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Johnathan Nightingale has seen first-hand how powerful a solid management structure can be for growing organizations.
“We grow so fast,” Nightingale says of tech companies, “and we’re often run by founders who have not themselves experienced great management. With that, the argument that they should put a people-managers on their payroll, where it sounds like their only job is for them to tell other people what to do, feels like a real waste.”
At Raw Signal Group, Nightingale conducts leadership and management training with hundreds of fast-growing tech companies. Before transitioning into coaching and consulting, he was the VP of Firefox for Mozilla through a period of intense turmoil (during which he helped build and launch the first Firefox offerings on Android and iPhone). He then took over as Chief Product Officer for Hubba, helping that team triple in size while improving its diversity stats. He also now sits on the board of Creative Commons and he co-authored the bestselling book *How Fd Up is Your Management? with his wife, Melissa Nightingale.
Nightingale recently sat down with GitPrime’s CEO, Travis Kimmel, for an episode on Software Engineering Radio. Their conversation covered everything from how startups should think about management and how to hire for it, to “troubleshooting” management. Below, you’ll find the highlights from their discussion (you can also listen to the full episode on SE-Radio here).
Why management matters
“Never in the history of the universe have eight engineers spontaneously self-organized and done well-aligned work toward the goals of the business in a sustained way,” Nightingale says. “In the absence of management, my assertion is you’re paying eight salaries but you’re only getting four engineers’ worth of work. Things are getting half-built and then abandoned because we don’t know what our priorities are. We’re building fully fledged things but they’re not the things the business needs, because there wasn’t clear communication between the different departments about what to do. Also we’re dealing with things like people stagnating, people checking out, people getting out because they don’t feel engaged.”
Having someone dedicated to management, Nightingale says, is the difference between a group of individuals and a team that’s unified in their efforts.
“Good engineering managers are also connecting individuals with new challenges,” he says. “They’re also helping lift them up and providing mentorship opportunities for them to either go deeper or go broader in terms of their skillset. You can get eight, nine, twelve engineers’ worth of productivity out of it because that investment starts to pay off. That’s the strictly cynical financial justification for where managers fit.”
A startup may have a founder or an early hire serving as the head of engineering and taking on some of those managerial duties. Nightingale recommends that startups add a layer of dedicated management by the time the team is at 8-10 people.
Eight to ten people is where most people max out in terms of their ability to be thoughtful, conscientious managers.”
“You want to be thinking, ‘How do we establish clear norms and expectations, and help people build something sustainable?’” he explains. “If your only job were managing engineers in a highly understood and parametrized system, maybe you could manage ten engineers and still have time left over for sleep. But eight to ten people is where most people max out in terms of their ability to be thoughtful, conscientious managers.”
Starting up with the “tree structure”
While being thoughtful about organizational structure can has proven to help companies better serve their customers, Nightingale cautions against reinventing the wheel — especially when a startup is just beginning to incorporate managerial roles.
“Don’t innovate on this,” he says. “You’ve got hard stuff you’re trying to solve, problems that have never been solved before. Go focus all your energy and innovation on that. When it comes to org structure, use the stuff that we’ve been using for a long time.”
The tree structure
Nightingale describes the ‘tree structure’ as one of the more common structures that companies adopt.
You’ve got individual contributors. When some of them express an interest in management or have some potential for it, they can step into the lead role where they’re managing four engineers. You have those leads report to a manager. You don’t want to overload that person either – each of them has a maximum of 6-8 direct reports.
That’s already a sizable engineering team if each lead and manager is fully loaded. Throw in a director of engineering to whom a maximum of 8 managers report, and then a VP to whom a smaller handful of directors report… and you’ve got a tree structure that can carry more than 250 people without struggling. Everyone knows who they report to. No one is overwhelmed with direct reports. And there’s no ambiguity along the line.
A small startup doesn’t need all those layers. “You can probably blend your leads and your managers and your different teams,” Nightingale says. “You might not have directors. That’s a pretty vanilla structure, and it allows a surprising amount of scalability. We didn’t even talk about senior managers or junior vice presidents or any of the other tiers you can introduce into the tree structure.”
Seniority in management
Each level in the tree structure comes with more than a different nameplate. There’s a difference between managing ICs and managing managers, and Nightingale holds that applying titles consistently and meaningfully will help make those people’s roles clear for others—both within and outside the organization.
- Managers: “A manager’s job is to make a team of individual contributors effective at accomplishing part of their director’s obligations,” Nightingale says. “The manager is the fundamental building block of organizations with more than eight people. The manager is situating their work within the broader organization, doing a bunch of work assignment and back-and-forths with other teams.”
- Director: “At the director level, we expect you to be informing overall strategy,” Nightingale explains. He understands directors as the basic level of deconstruction; generally, a director owns a function of the business, such as finance. Engineering often has several directors who own different pieces of it, such as platform, ops, front end, or science and analytics.
- VP: The VP is typically the highest point on the tree for gathering everyone in a function. “You usually only have one VP of engineering,” Nightingale says. “Generally a VP is part of the senior team and is charged with an entire section of the organization when divided by function.”
Not only are the job descriptions and responsibilities different at these most basic levels, but Nightingale points out that people experience a shift in operator context within the tree. Even in the entire Engineering tree, not everyone is dealing directly with engineering.
“Eventually, your team isn’t actually engineering,” he explains. “For a VP, yeah engineering is a crucial part of your work. But as the VP of engineering in a hundred-person organization, your principal obligation is to the other members of the senior leadership team. What are we doing as a business? What are we committed to? What are the strategic choices that we are making?”
In other words, leaders experience this shift from being more team-oriented at the junior manager level, to being organizationally oriented at more senior levels. In many organizations, this shift occurs around the director level. That’s when Nightingale expects a leader to embrace more strategic ownership and less day-to-day operational management.
Hiring leaders in your organization
Your managerial structure is all theory until you actually populate those levels with flesh-and-blood managers. It’s easy enough to put out a job opening for managers. Yet even Nightingale recognizes the struggle to distinguish between folks with managerial experience and folks who will actually thrive in your organization—and who will help your organization thrive in return.
“In a hiring context, I find it really difficult because you can look at someone whose resume says they have experience managing. Maybe they say ‘very high retention’ and ‘high performing teams’ and stuff like that. Those are good signals,” Nightingale says. “But I think that we shortcut it so much by saying, ‘Oh if you’re good with people then you’re going to be fine.’ I’ve met lots of charming sociopaths. That’s not a good way to hire leaders in your organization.”
Culture is set at the line manager level. Someone’s experience of working in your company is dictated mostly by their manager.”
1. Hiring for culture fit
Rather than hiring for years of experience, Nightingale boils down a positive managerial hire to two facets: someone who is a strong culture fit (some say that hiring for “culture contribution” is a better approach than hiring for “fit”), who also has honed their managerial abilities (like running effective meetings, building teams, etc.).
“Culture fit is a big piece of it,” he says. “Culture is set at the line manager level. Someone’s experience of working in your company is dictated mostly by their manager.”
Those managers have a sense of custody that really matters, and Nightingale finds that the keenest way to screen for that connection is a truly in-depth conversation around your organization’s expectations.
“It’s a detailed process to say, ‘Walk me through how you think about one on ones. Walk me through how you think about an underperforming employee.’ Stuff like that often flushes out a bunch of cultural assumptions that may or may not work in your organization,” he says. “It doesn’t leap off the page.”
2. Hiring for their approach to management
Next to cultural fit, Nightingale recommends hiring managers more on their skills than on the years of experience they tout.
“There is a lot of stuff that a manager needs to know how to do,” he points out—and he asks candidates about those things in the hiring process. “How do you run a meeting effectively? Talk to me about how you figure out ownership in a cross-team project. Talk to me about your hiring strategy. How do you think about distribution of seniority in a team?”
Fortunately, all of these skills are all learnable. If you’re hiring a senior contributor with a path to management, you can prepare to do a lot of this training on the job. But if you’re hiring a manager to put them in charge of a team right away, you might need someone ready to go out of the box.
“I think it’s really very possible to teach a broad swath of otherwise capable people the core skills of how to manage well,” Nightingale says.
Onboarding and training your management team
Whichever scenario you’re hiring in, you absolutely do not want to skimp on the onboarding and training portion of introducing managers into your scaling organization.
A 20-minute conversation
If a manager’s one job is to make a team more effective, they need to understand what their team is here to do. And that means they need to understand what they can do for their team. Where can they make choices? How much budgetary discretion do they have? How much promotion discretion do they have? How much work assignment discretion do I have?
And perhaps most of all, they need to know what “effective” looks like in this organization.
“It’s really hard to manage effectively if you’ve got no idea what effective means,” Nightingale says. “The foundational concepts to cover in onboarding a manager are, ’here’s what your team is here to do’ and ‘here’s why we hired you.’ Here’s the business case that I had to make in order to cover your salary and the people I know you’re going to need to hire. Here’s what we need from you. I think that conversation is often twenty minutes, but it doesn’t happen a lot of the time.”
The foundational concepts to cover in onboarding a manager are, ‘here’s what your team is here to do’ and ‘here’s why we hired you.’”
Your company’s honest norms
A second piece of successful onboarding is really a continuation of Nightingale’s hiring process: make your company norms explicit, because as a leader, your new hire has a disproportionate impact on those norms.
“Walk them through it,” he says. “What does it mean? How do you balance the tradeoffs? Every cultural norm means we’re doing some things, and it means we’re saying no to other things. You’re making choices, so it’s crucial to elucidate how you make choices.”
Nightingale encourages a bit of self-reflection in this process. You probably have a culture statement posted in the lobby or on your—great. But he uses the best-friend test to illuminate what a company’s true cultural environment is.
“Let’s say your best friend was coming to the organization,” he says. “They’ve just gotten a job and they take you out for a drink and they say, ‘I really want to succeed here. What do I need to do to succeed here?’ If you give them advice that’s different than what’s on your values poster, then that advice is true and your values poster is a lie.”
In which case, you may need to do some evaluating as an organization before you scale too large on false premises. Every manager who learns the culture you don’t actually want will embed that very culture into your organizational practices.
For completeness, the third piece of onboarding a manager is to go over the nuts-and-bolts of your organizational processes. How you style your sprints, how you administer your retros, and how you conduct post-mortems: these all matter. “All this stuff goes without saying,” Nightingale says, “because it’s the stuff most people would actually say. The first two pieces are the ones that get ignored a lot.”
Planning ahead for career growth
A huge benefit of joining a scaling company is the opportunity for career growth. It’s critical that you plan for that growth with your managers from the beginning, even if that’s not easy to do.
“It’s challenging because it is the nature of tree structures,” Nightingale says. “Part of the reason they scale so well is that you don’t need a bunch of people at the top to handle a lot of people at the bottom.”
He offers several pieces of wisdom:
- Set expectations up front about that career path. “Setting up what that timeline looks like in an honest way is important,” Nightingale says. “It’s not likely to go that quickly. We want you to master these skills. We want you to have some depth of expertise, and that takes a while. You need to live in the job for a while and move from unconscious incompetence all the way to unconscious competence. It’s a long trek.”
- Progress is attached to the growth and changes of the organization. So encourage and help your leaders to be prepared for it. “Are you equipped for a new opening?” Nightingale asks. “A lot of that career development is saying, here’s where we’re going to invest in broadening your context and depending your insight so that you can help be part of it.”
- Often, the most successful managers don’t wait for promotions to expand their roles. Those managers are the ones who say, “Hey, is anybody else bothered by the fact that we’re totally ignoring this piece of our engineering work? This piece of our deliverables to the business? I’m bothered by it and if it’s okay with everyone, I would like to spend some of my time working on that,” Nightingale says. “In the cases where people see that you’re taking the business seriously, that you want to go fix an important piece of it, people are much faster to say, ‘Oh, if she’s already working on it then let’s give her some resources, because it’s an important thing.’ That is totally how executives think about it.”
Troubleshooting to keep moving forward
Of course, the flip side of career growth also happens: you’ve hired managers for your scaling organization, and they’re just not thriving in the role. Rather than give them the boot right away, Nightingale recommends you learn from all that he’s witnessed while coaching tech companies on their management.
If I’ve seen a thousand performance problems in various engineering contexts, probably nine hundred-plus of those did not have the ‘failure’ clearly communicated. You probably need to be five times clearer.”
“If you have someone who’s underperforming in your organization, my first assumption is you probably haven’t told the person they aren’t meeting expectations yet,” he says. “Really, if I’ve seen a thousand performance problems in various engineering contexts, probably nine hundred-plus of those did not have the ‘failure’ clearly communicated. You probably need to be five times clearer.”
In other words, you can’t dismiss managers for their failure to read your mind. If you communicate clearly with them about their expectations and where they fall short, you’re enabling them to correct course.
And whether or not your managers are leading their teams to greater effectiveness, your organization always has room for troubleshooting and self-reflection. Nightingale’s five considerations for scaling engineering management don’t apply only to struggling companies. You can always evaluate how you’ve structured management, how you hire for it, how management fits your culture (both desired and actual). You can always troubleshoot. And you can always improve.
To return to the idea of managers being a valid investment—a 10x engineer only increases one person’s output. But if you can turn 1x managers into 1.5x managers, you’ve just increased the effectiveness of every engineer working with them.
And whether you’re an aspiring manager or a VP of engineering, that ability to power up is in your control.
“Train your managers,” Nightingale stresses. “In every individual contribution discipline, people expect that there’s some learning that you’ve done. That you have a set of legitimate, capital S skills. Yet so many people in management positions are just thrust into it because they were good engineers and seem okay with people. It’s a totally different job. You have to expect to skill up on it. Invest. It’s such a leveraged investment.”