If remote work is so awesome, why does it make my job as a leader harder?

Reading Time: 9 minutes

Last week we talked about why companies recall remote workers. Three companies cited a need for more collaboration. One company mentioned that there were too many occasions when they needed to tap someone on the shoulder.

Maybe you, too, have concerns about a dip in collaboration with a remote team.

Maybe you have experienced the frustration of wanting to talk to someone and then seeing their desk empty.

Maybe you notice other frictions when teammates work remotely. Does productivity seem lower among your remote people? Do meetings with remote members suck more than in-person meetings? Or maybe your company relies on technical collaboration, and pair programming proves much harder for folks who aren’t colocated.

We know that remote work doesn’t work for every company.

Books and blog posts promoting remote work often say ‘remote work isn’t for every company, but…’  and then keep going. They rarely discuss why remote work doesn’t work for every company. That seems important. Shouldn’t we talk about that?

In some cases, logistical matters make remote work a poor fit for a company: on a factory floor, folks have to interact with machinery. In coffee shops, folks have to interact with customers.

But I’m a programmer. If you’re reading this I suspect you’re also somehow in tech. In tech, a lot of employees interact chiefly with each other—not customers, machinery, or anything else defined by location. So why does remote work present us with frustrations?

It happens because there’s a breakdown between remote employees and colocated employees.

Perhaps you have personal experience with how that breakdown feels.

You walk in and the remote workers’ desks are empty. You’d love to share a piece of news with them, but they’re not here. You’re used to tossing around ideas with the team in the office, but now half of the people in the office are missing. How will you toss around ideas? Where is the spontaneity and creativity?

It’s also hard to know when people are available. Maybe your remote employees don’t tell you when they get in or when they clock out. You send them an e-mail to communicate, but you’re not sure when they will respond. What if it’s urgent? How do you escalate?

It’s time for a meeting. Audio issues. Always with the audio issues. Weren’t phones invented in the 1800s? Why do we still have audio issues?

Janna needs to pair with Joey, but Janna can hardly see what Joey is doing. It’s hard for Janna to connect with Joey when she can’t see him—all she gets is a screen. The experience is burning Janna out.

There’s a disconnect between the remote employees and the colocated employees. It happens because we’re used to business practices that center the colocated employees.

And therein, I’m afraid, lies the rub.

A colocated collaboration strategy only works for colocated members of the team. Remote work requires a different collaboration strategy, and it requires remote work skills.

Remember all those companies that recalled their remote work policies? What did we identify the same about them? Their remote teams made up a tiny minority of the workforce: most of the team stayed colocated. And with most of the team colocated, it seems unnecessary to invest in building remote skills for the colocated people.

But here’s the problem with that: once one person is remote, everyone is remote to someone. So everyone needs to build those skills. The people at the office have to do it, too; in fact, the whole company has to learn the same skills that the remote employees do. This is why Basecamp (70% remote) and Trello (60% remote) have a huge advantage on reaping the benefits of remote work: most of their people see themselves as remote and build skills accordingly, so they get a kind of herd immunity from that. The most common (and therefore normalized) business practices happen over remote channels, so everyone adopts them, colocated or not.

What do we mean by remote skills? Take overcommunication, for example. Lots of guides recommend that remote employees over-communicate when they’re available and what they’re doing. They ask those employees to communicate in the online channels: when they come in, what they’re working on, when they can answer questions, when they’re going home. The onsite employees don’t do this, so from the remote side the chat becomes complete radio silence.

Remote employees make sure their audiovisual equipment is working. Colocated employees don’t practice with their audiovisual equipment, so when meeting time comes around everybody waits while a colocated person figures out how to work video chat or screen sharing. The remote attendees get piped in on somebody’s laptop with no microphone affordance to help them hear people at the other end of the table. Somebody points the laptop at a TV where a powerpoint is showing. They might as well not: the camera + the reflection + the small type + the distance = the remote pipe-ins can’t see it.

Remote employees make sure their one-off conversations are recorded somewhere that others can asynchronously consume and contribute to them. But the onsite employees don’t do this. Instead, a lively conversation starts between a few employees sitting in a room together. Remote employees are none the wiser. This is not because it’s impossible to include remote employees: it’s because people either don’t know how or the inconvenience of the affordance is judged more important than the remote employees’ contributions.

This undervalues remote employees, and when people feel undervalued at work, they leave. Then turnover is higher for remote employees, and the company thinks remote isn’t working.

Maybe remote isn’t working, but it’s not the remote employees’ faults.

A remote culture starts at the office. If it doesn’t, even the perfect remote employee can’t fix it.

So how do you make it work at the office? What we’re talking about, here, are structural changes to your day-to-day operations—sometimes large ones. Embracing remote work for your company will mean doing things differently than they’re usually done. We rarely see models, in business or popular culture, of the practices we need to adopt to make remote work a launchpad for us instead of an anchor. Your investors may push back on you. Your board may push back on you. Other CXOs may push back, too. Even some colocated employees will not like it.

So why bother? What’s so great about remote work anyway?

Various blog posts will give you various reasons: hire from a wider geographic range of people, offer more flexibility for senior contributors with conference/teaching/consulting schedules (or children; senior people tend to be older and more having of children), take advantage of cost of living arbitrage, not rent office space, get closer to customers, yadda yadda yadda.

It’s not that I don’t care. It’s that these are well-covered in the existing bloggerature on remote work.

But it’s also a little bit that I don’t care.

Why? Because there’s another reason to embrace remote work for your company that is so important that it suffices by itself to justify the investment.

The biggest benefit of embracing remote work is also the reason that remote work sucks.

A remote culture forces operational practices that benefit the people you serve—employees, customers, investors.

Does remote work seem to be causing a productivity problem? It’s not; it’s revealing a preexisting management problem. Better to get that fixed than ignore it.

Do remote meetings suck? Remoteness is revealing things that already sucked about meetings—you just didn’t see them until remoteness exacerbated it. 

We will talk about these cases and many others in upcoming blog posts.

I’m not saying every remote work adaptation will require rethinking your operational strategies. Some of them will come much more easily, like choosing a videoconference tool.

But you’ll feel significant resistance to a lot of the adaptations I recommend. Your chest will tighten and your jaw will clench. Not because remote work is so objectionable, but because they challenge our assumption that our business ‘best practices’ are working just fine.

You will not like the ideas. You’re not used to them. They require dislodging your assumptions about how work flows.

But when you dislodge those assumptions, you’ll also find yourself dislodging obstacles to success that you didn’t even realize were there. You’ll discover new ways to get more work done, collaborate more effectively, make better use of employee time, and transfer knowledge more efficiently. More employees will have more agency, even if no one at your company ends up working work remotely. You’ll attract a larger hiring pool as people hear how great it is to work for you. And with a diverse range of perspectives and the ability to solicit those perspectives, you’ll do a better job of delivering for your customers and investors.

We’ll talk about several examples in their own blog posts, but in the meantime I’ll encourage you to do a short exercise. You’ll need a piece of paper and a pencil.

  1. Try to describe your physical reaction when you think about remote work. Do your arms tense up? Do you feel agitated? Do you squint your eyes? Write down those sensations on your piece of paper. This can be as short or as long as you like.
  2. What is it about remote work that causes you to respond that way? What, specifically, are you concerned will happen if you try to go remote? Write those down.
  3. Do any specific experiences spring to mind about remote work? Maybe when anyone mentions remote work, you remember that one time Ike worked remotely for a week and you didn’t hear from him the whole time. Or maybe there was that one awful meeting, and it always leaps back into your head when you think about things like this. List all of those experiences that you can remember. It can be as many or as few as you like.

You can keep this sheet of paper for later. We’ll get a chance to look at it again, and it will help us figure what might stand in your way of trying remote work and how you could address it to test the waters around whether you’re ready to support remoteness.

If you liked this post you might also like:

Why do large companies keep abandoning remote work?

Advanced Pair Programming: Pairing Remotely

Contributing to Open Source (which often means a distributed team)

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