Claire Lew

Remote managers need a new skill set

31 May 2020   |   Leadership Remote Teams

Claire Lew

Remote managers need a new skill set

31 May 2020   |   Leadership Remote Teams

What are we talking about?

Managing remote teams well.

Why is managing remote teams important for the future of work?

Managing remote teams takes a different orientation than being in the office. As more workplaces go fully digital, managers need a new set of skills.

What did Claire Lew teach us about managing remote teams?

Many people expected this transition to remote work to be quick. It’s not. It takes a lot of work and effort.

Most of the success lies in how well your managers and team leaders show up. Here are the things they need to focus on:


This is less about tools and more about good management practices. Share the context, build trust, have honest conversations. If you weren’t doing this before remote work, you are going to really struggle.

Remote work requires a lot more writing, so managers need to get great at that. A lot of it is asynchronous writing, which means you have to communicate clearly, provide even more context, and assume positive intent.

Interacting with team members

One of the most important jobs a manager has is to make sure people have a positive morale. There’s a lot of uncertainty and managers need to help ease confusion and fear.

Your role as a manger is to be constantly clarifying where people are spending their time. Keep up on your 1:1 meetings and identify what is getting in the way of others.

However, the success of the team isn’t only dependent on the manager. You should also allow the team to support each other and create a buddy system so not everything is reliant on one person.


When life gets hard in remote work, you are tempted to blame:

  • Remote work itself
  • The people
  • The systems you’ve set up


Great managers know that their highest responsibility is to focus on setting up great systems for the people around them to thrive.


More from Claire Lew

Know Your Team

The Guide to Managing Remote Teams


Today, our guest is Claire Lew. She’s back on the show. She’s the CEO of Know Your Team. This episode is Work Minus Remote Panic. Hi, Claire. How are you doing today?


Hey, Neil. I’m doing really well. How about yourself?



I’m doing great. It’s so exciting to have you back on the show. You are in my mind, my favorite management expert. I love the stuff you put out. You put out a lot of really interesting things and I feel like lead your community well. Thanks a lot for coming back on our show.


You bet. That’s really kind of you. It’s funny. When you asked “how are you doing?” my automatic response just I noticed was “well,” and then I realized, you know what? I am but I just feel really grateful given that that is the case during these times. A lot of people are really struggling. It was a funny thing to say, wow, that question. I think the answer to that has changed for a lot of people.



It’s true. That’s one of the things I like that you write about, too. It’s not just starting with, hey, how’s everyone doing? Fine. Okay. Great. And then moving on. I like that piece of advice you give.


Thank you.



So, Claire, like I said, you have a large community of people who are talking about these topics, wanting to know things. I want to hear from you, managements helping people be better managers, bosses, leaders is your core area. But remote is also a core expertise for you. You’re running a remote company, you have a lot of experience in this. So, over this last month that we’ve been involved in this crisis, what are the the areas you feel like people are struggling with the most? Where are they reaching out to you for help in the last month?


It’s really interesting with the pandemic in that, all of a sudden, people were just forced into something. Folks who’d never worked remote before were planning on it, kind of doing it, all of a sudden had to go all in on something. I think anytime that happens where you just rapidly have to switch your entire context for how your entire company works, and it doesn’t matter if you are a three-person team or 3,000 people, that’s hard. Folks are really trying to figure out that transition. I think one of actually, the biggest misnomer for the things that people run into is they expected the transition to be very quick. We’ll just jump on Zoom, and we’ll make sure everyone’s on Slack. And now we’re remote. The reality is that to actually run a remote team, well, it’s like any other work process or context or system which is it takes a little bit of time. So, that’s one of the first things I always tell folks is, don’t expect that in a week everyone’s going to get the hang of it, is that it’s actually pretty different if it’s something that you’re not used to or something that your entire team isn’t used to. Then the second thing that folks often run into is they go, well, yeah, the biggest problem I’m having right now is how do you even communicate in a remote team? Do you just take all your meetings they used to have and put them on Zoom? Or do you take all the back and forth that you used to have with folks and you send them all emails and Slack messages or whatnot? What at the end of the day enables remote work to be effective is less of the tools that you’re using and more so the actual management practices. In fact, that insight is not my own original insight by any means. There’s an incredible woman by the name of Dame Stephanie Shirley, and she back in the 1960s founded one of the very first remote IT companies in England, and it became massively successful. At the time, if you can remember, 1960s…



I don’t remember.


Here’s the thing. I mean, I wouldn’t either. But this is a time before email was invented. So, how do they run a remote company? And she said telephone. And she is really keen on emphasizing that remote work has very little to do with the tools itself and has everything to do with actually having good management practices. So, that brings us back to what folks are really struggling with, which is right now, if you have outdated management practices in the sense that you haven’t figured out a good system for sharing context in your team. You haven’t figured out a good system for building trust. You haven’t figured out a really good system for having honest conversations and one-on-one meetings, then you’re going to really struggle and particularly struggle when it comes to remote work. It’s almost as though the things that you were having a hard time doing in person are almost exacerbated when you’re remote. That’s another thing that’s been really interesting. More specifically, Neil, the things that folks have been struggling with the most I would say, number one, is just the fact you have to write a lot more, particularly writing asynchronously. The remote companies that are most effective are the ones that their leaders in particular are really focused not just on paying people all the time and saying, Hey, what’s the status on this, or, hey, we should do this, but being very thoughtful in their long form written communication. You can use a tool like, for example, here at Know Your Team, we use Basecamp to do this. But other folks will use tools like Notion or Asana or Trello, etc. But that’s one key thing. Here’s the thing. That’s based off a bunch of research that we did last year with hundreds and hundreds of remote managers and employees in terms of what really helped make them successful. The second, I would say, biggest thing, and once you figured out, okay, here’s how we just get work somewhat done in anyways and figuring out some system for communication, is the social piece. That’s probably the biggest noticeable difference for folks who are going remote. I would say in terms of frequency of questions I get right now, one of the most common questions that I get is, how do I help my folks have positive morale right now? How do I help them feel connected to the team while we’re all socially isolated? How do we do that? So, happy to go into more detail about any of those things, Neil, but those are some of the biggest things I’ve been hearing.



Yeah, I love how you framed it. I agree that remote work, I think, really exposes what your workplace was before. When you take away all the physical contact, when you take away all the things you were relying on, if you had bad management practices, they’re going to look a lot worse. If you had good management practices, it’ll still take some time to transition, but I feel like it won’t be as tough. Are you seeing the same thing?


Yes, I am. I will still say that I think it is difficult for even the folks who are having good management practices. The transition will be easier, but it is different. Again, I really emphasize this because I think if we as leaders, and if you don’t really also level set with your team, that the transition is going to take a little bit more time and be a little bit more rocky then you set folks up to get frustrated. Essentially, the expectations that you set as a leader are really important for what folks actually are going to be feeling on the other side. We did this, I may have shared a little bit about this, but we last year, Neil, we did this really big study with hundreds and hundreds of remote managers, employees. And I spent the better part about a half a year writing and researching about 11 chapters, specifically on remote work. Then in March, when all this craziness with COVID-19 happened, we actually opened it up for free. So, if folks are interested in diving into any of that research, that’s a great place to start. We had hundreds of thousands of people download it and read it and share it. I think that alone shows you just how hungry and how needed information on this topic is.



I love the resource. I’ve downloaded it, read it many times. Used it in my own writing, as we’re thinking about these topics. So, I’ve referenced you several times in there. It’s really a fantastic piece out there. So, thank you for spending that time. I know that doesn’t just happen overnight. I know it’s a lot of research, a lot of work to get that out.


Oh, thank you. I appreciate that.



Let’s talk about this timeline issue again. In my experience talking to people I know, I feel like the first few days of the reaction to the pandemic, everyone was freaking out. What do we do? We don’t know how to do this. And then they were were just, day long Zoom calls that were going on. Then after maybe a week or so it settled in and people realized, wait a second, this is not so bad. We can get used to this. We don’t have to meet all day, every day. There was almost this little bit of, like, you’re almost on vacation from the office and a little bit of hype around that. But then now, we’re about, for some people, four or five, six weeks into this. Now it’s really set in, like, oh, this is different. This is harder. How do you help people navigate those ups and downs of that remote work feel of trying to figure out, because when you’re in remote work, you solve one problem, but another one comes up. There’s a lot of work on the leadership side, on the management side of setting up those systems so that these things don’t become problems down the road. So, how do you help people do that?


It’s such a great question, Neil. I think there’s several layers here. If I just paraphrase what you seem to be asking is just what is the best way to support your remote team members as they and you go through these ebbs and flows, especially in the midst of working in a pandemic? I think, first and foremost, one of the things that is hard to do as a manager, but it’s so crucial, and this is regardless of whether you’re in person or remote, is making it extremely clear to folks. Here’s what needs to actually get done and why. When we’re working in a team, the whole purpose is because we’re trying to accomplish something that we alone wouldn’t be able to accomplish. The role that we play as managers is, first and foremost, how clear are we making that for people? In a remote environment, this becomes even more critical. For example, have you answered the question, what does a picture of success look like? How will you know you will have been successful? How will you know something is good enough? What is the expectation to respond to messages back and forth? What’s the expectation around how often progress will be shared? What are the milestones that are expected to be hit in order to get to that place? What do they anticipate the biggest hiccups are going to be? I could go on and on and on about different questions that you can ask folks, for yourself and for your team member to make that clear. But I think one of the things that gets lost is it may be clear to you as a manager, but your role as a manager is to be constantly clarifying what it is that is most important or where people should be spending their time. So, that’s one.


The second thing is, as a manager, especially remote, you have to become almost militant about trying to figure out what is actually hurting folks and holding folks back. And this is also harder to do in a remote environment. Part of your job as being a manager, and again, this is regardless of if you’re in person or remote, is trying to figure out, how can I actually help this person accomplish the thing that I said very clearly that needs to get done? In order to do that, you have to figure out what’s holding them back? What’s getting in the way? Where are they stuck? What do they not have enough information on? What do they not have enough skill on? What is it? This is where having regular one-on-one meetings is crucial and structuring and preparing for these meetings in a way that’s actually going to help you get the most out of them. So, it’s why, with Know Your Team, for example, we built a one-on-ones tool that helps you ask these questions, prepare for them. We give you hundreds of agenda questions and templates. And this is probably our most popular feature in the tool. It’s what I use almost every single day. You don’t have to use our tool. You could use anything. But the whole idea is, are you creating a system of regular check points, one-on-one where you can have a conversation to be able to uncover what is it really, that is getting in the way and that’s a second big piece.


The third big piece that’s massively important as you think about supporting and creating a strong environment for your team as they’re remote is trying to find ways for your team to be able to support each other. So, what ways and opportunities are you creating for your team, to feel connected, to laugh, to smile, to just actually enjoy getting to be around folks when you’re not even in person. There’s some really fascinating research that’s been done, Buffer actually put out a 2020 state of remote work report where they interviewed, or rather surveyed, I think it was over 35,000 remote workers. They found that the number one problem and struggle that remote managers and employees faced was loneliness. So, feeling socially isolated. You paired that with the fact that there’s a study that was done, I forget what year it was, sometime in the past five years, but it was done with about 15,000 call center employees and they found that 15 minutes of socialization with folks actually increased performance by 20%. If you pair those two things, which is that loneliness is a huge problem for folks who are working remote, that it’s the number one thing that remote workers wish they were able to overcome. It’s contributing to potential attrition. Then you have the fact that the upside is that having a little bit of socialization and connection actually helps to increase performance. As a manager, you have this incredible opportunity to try to figure out, how do I do that in my team? Lots of different ways, any everything from, this is stuff I’m sure you’re doing within your own team, from having a non-work chat channel, whether it’s a Slack channel about everybody’s pets, it could be Zoom calls where you have coffee and book clubs and play video games or whatever you want to do that’s fun and fits with the culture of your team. Then there are things that other remote teams do like creating a buddy system, or really investing in the onboarding process for folks or icebreaker questions. In Know Your Team, this is why we have a feature called our icebreakers feature and our social question feature that are all about building social connection.


That’s a third piece that I think is absolutely crucial for creating a strong environment for remote employees. And then the last thing I would say is to actually make sure that you’re taking care of yourself as a manager. I think this is something that’s often overlooked, especially during this time, which is that you usually, as a manager, you’re in that position because you like helping others. You give and you give and you give, and sometimes you forget to take care of yourself. It sounds a little cliche, I suppose. But I know for so many managers, and I get a ton of emails about this. I’m feeling not as motivated. I’m feeling depleted. Especially for folks who are caretakers, they’ve got kids, they’ve got parents living with them, etc. Taking a moment to realize that you can only be as good, in terms of helping others, to the extent that you are nourished and energized yourself, and so finding that time in the day for yourself, whether that’s literally 10 minutes in the morning, or doing a 20-minute workout or jumping jacks or whatever, going for a walk, whatever it is for folks, but making sure to take care of yourself, too.



I think that your fourth and third points really play into each other, especially because at the start, you said it’s not about necessarily you need to be the one supporting everyone on your team. The team can support each other. I think a lot of people as managers may feel like, oh, I got to be the one calling up everybody every day having these conversations, and that does drain you. Losing that the world is stuck on your shoulders. I feel like another thing you said when you were talking about being militant about systems setting up, there’s something to me in my experience working remote that as I’m interacting with people on my team, taking away the office environment helps me to focus on the fact of the person is not the problem 90% of the time. It’s the system that’s the problem. I feel like remote work exposes that and helps me as a manager to focus on, okay, if this person is not getting work done, if there’s a problem, there’s probably something in the way that focuses there. Have you found the same thing?


I think it’s extremely astute of you, Neil, to see that. Truly, because I think the way systems operate is that they’re almost invisible carriers of our actions. The fact that we can see them is, I always find it revelatory. I always find it surprising to folks and I think it’s always hardest to see when you’re in it. I’m encouraged by the fact that you think that’s true. I don’t know if broadly speaking, but that’s something that folks pick up. It would be great if that was the case. But I do think, at the end of the day, here’s one common reaction actually, sometimes is folks sometimes have the opposite insight you do, which is, oh, I’m seeing now that we’re working remotely, I’m seeing all these things that are broken. So, the fault is that just remote work doesn’t work, period. So, it’s not our systems or the way that we’re doing it. It’s just the fact that you can’t run teams not being in person. People have another way and lens of looking at it, which I think it always reveals that our tendency as people, whether or not we’re managers or not, our tendency as people is to figure out a convenient story to explain whatever is in front of us. It’s much more convenient to say that there’s this thing called remote work that we just can’t really control that is the problem versus looking at, oh, I might be the problem. It’s because I’m not holding regular one-on-ones. It’s because I haven’t created a strong system of accountability. It’s because I haven’t found a way to clearly share progress. It’s because I haven’t done a good job sharing expectations. That’s a harder thing to admit than just to point and say, you know what? It’s remote work. Again, this isn’t to disregard the fact that moving and transitioning to remote work is challenging. It’s what I began everything off with is don’t expect this to be a two-week thing. It’s going to take months to really feel like you are transitioning into it well, but I think the unfortunate results would be to, while you’re experiencing some of these struggles is to blame the remote work itself versus using it as an opportunity to put a magnifying glass up to, what are the systems that we could be improving internally better?



This really got me thinking a lot of great things. I feel like the theme of the show should just be remote work exposes lots of things, or at least gives you a new view on the work you’ve been doing, on the team, on your own leadership style. Obviously, things are different in remote work, but it does also reveal some core things that are good about what you’ve been doing, how you can replicate those in a digital environment, but also ways that you can improve. So, let’s hope we can be self reflective during this time and find those new ways to move forward. Claire, it’s been great to speak with you and have your insights on this. You mentioned several resources and tools. Where can people go to find all those?


If folks want to go to, we have something in there now that says remote managers. If you click on that, you’ll see all of our resources for remote managers. So, everything from all of the tools that I mentioned, so we have tools for social connection, for one-on-ones, etc, for remote managers. You can view the guide that you talked about, Neil, and that thousands of other folks have read and downloaded, which is completely for free. Then the other thing that we offer that we opened up for free is I recorded a 60-minute deep dive online workshop on how to manage remote teams. There’s a pretty good Q&A section in there. We had hundreds of folks from around the world tune into that, and so, you can also view that session, too. You just head to



Well, great. Like you said, this is going to be a long walk towards remote work. It’s not something we can just learn and move forward. So, we look forward to continuing to learn from you and the things you’re learning and share those with others and thanks a lot for being on the show, Claire.


Absolutely. Thank you so much for having me, Neil. A real pleasure to get to chat with you.


Claire’s mission in life is to help people become happier at work. She speaks internationally on how to create more open, honest workplace environments, and has been published in Harvard Business Review, Fast Company, Business Insider, Fortune, Inc, Forbes, among others. She writes regularly on the Know Your Team Blog, and is an adjunct professor in entrepreneurship at her alma mater, Northwestern University. Follow her on Twitter, and email her at [email protected].

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