How to Measure Remote Team Performance (Without Spying)

In today’s episode, you’re going to discover how you can really know if your team is performing at full capacity, which, to be honest, is one of the trickiest parts of leading a remote team.

Welcome to the Eric Dingler Leadership Podcast, where I am committed to helping you build and lead a successful, efficient, and effective remote team. So if you are looking to start a team, if you are already leading a team and they are remote, virtual, or hybrid, and you want to skill up your leadership, you’re in the right place. What I’m sharing with you comes from in the trenches experience. I have been leading since I was 20. I am currently 50. So for 30 years I’ve been leading in the trenches. 15 of those years was at a summer camp where every summer we hired staff, and we would have to hire 30 to 50 staff to come on board and take care of other people’s children. Then I transitioned into local church leadership, and then church planting. And now, for the last five years in the marketplace, while leading in the marketplace, my team has been fully remote. So I’ve had to make that transition from leading in-person to remote, and I’ve learned a lot about what it takes to do that. I’ve had to recontextualize my approach to leadership, which is really exciting for me, because one of my favorite leadership axioms is the principle behind the practice, and I’m going to unpack that as well as how you can measure the performance of your remote team.

In today’s episode, I’ve got three things I want to cover with you. Number one, we’re going to jump right into the content. I’ve got three things I want to share with you on how you can ensure your remote team is performing and working when they’re supposed to be working. Then I’m going to share with you a leadership nugget of the week. I love these little leadership sayings and nuggets, avoiding cliches but really trying to boil things down to a statement of truth that helps you and I and others remember a leadership lesson. Some of these I create, and the vast majority are ones I’ve learned from other leaders as I’ve been mentored and coached over my career. Finally, the third thing I want to share in today’s episode is a final travel update.

If you’re new to the show, you’re going to be like, wait, what’s this travel update? Well, I started the podcast when I was a digital nomad. My family and I, my wife and our four kids, would change locations every couple weeks to every couple months, and we were building our business and traveling the world. Well, time has come after almost four years for us to settle and set down some roots as our kids are starting to transition into young adult life. They’re between the ages of 12 and 18, our two oldest being 18 and 17. It’s just going to be easier for them and better for them if we are living rooted as a family, for them to start transitioning into their adult life. So we are going to stop traveling. I’ll give a quick travel update and then this podcast moving forward is just going to be leadership focused. But I’m never going to stop traveling, just not full time, and I’m always happy to speak with those who want to know more about how to travel full time as a digital nomad and build and run your business. So if that’s you, feel free to reach out. Always happy to talk.

Okay, so let’s get into this week’s content. How do you measure your team’s work, their output, their performance? Now the thing is, most people, when they try to start tackling this, and I have seen it, I get bombarded with advertisements for some of these tools, and I hear people talk about these things, and it makes me cringe. But I understand where it comes from, because I used to, for a short period of time, think I had to have these things. There are tools and technologies out there that people think they need, such as screen recording, where every time a team member is logged in and working, a digital trail is being created, their screen is being recorded, keystrokes are being recorded and measured. I know some companies where you have to register a certain combination of keystrokes and mouse movements within a certain time frame. If your computer doesn’t register that amount of activity, an alert goes up, sirens start ringing somewhere halfway around the world. People think they have to have some type of time tracking software. And a lot of these things come from fear. I’ve got a group I’m coaching right now, and one guy in the coaching program has asked me two or three times, do you ever worry about somebody taking advantage of this? What if something goes wrong? What if you hire a freelancer and they mess up? There’s just this scarcity mindset and this fear that’s holding this person back. A lot of us have this. We don’t like giving up control, and so we want to keep control. What we have to do is we have to wrestle with the principle behind the practice.

You see, when you’re leading and managing an in-person team, you can manage by walking around. You walk around, you get a feel of the environment, you can see what people are doing, you can sense the activity. You can have stand-up meetings, there are all these things you can do. But these practices you have in place are all guided to help a leader make sure things are moving forward, to help a leader make sure there are no bottlenecks, to help a leader make sure there are no barriers in people’s way. One way to do that is a lot of leaders employ managers, and managers are tasked with keeping the trains on track, keeping things moving, keeping everybody regulated. So when you start to disperse people into a remote team, we want to replace those practices, or contextualize the practice from an in-person environment to a remote environment. And you can’t do that, you can’t contextualize the practice, until we stop and ask ourselves, what’s the principle at play here? What are these practices that have served us well for this environment trying to achieve? Ultimately, what you’re wanting to do is make sure there are no bottlenecks, that your team is empowered, equipped, that they understand what to do, when to do it, and why they’re doing it. You want to make sure things are moving forward. You have to trust your team.

Well, it’s really easy to trust your team when you’re physically in one spot. And when Covid happened, some businesses adjusted really well and some businesses never have. Even some really big businesses have struggled with this, and they’re forcing their people to come back to the office because they say it’s just better, remote doesn’t work. And they’re wrong. Remote does work. They just suck at leading remote teams. They didn’t change the practices, because they never took the time to wrestle with the principle behind the practices they were using. So they tried to figure out ways to micromanage people’s time. It was this focus on time. What are you doing with your time? How are you maximizing your time? If we can record their screen, if we can record their keyboard strokes, if we can measure their mouse movements, how many pages they work through, if we can measure these things, these are indications of progress. And that’s just wrong. It doesn’t work that way. It doesn’t have to work that way.

So what do we do? What are the three things you can do to make sure your team is functioning at their fullest capacity? Here’s the thing you’re going to learn. People who crack this nut over and over all say that their remote teams are actually more productive in less time, because they stopped measuring time and started measuring productivity. They measure the productivity by the outcomes, and what they found is people got very creative in reaching outcomes when the outcome was clearly articulated. So how do you do this? What does this look like? I’ve got three things for you.

Number one: you need to create a virtual office. Now I’m not talking about using augmented reality and having your team wear headsets. But I do think having a virtual office is crucial. Your virtual office can be made up of a few different tools connected together, or you could use just one tool. You could successfully create a virtual office with Slack, with a WhatsApp group, with a Facebook group, with a membership software like Circle or Kajabi, or something like Searchie. The idea with the virtual office is again the principle behind the practice. What was the principle that having an office was delivering on with managers and leaders? Being able to see people in their space. They weren’t walking up and staring over somebody’s shoulder monitoring keystrokes, that’s not what people do. In those environments, what starts to happen is over time, as a leader, you start to pick up on all kinds of overt and covert cues and messages that sometimes you’re not even aware of. It can be the volume level in an office space. There’s this intangible feeling you get when you’re in an office space, and every office space is unique, and employees and teams have unique feelings to them. As you’re there, you get this sense that things are happening. If you’re in a keyboard-heavy office space, you’re going to hear the clickety-clackety of keyboards. If you’re in a creativity-heavy space where people are collaborating, you’re going to have a level of murmur. There’s going to be visual cues too, you’re going to be able to tell things are happening just by the movement. People develop these rhythms and this cadence of movement that you’re not even going to be fully aware of. When I was running the camp, I could tell by just the sound of camp if things were going well. At different times of the day, the camp had different sounds and a different feeling to it, and when all of those things felt right, I knew things were going really well. A virtual office lets you do the same thing.

For my digital marketing agency, we use a tool called Hive. It’s our project management app, and it’s got its own built-in Slack functionality. We don’t use Slack, we just use what’s built into Hive. There’s a level of activity in Hive that happens when things in my business are running at the right pace. If suddenly I notice the notifications seem less than normal, or there’s a lot more than normal, I get a sense over time by just scrolling and looking quickly. The amount of questions I’m being asked, or that I see the team asking each other, is even more telling of how things are going. In our system, when somebody is online and logged in, there’s a green circle around their picture. There’s a yellow if they’re on but haven’t been active. I don’t measure that, I don’t calculate it, but I have a pretty good idea at this point of my team’s working rhythm. There are times of day I expect to see certain people’s green circles, and when that changes, I notice it. I haven’t kept track of it or created a log, but over time you start to notice these things. That doesn’t mean I do anything about it in the moment, I just make a mental note and look to see if it’s a new pattern or maybe just a blip. But having a virtual office lets you do that.

You need a virtual office that you require everyone on your team to use. Whether it’s Hive, Monday.com, ClickUp, Asana, or even Google Spreadsheets and Google Docs and email, it doesn’t really matter, you just need a system in place that collectively is your virtual office. 99% of ours is in Hive. The other part of it is we have a virtual break room, a WhatsApp group where we post more personal things. I’ve talked about that in previous episodes so I’m not going to spend more time unpacking it.

Number two: you have to develop as a leader, and within your leaders, the skill of communicating via delegation at a higher level than you do in person. When I would delegate tasks with an in-person team, as I was explaining it to them I could read their body language. I could tell whether they were picking up on it or not. When they walked away, I could tell if they walked away with confidence or if there was still hesitation. I’d be able to oversee as they were working, whether they were moving in a direction that showed clarity in the instructions. In leading a remote team, you can’t do that. My wife and I often say balance is where the pendulum swings through on its way from one extreme to the other. In person, I’ll see leaders under-communicate when delegating. When they switch to leading remote, sometimes they either continue to under-communicate because they don’t realize they need to communicate more, or they hear that they need to communicate more and then it swings dramatically to over-communication, sharing so much content and written instruction that it’s overwhelming and nobody can remember all of it. It creates confusion. So you have to find the balance.

What I’ve discovered is when you delegate a responsibility or a task to someone, you have to be really clear that you paint a picture of what the finished result is going to look like. If you have a very specific picture in mind, and it’s important that something is a certain color or has a specific visual look, you need to paint a very clear picture of that. If you don’t care what the detail looks like at the end, you just want to see something that resembles this thing and it’s done, then you need to clearly articulate that. You have to learn how to be way more clear delegating to a remote team than you do an in-person team. It’s just different. You have to set very clear expectations with very specific deadlines. And if your team is remote to the point where you’re in different time zones, you need to have a specific agreed-upon time zone for everybody on the team. In my agency, our time zone is East Coast USA. So if I say something has to be done Wednesday at 3:00, I mean Wednesday, 3:00 pm Eastern Standard Time. It doesn’t matter if you’re in India, Bulgaria, El Salvador, California, Ohio, it doesn’t matter. It’s 3 p.m. East Coast USA time. You don’t have to be that specific in an office. If you tell somebody, can you have that to me Monday by nine, they don’t think Monday at nine in Japan, unless you’re in Japan, it’s Monday at nine wherever you’re living. For a remote team, you have to be very specific. And if your remote team’s primary language is different than yours, you have to make sure you’re clearly articulating in a way they’re going to understand. You have to avoid cliches and idioms. You have to be very specific when delegating. Dave Ramsey and his organization have a core value that says to be unclear is to be unkind. I really like that, and it plays out even more so in remote teams.

Number three: you have to set a cadence of communication, because bad things grow in the dark. It is so easy to have communication voids in a remote team, because you are living with something your entire workday, and because it’s in front of you and you’re thinking about it and working at it, you have situational bias where you think everybody else on your team is also thinking about that same thing and seeing it the way you do. That’s just not true. So you need to fill in these voids by having a cadence of communication. What your cadence of communication looks like is going to depend on you, you get to determine that. I’m going to share ours, but not as a practice to copy, you need to understand the principle behind the practice and then contextualize it to your team. Our cadence of communication is made up of three things.

Number one is the daily update. Every single project we have in our project management system, and for us a project is something we’ve been paid to do that has a deadline, whether it’s building a website, managing somebody’s monthly Google Business Profile, an ongoing service, a local SEO boost, remediating the accessibility of a website, or building a new one, has its own action card. There’s a card called Daily Update, and we even invite our customers to be a member on that card so they can see these daily updates from the team. Every single project is assigned one person on the team who owns that project. Now they don’t own the whole entire project, they just own the ball on the project at this point in time. Every project has somebody on the team who owns the ball, meaning at the moment they’re the person responsible on the team to move the ball closer to the goal line. They may eventually be the one that carries the ball across the goal line, but they’re just as likely to pass the ball to somebody else on the team, get it passed back to them, and pass it on again. Every single project has a tag with a team member’s name that says owns the ball. If you go into our project management system and go down through our list of active projects, you’ll see some that say Eric owns the ball, meaning I’m currently responsible for making sure we’re moving the ball toward the deadline. Some will say Marissa owns the ball, Peter owns the ball, Katie owns the ball. When you own the ball, you’re required to make a daily update on the project.

So every single day, one of the first things I do in the morning is sit at my computer with a cup of coffee or tea, take a sip, and start scrolling through every project reading the daily update. It’s been 24 hours, so every project will have had one. For the majority of them, other people own the ball, and I’m going to read an update that tells me three things: what has happened since the last update, what will or should happen next, and when that’s going to happen and by whom. The project may say, sent the link to the client for approval, we should hear back from them by Friday, I will reach out to them Thursday to remind them if we haven’t heard back. So: here’s what’s happened, here’s what should happen, by who and when. That’s the update. It could be, I’ve finished steps one through three and tomorrow I’ll do the final two and have them done by 5 p.m. Or, I’ve finished my part and I’m now handing this off to Peter, and Peter will take this through the next stages, or Peter can give an estimated time of when that will be done because maybe he doesn’t know yet since he’s just receiving the ball. Within about 20 minutes, I know exactly where every single project is and where it’s going. 24 hours later, I look again, and I can start to look for bottlenecks, like, that shouldn’t be holding us up that long, or here’s how you should handle this next time. I can see patterns develop and think, hey, we need an SOP here, we don’t have one, and I can step in and ask somebody to create one or refine something. These are golden for me. This is the most powerful management tool we deploy. This isn’t leadership, this is management, but we’ve got to have it, it’s super important.

Our second cadence of communication is the weekly report. On everybody’s last day of the work week, they have to submit a weekly report that asks them to score their workload, stress, and morale from the week using emojis, one through four, and then answer three open-ended questions about what they were most excited about and what was frustrating or got in their way. I read down through the team reports every Monday morning, and I have a very good sense by the end of that of how things are going with my team. Some people share personal things, the worst part of their week was their cat getting sick, or a storm came through their area, it’s not always just work related. The weekly report is very powerful. It takes most people less than three minutes to do.

The third and final piece is the weekly one-on-one. Everybody on your team should meet with somebody else on the team, via Zoom or whatever your video preference app is, at least once a week for a conversation. This isn’t project updates, that’s happening on the update cards. This is checking in with them about how they’re doing, how they’re feeling, how they’re coping, what they’re wanting to learn, where they’re looking to grow, how you can clear boundaries, whether there’s a tool that’s not working for them, what new opportunities they may know of. There’s lots of things that can happen in those weekly one-on-ones, but it’s really important that you’re checking in with your team and having these conversations.

So there you go. How do you measure performance in a remote team? You’ve got to change your mindset. It’s not about measuring time. It’s not about time tracking software, screen recording, or keyboard stroke measurement. None of those things. It’s about the principle behind the practice of an effective in-person team: having a virtual office that lets you and your team create and get into a rhythm and a pattern you can see and sense through a shared work environment. Number two, you have to learn to become crystal clear on what an outcome is that you’re looking for and when you want it done, and as you’re doing that, you’re going to be thinking through what obstacles could come up, what problems your team may encounter, and you’re going to help address some of those things because they’re not going to be able to just stop by your office and ask. You have to pre-plan some of that stuff you didn’t have to when leading in person. And the third and final one, you have to set a cadence of communication.

I’m telling you right now, the game changer for us was the daily updates. The team loves them because they now feel empowered, they know how to share, they know where to ask questions. The weekly reports are great, and the weekly one-on-ones are totally invaluable. Do those things and your team is going to perform. Don’t worry about time. Focus on output, focus on winning together, focus on moving things across the finish line by removing obstacles and barriers. That’s how your remote team will deliver over and over again.

Now see how this all came back to a mindset change? That’s one of the biggest keys here. And to help with that, I’ve created an 11 Day Leadership Reset, 11 prompts I’ve created to help you think about how you lead, about your leadership style, about leadership in general. I’ll send you one a day by email, and I’m going to encourage you to write down and journal your answers, even if you’re not a journaler. Type them, write them, speak them, I don’t really care. Just work through them, because it’s going to help you start to see yourself as the leader of a remote team, and help you step into that in a way that’s going to make you, your team, and your company more successful. Remember this about your business: your business will never, ever outgrow your leadership. Your leadership skills are the capacity of your business. Lead better to have a better business. It’s that simple.

Sign up today for the 11 Day Leadership Reset. Go to EricDingler.com, scroll down until you see it, click on it, fill the form in, and you’re done. You’ll start getting those emails. I’m hearing back from people generally after day three or four saying this has been hugely beneficial.

This week’s leadership tip of the week: what gets rewarded gets repeated. This is why you need to take time to think about what you’re rewarding. If you’re rewarding meeting deadlines, your team will start to take shortcuts to meet the deadline, because what gets rewarded gets repeated. So you’ve got to be careful what you reward. I don’t reward meeting deadlines, that’s the job. What we reward is meeting a deadline without mistakes, delivering a quality product on deadline. We focus on the quality, we focus on the client’s response. You can’t say, I met the deadline, the website’s built, it’s done, and then go in and the links aren’t working, or the form doesn’t submit, or there’s misspellings or the wrong picture. You can’t say you were done. So be careful what you reward, because what gets rewarded gets repeated.

Here’s a bonus tip: how you reward it makes all the difference. You may have heard of the five love languages, gifts, words of affirmation, quality time, and so on. Those same languages are used by people to receive appreciation. I used to have a boss when I ran the summer camp who said thank you to all three camp directors the exact same way, always the same gift, and I would leave the meeting annoyed. He’d give us a gift card to a restaurant, and I didn’t like it, I lived an hour out in the middle of nowhere, going to a restaurant was a pain. I know he was trying to be nice, but it wasn’t landing. Another one of the camp directors loved every single gift, that was her appreciation language. My appreciation language is words of affirmation. Compliment me genuinely, specifically, in public, and I’ll absolutely feel appreciated. Send me a gift, and I don’t really care. Your team is the same way. I’ve got people on my team where if I want to say thank you, I send a gift card to Starbucks and they’re thrilled. I have another guy whose appreciation language is words of affirmation, but expressed to the people that matter to him, so when I send a thank-you gift to his family with a note about how much he’s contributing, he goes nuts over that because his boss appreciates him in front of the people he cares about. Learn the appreciation language of your team. Speak the appreciation language of each person. Be careful what you’re speaking about, too, because what gets rewarded gets repeated.

Well, here we are, the final travel update. Every country we’ve been to, I’ve collected a patch, generally a version of their flag, from all 24 countries we’ve visited in the last four years. Last week we were in Germany, and when I got that patch, driving home, it dawned on me that was the last one. We were leaving Germany headed to Paris, I already have the patch for France. And then we’re headed to the United Kingdom for six months, I already have that patch too. In January, we’re going to stop traveling and be permanently rooted somewhere, we’ve got it narrowed down to one of two places. This season of our life is coming to a conclusion, which is why I’ve rebranded the podcast from Digital Nomad Entrepreneur to the Eric Dingler Leadership Podcast. There’s no sense giving travel updates anymore since we’re not traveling full time. We’ll still go on trips, that’s the benefit of having a location-independent business with a remote team, but we’re no longer going to be digital nomads.

Right now we’re in Paris having a great time. My wife and I were talking last night, the first time we were here we brought our two youngest children. The second time, we had our two oldest as well after adopting them, so all four kids. This time, my mother-in-law was with us too, seven of us total. Each time we’ve gone to the Eiffel Tower in the evening to see it light up. The first time we brought two people, the second time four, this time five. Who’s going to come with us next time? We’re going to need to bring a couple more people or another family with us.

From here, we’re headed back into the United Kingdom for the rest of the year until we root in January. For those of you who have been listening for 40-plus episodes, who started back when we were traveling full time as digital nomads, following the adventure from Costa Rica to Argentina, El Salvador, Italy, Ireland, and everywhere in between, thank you for listening and tracking our trek. We’ve had an amazing time exploring the world.

From here, the next episode will be solely on leadership. So until then, my friend, chase the big dream, lead with courage, and safe travels.