Don’t ask if remote work is right or wrong. Ask this instead.

I started working remotely in 2006 or so, hacking my own career via freelancing and consulting. Nothing against the office: it just wasn’t a good environment for me and my unique brain.

At the time, my choice confused a lot of people. “How can you have a career if you don’t get a real job?” was a common one. I tried not to take it personally.

Despite the haters, remote work was taking off; by 2020, I had a well-paying, rewarding job that existed entirely inside my laptop. And I now had the depth of remote-work experience — as well as passion for its potential — that I actually got a job offer to use that expertise full time. Darren Murph, the first-ever “head of remote,” hired me on at GitLab. Our mission: to teach the world how to work well remotely. I started that job on March 2, 2020; eleven days later, the whole world was working remotely.

I talked to scores of business leaders during the early pandemic. At the time, the most common question we got was “will people actually do their jobs if they aren’t in an office?” By the end of 2020, that question faded into the background as companies saw a massive surge in overwork. Corporate employees stopped commuting, and they put in longer hours instead.

Again and again, we ask the same question about remote work: is it real? If you work from home, is that a real job? (so many implications here for how we talk about motivation and purpose, but that’s a separate post)

Four years into the pandemic era, it’s still that same question. The debate is circular and intransigent: execs say it’s not possible to manage people remotely. Workers say they’ll quit if they’re forced back into the office. Remote-work advocates say returning to the office is a bad business decision. Tech bros say you can’t be successful without getting face time. Researchers say remote teams are happier and more productive. Real estate investors say it’s all a fad that’ll blow over.

So who’s right?

Everyone. Everyone is right.

This is not a binary situation. There’s not one single answer, and it’s certainly not a yes/no question. Can your organization work well remotely? It depends.

• It depends on what your company does. Are you SaaS? Yeah, you probably can do it remotely. You run a hospital? You should probably be there in person.
• It depends on who your team is. Do you have a high proportion of engineers, subject matter experts, and individual contributors? You can do remote. Do you hire early-career people for (e.g.) sales jobs? Get them in a room together.
• It depends on your organizational culture. Do you have efficient processes and clear roles? You’ll work great async. Do you do a lot of discussion and make decisions by consensus? Probably need a big conference room.

And more importantly than anything else: it depends on your appetite for transformation that might be chaotic, disruptive, and lengthier than you would prefer.

During the pandemic, several companies decided to never go back to working office-first. Then, several of those companies reversed their strategies and returned to the office — often to great consternation from employees who felt it had been a bait-and-switch. But it probably wasn’t a bait-and-switch. It was probably an honest realization that transforming a company is hard, and perhaps the moment wasn’t right.

Prediction time.

Here’s what I predict we’ll see in the next three years: Companies that rolled out return-to-office (RTO) policies will now start rolling out their transformation plans. We’re going to see well thought-out, long-term strategies for transitioning away from office-first work and toward greater distribution of the workforce.

Just because it wasn’t the right time to switch to remote-first work, doesn’t mean it wasn’t the right strategy. I guarantee you that every executive team talks about it, and I guarantee that several major companies are quietly working on their plans.

So, what’s the right question?

The next time you’re in a discussion about distributed work, ask one of these and see what you learn. All of the questions below have answers, and you’ll be surprised — on many of these answers, a lot of people are in agreement.

1. What’s easier to do in person, and why?
2. Why were some companies more productive during the pandemic, while others struggled?
3. What’s the business case for working remotely, and do we have enough data to prove it yet?
4. Who benefits from being able to work from anywhere? Who doesn’t benefit?
5. Who benefits from working in an office? Who is disadvantaged by in-office requirements?
6. Why did so many companies struggle with meeting overload when they tried to switch to remote work?
7. How do you create a great culture without regular trips to the office?
8. Which types of companies are succeeding at remote work?
9. Why are executives saying such different things than employees and researchers are?

Feel free to ask me any of these — or leave a comment with your thoughts.

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By the way: I now run remote organizational effectiveness at Upwork — one of the companies that decided to transform to remote-first, and stuck with the decision. Yes, the transformation is still ongoing. But, a few years into it, I can attest that it’s working. More on that soon, along with what we’re working on.

Featured image by ThisisEngineering RAEng on Unsplash