Read more about Scott Berkun in “Observe, Don’t Surveil: Managing Distributed Teams with Respect.”

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Scott Berkun wrote the book on distributed teams. Literally. He spent a couple of years at Automattic and wrote about his experience as a manager in a distributed company. In this episode, Scott talks about that experience, discusses how things have changed since, and explains how today’s managers can cultivate a shared vision in a distributed team.

The full episode transcript is below.

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Matt Mullenweg: I want for you to imagine that you’ve been hired as a manager at a scrappy startup where there are no meetings, no hierarchy — not even an office. How do you make people feel like they’re part of a team? How do you brainstorm, and how do you make sure the work’s getting done? Is it possible to cultivate a shared vision, structure, and goals by only meeting in person twice a year?

That’s what Scott Berkun faced nine years ago, when I hired him to join a little company called Automattic, which is the parent company of WordPress.com, which I founded in 2005.

As you know from listening to this podcast, Automattic is fully distributed, with no central office and more than 900 employees working from 68 countries. When Scott joined us, we were quite a bit smaller, we were using IRC instead of Slack, and there was a lot that we were still figuring out.

Scott wrote a book about his experience at Automattic called The Year Without Pants, and since then he’s written a whole bunch of books about management, culture, and how we work. Today he’s a sought-after speaker on creativity and innovation.

I caught up with Scott in Seattle to talk about his experience at Automattic, and everything he’s learned since then. Has the future of work panned out like we first imagined it?

Matt: We used to work together, actually.

SCOTT BERKUN: We did used to work together. I used to work for you. [laughs]

Matt: Well let’s talk a little bit about how that happened, because that was an interesting arc in the story.

Scott: Yes. That was probably 2009 that you asked me to come to an Automattic Grand Meetup and you wanted me to advise on the team or lack of team structure at the company at the time. That was the first time that we officially were working together.

Matt: That’s an intriguing hook.

Scott: Yes.

Matt: And I guess that was a point when Automattic was totally flat, right?

Scott: Yes.

Matt: It was like 50 or 60 people all reporting to me. I don’t know how that worked, actually.

Scott: That’s right, yes. [laughs]

Matt: I don’t remember.

Scott: We talked a few months later about me joining Automattic as a lead of one of the newly formed teams at the company.

Matt: Before that you had been at Microsoft for a while?

Scott: I was a team lead, a project manager guy for about nine years there and I wrote a book about it, which is — probably how we first knew of each other is that you were on my mailing list that was about project management.

Matt: Oh was that the Art and Science — the Project…

Scott: Yes. That’s how we first titled the book. And then when WordPress launched I used it for my blog and that’s how we got to know each other.

Matt: Can we plug that book really quick? What’s the new title?

Scott: The title is Making Things happen. That’s the title of the book now.

Matt: I highly recommend it. That’s the one with the matches on the cover, right?

Scott: That’s right.

Matt: I really enjoyed that book.

Scott: But that was the beginning of my full-time remote work experience was working for you at Automattic. And I remember one of my biggest reasons for wanting to do it was that it very clear in your mind and in my mind that this was an experiment. Can we bring this experienced manager from a traditional company into a company like Automattic that has all these special things — being remote is one of them — but the high autonomy that every individual employee had — continuous deployment, was another. And then the notion of teams itself was an experiment. And then there was also this other notion that you knew that I was going to write a book about this, which was this other curveball to the whole thing.

Matt: Yeah.

Scott: And that combination of experiments — I love the word experiment, and when you used that word, I felt like no matter how this went, it was going to go well. For one of us, at least. [laughter]

Matt: Yeah, sometimes those book documentary projects don’t go as well.

Scott: No. The distributed work element wasn’t my greatest concern. I was worried about that but I was more worried about — do my skills as a manager in a traditional company where it’s an open office — you see people everyday. Could those skills transfer well to distributed work and to a far more autonomous culture in terms of the individual’s relationship to their work — how much control they had. I was more concerned about those things than distributed work.

Matt: I think this is a big concern of a lot of managers who have worked one way their whole career and then might be thinking about joining or starting or working in a distributed fashion. What did you see your superpowers as when you were in these in-person cultures?

Scott: I don’t know that I ever thought I had a superpower. I thought —

Matt: Well you’re a modest guy so let’s call it “medium-powers,” that made you effective at what you were doing.

Scott: I thought that, and I still think this, that most managers are really not very good at managing. Most people you talk to, when they come home from work, they’re not that happy about how well they’ve been managed — they have complaints. And that may extend out to the way the team is organized or the way the goals for their product has been set.

I thought that I was a good team manager in that I remembered all of my bad experiences as an employee and I tried to work really hard not to repeat those mistakes. And I gave a lot of autonomy to employees because I was one of those employees who liked a lot of control. Once I’ve earned some trust I wanted to be able to run and go at full speed. And the best managers I had are ones who are comfortable giving me that much control. And I tried to rely on that as a strength coming to Automattic. Because everyone was already independent. I have to start out by saying I may not actually add any value at all. I need to observe first to see how things are going before I have any reason to change anything.

And that’s a common mistake that new managers make everywhere, that they come in and they’ve got this new salary, this new job title, and it kicks their ego in and now it’s about them — How am I going to change the team, how am I going to change the organization? But you don’t know anything, you don’t know these people, you don’t know what their strengths or weaknesses are, you have no data.

So the best thing you can do — and this comes up in the book that that was what my strategy was for two months — I’m just a note taker. When we have meetings, I’m just going to take notes. I’m going to observe, I’m going to reflect back. And then little by little, once I have something useful to say, I’ll put it into — well it was IRC then but it’d be Slack now — little by little I’ll just try to show, A, I’m not stupid, B, I’m not trying to get in your way, and C, I may actually have some insight that will help you be more productive or successful or happier. And you have to earn that even if you’re the most senior person on the team or the company or whatever.

Matt: How do those meetings happen?

Scott: Well obviously there weren’t teams yet so there were no meetings. [laughter] So what we agreed to do was —

Matt: Were those Skype calls?

Scott: It was all text.

Matt: Everyone would be there at the same time, once a week?

Scott: Yeah. And we would chat about whatever everyone was working on. And it started off really short and little by little we added more structure, then we moved to Skype and then eventually the big breakthrough was we switched to audio! Woohoo! It was a big deal because everyone was fully paying attention.

Matt: We’ve had different experiences on audio meetings.

Scott: Yes…

Matt: Just to define some of those terms…

Scott: Yeah.

Matt: IRC is a text-only chat.

Scott: Correct.

Matt: Think of it like Slack but with a really old school version, like almost terminal-like interface.

Scott: Old school, yes, old school Slack.

Matt: Skype is a messaging platform plus voice.

Scott: Yup.

Matt: And is that what you did the voice meetings on?

Scott: Yeah. We agreed we’d keep the meetings really short but every communication tool is good for some things and bad for others. And text has the advantage that you have time to think but the downside is that written language takes away a lot of data. You can’t hear someone’s inflection in their voice, or pick up on how loud or quiet they are. There’s a lot of data that you lose.

And having a moment every week where we were on audio, even if it was just for five minutes or ten minutes, emotionally, in terms of your relationship, in terms of understanding people’s nuances and sense of humor, their sarcasm — you could only get that through audio. And you don’t need that much, you don’t need to have two-hour meetings, but ten minutes a week to hear everyone, what they’re talking about, what they’re excited about — you get more data. And I think that helped us throughout the rest of the week.

Matt: That was enough for you to get what you needed to be an effective manager to this team?

Scott: That was enough to help prove that I had some value. Because people would leave those meetings when they were run well saying “Yeah that took 25 minutes but now I understand what Andy is working on, and I see now that’s going to help me later.” That was 25 good minutes as opposed to the typical way people feel about most meetings, which is [that] it’s about other people, it’s all just FYI, stuff that doesn’t go anywhere and it seems that the person running the meeting cares a lot about having them, even though no one else really is engaged.

And then little by little it became natural for the team to look to me to set the goals and to help decide what features should be next or what things should be built. But you can’t do that as a leader without having some forum for those things to happen. And that’s what the weekly meeting was for us.

Matt: Is that how you saw managers come up in Microsoft as well or was this a unique approach you created for this opportunity?

Scott: I saw a wide range of styles at Microsoft. And this was more like the style that I preferred. I wanted to start off by trusting everyone and extending trust before I ask them to trust me. That’s just good —

Matt: That’s a really powerful concept, yeah.

Scott: That’s good relationship management. But I knew there has to be cadence. That’s the fancy word. There has to be a rhythm. If you’re on a team there’s a rhythm. You think of people who are competitive rowers, and there’s that person at the front of the boat who’s just — their job is just to yell out the rhythm, that’s all that they’re doing, the coxswain, right?

Matt: Yeah.

Scott: They’re taking up weight on the boat simply to be the person who’s controlling the rhythm. And any team, even if people are working individually for the most part but there’s some things that overlap, someone has to be setting the rhythm for the week, the rhythm for the month, and to help people set their own rhythm for the day. And that’s what I thought my job was.

Matt: One thing I hear a lot about people who have had a lot of experience in a physical office is they get so much value from the kind of drop-in or walking around because you get — what you said you get with just a little bit of audio is an even higher bandwidth, right? If we go text, a little bit, audio better, video more — you can see faces — and then in person. Let’s call that the best. How do you deal with not having that?

Scott: All the claims people make about serendipity, you’ll lose all the serendipity of meeting people in the hallway or — you can replicate all that. That’s what the group chat rooms are for where you jump in and you’re bored and you see all the other people who are procrastinating on something. You don’t see them but you can chat with them. There’s randomness and surprise that can happen in any group situation.

And all the one-on-one direct, more intimate communication, you have now fifty different tools to do that. You can send someone a private text message. “Hey, it seemed like you were upset in that meeting, should we talk?” Or you can make a Skype call. You have all of these tools to make the equivalent of what I would do at Microsoft, which is to go down to someone’s office and say “Hey, can I talk to you?” and close the door.

Matt: What about when that trust gets broken [and] someone doesn’t follow up on what they say they’re going to do? How does your approach there vary when you were an in-person manager versus being a distributed one?

Scott: I really have become a universalist about this, that as the manager — not even the manager — as a person, if someone has made a commitment to me and they’re not honoring it, part of my first thing to do is check in. “Hey, how’s it going, are you still on track for this thing on Friday?” I’m just checking, is my sense of the world in line with your sense of the world? If you do that periodically, especially when you don’t see them posting on Slack or giving any visible — you have no passive indicators that they’re following up on this…

Matt: So is quietness a warning flag?

Scott: It is a warning. And this is one of the things that I learned from you about Automattic was that if you don’t make your work visible it’s invisible. No one can see it. And if you’re not over — what feels at first like over-sharing — or making sure that your code commits show up in the team channel, [or] whatever you’ve agreed on, then that puts someone who is the manager and the responsibility now going, “Well that person’s been quiet for four days, I have to reach out.”

So my first thing is just to check in. Do we still have the same expectations and view of the world? Yes. That sets me up then to come back two days later and go “Hey, we talked a couple days ago, we have a problem here because if you don’t get this done then Sally can’t get her thing done and now it’s going to cascade. So what’s going on?”

90 percent of the time, there is a reason. “Oh, this other issue came up that was more important, I forgot to mention it to you.” I’m like, “OK, great, now I understand, I can recalibrate.” But someone has to be that check-in maintainer that is driven by whoever is in the leadership role. The hard part is when you check in on someone and they keep — there’s something broken still. They’re not getting their work done, they’re frustrated —

Matt: Or there are broken things in the past. It was due on Friday and now it’s Tuesday.

Scott: Right. You really want to avoid having deep, personal conflict conversations over text.

Matt: Why? It seems so efficient.

Scott: It’s efficient until it’s only making things worse.

Matt: Ping, Berkun.

Scott: [laughs] It’s what I mentioned before about what you lose, that you don’t get the nuance that is so important to empathizing and understanding what someone is trying to say. And if I have an employee who [has] some issue that’s going on that’s personal that’s got nothing to do with work, they’re less likely to type that in.

But if I can get them on the phone and they hear my voice, and I can offer them my true empathy for — “I want you to do well, my job is to see you do well.” They get that empathy. Our brains respond to that more directly through voice and eye contact and facial expression. They’re more likely to respond back and share a little bit more about what’s really going on, which could turn out to be something simple, that the way that I assign work or the way that I make decisions bothers them in some way, but I didn’t know that. And they were afraid to offer that to me before.

Matt: So you created that safe space for that to be communicated.

Scott: Yes. I also think that even if you don’t agree with my point about intimacy, I think that every medium has strengths and weaknesses. And just by switching the medium it changes now what the strengths and weaknesses are going to be. To switch from Slack to SMS, although they both seem like text, there are subtle differences in the way people think and translate what’s in their head into communication. And so whenever I am stuck, I will always try to — and I feel like I don’t really know what’s going on here — try to switch the medium. The one that I always feel is the go-to one if I’m confused is voice. And often it’s faster.

Matt: I think that’s great advice and it’s a cool feature of the new tools, like Slack. They have audio built in so you can initiate a call right there.

Scott: I have this experience with my friends. We’ll be going back and forth on SMS on something we’re not agreeing about and I know from all my experience at Automattic, I know that sometimes a 30-second phone call —

Matt: Would fix everything.

Scott: Instead of a 20-minute — yes, we are asynchronous, I’m half watching TV while I’m doing it. But it is 20 minutes of time spent arguing about something that’s a nuance that would be completely obvious if we spoke on the phone for 30 seconds.

Matt: It was interesting, we just had a leadership summit at Automattic. It was a training one, and we decided that the focus for the week would actually be feedback. And in my mind going in, it was more about how to give good feedback, some of what we just talked about. But the facilitators, who were quite good, ended up focusing probably the bulk of it on receiving feedback. Let’s say you’re on the other side of things and you’re getting some feedback over text or something like that, what have you found works well or poorly for that?

Scott: I think that you have to start from separating out your personal identity with the work that you’ve done.

Matt: Hmm. What does that mean?

Scott: Well I’m a writer, so that’s the easiest place to start. I’m a writer, I write books. And people write reviews of books and a lot of them are really mean. Making Things Happen has a two star review on Amazon where someone says it was about as useful as a piece of toilet paper or something like that.

Matt: By the way, toilet paper is super useful.

Scott: It is super useful. [laughter] It’s all context-dependent though, right?

Matt: It’s interesting though, every author I know has this where at some point, even if they know they shouldn’t, they’ve read the bad reviews and they can usually quote it word for word.

Scott: Yeah. Oh yeah.

Matt: But maybe you can also quote a really good review but they typically don’t have that same vividness to the probably 10 times more good reviews that it’s gotten.

Scott: Yeah. I read every review.

Matt: Yeah?

Scott: I think every review… not all the GoodReads ones but every Amazon review, every magazine review, and I feel like that’s part of my job. So I write a book and I do work knowing that there are going to be people who have valid criticisms of what I have made. And it doesn’t necessarily mean that what I did was bad, it just means that there’s many ways to decide what good is. That’s part of the job.

And I feel like that’s part of the job as a manager, that’s part of the job as a developer, that’s part of the job as a designer. You are making stuff and putting it out into the world. That’s what I mean by splitting out my personal identity as Scott from “I made some thing that someone might not like”, or in the management case, “I made a decision that someone really is upset about.”

Matt: So if I were to rephrase that — you created something that someone thought was worthy of two stars but that does not mean you, Scott Berkun, are a two-star person.

Scott: Correct. I might be a two-star person but not just because of —

Matt: Of this one review.

Scott: Right. Not just because of that book that I wrote or a thing that I did.

Matt: Or a thousand two-star reviews, ya know?

Scott: Sure, yeah.

Matt: That sounds hard though. You even started with saying, “I am a writer.”

Scott: That’s why feedback is hard because we, especially people who are passionate about their work, they don’t have much psychological separation between their identity as a worker and their identity as a human being, and that is a kind of maturity that you need to have.

The helpful thing [is], I have a curious mind to ask clarifying questions. I’m not going to defend anything. I’m going to run with the assumption that they are correct. There’s something flawed in the decision that I made. But I have to be an investigator now. I have to — “OK, when you say this, do you mean that or that? When you say that you thought the decision was unfair, did you mean it was unfair just to you or to the team or to — ” I have to go into that —

Matt: That’s a tough one because it can feel aggressive.

Scott: Yes.

Matt: Because on the receiving end it’s like, “Oh I’m doing all this extra work to justify my feedback I’m giving you.”

Scott: Yes. I think you’re pointing out how much trust is required to be a good leader, that I have to somehow convince someone who thinks I have done a lousy job that I genuinely want to learn more about why they feel that way and how they think about it. They have to trust me and I have to have earned that trust, that they’re willing to make themselves vulnerable and telling me more about this very uncomfortable thing.

Matt: So how do you build trust besides giving it? Or is that the only way?

Scott: The last therapist that I saw, she said that that’s the only way. [laughter]

Matt: Oh!

Scott: She told me and my wife, we were in marriage counseling, that that is the way. If you want to trust someone, the only way to do that is to give them something that you’re entirely sure you should trust them with. There’s no other way.

Matt: Hmm. That’s powerful and terrifying and everything all at the same time.

Scott: It is, it is. But if I have a dog and I need someone to watch it and you’re the only friend I have around — I’m not sure how good you are with dogs, I can’t half-have you watch the dog. Like, either you’re going to watch the dog or you’re not. Or either I’m going to let you cook a meal for me or not. Or I’m going to let you drive my car or not. There’s no — you can do things to insure and mitigate the dangers but either I am trusting you to do something or I am not.

Matt: I will say also that’s something I learned a lot when you joined because as one of the first middle managers, it was a lot of letting go for me.

Scott: Mhm.

Matt: The book is so interesting, especially looking back at it now, because it was a vignette in time and so much has changed since then. In fact, some things in the book quite embarrass me now. I was like, wow, I can’t believe we did that or like, we were so early in our journey in a lot of ways that the company in a ton of ways is unrecognizable in a way I think is really positive.

You mentioned earlier that people still ask you about the book, you still get questions about it, so I guess people are still reading it, which is cool. How have those questions changed or what have you seen as the things that you look back and are like, “Oh, I’m glad that that’s better now,” or that we know more now?

Scott: I get asked a fair amount about the genderedness of my point of view. And it’s a regret.

Matt: I think it’s also a mistake I made when creating that team.

Scott: Well, maybe. That’s for you to — [laughter] I know that — I thought about it in writing the book and I knew the culture of our team was a particular way because of its makeup. I should have put that in some kind of context and I didn’t. And part of that was — the book was supposed to be this insider view and I don’t do that much context-setting about these wider issues in not just tech culture but culture at large. I totally understand that perception and I’ve tried to explain it. I don’t think that was an accurate reflection of the whole company. I was trying to reflect what was going on in my team and I didn’t do enough to set that in some kind of context. I regret that.

But people ask me about the book because they’re switching to a remote company or they’re thinking about going to work for a remote company and they want to understand [what it’s] like. A lot of my answer is I don’t think remote work is that big a deal. I don’t understand why people obsess about it. I was at the gym today walking around the gym, I see people who are on their phones, people who are talking to their friends, they’re not necessarily doing remote work, they’re doing remote interaction with other people.

Remote is such a part of our culture now. Anytime you’re on your phone, interacting with another person through a screen, and it could be an iPad or a laptop, you’re doing remote work. People do remote work at their non-remote jobs all the time and in some cases it’s 50 or 60 percent of their time at work.

Matt: They’re not always talking to people presently, they’re often chatting or emailing with them.

Scott: Exactly, yeah.

Matt: They just happen to be in the same building.

Scott: Just email alone, ask people how much time of [their] day is spent on email. Guess what, that’s remote work. Remote work! But somehow there is this phobia and stigma around it that is really still strange to me. There’s this fear of it being this completely different way to work. Now it could be if you took a centralized team and one day just said everyone you’re going to go to different countries on the planet, that would be a radical difference because people’s lives would change. But in terms of how work gets done, we’re already remote workers. Everybody.

If you do email, if you’re on the — you send text messages, Skype meetings, Zoom calls — to me it’s all remote work. And I try to tell people that and they still think there’s some other magical secret. And I’m like, no, I don’t think your problem with remote work is about the remoteness of it. Your problem with remote work is probably you don’t trust your team, your boss is a micromanager, you don’t have clear roles, you don’t have a good way to define who does what projects or to track them. And that’s got nothing to do with remoteness, that’s just basic competence as a team.

Matt: I think part of it is it’s tied in with a bunch of other things. I like to say any organization over 25 or 50 is distributed already, they’re just maybe not conscious of it. But people, when they hear remote, they also think “Oh I’m working from home.” And their context of what they do at home is very different from what they do at work and sometimes it’s hard to bridge that. Like, how could I work at home with my cat bugging me all the time, or my kids knocking on the door and wanting to play? So that all gets bundled in with some of that. And some of those are real challenges.

Scott: Sure. Part of the stigma around this topic, it’s there is a totality to it that people feel that somehow they’re going to be forced to do things they don’t want to do. I have friends who commute to work and it takes them an hour and a half to go each way to work. I would never do that. There are so many different styles and formats and the demands on you as a person, what you have to wear as a dress code — No job is perfect for everybody. And so I’m an advocate for remote work, I think there are so many advantages to it, but I would never say that everyone is going to love working remotely all the time. I know this is true at Automattic, that some people join and after they’re there for six months — or any distributed company — they discover some things about their own needs they didn’t know before. They need more social interaction, they need more this or that.

Matt: Yeah. In-office work bundles a lot of things and for many people it also becomes, like you said, part of social — people you get lunch with everyday. It’s your connections outside of your normal circles. It’s maybe, depending on where you work, who you play volleyball with or who you exercise with or all these number of things. I think that’s actually one way that companies draw people in quite a bit. I frequently give the advice when someone joins to get some hobbies, go to some meetup groups, find some things where you can interact with other homo sapiens outside of this remote, computer-mediated interactions.

Scott: Yeah.

Matt: The people who often have the most trouble with it are [the ones] where it’s their first job out of college.

Scott: Interesting.

Matt: You probably remember some of this. You wind up with this thing where someone is not being as productive after a little while and you’re like — I mean it’s a little silly but like, “Are you leaving the house?” [laughter] “Are you showering in the morning, are you eating things other than pizza?” You do need a level of discipline and an approach to healthy habits.

Scott: That is true.

Matt: Another key point and a prominent feature in the book and your experience at Automattic that you helped create was meetups. So we’re distributed, why do we need to get together?

Scott: That’s a bigger version of the voice comment that I said before about how our brains have old programming, we respond in certain ways regarding intimacy by being around people. Facial expression, body language, sharing a meal together.

Matt: Breaking bread, yeah.

Scott: Breaking bread, yeah, there’s a real power to that that you can’t quite replicate it, not in the same way. And so the meetup thing was something that you offered as a policy. It just so happened that me and my team decided to be the — [laughs]

Matt: To really take off on it.

Scott: To run with it. But I thought it made total sense to me, that at least a couple times a year, get everyone in a room together, and then we could flip the way we work and we could work more like a traditional team and take on a bigger project where we all have to be working on the same thing together for two days.

There’s a different way you learn to work with each other when you have that kind of commitment. I think that helped us a lot as a team because then we’d go back to our regular style of working but now we just spent two days really working hard on something that stretched our relationship and our working styles in a very important way for us.

Matt: How was your trust before and after those meetups?

Scott: Probably better. This gets back to human psychology again. When you share a house with someone, you share a meal with someone, you trust someone to go get the groceries or pick up the car or do a dozen logistical things that happen to be required. It’s a little bit different than this person that you work with but it’s all through digital and virtual stuff. And I don’t know that a team needed to meet up as often as we did. We probably met three times a year and then there’d always be the grand meetups. That’d be the fourth, but we all really enjoyed it and we were all mostly — we didn’t have kids or families so it just fit our team style for the most part. That would change more as the team got bigger.

Matt: I think this is probably an independent variable from being distributed or not but I’m a big believer in it, that if you give teams autonomy to try things out, hopefully the best practices then spread organically. And then occasionally you might come down from on high and say okay, everyone must do this.

Actually the last time I remember that was with Slack because we had portions of the company on IRC and Slack and the network effects of having everyone on the same communication tool was too big, too important to let that be too balkanized. But the initial adoption of Slack was just on a team here or there.

Scott: Yeah, that’s smart how you’ve managed that. I think the autonomy is really important to creative people and not in a superficial way. I think that their tools are so important. A big corporation that hires programmers and tells them you have to use this old computer or something, that’s a lack of respect for what you hired them to do. They’re going to be really tuned in to what tools are going to make them most efficient. Continuing to have that flexibility as Automattic has grown — that’s a cool thing. A lot of companies struggle with that as they grow.

Matt: One thing that comes up a lot is people not sure how to do — is like, “OK. my team is in five different countries, how do we brainstorm? How do we do that sort of creative frisson that seems much easier to spark when you’re in person and have that white board on the wall?”

Scott: For me, I didn’t struggle with that that much. I felt that if I have good people, and there’s a clear goal, then there will be an abundance of fodder. As long as stuff is being offered, as long as there’s that loop of feedback: idea, opinion, critique, new idea. You’re doing above the bar for most teams at most organizations.

Matt: Similar to one of your earlier answers that maybe it’s not as big a deal as people worry about.

Scott: I don’t think so.

Matt: So they should just try it.

Scott: I think they should try it. But again the things I mentioned are not common. Talented people? Not common. People who are comfortable offering an idea and getting feedback on it? Not that common. People who are good at giving critique? Those kind of conversations? Most organizations don’t do that well. That’s really the problem to me. And no tool is going to solve that. It’s these other factors that are harder to deal with and probably have a lot to do with you as the boss.

Matt: I’m a new manager at a distributed company. What should I do every day?

Scott: Lurk where your team communicates. Just lurk, just hang out. Spend an hour not jumping in. It’s very easy to jump in. Just observe. Because you may observe the team is just fine without you jumping in.

Matt: And then do you stack something on top of that later?

Scott: The thing that’s coming to mind is whatever feedback loop you have with each individual person on your team — and there is a set of questions that I developed. It’s in the book. I think the four questions were: what’s going well, what could be going better, what do you want me to do more of, and what do you want me to do less of as a manager? That’s how very one-on-one conversation I’d have — which would be like a half an hour, whatever, once a month or so — would be framed in those four questions.

Matt: Twenty years from now what percentage of jobs do you think will be distributed?

Scott: Well, so I spent a fair amount of time, not recently, with some of these statistics because I get asked a lot and it’s weird how they measure these things. This will be my way that I dodge the question is to talk about survey design instead.

Matt: Telecommute.

Scott: A lot of the surveys are designed, they ask the question in the sense of you being a hundred percent remote or days where you’re a hundred percent remote. So it’s really weird because there are some companies that have liberal policies for you taking one day a week to telecommute. Is that remote work? Well it is but how does that fit into a percentage, like what you’re asking? It’s a weird thing.

Matt: We can make our own definition here. If you were to pick an integer that was a percentage and let’s say people who work not in an office the vast majority of the time, the plurality of the time…

Scott: Yeah I think all the numbers will go up, to cut to the chase. I think it has to. The tools — I’ve already made the joke that most people are already doing remote work even though they don’t call it that. That’s just continued to grow. The tools will get better and better and all the things that can be done digitally, which is the cliff to get over, the curve to get over before you can do it on your phone or your tablet, will continue to grow as technology gets better.

Matt: So a hundred percent? Wow.

Scott: Well it can’t be a hundred percent because you don’t want your brain surgeon working remotely or your —

Matt: There was famously the doctor that wheeled in on one of these iPads-on-a-wheel thing and delivered a terminal diagnosis and the person was upset.

Scott: Yeah. I see. Yeah that’s a tricky one. That’s a whole other case though where —

Matt: It’s a good chance to switch mediums.

Scott: Yes, that is a good chance to switch mediums. Someone else should’ve given the diagnosis I think. Yeah. But I’m very positive just because I think that more worker autonomy just makes for better work. I really believe that.

Matt: Just pick a number off the top of your head.

Scott: What do you think, this is five percent now? Of jobs that are distributed?

Matt: Sure.

Scott: I don’t know, ten percent? I don’t know, twice that, maybe three times that.

Matt: So somewhere like 25 to 35 percent?

Scott: Yeah. I think it’d be. And that’s enough for it to be normal.

Matt: All right, we’ll get you on Episode 15,000 of the podcast and we can check it out.

Scott: [laughs] Reserve my slot for that.

Matt: Where can people find you if they want to hear more?

Scott: I am ScottBerkun.com and I’m @Berkun on Twitter.

Matt: Scott, it’s always inspiring. Thank you so much for talking with me.

Scott: Thanks for having me.

Matt: That was Scott Berkun. His latest book is The Dance of the Possible: The Mostly Honest Completely Irreverent Guide to Creativity. You can find him at scottberkun.com.

Thank you so much for joining us and see you next time.

2025: Expectation vs reality