Remote Work Best Practices (ft. Chris Dyer, #1 Forbes Leadership)

Chris is a recognized company culture and remote work expert who consistently creates the "best place to work" for thousands of workforces.
Daan van Rossum
Daan van Rossum
Founder & CEO, FlexOS
I founded FlexOS because I believe in a happier future of work. I write and host "Future Work," I'm a 2024 LinkedIn Top Voice, and was featured in the NYT, HBR, Economist, CNBC, Insider, and FastCo.
May 23, 2023
min read

In this episode of the Future Work podcast, I speak to Chris Dyer, one of my favorite thinkers about remote work.

Chris is a recognized company culture and remote work expert. He has been a CEO with a workforce of thousands and consistently creates the "best place to work." Chris is an International Keynote Speaker ranked #1 by Forbes. He has two bestselling books, The Power of Company Culture and Remote Work, and has been named #5 on the Leadershum Power List, a Top 40 Change Management Guru, a Top 50 Global Thought Leader, and a Top 50 leadership podcast just this year. He is one of our Top 55 Remote Work Thought Leaders 2023.

You can find this interview and other episodes of the Future Work podcast on Spotify, Apple Podcasts, and YouTube.

This week's newsletter is sponsored by Coursera. Managing remote teams isn’t easy, and Coursera hosts some of the best courses to level up your leadership game. GitLab’s How to Manage a Remote Team and University of Toronto’s Communication Strategies for a Virtual Age are universally acclaimed, and best of all, free to take. Start learning today.

Hybrid and remote work is not something new

Chris, you've been researching, writing, and speaking about company culture, remote work, and the future of work generally. Recent research by another great work-from-home researcher from Stanford University, Nick Bloom, showed that while not every company in the world is remote or hybrid yet, almost every company has at least some remote or hybrid employees. 

That begs the question: If almost every company has at least some hybrid employees, how do companies deal with this? What's the way to run a company in this day and age?

To set the tone, we have had hybrid and remote work for a long time. COVID just democratized this experience for employees. Companies always had sales teams, trainers, and technical people that had to go to their clients on-site or do different things. 

They had to figure out what to do with a hybrid employee who was sometimes in the office or maybe never. You might never see that outside salesperson, except at all staff or the company holiday party. So, this is not new for employees and some groups. 

Now companies were forced to do it. So they realized, "I really can't manage these people." It's so simple to say, "Is this salesperson meeting their quota? I don't care what they're doing with their time." They meet the number, or they don't. But that's not the metric we use for a customer service agent or a technical person.

"We don't know how to manage employees? What did we do?" That was what we spent a lot of time during COVID and after helping companies. What are those metrics, and how do you decide what's good, what's bad, and what needs to be worked on?

Remote Work Best Practice #1: Set and measure team goals

A lot of companies were never built from the ground up for remote and hybrid. Everyone is trying to figure it out as we go along. You mentioned something really interesting about salespeople being very easy to measure their performance. You know whether they made the appropriate amount of outbound calls. You know whether they contributed enough revenue, as per plan. We could say the same for engineers. Within IT and engineering companies, typically, the transition to hybrid work wasn't that difficult. Because they were quite used to thinking about what needs to be built, what are the story points, and how we track whether people deliver on that or not.

But there are so many people where companies don't know how to measure it. What are some steps that companies could take toward solving that problem? So that we go away from, as Microsoft calls it, productivity paranoia, where just because we don't see people, we assume that they're not working.

It is a varied response or varied approach for every company in every position. And one of the hardest people to figure this out for is mid-level managers. Because how do you measure that when you're managing people? Are they on call? Survey results? It can be really tough. If your job consists mainly of managing and sitting in meetings, it's hard to put a number on that beyond a team satisfaction score.

I suggest looking at the metrics they can put towards that person that makes sense. If there is a manager's opinion of their performance and productivity or how they are on the team is a part of it, they should be a part of that [metric]. 

But sometimes, you can't look at someone and say these metrics equal a good job because they're impacting the organization in such a soft and generalized way. Occasionally, a client calls and says, "Wow, Suzy, you're really getting great for me." But do you give them a raise because of that? Does that mean all of a sudden they're good? And if they didn't get one this year, they're bad? 

I have often set team goals with those groups of people. We look at the team holistically. Ask if the team met their goals, and mix that with some manager's review. That's how we determine it. If it's too squishy and hard to say that person needed these specific things, we can look at the team goals. If the team goals are met, doing great, then we leave them alone. And if the team goals aren't being met, the team is failing, then we can get in there, start micromanaging, start picking out what's happening, and really don't worry about productivity. 

Absolutely! That's super interesting to think about the team as the units and what they should deliver.

If a company doesn't know what individual teams are supposed to deliver, probably there's a bigger problem altogether. Because, at least at a team level, you need to understand what we are here for. What work would contribute meaningfully to the company's goals and mission? Therefore, that's something you can measure.

Remote Work Best Practice #2: Be explicit about performance metrics and remove unnecessary approvals

The topic of teams also raises another question, moving away from the metrics to another area where you're also doing a lot of research. How do you build teams? And how do you maintain teams? How do you do that in a world where we're not sitting side by side, 9 to 5, five days a week? That's a big challenge for a lot of companies right now.

Well, it depends on the different metrics of that team. If you and I are on a team, we have about two hours a day, so we could have a Zoom call. Otherwise, we're going to be working on anything. 

It takes a custom approach. But aside from that, we have to make sure that everyone agrees on what success looks like. What are the goals we're trying to accomplish? Who is specifically in charge of what? How much autonomy? Where do we give them autonomy? Where are they allowed to meet? And be explicit. Don't just assume. We have to be a leader explicit about what areas they have autonomy to make decisions, think independently, and get things done. They need to let us know. We need to make adjustments that they need to make a decision. 

But we want to remove barriers and unnecessary approvals. Great teams understand at a very deep level how to get work done, what they are allowed to do, and what requires approval. Then we can energize them with good leadership to move forward and accomplish their goals. 

Bad teams typically don't understand. It's like a mystery to them about what we're supposed to be doing. When am I supposed to go to my boss and teammates for guidance? They're walking around trying to get work done with the lights on because they haven't been in other roles.

Super interesting! Immediately, when we're talking about team building, we're talking about running some fun activity. But you're saying there's also a lot of importance to start with the work. Because, at the end of the day, that's why we show up in the first place? And do I know what's expected of me? And can I be a good part of this team? That could be a much better starting point than starting by running fun activities and doing icebreakers. 

Remote Work Best Practice #3: Start “Cockroach Meetings”

Then within that, obviously, there's a big role for the manager. I think a lot of the conversations always come back down to the manager. How does someone manage that? We're running a lot of first-time managers who are transitioning from an individual contributor to a manager. They have to figure out how to manage, but now suddenly, they're in a context where they cannot rely on the office as a crutch to seeing people constantly and being able to give feedback on the spot and course correcting in real-time. 

Are there some management principles that managers can use when managing these kinds of hybrid Zooms?

Sure! Again, be explicit with people on how they get the answers to their questions. Is that always in Slack? Is that always on email? So we used to do these meetings, and I've taught this to hundreds of companies, something called a "Cockroach Meeting." 

If you have a cockroach in your bathroom, it's a small problem. You may not want to be the one who cleaned it up. But it's a single small issue. So you would quickly run downstairs and tell everyone there's a cockroach in the bathroom. Could someone come to help me catch this thing and get it out of here? 

As opposed to it, we have this other meeting called a "Tiger Team Meeting." Imagine what happens when you get a tiger in your bathroom. That's a totally different reaction. 

In the cockroach meeting, we told people you are allowed to call a meeting. Any person can call the meeting. You can invite anybody you want. We suggest five to seven people. It is totally optional, though. If you are invited to a cockroach meeting, it is totally optional for you to show up. So, if I invite you, it's morning time for me, but if you're sitting down for dinner with your family, you don't have to feel any pressure to show up. But if you happen to be sitting on the train, and you're like, "I can pop in this meeting for really quick. I could help this person out." You could do it.

The meeting is no more than 15 minutes long. We always strive for it to be less time. Our average cockroach meetings are seven or eight minutes. There is no "How's it going?", no icebreakers, no "What's the weather like?" But instead:

  • Caller: Here's my problem.
  • Supporters: This is how you solve it, or this is who you need to talk to.
  • Caller: Great, thanks, everyone! Bye!


Creating that empowering solution allows employees to deal with their issues and let the team help them. They don't have to wait until they get their boss on the phone or until a weekly meeting with the team, or the worst is, go around calling or slacking every teammate one at a time trying to get a question answered. Then, they're bogging down the entire organization. And they're not getting any work done or spending three hours Googling the problem when they could have just asked. For example:

  • Caller: Hey, can anyone pop on a quick call with me at 1:00? I don't know how to do a pivot table. Who knows how to do a pivot table in Excel?
  • [Three people will show up.] Oh, I know how to do a pivot table. Let me show you and quickly show them how to do it. Here's a cool video you might be able to use.
  • Caller: Okay, thanks, everyone. Bye, awesome!

In 15 minutes or less, we saved the organization 20 hours because you probably had them bugging people one at a time, bouncing around the organization, and being in all these meetings.

That's how we create efficiency and opportunities for people to get things done. If the managers can empower their people with the strategies and how they can get things done, that's really big. Making sure they have the right cadence for check-ins. I love companies utilizing Scrum, Agile, or Kaizen. These naturally have these built-in meetings.

But if you're not doing that, if you're like, "I'm just a regular manager who's got five customer service employees that we don't have a system," read some leadership books. Keep asking and talking to your people about what they need, and give them clear direction on how you want them to ask for help.

Yeah, I love that! I think the practical approach to solving problems is powerful. Because what we hear a lot is that people feel too big of a barrier to reach out to ask small questions. They start lingering or festering, and maybe one cockroach becomes a whole army. 

That barrier seems to be there because when you're sitting in an office, side by side, it's very easy to see if someone would be receptive to you asking a quick question. You can see whether they're in deep focus mode or whether they're in another conversation. You don't want to bug them about it. But if you see that they're just answering emails or doing small work, you don't mind that much stepping up to them and asking the question.

Now that we're remote, we don't have any context. We don't have any visibility into what people are up to. So can I really bother them with this question? That's something that we hear a lot. 

So, the manager's role then being the one to say, "No, actually, I want you to reach out, and here's a format in how to do that. And if you don't, here's a cadence of other meetings in which we'll get in touch, and you'll have the opportunity to ask those questions." That can be very, very powerful.

Remote Work Best Practice #4: Let people know where to find information, and make it a habit to capture every learning

Any other tips and tricks? We can learn a lot from you in terms of just practically how to communicate better. How to collaborate better in these remote contexts?

Well, a lot of times in these little questions that come up, the leader, if they hear about it or if a team member identifies it, it's great to create a Loom or a Vidyard. Usually, 99% of the time, when someone has a question and runs into a problem, it is not the first time that has come up, and it's not the last. Rarely do brand-new original problems suddenly show up. When they do, it gives you to land on the manager's desk anyways. 

So, take extra seconds to create that content. Someone asked this question, here's how you solve this problem. Here's where you go with our software, or this is what you do, when you talk to IT or whatever. And the next time it comes up, someone can literally grab that link to that video to solve the problem. We don't have to meet. We wouldn't have to talk.

In organizations, we've created internal FAQs and videos next to them. It takes time. But in about six months, they have so many videos and repositories for employees to shift from "who can help me" to "I actually have a place to go" and "I can look up this question." ChatGPT and AI have started helping organizations look at their emails, transcribe their calls, and create an FAQ system. Employees don't even have to stop what they're doing to write it down. AI will make just naturally go. If you keep hearing that people don't know how to get their password, create that FAQ. I think that's really important.

I love the idea that this is probably happening anyway. Even if you think about a simple exchange on Slack or within a team about a specific issue that some one runs into, a co-worker who's been there before tells them how to do it, maybe a link to a resource or a video. That is all happened already. If there's a smarter way to tap into AI, then compile that into an FAQ, so that the next person can also find the answer. That makes a lot of sense.

Generally, the idea you boast about is not the first time this problem has come up. That's obviously the old way of doing things, and the old way of thinking is very much that I step into a role managed by someone who's done that role before me, and they will cascade down, "Oh, I remember two years ago when I took on that role, here's how I did that." You'd take some of that knowledge and then put some of your own spin on it. That becomes your way of working, which you pass on to the next person, which is very linear. This knowledge base and inventory of all the answers to all the questions and challenges means that you can distribute the work much better.

As organizations start to think about not just hiring a few people under a manager, but also tapping into gig workers and skill marketplaces, whether it's internal or external, that really helps build the organization of the future. I think that's very interesting.

Yeah, we used to know that people always need to be trained on certain things. They would always have certain questions. We created folders and really made them organized. So employees could go in at their own speed. 

Remote Work Best Practice #5: Automate onboarding and training process

Even though employees enjoy asking their fellow employees and having that time to connect and be human, when we send them a video, they watch it an average of 15 times. 

The answer was twofold. One, they could watch it at their own speed. They could tell us they understood, but they didn't really understand. And so when they got the video, they could keep re-watching it and realize they're getting deep learning, deep understanding because I'm watching somebody do it. What would happen as a few days goes by and they would forget some of it? They will go back and watch the video a few more times again. And it cut down on the amount of time that our key staff and managers had to spend training new people. 

"A" players tend to get called into these training because they're the ones who know how to do it best. But now you're sucking all of the juice out of them for the wrong thing because they should be doing the work, not all the training. And the managers get bogged down in the situations. 

We also created automation for marketing, sales, and things like that - employee automation. So when they started on day one, we had an intro email to welcome them and tell them what they should think about for today. On day two, they would get another automated message from the bot or from Human Resources about what they should know about Spark, for example. Day three, here's a cool thing you can do in Slack or what you need to know about this. Slowly day by day, they get an email. But we can automate the process. We know the things that need to be learned over time and that need to be introduced to help them get integrated into our company. We didn't leave it to the team or each individual manager to do in their own way. We created it the way we wanted it to be done and automated it with consistency and persistence for every employee.

It makes so much sense. We were joking early on about TikTok. When you think about especially younger generations and how they come into the workforce, there're organic media-consuming habits. That idea of watching a video and watching it 10-15 times is so much more natural towards how they already consume not only content but knowledge. They learn through 15-30 second little videos in which you talk about one little thing, for example, company culture or three tips for positive leadership. That's how I learned, and maybe I bookmark that video and go back to it when the situation arises where I actually have to apply it. That's so much more logical. 

And again, the barrier is so much lower to getting that instruction up to 10 times than constantly having to go back to your manager and say, "Oh, I'm so sorry. I know I said I understood it. But actually, I didn't really get it. Can you explain one more time?" Because at some point, you're just not going to ask anymore. And for some people whose tolerance is very low, they will only ask once or twice. Then you get people spinning their wheels doing a lot of work that doesn't contribute to anything because they may have gone down the wrong path. These little micro tips can help solve big problems for a company at a very granular level. 

I also really liked the idea of the automation. Because we live in a day and age where so much can be automated. In everything besides work, so much is automated, data-driven, and personalized, like that drip email idea. But it's still very much one-size-fits-all in the workplace. And everyone gets the same experience. Everyone gets the same onboarding, which doesn't make sense, and we're wasting a lot of time.

Expert Advice #6: Just try to be able to accomplish things outside of your comfort zone

Just one question to end: If there's just one piece of knowledge you could get across to the world, what would it be?

Wow, one thing to get across to the world. I really wish people knew that they just have to try to be able to accomplish something. 

Many people say to me, "I can't believe that you've done this, or that you've written this book or whatever." And I'm like, "I just try." It wasn't because I was going to ask my teachers. None of them would have told you I would be a writer. They would laugh at you if you asked them that when I was in school. That was not my jam. But I went and wrote books. 

You just have to try and taking that first step and being brave enough to be okay that you might fail. I've literally tried 1000 things that did not work out. But for some reason, I don't have a problem trying. But I'm always fascinated by how many people around me are so afraid. Just try outside their comfort zone or outside of what is the normal thing they're supposed to do and get failure. And so let's go get a 9 to 5 job, whatever. Just do try the thing. That way, the world would be a lot better. A lot of people who were out there trying to do something else that makes them happy, makes them more money to help their family and society. Just go out there and try.

Beautiful, and what is there to lose? I love that idea. Okay, everyone. So you've heard it from Chris, the expert, just go and try. And hopefully you will become as successful as him one day.  

Thanks Chris so much for joining us today. We'll post all the links to all your accounts in the show notes. People, go and check out Chris for much more advice and insights.

Thank you for having me.

Find Chris on, Linkedin, and other social media channels to learn more from his expert.

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Future Work

A weekly column and podcast on the remote, hybrid, and AI-driven future of work. By FlexOS founder Daan van Rossum.