8 things remote CEOs do differently

If you’re thinking of going remote, here’s what successful remote leaders do…

Earlier this month, I spoke with a CEO who’s looking to transition her company to become remote in the upcoming year. I could tell she was hesitant — perhaps even nervous about it. She’d never run a remote company before.

She asked me:

“Claire, what do CEOs of remote companies have to do differently?”

“Do I need to shift some of my attitudes or behaviors?” she elaborated. “What do I need to do as a remote leader to make sure we’re as successful as when we were co-located?”

I had to pause and think about her questions for a minute.

Even though I’ve been a CEO of a remote company for the past almost four years, I’d never explicitly thought about the difference between what a remote CEO requires vs. what a co-located CEO requires. But when posed the question, I realized there are certain things I deliberately focus on as a remote leader. And, I’ve noticed other CEOs of remote companies focusing on similar things, too.

This isn’t to say that co-located CEOs are a world apart from remote CEOs — it’s just to say as a remote CEO, you cannot survive without doing certain things. You have to do things a little differently.

Based on what I personally strive to practice and what I’ve observed from other CEOs who lead remote companies, here are 8 things that remote leaders do differently…

Write it, don’t say it.

As a remote CEO, I spend 90% of my day writing. Sure, I’m writing blog posts, notes to prospects and customers etc… But I write a lot to our team. I’ll write up our strategy around business development, how we’re doing financially, or a new experiment we should try with marketing. I’ll riff on a new product concept or critique a customer service approach with a co-worker — all in writing. If we were a co-located company, most of this stuff would happen in the form of meetings or chatting someone up by their desk. Or maybe I’d pick up the phone if the person was on a different floor. But in a remote company? You write it out.

“Being a good writer is an essential part of being a good remote worker.” — Jason Fried & David Heinemeier Hansson, co-founders of Basecamp

Jason and David, the co-founders of Basecamp, espouse this in their best-selling book, Remote. But being a good writer is not just an essential part of being a good remote worker — it’s required for being a good remote leader as well.

I’ve observed this firsthand in the way that Jason and David both lead Basecamp, as a company. I’m looped into their all-company Basecamp HQ Project, and I remember being floored when I first saw how Jason wrote up a new idea he was introducing. His written message was crystal clear, well thought-out, and succinct. In other companies, I imagine the same message might get communicated at an in-person meeting — more off-the-cuff, haphazardly, a little all over the place. Here, I saw the power of clear writing as a means to get everyone on the same page, articulate a complex thought, and not waste a bunch of people’s time. Great remote leaders understand this, and utilize writing as a tool.

Commit, don’t dip a toe in.

You can’t half-ass running a remote company. I’ve noticed this in watching other CEOs try to transition their company into becoming a remote company… They only let a select few people work remotely, or they don’t make writing things up a priority, or they don’t make what’s going on in the company accessible to their remote team members. That doesn’t cut it. The remote folks get treated like second-class citizens. Over at Help Scout (a Know Your Company customer, no less!), their CEO Nick Francis says exactly this when talking about their remote culture of 60+ employees world-wide:

“A friend and investor in our company, David Cancel, once told me that you have to choose remote culture or office culture and stick to it, because there is no in between… Trying to optimize for both will likely result in remote employees feeling like second-class citizens.”
– Nick Francis, CEO of Help Scout

Similarly, Help Scout’s Head of People Ops Becca Van Nederynen shared that, “You can’t dip your toe into remote work, it requires 100% commitment.”

At Know Your Company, there’s no way we’d be successful as a remote company if it was just something we tried out part-of-the-time, or only allowed some employees to partake in. Someone, at some point, would have been left hanging. I’ve found being 100% committed to remote work from the get-go has been an advantageous choice to make as a CEO.

Respect the quiet.

Effective remote CEOs understand how quality work happens: People need quiet, uninterrupted time to get things done. That’s how people get into a state of “flow,” which is crucial to thinking creatively or building something from scratch. Remote CEOs recognize this, respect this, and encourage this. Paul Farnell, Co-Founder of Litmus (also a wonderful Know Your Company customer), embodied this when he wrote:

“It’s more important to give employees quiet time than it is to cram them into an open office.”— Paul Farnell, Co-founder of Litmus

This sacred “quiet time” that remote work enables is possibly the biggest reason I personally love being at a remote company, myself. I can’t imagine Know Your Company being co-located and getting even half the amount of stuff we get done today. I attribute the uninterrupted periods of “quiet” time as to why we can be so small as a team (just 2 people!) supporting over 15,000 employees in 25 countries. As a remote CEO, you must embrace and respect the quiet.

Communicate well, communicate often.

Communicating as a remote CEO isn’t just about writing — it’s also about how well and how often you’re communicating. While communication is critical for CEOs who have co-located companies, the importance of communicating well is amplified in a remote company. As Jeff Robbins, founder of Lullabot (another fantastic Know Your Company customer), has said:

“If you don’t communicate well at a distributed company, you don’t exist.” — Jeff Robbins, Founder of Lullabot

In other words, if you don’t say or explicitly communicate something as a remote CEO, your team has absolutely no idea what you’re thinking. Unlike co-located CEOs who might rely on small talk or one-off conversations to gage the pulse of an employee or relay an idea to, remote CEOs must be much more intentional about communicating.

Relatedly, communicating your company’s values becomes even more significant in a remote company. As a remote CEO, you can’t rely on your body language, tone of voice, or physical office relics to communicate values. You have to explicitly state them over, and over, and over. Wade Foster, CEO of Zapier has highlighted this, saying: “You really need to set the values of what your company is going to look like. The high-level things that you care about.”

This sometimes means over-communicating. In her research, Mandy Brown, co-founder and CEO of Editorially and an editor of STET, found that, “Perhaps the most persistent bit of advice I gathered — and in some ways the most counterintuitive — is the need for remote teams to over-communicate.”

As a remote CEO, I definitely default to over-communication. If I’m unsure of something, I ask questions about it. If I’m wondering if a team member understands what I mean, I share greater detail and context. This isn’t to belabor the point or to create extra work for myself or others. Rather, communication is the oil of the machine in a remote company. Without it, things simply won’t run.

Know exactly who to hire: Self-directed, highly-empathetic people.

Jason and David of Basecamp have famously talked about hiring “managers of one.” Other leaders of remote companies advocate for the importance of self-driven folks. Becca of Help Scout has made clear that remote leaders should hire people who are “are mature enough to work well without a ton of structure.” Jeff of Lullabot echoes this in saying, “We need people who capable of thinking about the big picture and self-managing to some extent.”

Here are Know Your Company, we not only seek out self-directed people when we hire — we look for folks with high degree of empathy. People who don’t take things personally, genuinely care about others, and have a deep, intrinsic desire to help. Wade of Zapier describes this necessary empathy well:

“We like folks who have a lot of empathy and are really good, just helpful people because you’re working in Slack and in text all day. You need to be able to empathize when maybe a sentence doesn’t come off quite right, or whatever, you’d be like, oh, I trust that they had good intentions here, this wasn’t meant to be, you know, harsh to me or whatever right. Those are important values that we have that lend themselves well to remote environments.” — Wade Foster, CEO of Zapier

While c0-located companies may value self-direction and empathy in new hires, at remote companies they are an absolute must. As a remote CEO, it’s imperative to discern for these two characteristics while hiring.

Trust your employees… for real.

As a remote CEO, I couldn’t operate day-to-day if I didn’t trust my employees. If someone goes out and runs to the grocery store in the middle of the day… so what? If someone takes the afternoon off to go watch their kid’s school play… so what? In fact, it’s great that they get to do those things, live their life, and get work done too. It doesn’t matter how many hours are being put into the work or when the work is being put in. All that matters are the results — and I trust our employees find a way to make the results happen.

Leon Barnard, a UX Designer and Writer at Balsamiq (another Know Your Company customer we are proud to serve), talked about how their CEO trusts their employees:

“Our founder and CEO, Peldi Guilizzoni, shows a lot of confidence and trust in us. I would guess that we all actually work more effectively than we did in previous jobs where the most important thing was “looking busy” for the boss… Being so distributed, we couldn’t function without valuing trust and autonomy. Peldi doesn’t micromanage. At this point he couldn’t, even if he wanted to.” — Leon Barnard, UX Designer and Writer at Balsamiq

Paul of Litmus put it succinctly: “Trust your team… Work only gets done when you allow people to make mistakes.”

Have a strong, hands-on onboarding process.

Remote CEOs readily acknowledge a key challenge when hiring folks who aren’t all in the same physical place: Getting up to speed as a new employee is key. This means giving new hires the exposure, resources and support they need to be successful. To do this, remote CEOs often focus on having a strong, hands-on onboarding process that’s often partially in-person. Wade of Zapier, explains how they onboard new hires:

“AirBnOnboarding, which when we hire folks within the first month, we actually do like to have them spend a week in person out here in the Bay Area. So we’ll rent an Airbnb, we’ll bring their manager out here, them out here and then spend a week working alongside them.” — Wade Foster, CEO of Zapier

At Help Scout, they give the new hire a buddy — or a new “work best friend” as they like to call it. You can read a wonderful in-depth write up of how they onboard folks here.

Find ways for people to interact who usually don’t interact.

Fostering a sense of connection across the company is a vital part of your role as a CEO — whether you are remote or not. There is literally no one else whose job it is in the company to unite people and ensure they feel they’re heading in the same direction. Doing this in a remote company is admittedly more challenging than in a co-located company where everyone is physically in the same place, bumping into each other, or at the very least, seeing each others’ faces.

Paul of Litmus emphasizes the importance of finding ways to “make time for socialization.” He describes at Litmus how “a few times a year, we have company get-togethers and smaller teams meet in-person more often. Week to week, we get Coworker Coffees, drink beers on Skype, and play video games online. And we invite local employees to the office every Thursday.”

Most remote companies host some sort of yearly or a few-times-a-year meet-up. At Know Your Company, we try to get together at least twice a year in-person. Balsamiq is known for their all-team retreats that focus getting everyone together to have a good time. In addition to in-person meet-ups, Buffer has helped people get to know each other through personality tests, and Help Scout organizes 15–30 minute coffee breaks between randomly assigned team members called Fikas.

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