who’s on your team who’s not able to do the role, or they’re they’re not doing well in the position…taking a moment and stepping back, and seeing: Were they operating from a different set of assumptions? Are they thinking about the business six months ago versus where the business is now? Where are there places where I can provide clarity and connect those dots? Because generally, folks don’t show up wanting to do a poor job at work,


Absolutely. Why don’t you close this out with maybe a story or two – and I know there’s no perfect companies out there – but just a few examples of companies who have done this well, maybe have made the transition from a mind reading culture to one that’s more explicit in what they’re expecting? Do you have any stories you can share?

J: Yeah. One example that I point to from time to time is the work that Glitch in New York – Anil Dash’s company – has done around salary transparency. Compensation is one of those things there people have very strong feelings about. And one of the real challenges as a manager, or as an individual contributor, in any organization, is that negotiation around: Am I being paid fairly? How does ‘fair’ change over time? What’s ‘fair’ based on the work that I’m doing and it’s evolution? That’s a really unbalanced conversation. And I think junior managers can feel like their job is to hoard that information, and find the minimum number that’s acceptable to the employee. And it creates a bunch of awful game-playing, and just basically a lot of mind reading. A lot of guessing about whether this is the final offer, about whether they’re really going to quit, or whether they’re really unhappy or just trying to haggle. Salary is, on the flip side, is not something where you can just turn around and say: Alright, the salary spreadsheet is public, everybody can see what everybody makes – problem solved. A thing that I think Glitch did really well was that they embarked on a process around it. They spent most of a year, from what I understand, talking with every individual about what this would mean, figuring out what the right level of salary transparency was. I think they settled on making bands of salary available publicly, or within the company, for every role. And it meant that for some people you could basically figure out what they made, and for other people – they disappeared into the noise. But it created an explicit set of conventions where previously it had been just guesswork and mind reading, about whether a manager was was telling the truth or not. I think it’s an example of something that was, I’m sure, scary for them – but took them out of a mind reading place and to a certainty place. And it’s just one less thing for them to be freaking out about. It’s a powerful move.  


That great. It’s a great example. Well, it’s been great to talk to you guys. I wish we could have a little bit more time, but hopefully we’ll have you on the show again. Where can people go to to get in touch with you, if they’re wanting to know more about what you guys are doing?

M: Our company website is, and the book is


Alright make sure you go check that out. Jonathan, Melissa thanks so much for being on the show and we hope you all have a great day.

M: Awesome, thanks Neil!

J: Thank you!

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