This time, we’re speaking to Johnathan and Melissa Nightingale of Raw Signal Group, and best-selling authors of How F*cked Up Is Your Management? An Uncomfortable Conversation About Modern Leadership.
Johnathan and Melissa have been building tech companies for 20 years. They met in the early days of Mozilla — Johnathan in engineering and Melissa in marketing — and learned to lead as the organization grew from under 100 to over 1,000 employees in about three years. Since then, they’ve run nearly every part of a start-up (including product, engineering, data, design, marketing, pr, community, customer success, trust & safety).
Johnathan and Melissa kept seeing founders get frustrated at how hard it was to get things done and leaders running as fast as they could to figure it all out from scratch. They started Raw Signal Group in 2017 with the central belief that it doesn’t have to be that way—all that stuff is learnable and that great leaders are made, not born.
Tell us about Raw Signal Group
Melissa: Raw Signal Group builds better bosses. Johnathan and I were both 20-year veterans in technology organizations and, throughout our careers, we had both been promoted several times. But we realized that, especially early on in our careers, we were often put into positions of management with no training, no skill development, and no real understanding of what we had said yes to. People getting promoted without really understanding what their new role entails and the skills required to do the job well is a pattern we’ve seen repeated across the board in technology companies and other fast-moving organizations.
Johnathan: When we founded Raw Signal Group, we were both executives in Toronto start-ups and were watching our industry make the same mistakes over and over again. There was a real lack of understanding of what it means to be a leader in an organization. People didn’t know what to do when their employees brought genuine concerns to them about issues like sexual harassment or bullying. They didn’t know how to do career pathing or how to give hard feedback. For us, the pull wasn’t just that we saw an opportunity there, but we also felt like we needed to address it.
Melissa: We felt like we were uniquely positioned to address these issues. There are so many people out there who work with organizations to upskill managers and leaders who have deep expertise in training and organizational development but don’t have the lived experience that we do of what it’s actually like to lead and manage teams in a growing organization.
Johnathan: Credibility is a big part of it. A lot of the management training out there is not very good. It’s out of date and not very informed by modern conversations around diversity and inclusion. A lot of the clients that we work with, especially in bigger companies, have had other training in the past and hated it. All we can say in that moment is that we understand. We’ve been through a lot of those programs ourselves and we didn’t love them either. It’s part of why we built Raw Signal Group in the first place and it’s why we index so heavily off of how people feel about the training. When you get it wrong, it’s not just that you fail to teach people, it’s that they internalize this idea that learning about management is awful and if that happens, they’re never going to get better at it.
Do you focus solely on tech companies?
Melissa: Early on, we thought that’s where our focus would be because that was the industry where we had spent so much of our careers. But as we’ve grown, we’ve worked with everything from nonprofits to a rapidly-growing physical therapy practice. The markers we look for are organizations that are growing and expanding really quickly and want to maintain some level of operational excellence as they do.
We started experimenting with ticketed events and we realized our impact is much broader than we thought.
Johnathan: Most of our work is with one company at a time where we go in, get all the leadership together, and build a cohesive management team. But this year, for the first time, we started experimenting with ticketed events and we realized our impact is much broader than we thought. We had attendees coming from agriculture, from non-profits, and even people coming from other countries. That inbound interest has been really exciting for us.
Do you train HR professionals too or do you solely focus on people managers?
Melissa: We feel like it’s really important for HR to be in the room with their people, because part of what we’re covering is, what happens if your folks are struggling? What happens if somebody comes to you and says that they’re suicidal? What happens if somebody comes to you and says that they’re experiencing sexual harassment? Every one of those conversations involves a partnership with HR so it’s been incredibly powerful to have them go through the programs alongside their people, even when they don’t necessarily have direct reports.
Johnathan: We’ll often go into an organization where HR has been trying to make this happen for a while. They’ve been trying to get the managers to have a monthly meeting, they’ve been trying to have skill-sharing sessions, and they’ve been trying to figure out how the company develops a sense of what their own management culture is. And it’s hard. Building out the training content is really hard work and HR folks are often overtaxed. There is also a credibility issue. HR is incredibly knowledgeable about how to how to run the people aspects of an organization, but a lot of the time, people aren’t looking to HR for specific subject matter expertise. The engineers feel like engineering management is something that only an engineering manager can understand and the sales managers feel like if you don’t come from sales, you’re not going to have anything useful to say.
A big part of our work is to sit at the front of the room and tell people that, for almost everybody there, we’ve done your job or have managed the people who do your job. So we have a level of credibility. But we also want to have HR in the room so we can reinforce to the management that HR is a partner and when any issue arises they should be bringing them in early. That gives the managers in the room a framework for understanding where HR plugs into the work they’re doing. It doesn’t mean that an HR person necessarily understands the mentorship challenges that come with being an engineering manager or the burnout challenges that come with being a sales manager. It’s not really about that. It’s that, fundamentally, an organization is built on people and HR folks are very strong in that regard.
If you have a management core that’s willing to work with HR, and can do things in partnership, you go so much faster.
Melissa: One of the things we’re proudest of is that, if you didn’t know how to partner with HR before you walked into a program with us, you do after. HR are often the ones who bring us into an organization and when we follow up and ask them “what’s different, what feels like it’s changed?”, one of the things that they point to is that they now have a management core that understands when to bring them in. They have a management core that respects their function. It tends to be a really powerful shift for an organization—if you have a management core that’s willing to work with HR, and can do things in partnership, you go so much faster.
This isn’t a traditional business and there aren’t a lot of examples out there to model your business after. What gave you the confidence to take the leap?
Johnathan: I think the confidence to take the leap was because we felt like we had to. And it was a leap. We’re co-founders but we’re also married so it meant taking our household income to zero.
Melissa: We had run businesses before where one or the other of us was still working in an executive role while the other one was starting something, but this was the first time we were doing it together at the same time.
Can you talk a little bit about how you define roles and address conflict?
Melissa: We looked to other folks who are married co-founders, because there are a lot of examples of family-run businesses out there, and we asked them what some best practices are. Most people said to us that, early on, you need to have a clear definition of roles. But in our experience with early-stage start-ups, clear definition of roles tends to come later. We were both okay with throwing ourselves into everything that needed doing and figuring it out as we went along. As the business got more mature, our roles became much clearer.
Johnathan: We discovered which of us was lit up by tracking the financial elements of the business, or which of us was lit up by opening the conversation with a new potential client. Even before we knew we were going to start the business, we were writing together. And it’s also worth saying that Melissa and I met each other when Melissa was running global communications for Mozilla and I was working on Firefox. Anytime there was a security issue, we needed to work together to figure out how to communicate that to hundreds of millions of users and to let them know what we were going to do about it. It was pretty high-stakes and high-visibility collaboration so it’s a muscle we’ve been working on since the beginning.
Melissa: One advantage that we had going into founding Raw Signal Group was that we already knew that we liked working together.
Johnathan: We joke about it sometimes when we talk to other founders that we don’t know how you could found a business with someone who isn’t your spouse. It feels like I spend so much time talking about the business that, if I was married to someone else, that person would hear about my work all the time anyway. In that sense, I feel like the interplay works really well. We got a bunch of terrible advice from people who said that founding a business with your spouse never works and we’re just out there proving those people wrong.
Melissa: Another piece of advice we got was to make sure you keep really clear lines between work and home life, but I don’t know any entrepreneurs who live that way. It sounds good on paper but I have a really hard time finding founders, even founders who aren’t married to each other, who never talk to each other after eight o’clock at night. That seems unreasonable.
I think I’d be remiss if we didn’t talk about your newsletter—“The World’s Best Newsletter”
Johnathan: That’s what happens when you have two early-internet nerds found a company together—Friday nights are for weird-URL shopping. When we found out worldsbestnewsletter.com was available we knew it had to be ours forevermore.
Melissa: I love that we got that URL. A year-and-a-half ago, we challenged ourselves to see whether we could keep it up bi-weekly and we haven’t fallen off yet.
If we’re teaching people how to be better bosses, we need to have a really deep understanding of what’s going on in work, in leadership and management, and what’s going on in the broader tech community.
Johnathan: Melissa and I try to stay in our lane and we don’t presume to give advice on stuff that we’re not qualified to. But when your lane is people’s experience of work, there’s plenty of material there. The structure of the newsletter is pretty straightforward—one or both of us will collaborate on an intro and then we’ll each talk about something we’ve read recently and our reflections on that. We’ve never come up dry when it was time to write the newsletter.
Melissa: If we’re teaching people how to be better bosses, we need to have a really deep understanding of what’s going on in work, in leadership and management, and what’s going on in the broader tech community. That’s what enables us to be credible.
Johnathan: Anil Dash wrote an essay last year that says the price of relevance is fluency. If you want to be relevant in your industry, whatever your industry is, you have to be fluent in it. You can’t rest on your laurels or rely on the fact that, 20 years ago, you had some good ideas about something. You need to understand the current state of your industry. It’s so hard to be credible if you’re not showing your work and if you’re not like engaged with it. That’s why Melissa and I will read research papers and books by incredibly accomplished CEOs but we’re also paying a lot of attention to Girlboss, Refinery29, and Teen Vogue and the people who are talking about what it feels like to be 24 in the workplace.
Melissa: It’s hard to talk about your art and though it might sound a bit silly to talk about a newsletter as art, that’s really what it is. It can be shaped by many things. Sometimes it’s shaped by recent news articles, sometimes it’s shaped by a current conversation, and sometimes it’s shaped by a nagging idea that keeps you awake at 3 am. From a tech perspective, there’s so much pressure to optimize the shit out of everything but that’s not the approach we take with our newsletter. It’s been really freeing to just think about what we need to say to the world about management and leadership right now. What’s the thing that the bosses out there need to hear?
I’d love you to talk a bit about one of your recent newsletters where you spoke about the sexual harassment allegations by a former Planswell employee known as Jane Doe and the company’s response to that
Johnathan: That was the first time in more than a year that we’ve written something and put it up on Medium. We stopped posting there in part because Medium’s paywall meant that not everyone would be able to read it. But a few weeks ago we read this Jane Doe post about a young woman having a crappy experience at Planswell and we knew we wanted to respond. Melissa and I have a fair amount of privilege in the Toronto tech world and we feel like, if we make noise about something, a lot of people are going to pay attention.
Melissa: We’re also in a unique position where we can speak freely on issues in a way that I don’t think I have been in prior roles.
Johnathan: Having the freedom that we do and also feeling a sense of obligation, we signal boosted Jane and tried to make noise so she wouldn’t have to. But we also checked in with her before we published anything to make sure she was comfortable with that.
[We] have a fair amount of privilege in the Toronto tech world and we feel like, if we make noise about something, a lot of people are going to pay attention.
Melissa: We were in constant communication with Jane throughout and didn’t write a word until we had that conversation with her.
Johnathan: Anytime something like this comes up, there are a bunch of people who rally and who feel like they need to act. I like that instinct, but it has to be survivor-centred. We only act if the person at the centre of this wants us to. In the midst of making that noise, the CEO of Planswell called our office to talk to me. I told him that if he sincerely wanted my advice then he should apologize completely, don’t sugarcoat it, don’t write a half-apology that you’re going to have to elaborate on later—just get it right. But he didn’t do any of that. He wrote something that I found pretty unimpressive. But again, it’s not about what I think, so we checked in with Jane again and told her we were pretty unimpressed by his response but that we wouldn’t write anything about it if she didn’t want us to. She said she would welcome us adding our perspective so we wrote a few pieces and showed them to her ahead of time.
Our book is called How F*cked Up Is Your Management? —that’s not a cheery title. But if you read it, we try very hard in every chapter to have something constructive to say—here are things you can do to change your ways, here are things to think about when building your business that will make it better etc. But in the course of writing about that interaction with Planswell’s CEO, it was difficult for me to be constructive so we split our response in two because Melissa had a lot of things to say that could make the world better.
We’ve seen it happen a lot that business owners say, “Well that’s unfortunate, but we can’t do anything until after it happens.” I think that’s bullshit.
Melissa: “Does that actually happen in Canada?” is a question I got a lot following the #MeToo movement. When Jane’s post hit, the response was really fast but the quickest response I saw was from women in the Toronto tech community. This kind of thing not only happens here in Canada, it happens here in such a widespread and prevalent way that somebody writes a post like this and the immediate response from the women in this community is to put a hand up and say, not only do I believe Jane Doe, I’ve also experienced it.
We’ve seen it happen a lot that business owners say, “Well that’s unfortunate, but we can’t do anything until after it happens.” I think that’s bullshit. There’s so much preventative work that you can do. You don’t even have to think very hard to come up with several things that you could do right away to ensure that people have a better experience in the workplace—particularly women and marginalized groups. In my post, I wrote up a bunch of really simple questions that you can ask people who are entering into a leadership role within your organization. This is where we most frequently get ourselves into trouble in tech—we skip over having those conversations and that feels like a massive oversight.
A lot of organizations tend to put that kind of behaviour down to one person being a bad actor—all the other people in the company are great…except for that one person. They also hide behind government compliance
Melissa: The thing that seems to be unique to start-ups is that we’re often not compliant. We have not even hit that minimum bar yet. Most of us, when we’re starting an organization, completely punt on any HR obligations. We tend not to bring HR into organizations that are growing until they reach at least 15-20 people. It’s all part of the “move fast and break things” ethos. As an industry, we’re still well south of minimum compliance. When the CEO of Planswell was faced with a harassment complaint from somebody on his staff, he didn’t know what to do with it and ended up doing several things that are out of step with minimum compliance.
We’ve discussed a lot things you’ve learned from your unique positions in the tech industry, but what would you say are the most powerful lessons you have personally learned as entrepreneurs?
Johnathan: Entrepreneurship is different from every other job in terms of how much it sits on your chest. It’s your business and the buck doesn’t pass to anyone else. Melissa and I both feel very strongly that if we don’t push it, it doesn’t go. That feeling can make you want to try and control everything. It’s why people say that you’ve got to be able to delegate, you’ve got to be able to give away your Legos. We run a management training company so we should be good at delegation, but the impulse to keep everything under our control is strong. The experience that someone has at a Raw Signal Group event is something that we own, from top to bottom and we take that trust very seriously. There’s such a temptation to do all of it—we’ll buy the hotel, we’ll run the catering company, we’ll do the whole thing if that’s what it takes to nail the event! There’s a tension between caring a great deal about putting together the best possible event and recognizing that you can’t do it all yourself. We’re in our third year and I still feel like we’re working on finding the right partners and vendors. “Do your diligence” is a really good way to frame it. You will need partners, and you need to understand what you need from them and how you’re going to vet them ahead of time. That’s something we’re definitely working on.
We’re really proud of our operational chops and we’ve carried that into our entrepreneurial roles. We are entrepreneurial and visionary, but we don’t lose touch with the operational side of the business.
Melissa: I think the biggest lesson for me to date is that we never say “we’re only a three-person organization” and use that as an excuse to not deliver our very best work. We treat our business very seriously. People can see that we punch so far above our weight and that there’s a polish to what we do. We’re really proud of our operational chops and we’ve carried that into our entrepreneurial roles. We are entrepreneurial and visionary, but we don’t lose touch with the operational side of the business. There are many ways to run a business and give yourself blanket permission to be sloppy, to just get a product or service out the door and worry about fixing it later. I understand that, but I like that we only put things out into the world that we’re really proud of and can stand behind. All the work we’ve done over the past three years looks like a really polished body of work and I love that. I don’t want to ship garbage.
If there’s one task or responsibility you could remove from your day-to-day, what would it be?
Johnathan: This year we started doing ticketed events and we love them. We ran the Betterboss event back in September and we’re probably going to do it again in 2020. That room had such energy, just because it was buzzing and active because the attendees were changing—they were bosses who came in underwater and left above water. It was so cool to see and I absolutely loved it. But to get those people in that room, we had to sell tickets. I’m not opposed to sales but it’s a lot of work. If there was some Genie who could show up and say “You worry about the training, I’ve got your ticket sales covered.”, I would accept that Genie into my life in a second.
Melissa: Somebody else filing my receipts would be good. I know that’s silly but I didn’t like doing that in my last job either! Shopping for event spaces is also hard. So much of venue shopping is waiting for somebody to check their email account, which only gets checked once a week, or calling them and having it go to voicemail. I would totally outsource that.
When it comes to operations, what are some of your biggest pain points?
Melissa: Figuring out the seasonality of the business is so hard because in your first year you don’t know anything and in your second year you’re not sure what’s signal and what’s just noise. Because we’re married and running the business together, figuring out when to take family vacation and how that corresponds to the school schedule for the kids has been a little bit tricky.
This business is not going to fail because we pay an operations person’s salary, but this business may fail if we have poor operations.
Johnathan: The first hire we made as an organization was on the operational support side. As Melissa said, we’re both operators and we enjoy that, but we want everything we put out in the world to be of very high quality. The first engagements we had were with operational support and design to make sure that we’re telling our story in an effective way. The reason we don’t have a laundry list of things that are very difficult for us operationally is that we have a phenomenal operations manager, Adrian. When we set stuff up, she knocks them down. So much of the business runs more smoothly because we made that staffing choice early on. I remember us talking about it and saying that this business is not going to fail because we pay an operations person’s salary, but this business may fail if we have poor operations. For us, that math was very straightforward.
Melissa: We started working with Adrian for just five hours a week and were doing this all over the internet for the first six or seven months before we actually met in person. We were able to build trust as we went.
Johnathan: Both of us had managed remote teams for a long time so we weren’t hung up on the idea that the person needs to show up in our office every day in order for them to be productive.
What’s the best part about being an entrepreneur?
Melissa: One of the best parts for the two of us is having folks come back to us years later and tell us that the work we did had a lasting and profound impact on their career. We’re now in our third year of business and we have people coming back to us who we worked with two years ago who have been promoted, who are doing bigger and more impactful work, and who now have a whole new set of questions and challenges that they’re facing. We had somebody who attended Betterboss come back a couple of weeks later and tell us they had the most effective one-on-one with a direct report they were having a really hard time with. I just think that’s so cool.
Johnathan: I feel like in every other job, you can get away with just doing your job—even at a very senior level. I was General Manager of Firefox for a while where there are half a billion monthly active users and $300 million in annual revenue and still there were days where I just managed my direct reports and focused on my own thing. The disconnect between “just doing your job” and what the organization needs can get really profound. As an entrepreneur, you can’t let that happen. If you start working on stuff that isn’t what the business needs, then you don’t have a business anymore. When Melissa and I decided we were going to found Raw Signal Group, we weren’t sure how much of it was going to be consulting versus training versus public speaking. We get to shape how that looks by pursuing the question of “how do we achieve the impact we want and not go out of business in the process?”.
What are some of the tools you rely on to either make your job easier or to inspire you?
Johnathan: A tool that nobody seems to know about is the Hemingway app. It’s a text editor that highlights all the things you need to work on like “This sentence is hard to read,” or “You used 78 adverbs, stop doing that!”. You’ll paste some text in that you thought was pretty clear and it’ll come back and tell you that it’s at a postgraduate reading comprehension level when you should be aiming for grade five or lower. Getting practise in clarity of communication is really useful. I learned a lot about how to write from Melissa when I was the spokesperson for Firefox but I still lean on tools to just spot the places where I thought I was being clear, but was only being clear to myself.
Melissa: Similarly, there’s a tool called Textio that’s really helpful when you’re writing job descriptions because it flags where you’re using very gendered language that’s likely to skew your applicant pool. You can paste in your text in exactly the same way you do in Hemingway and it will tell you “These sentences are too long,” or “This is sexist garbage and you should probably consider rewriting the following sections”. It’s something we’ve talked to hiring managers about a lot because they often say they’d like to hire a more diverse team but when they post the job, they only getting a very homogenous group of people applying. Textio also has a really lovely blog that’s worth checking out.
Johnathan: There are tonnes of management books out there, but if I was going to suggest a few that people might not have read…The Art of Gathering by Priya Parker is a book about hosting and bringing people together. She coordinates corporate gatherings and government meet-ups and what I like about her book is that it’s very opinionated. She says “you should do these things”, and they’re not the things that you would naturally expect but they are right. It’s very provocative. Another book that I’d suggest all leaders read is So You Want to Talk About Race by Ijeoma Oluo. She’s just such a lucid writer about race issues. A lot of it has an American lens but it doesn’t matter, It’s absolutely worth reading.
Melissa: The Messy Middle by Scott Belsky is a book I’m currently reading. I love half of it and I hate half of it and the part that I hate is often because it’s really true! There is some stuff in there that I don’t agree with at all, but most books have something that I don’t agree with. It’s a good read, especially if you’re in the throes of entrepreneurship and want to read about people who are not giving you the glossy version of their story. This book is more about the journey of being an entrepreneur and the lived experience of it.
If you have reached a point where your intuition pulls you somewhere, just let it. Whether you can turn it into meaning for your business or not as it is a different question, but I think it’s worth listening to.
Johnathan: This isn’t a book, it’s a series of articles from the guy who does a lot of the content coordination for Burning Man, Benjamin Wachs. The theme for Burning Man this year was “Metamorphosis” and he wrote this series of articles about why so many people leave Burning Man feeling changed. He gets into a bunch of psychoanalysis so it’s not going to be for everyone, but for us, who host events and try to cultivate a space where people can come in, engage with the work and leave feeling different, it’s really interesting stuff. I suspect some people might read it and decide that it’s not for them, but we found it really substantive. If you have reached a point where your intuition pulls you somewhere, just let it. Whether you can turn it into meaning for your business or not as it is a different question, but I think it’s worth listening to.
Melissa: There are so many places you can find inspiration. One of the things we do that I give us a lot of credit for, is that we look at different places. So much of tech only looks toward tech but we have a real appetite for this kind of stuff so we’re not just pulling from the TechCrunchs of the world—which are totally fine—but also from things like Burning Man’s Travel Journal.
Johnathan: When it comes to software, Microsoft bought this company a little while ago called MileIQ that automatically tracks mileage and that’s really handy. We also recently picked up a subscription to OpenPhone, which is a startup based out of Waterloo. It gives your business a 1-800 number through an app on your phone and you can have multiple people install it so when it rings, anyone can answer. It lets us put a phone number on our webpage.
Melissa: Somebody asked me recently about workplace culture in remote teams. We obviously use Slack—I think everybody uses Slack at this stage—but one of the things we do if a big moment for the company is dial into a Zoom call and have the high-five be one where you can see everyone’s face. It’s just a nice moment where you can feel connected even if you’re not in the same space.
When we first got started with the business, we were trying to be very clever and scrappy and not use Salesforce. Now we use it all the time and it’s much better. Switching over to Salesforce has saved me a lot of time so it’s well worth the 70 bucks or so it costs each month.
Johnathan: I’m loath to say this one but it’s true—my own personal ability to be relevant comes through Twitter more than anything else. Instagram’s way too shiny and Facebook is poison. Twitter’s awful—there are a bunch of awful people on Twitter—but I have learned more and been pushed more and had more diverse voices come into my daily experience of the world through Twitter than anything else. As problematic as that company is, and as unimpressive as their actions have been with regard to a lot of the abuse that happens on their platform, it’s where a lot of my own education on diversity and inclusion comes from. If I feel like I don’t understand enough about the process of reconciliation in Canada from First Nations perspective, for example, I can go and read a whole bunch of reports on it or I can go to Twitter where indigenous people are writing about their own lived experiences. If I don’t understand an issue, I can bring in the voices of people who do.
Melissa: That’s what Twitter is good at—it gives you the opportunity to bring in voices that are not like yours and prompts some useful reflection.
*****
Raw Signal Group are running their second Betterboss series from March 2-4, 2020 in Toronto. Check out their website for more details or head straight to the Eventbrite page to secure a spot (early-bird ticket prices expire in less than a month so act fast!).
You can follow Raw Signal Group on Twitter and Instagram and check out Melissa and Johnathan’s personal Twitter pages.
Their newsletter is The World’s Best Newsletter, so naturally, you can find it at worldsbestnewsletter.com
For everything else, check out their website https://rawsignal.ca
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