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Basecamp’s Jason Fried on the Learning Curve of Remote Work

The co-founder of Basecamp reflects on two decades of remote collaboration, giving advice on how to manage expectations during transition.

Last week, I reached out to Jason Fried, CEO and co-founder of Basecamp, which provides collaborative software to remote teams large and small. He and his team have been working as a fully remote company for over 20 years, first as the design shop 37signals (also home of Ruby on Rails), now focused on the project management-plus-chat software Basecamp with 3.3 million user accounts.

Fried and I had a conversation on March 16, as many creative workers across the U.S. were starting what was likely the first of many WFH weeks.


Q. Tell us about Basecamp and your advice to people newly working from home.  

A. We wrote a book about this called Remote: Office Not Required. A lot of what we put in the book is what we’ve lived. We’ve been a remote company for close to 20 years, so we’ve learned a lot. 

This is actually a moment to reconsider how people work. Where people go wrong is when they try to simulate working in an office, but just remotely: same number of meetings, same number of people in meetings, just via videoconferencing. That’s not taking advantage of the potential benefit of remote work: asynchronous work, meaning that you don’t have to do everything in real time anymore. You can give people more time back during the day—long stretches of uninterrupted time where they can do more creative work. 

An advantage of remote work is that it (typically) eliminates many of the interruptions of the office: noise, people tapping you on the shoulder, and intermittent meetings.


Q. What would you say to managers and others who are unfamiliar and potentially uncomfortable with this setup?

A. Some managers may wonder how you know work is getting done if you can’t see people. The only way to see if work is getting done is to look at the work. Since people don’t have to look “busy” at home, they can produce work on their own schedule—so it should be a more relaxing way to get work done, once you get over the hump of the unfamiliar. You realize it’s quieter, with fewer interruptions, less distraction, and you have your own time and space. Under typical circumstances, those are the real benefits of remote working. And I encourage people to seek those moments out and not try to simulate what you do in an office (in terms of meetings and daily structure). It’s funny, most companies outsource lawyers or accountants which means they work remotely. We trust professionals to get their work done, and that’s how we should be treating employees. Trust your employees to get their work done. 


Q. How do tools fit into the work from home experience?

A. The tools you choose have a big impact on how much work can be done. If you’re expected to be communicating constantly, people will feel more distracted than before, and it will chunk their day up into smaller and smaller bits. So my suggestion (of course, I’m a bit biased because we make Basecamp) is to find a tool that allows for asynchronous work, long-form writing, and collaboration, in your own time. Continuous meetings plus the expectation of immediate answers is why many of us don’t really have time to get actual work done at work anymore. Remote work allows for people to get work done. Encourage slowing things down. Speeding things up and working remotely is a bad combination. 

“We trust professionals to get their work done, and that’s how we should be treating employees. Trust your employees to get their work done.”

Q. What kind of companies or teams does this model work with?

A. Any creative or “information” endeavor, such as software development, journalism, design, consulting, even accounting and law. Once you get used to it, you can actually get more done and do more creative work. If you’re sitting in front of a computer all day, you likely can work well remotely. 


Q. What kind of framework do you put in place for a new team member who isn’t used to working remotely and having an unstructured day?

A. As a team lead or a manager, you want to understand there’s a bit of a learning curve. It’s the same as handing someone a guitar who’s never played it before, we shouldn’t expect them to strum a tune right away. Give them a chance to think things through deeply. Compose teams of people who have experience, empathy, and teaching ability to help people along who are new to remote work. Also: lower your expectations of people, especially in the beginning. When we hire someone new, we say the first 90 days are not about work but about getting to know the place, the coworkers, how we get work done, and our values. The same is true for remote work. It will take a few weeks to understand the surroundings, the tools, and the things you’re not going to do well. Managers need to make sure people have enough space and leeway to practice this. Play up the good sides: you have three to four hours to thoughtfully work on a problem, rather than 15 minutes to quickly produce something in between meetings.


Q. What do you say to executives and managers who want to support their newly remote team/company?

A. This is going to be a challenge for people. Full-time work may not be possible for a lot of people with school off and daycare closed and roommates and partners home—though you should still pay them as usual. Recognize the reality of the situation: people may only be able to work 60% of the time right now. It’s important for owners to have an understanding approach [Basecamp sent out the following memo to their team last week to share how they’re handling the situation].

People will have less time, because of family and home life being so different. We’ll have to trim down our days. I hope this experience is going to change some minds, of bosses and managers, who think they couldn’t survive without a certain number of meetings or that people won’t know what to do unless physically in an office with a team. Though we are forced to work from home now, I think it will remain at least optional in the future, which would be a huge collective step forward. 

The important thing is not to try to simulate what you do in the office, but pull back on the number of things you think you need to do. We have to curb our ambitions right now, and be empathetic about the situation we’re in. You can’t expect that everything is going to be normal.


Q. And what do you say to people who now are home with kids, parents, roommates, partners, when they’re not used to that as a work environment?

A. This is a renegotiation of boundaries and space. It’s new territory, even for the Basecamp team that’s been doing this for 20 years now. Our head of operations was talking about how she now has her husband and child home with her and it’s chaos. Companies need to be fair and realize that they’re not going to be able to do everything they want over the next few months given the reality of what’s going on right now. It should help the transition into remote work when people (and their managers) realize they will not have the full day to themselves of working that they’re used to.

“We have to curb our ambitions right now, and be empathetic about the situation we’re in.”

Q. So you see a more empathetic approach, as you mentioned before, to be necessary in this moment?

A. It’s more flexible, and in some ways it’s really healthy. It just goes to show, work is not that important. We like the work, but if we slow down for 90 days because people have other things going on in their lives, things are going to be fine. This is a good reminder that we don’t need to be going full-speed all the time. This is obviously a very scary moment, but hopefully we can realize that work can be different, in a good way.


Q. What does this moment signify for us, in terms of the nature of work and our perception of it? 

A. This is a break in momentum, which is the healthy side of what’s happening. Momentum can be powerful: doing today what I did yesterday because it worked. A lot of companies are on autopilot, without taking time to reconsider how they do things. When something knocks you off course—this is as off-course as we could imagine—it gives people a moment to look around and see what needs to change. We don’t need to do everything as we did in the office. What happens if we don’t? 


Q. What would you say to managers who may be using this as an experiment as to how valuable WFH is to their team or organization?

A. My take on how to evaluate this is: how does it feel? It’s not about numbers or measuring productivity or deadlines or number of meetings. When this is all over, do we feel like we want to work from home more, maybe two days a week? It’s a shock to the system and it’s awkward right now, so we need to take some time to get used to it. But when this is over, will people want to go back to office work only?  


 Our takeaways:

  • Reconsider how we work: as an individual, as a team, as a company. What policies can you collectively reevaluate? What meetings are expendable? How can you trim down the must-dos in your day?
  • Flexibility and empathy are key. This is new for a lot of people, and these are without a doubt extenuating circumstances. Be patient with yourself and your teammates. 
  • Adjust expectations as a manager: how many meetings are necessary, how heavily to rely on chat software, how productive people will be when faced with a huge shift in home and work environment. Lower your expectations and be flexible.
  • Evaluate how it feels, not how the numbers look. 

More Posts by Chrysanthe Tenentes

Chrysanthe Tenentes is Editor & Head of Content at 99U. She is cofounder of Brooklyn Based and The Shed story salon. 

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