What Makes a Good Remote Team?

I don’t know how you do it, but everyone you hire is so kind and empathetic. It’s crazy.

One of our principal engineers gave me that feedback in a recent one-on-one, and it might be the best compliment I’ve ever received about Simple Thread.

As a consultancy, our team is literally our product, and it’s the part of this company that I’m most proud of. Our business is not perfect. I certainly have room to grow as a leader, our internal processes can mature further, etc. But I cannot imagine having a better team in place to support each other and deliver for our clients.

I agree with the engineer’s feedback above. We do have an unusually kind and empathetic team, and I think those attributes make our remote team run more smoothly than most. But the interesting part is how we ended up here.

Kindness has never been an explicit goal of our hiring, and empathy is not something you can test for easily.

So how do we hire for remote work?

We started as a remote-first company a decade ago, and I think that has made us come to value certain non-technical skills more than traditional workplaces. There is a bit of nuance in what we look for, but the criteria that differentiate us can be distilled to three main points:

• Written Communication

• Humility

• Generosity

Let’s look at each of these in more depth.

Written Communication

If you ask any seasoned leader what they look for in a teammate, good communication skills are often towards the top of the list. Yet if you press for details, you often find a nebulous idea of what that really means. You know, the ability to, uh, communicate clearly, uh, about stuff.

Furthermore, there are many different forms of communication with skills that often don’t transfer. The person who can comfortably run a conference call may not be the same person who can give a good presentation. The person who can expertly draft a detailed, succinct technical email may not be able to explain their thoughts in a video chat.

The form of communication we choose to emphasize in hiring is written communication, typically in the form of emails and problem descriptions. This is for a few reasons.

Writing is the backbone of a remote company. Emails to clients. Slack messages. Commit messages. Design feedback. Pull request comments. Most of our workflows are rivers of text. If this form is a struggle, it almost doesn’t matter how charismatic you are in a meeting or how quickly you can think in an interview.

Another big reason is that writing requires one to order their thoughts and gives us the clearest picture of how their mind works – without the distractions of nerves or stutters or shyness or any of the myriad challenges one can face in answering a question in real-time. Writing cuts through all of that noise to reveal pure signal.

If you think without writing, you only think you’re thinking.

Leslie Lamport

A slightly less obvious reason is that it shows an attention to detail. Is this somebody who just reads an email until they get to the first question and then replies, or do they read the full email? Are they asking questions that have already been answered?

Lastly, of all the forms of communication, written communication requires the highest form of empathy, I think. When you’re talking in person, you have so many nonverbal cues to provide feedback. Even when you’re talking on a conference call, you can hear tone and get a sense if you’re losing people. But with writing – good, effective writing – you have to understand your audience well enough to steer through the pitfalls of not talking over them but also not talking down to them, landing a joke without resorting to an emoji, structuring your writing so a skim gives the important details but a longer read rewards those who need to know the details, and so on.

To be a skilled written communicator, you must have a moderately high degree of empathy.

Humility

One of the mental framing tools we use a lot at Simple Thread is the idea of tradeoffs. This comes from our background as engineers and designers. When you are creating a product, you are often balancing competing needs. The product needs to be usable but also secure, scalable but also simple to operate, flexible yet opinionated, etc.

If you asked hiring managers whether they wanted employees who are humble, i.e., “free from pride or arrogance,” most would say they do. However, if you phrase it as a tradeoff, the answer is less clear. Would you prefer an employee who is passionate or humble?

There are legitimate arguments to make on either side, and I think we’ve been lucky enough to find team members who are both. But if I had to choose, I’d pick humility over passion every time.

Humility is not thinking less of yourself, it’s thinking of yourself less.

C. S. Lewis

You can keep your genius ninja rockstar programmers who insist on using complicated, unproven, bleeding edge tools. I’ll happily take developers who are merely smart, a joy to work with, and care as much about the real-world business problem we’re solving as the technology we’re using.

For me, humility is not really about how you view yourself; it’s about how you view everyone else. It’s whether you are wise enough to realize you can learn something from everyone around you. It’s whether you are empathetic enough to realize your view of a problem, regardless of how clever and experienced it may be, is still only a small sliver of the world.

Generosity

This isn’t exactly the right word, but words like tolerant or liberal aren’t quite right either. I mean a generosity of spirit, acceptance akin to the robustness principle:

Be liberal in what you accept, and conservative in what you send.

Postel’s Law

This is almost an inevitable character trait if you excel at written communication and have a humble perspective, but it’s worth calling out separately. It manifests in a few ways, but it can be summed up as giving people the benefit of the doubt.

This is valuable in every setting, but I think it’s especially important in remote companies. With so much text flying around, it’s extremely easy to misinterpret tone. It’s easy to read a short reply as rude, when maybe somebody is just extra busy. It’s easy to read a detailed reply as patronizing, when maybe someone just doesn’t know your familiarity with a problem.

If I’m driving and somebody cuts me off in traffic, I get angry like anyone else, but I try not to dwell there. Instead, I try to imagine what’s going on in their life that’s making them drive that way. Maybe they’re late to an important job interview, the first they’ve gotten in months of searching. Maybe they’re rushing to the hospital to meet a family member who had an accident. Maybe they’re just young and feel invincible. I don’t know.

The point is that the other person’s behavior is usually not about me, and this is also true in the business world more often than we realize. How someone engages with you is often as much about the day they’re having as it is about your actions – especially in 2020. I want teammates who understand that.

Conclusion: Back to Empathy and Kindness

We don’t test for empathy, but it’s the essential ingredient underpinning generosity of spirit, humility, and an ability to write well.

We don’t hire for kindness, but it’s the inevitable outcome of empathy and fostering a culture of humility and generosity.

I don’t know if empathy and kindness are requisite pieces of a successful remote team. Everything is a tradeoff, and I imagine there are remote teams who succeed by prioritizing assertiveness and radical candor. I haven’t worked in a culture like that and don’t know.

But I know this works for us, at our size, at this moment in time. I’m proud of the technical prowess of our team, and I’m proud of what they deliver for our clients. And I’m even more proud of who they are and how we all work together.

Many years ago I read this Vonnegut line that stuck with me – and it’s been popping into my mind lately. I hope it sticks for you too. This year especially we all need a bit more kindness.

There’s only one rule that I know of, babies—God damn it, you’ve got to be kind.

Vonnegut, God Bless You, Mr. Rosewater