Distributed FAQ: Should Companies Use Software Tools to Monitor Remote Workers?

In Distributed FAQ, Matt Mullenweg addresses some of the most common issues companies, executives, and individuals face as they consider transitioning to a distributed model.


Q. At distributed companies, managers can’t always see when — or if — employees are working. Do you recommend using monitoring software to ensure people are productive?

A. No.

I don’t advocate for using this type of software at all. Instead of monitoring progress, you should focus on outcomes. Respect the outcome and trust that your employees will do their jobs.

Culture is what you do when no one is looking — it’s something I firmly believe in, and it’s especially true in the context of trust in a distributed setting.


Even in companies that thrive on mutual trust, different communication styles and social-interaction preferences can lead to friction. Listen to Matt’s conversation with Morra Aarons-Mele about introversion and anxiety in distributed companies.

Are We at the End of the “Culture of Presentism and Micromanagement”?

Back in April, when entire sectors of the economy had just recently — and abruptly — transitioned to remote work due to the COVID-19 pandemic, Matt Mullenweg shared an aspirational roadmap, describing the five levels of autonomy companies go through along their journey from fully colocated to truly distributed. With increasing signs that we might never go back to the old normal, Enrique Dans, at Forbes, reflects on what executives and employees alike have learned in the intervening months. He takes Matt’s five levels as a starting point to ask how our collective understanding of remote work has changed as well, and what the near future might hold.

Where are we headed? Toward levels 4 and 5, characterized by the optimization of working practices, which means changing the synchronous-asynchronous balance: fewer rounds of endless video conferences and more short videos recorded for later viewing, much more Slackand similar communication tools, along with less time spent sitting in front of a screen listening to other people. Shared documents people can work on synchronously — coordinating in the chat window — or asynchronously are infinitely more effective than a marathon video conference. A spreadsheet, text document, or presentation that requires input from several people is an ideal solution for Google Docs, Office 360, or any of their competitors.

Head to Forbes to read the rest of Enrique Dans’ article.

7 Remote Work Lessons for Managers During the Coronavirus

During this time of tremendous change, here is some timeless advice from leaders who have worked with their own distributed teams. For more, check out their individual Distributed podcast interviews.

1. Make time and space to listen

“As a manager, the best thing you can do is train yourself to hold space for yourself so you are not having a million things that you need to unload onto your employee, to keep making more room, to keep letting more things bubble up that can be resolved. Keep it with open-ended questions and to let advice maybe only come in at the very end.”

Leo Widrich, cofounder of Buffer 

2. Trust each other

“At distributed companies, you can’t tell really if someone doesn’t show up to work. I mean, you can eventually tell, but it’s much easier to disappear. The level of trust required is much higher. And so there is a portion of the [hiring] process that is earning that trust. We really believe that people can be successful and we’re looking to make people successful. There is no ‘prove it again’ after you get hired. I think that’s really important.”

Cate Huston, Automattic

3. Know your role as a manager

“I think part of my role is to explain why things aren’t impossible. And I see increasingly with a lot of projects we have done, the first response is, ‘That’s just impossible.’ …  I am happy when people say that. When I’m not happy is when people say, ‘Oh sure, we’ll do it,’ when I plainly know there is no way they can do it, it’s too hard. And so then I’m trying to figure out, ‘OK, so let’s see whether we can figure out how to do it.’”

Stephen Wolfram

4. Give yourself the structure you need

“When I got here, everyone was like, ‘It’s great because you can work in your pajamas if you want to.’ And for the first six months I did. I didn’t have a dedicated office area and I just sort of got up and started working whenever I felt like it, and finished working whenever I felt like it. And I found that that was not a good choice for me, especially in the work that I have to do. It ended up making me less resilient, more reactive, and also I had no concept of when work started and stopped.” 

Josepha Haden, Automattic  

5. Blog your experience 

“My wife will always say, ‘You’re staring off into space like you’re writing something.’ She just knows that it’s this thing where I’m collecting my thoughts….I think better and organize my thoughts better and share my ideas better when I write it, and it introduces a rigor to what I’m sharing. I love that push to accuracy and push to quality. It makes my thinking stronger.”

Anil Dash, Glitch

6. Rethink your meetings

“If you’ve taken three days to think about something and you say it in a meeting and people start just throwing stuff right back at you — in some ways you’re asking them to because you’re sitting at a table, what else are they going to do? But it seems unfair to them, in fact, for them to have to react to this thing that you have thought about for three days or three weeks or three months, for them to have 30 seconds to say something back seems unfair.”

Jason Fried, Basecamp

7. Consider what questions you’re asking

“An effective manager in a distributed work environment needs to develop the skill of asking precise and information-gathering questions to elicit this kind of information. Because even if the employee might not be able to produce this information on their own, or might know it but not necessarily know how to communicate it in a way that would be applicable and useful in a work environment.”
Lydia X. Z. Brown

For more insights, subscribe to Distributed on Apple Podcasts, Spotify, or wherever you like to listen.

Photo by Alexas Fotos / Pexels

Observe, Don’t Surveil: Managing Distributed Teams with Respect

Like any new employee, Scott Berkun had the jitters on his first day at Automattic. He was a little older than most of the people at the company, having spent the previous nine years at Microsoft. Although he witnessed firsthand the excitement of the tech giant’s glory days, office life was still rather conventional.

Now, in 2010, Scott was joining a young company with no offices, and — prior to his hiring — no managers. Before Scott joined, everyone in the company reported more or less directly to Automattic’s founder Matt Mullenweg and then-CEO Toni Schneider. Scott had been hired based on his own advice as an Automattic consultant. He had observed that the company had grown too large to operate efficiently with a flat structure. Scott suggested a turn toward a more conventional approach — the company needed hierarchy. 

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