High-touch leadership in a fully-remote culture
When you’re running a startup company, things just work differently than they do in a more established one. You’re all in each other’s faces and spaces. You know almost everything your coworkers are doing at work, not to mention what’s going on in each other’s lives. And that intimacy often breeds strong camaraderie.
But as you scale, it’s impossible to know everyone that thoroughly, to support them that closely, and to grow into your careers together the same way. But interpersonal connection and working in an environment that encourages growth are still critical, even when your colleagues are out of your sphere.
Katie Womersley, Director of Engineering at Buffer, excels at discovering additional ways to support her team – it’s part of her philosophy of building a great company instead of just focusing on building a great product.
The name of the game here is mental health. That means on a day-to-day level, a career-path level, and a living-breathing-creature level for every one of your engineers and managers.
“People don’t talk about mental health aspects at work,” Womersley says. “I wish we’d all talk a lot about it a lot more.”
At Buffer, everyone works remotely, and Womersley’s perspective is unique to maintaining mental health for remote workers. But the same principles apply whether your team has an office or you’re scattered around the world.
Here’s what Womersley shared with us about promoting the health and fulfillment of the individuals on her team throughout the development of their careers—in a company that has no offices.
Engineers need time to focus—and to connect
Perhaps the most valuable resource for engineers writing code is uninterrupted time. But if you work with distributed engineers, as Womersley does, then you probably don’t have to worry as much about managing their interruptions.
“With engineering, specifically, remote work is fantastic for helping people have a lot of heads-down time,” she says. “You hear a lot of talk about never interrupting engineers, not disrupting their focus. While this still happens with remote employees, the challenge tends to be more on the opposite end of the spectrum—with not having enough interactions.”
One of the greatest challenges remote workers face—and it’s not unique to remote workers, though it’s often exacerbated for them—is loneliness.
“It’s one of the main health risks of remote work,” Womersley says. “Loneliness is one of the main triggers for anxiety and depression, but you don’t hear companies talk about it very often. It can be an uncomfortable topic, but the fact of the matter is that human interaction is important. So if we’re going to do remote work right, and have happy and productive employees, we have to take these things into consideration.”
“It’s always difficult to talk about mental health, but we try to be quite intentional about that.”
So she ensures that her remote teams socialize together, no matter where they live. And it’s intentionally done—think more the office lunch out, more so than the water cooler banter—because socialization is necessary for even the most introverted human beings.
“We have informal chats where the only goal is just to hang out and connect,” she says. “And we also reimburse employees for using coworking spaces, and even for their coffee when they work at coffee shops. So if you’re working at a coffee shop, you can reimburse your coffee, because it really helps to just get out of the house and be around other humans. It’s essential that people are actively supported in doing that.”
But sometimes, all the socialization in the world won’t counter depression and anxiety. This is where Womersley’s philosophy of actively discussing mental health comes into serious play. Managers can hold space and build a culture where mental health is prioritized, and being frank about promoting it sure helps. But managers are also not mental health professionals, which is why Buffer offers employees other avenues for seeking professional assistance and guidance.
One resource that they provide to all employees is Joyable, a digital therapy solution that offers access to personal coaches. “You can talk to them about how you’re feeling, and you can talk through things,” Womersley explains. “That’s just one way we provide psychological support for teammates, but it goes a long way.”
Buffer’s healthcare plan also supports in-network psychological support, including psychologists and psychiatrists in the United States and the equivalent providers for international teammates.
“It’s always difficult to talk about mental health, but we try to be quite intentional about that,” Womersley says.
In effect, there’s no team that wouldn’t benefit from access to mental health professionals. Even if your entire team is in the office, even just having access to the resource (and the encouragement to tap into it) is a boon to their well-being.
Two (equal) leadership paths
Let’s be perfectly honest: managing discussions about mental health with coworkers isn’t everyone’s cup of tea. But engineers get promoted to management all the time with little comfortability (or training) in how to do so.
The problem isn’t promotions. The problem is that, traditionally, there’s only one upward route in a career, and that’s into management. Womersley’s team sees another way—or, more accurately, two more ways.
“We see two routes towards leadership,” she says. “We see people leadership, which is what traditional management might look like. It’s very people-centric. It’s very much about empowering people, removing blockers, enabling them to do their best work.
“Second, we see technical leadership as an equal track,” she adds. “You can become an expert and lead through having an impact in your technical work without ever having to have direct reports, do one-to-ones, coordinate schedules, or plan which team’s going to do what, because it’s an entirely different skill set.”
Many engineers understand the dread of facing transition into management: you’re no longer doing the work you’re good at, what you care about, and that got you started coding in the first place, because now you have to manage people. Imagine the fulfillment of engineers who get promoted into more ownership of their engineering and a greater scope of influence—up to whatever point they’re happy with—and are treated with equal pay and respect as those managing people.
“We try to have relatively few passionate people managers who really care about enabling others, and more technical leaders who are becoming experts in their field and very, very good at doing the work that they are passionate about,” Womersley says. “It’s different than the traditional one-dimensional hierarchy where people are doing a job and they are aspiring to supervise doing that job—and it works for us.”
Moving people into—and between—those roles
So engineers can advance on two paths. But how do engineers truly know if they want to tackle managing people or not, if they’ve never done it? Fear and uncertainty can hold a lot of people back from taking risks or making moves that may ultimately make them happier in their careers.
Womersley relies heavily on transparency. “When we want a new engineering manager, we’ll advertise it to the team internally with a description of what management really looks like right now,” she says. “We do our best to be super up-front with all of the aspects of what the job is really going to be like.”
She’ll even take screenshots of her calendar and share it with the team. “A lot of developers like the concept of serving people and enabling people, but actually seeing how your time is no longer your own can be a deal breaker.”
This process helps give a clear picture of what management looks like. Still, Womersley has had engineers switch into management, realize it’s not for them, and switch out again.
“We want to play to your strengths. Let’s change, as opposed to blazing on.”
In a lot of organizations, that re-transitioning would put employees backpedaling. However, one of the benefits of Buffer’s two-track system is that switching back and forth is a lateral move. Trying out a new position, and maybe moving back again, is something you can do without any sort of career penalties—no loss of compensation or face.
“It’s quite okay to lead a team for a while and decide you’d rather not have that people leadership,” she says. “It’s actually fantastic that you discovered that. We want to play to your strengths. Let’s change, as opposed to blazing on.”
Then, of course, there are the engineers who take well to management and its schedule. They’re still new to the job no matter how much they like it, and they’ll need support if they’re going to really inhabit the role.
So Womersley will offer managerial resources, many of which she found—through research and her network—and used when she switched from being an individual contributor to being a people manager.
“I saved a lot of these resources so I could pass them on,” she says. “But I’ll also make sure that I prepare new managers for situations that can at first be uncomfortable. I’ll say, ‘Okay, this is the situation you’re in, it’s your first one, so here are great questions to ask. Or, it’s the first time you’re giving serious feedback, let’s role play that conversation.’”
And she’s still learning on the job too. “Initially, we were a lot of startup-starts-to-grow-up accidental managers, just finding ourselves managing people and wondering what we should do,” she says. “We’re doing a better job now because we’ve had managers go through these pains, pass on that knowledge, and come up with better ways of doing these things.”
They won’t always get it right—and neither will you
You’re always learning on the job. Just like Womersley’s new managers, and just like Womersley herself. Because no matter how many manuals someone hands you, you’re still going to screw up — a lot.
“I tend to tell my team, ‘I guarantee you that I’m going to mess up. I’m going to make mistakes, and I’m going to make decisions that are wrong, but I promise you that if you come to me and you explain to me why it’s wrong, I will listen, and I will fix it,” she says. “I can’t promise to not make bad decisions because I absolutely will. I have blind spots. There are things I don’t know.”
For Womersley, earning her teammates’ trust is all about admitting her failures and making her failure public. That way, she says, she’s able to share what she learned and what didn’t work with the entire group. It’s a learn-from-my-mistakes model.
“The only problem with making mistakes is when you double down on defending them.”
There’s no shame in acknowledging that you thought you had a great idea that ended up with detrimental consequences. She actually turns these mistakes into opportunities to thank her team for pointing them out to her.
“It’s really uncomfortable at first,” she admits, “but once you get into it, it’s almost sort of thrilling.”
And it’s not just the vulnerability of admitting mistakes made. In fact, the ability to do so openly and bluntly acknowledge her mess-ups is a product of the entire system of maintaining interconnectedness that Womersley works so consciously to maintain.
Ben Thompson is a co-founder at GitPrime where he leads design and customer experience. He is a Y Combinator alumni, with a background in product design, branding, and UX design. Follow @thebent on Twitter.
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