How to evaluate the performance of your remote team with Rob Rawson from Time Doctor and Running Remote

Speaker A: You must disagree with me at certain times, otherwise you're not doing your job properly.

Speaker B: Welcome to Building Remotely. Our goal is to create the world's first guide to building a remote company. Inspired by founders and leaders at remote startups. I'm sandraj, the founder and CEO of Safetywing, the company offering global health insurance for remote teams. Let's begin. In this episode, I'm joined by Rob Rossen. Rob is the founder and CEO of Time Doctor, a productivity software for remote teams. He is also the founder, famously of Running Remote the conference, and also co author recently of uh, Running Remote the book which was released last month in August 2022. Welcome to the podcast, Rob.

Speaker A: That's awesome to chat with you.

Speaker B: We will discuss how you can manage and hire globally distributed team across many cultural differences, as well as the learnings he has made from Running Remote and Running Remote the book. But before we get into there, I would love to hear your personal journey to where you are today. So you founded your first business while studying medicine, presumably to become a real doctor, and now you're a time doctor. So what was the journey from here to there?

Speaker A: I was always very entrepreneurial, so I started actually quite a few businesses. Even in med school. I took a year off and became a marketing consultant of all things, which is pretty crazy considering I had no training, no formal training in marketing. But I was so driven by the idea of actually being able to work remotely around the world to work from my laptop. I love that concept of traveling and working. So I tried a bunch of different things and I was just excited about entrepreneurship and I was drawn to online entrepreneurship because it's fits my personality. I don't actually like selling things, uh, face to face. I felt uncomfortable with it. So I like the idea of having a website that just sells for you and you don't have to do any, uh, kind of day to day selling. So that's how I got drawn into Internet business in general.

Speaker B: You were early discover the remote world, you know, with Running Remote the conference. So how did you get started with that? And I understand now you discovered it for yourself even earlier. Could you just walk us through, like why were you early?

Speaker A: Well, I actually thought that the way that you had to run a business was to have an office. Like that's how you do it. You get an office, you get people in the office. And I didn't even think of a scenario where people would be working from home. It didn't even enter my head. But then I actually had a team in the Philippines, so I went to get an office in the Philippines because it was a great talent there. Lower cost, it was working really well. I had an office in over 30 people, but it was quite expensive. And my. This is before I had time Dr. I was doing like an SEO type of business and it was doing okay. But business started to flounder a little bit and I decided that I wanted to get rid of the office, save the expense. Mhm. Very expensive. And also I just didn't want to keep coming back. Like I actually was sick of going to the Philippines. I wanted to travel the world. And if you have an office and you're not showing up as a boss, like it doesn't look very good. It's like, well, how come the boss is not here? Mhm. So we probably don't need to work either. That's why I decided to get everyone to work from home. And that's where the genesis of the software that I actually created, Time, uh. Doctor Came out of that is well, let's create this software for my own purpose. And then I had similar types of companies that might have a team in the Philippines quite often that would use our uh, software. At the moment our software is really targeted mostly to BPOs, to companies that have an outsourced or um, offshore team.

Speaker B: What was the learning experience with the conference? And you know, what did you learn from seeing the companies who participated there, the talks? What was your big takeaway from that time?

Speaker A: So we've had our own remote work experience. We did that before we created the conference. We decided to create the conference because we just saw that great opportunity. A lot of people that are interested in remote work. So we actually initially had a conference in Bali of all places. It's just a cool place to go, just uh, a fun place to travel and see other people who are interested in remote work and learn from those leaders. And I think one of the key things we were learning personally is about culture because I didn't focus on that as much. And also that these very big companies that took a different approach to us were working remotely. GitLab is a huge billion dollar company and several others that are just massive companies now. Like they're hundreds and thousands of workers that are all completely distributed working from home. So it's a very, very remote style.

Speaker B: Mhm.

Speaker A: And we were learning from how do they do that? Because we had a much smaller M company. We only had, you know, 10:30. Now it's grown to 130 people. Imagine trying to have thousands and they're all working from home. So how do you put that all together? And, uh, larger companies, they've been forced into it from the pandemic, but they haven't actually really got their head around it in the same way that these remote first companies have.

Speaker B: Yeah.

Speaker A: And that they've, they've really thought about it at a deep level. The key factor from a company point of view and the reason to go remote is the hiring. It's the fact that you can get people and talent from everywhere. And as a company owner, you don't want to lose sight of that. That's what you're actually doing it for. Because there's downsides to remote work as well. It's not all perfect, but having that talent anywhere is just amazing.

Speaker B: I fully agree. That's also like when I hear a sentiment that you might have heard, which is something like, oh, uh, remote is like a fad that will go away because people don't like it. And the thing that that really misses, even if that is, I don't think that's true. But even if it were, I don't think that's the determinant. Right. I think that what you're saying is that's the economic driver is the fact that you as a hirer and employer have a very large labor market. You as a job seeker have a large set of potential jobs. Uh, that's a, ah, very powerful economic driver that will overshadow these other things. It's like the economic difference between starting a company in a city with 400 people in it in a town, versus Tokyo or New York City. It's large. A, uh, talent access is not some trivial thing that barely matters. It's the thing that drives economies.

Speaker A: Exactly.

Speaker B: Okay, let's get into the book. Why did you write the book? What's in the book?

Speaker A: So the book is called Running Remote, and it is about these interviews that we had with these companies that we've had at the conference. So these are top companies that know how to work remotely, and we're trying to figure out what do they do to be effective at remote work. And one of the key themes that we pulled out is asynchronous work. So this is a new concept, I think for a lot of companies, it's that, uh, instead of working only with meetings where you're just talking face to face or via Zoom or Google Hangouts, you're actually working asynchronously. So you send a message the other person then has time to think about. First of all, they can listen to the message or read it or watch it when they have time, which is huge in terms of not interrupting their day. Right. If it's synchronous, you have to coordinate everything, which is sometimes a nightmare. You can also, when I'm listening to messages on video, I put it on double speed. So it's double the efficiency for me as the listener. And so there's a lot of efficiencies there. Of course, you lose that synchronous vibe of the conversation that goes back and forth. So you still want to have synchronous with some things. But the asynchronous is a really common theme of these companies that they remote for a long time. How do they communicate effectively across time zones without interrupting the person? And so that's what we talk about a lot. And how do you do that and how do you make sure that people are getting the message effectively?

Speaker B: Why do you think that is? I have a guess, but I don't know. I guess my guess of why these first remote companies were async is because they often, they have like, routes to open source, you know, which had this thing built into them that it kind of had to be like that, obviously, because while it was built before video, you know, talk was even possible and you know, it has long roots back in time of organizing a crowd of volunteers to cooperate on something. So that was my hunch. It's like, oh, yeah, it's because they have roots in open source. And my previous company, we also made it kind of async. Although what I mean by async is we made it full async, meaning we didn't have a, uh, one meeting. It's often, I've heard people call async just having less than meetings that they could have had. Meaning. It's a relative term. But, uh, we were async in the meaning of, like that we never had one meeting. And it's a lovely thing. You free up your entire day and just so much time for like peak productivity could be so high when it wasn't eaten up by meetings. But of course it did have a downside with Safety Wing. We ended up at a bit of a middle road where we actually did not go for the full async. We have three days a week, we have three hours, 8 to 11am PST, Monday, Wednesday, Thursday, you can book meetings. So we kind of cap it, but we then get back some of the speed in some cases and also maybe the cohesiveness. Although I would love to hear your take.

Speaker A: Yeah, well, I think time zone is obviously a Huge factor. Because if you're in multiple time zones, Europe, Australia, you know us, then meetings are a nightmare. And so you don't want to minimize them for that reason. I think meetings are important in certain aspects, like just the connection. Like it's hard, you don't connect when you're just talking, you know, asynchronously. Obviously the best thing is to connect in person, to meet in person, but the second best would be a video chat. And so a little bit of that is important, I think. M and that's why for one, on ones, I think having a video meeting is quite a good idea. And sometimes the complexity of the conversation is too difficult to get across, but then sometimes it takes a lot more time on the meetings because people are blabbing on and it's ineffective. If you're running an effective meeting though, it should be a, uh, bit more effective than the constant communication of I've got to write this, then I've got to wait, then I've got to write, etc. So there's pros and cons of both. But if you've got multiple time zones, then you have to do the async. And what you said exactly is that it frees up your time and it gives you control of your schedule so that you're. That's a really huge advantage. We're trying to still balance it in our company. So one way that we try to balance it is we have a no meetings weekly. So every month we have one week where it's basically like you just minimize to zero if possible, the number of internal meetings. You still meet with clients, but your internal meetings are basically zero. And that way you free up that week. You kind of evaluate, did I really need that meeting? And it keeps that balance there. Yeah, but I like the idea also of the three hour crossover. That doesn't work though if you're having multiple time zones because you need to have crossovers that are going to work for all of the time zones. So it's good if you're all in the same time zone to maybe only have certain hours where you meet.

Speaker B: Yes, the 8 to 10am PST we did chose because it's the one that captures the largest population because it's night in the Pacific Ocean essentially. But it still is pretty late in Australia. You mentioned hiring. So this is, you know, obviously someone who is starting out or listening to this podcast. You know, hiring remotely is a big question. So what is your answer to that? Like how would you advise companies to hire remotely?

Speaker A: Well, first of all there's the sourcing and there's the type of role. It's a complex answer, but previously LinkedIn didn't really work because you didn't have a remote option. It wasn't as effective. You had to pick each city. LinkedIn now is giving you that option of remote. And so I find that LinkedIn is one of the top sources and I think that's actually similar now for in Office and for Remote is that you're using LinkedIn a lot in terms of posting jobs, but then you've got all the other methods of sourcing as well. Obviously you've got your network, etc. M There are a number of job sites that are really specifically for remote which you can try. And I think they're still effective, but not necessarily things like we work remotely and there's a bunch of others. And then once you've got your candidates coming in, it's like, how do you talk to them, how do you evaluate them? Um, getting engineering candidates obviously really hard. If you're looking for remote work in other areas, like for technical support and you're opening it up to the right regions, then you can get thousands of applicants. We still get thousands of applicants to some of our jobs that we post. We also look at the region in terms of where to hire from to get the most effective talent for that type of thing that we're hiring for. So we hire in the Philippines often for any kind of support role. That's really fantastic that their English skills are great, technical skills great for developers. We're hiring in multiple regions which try to get people from wherever we can.

Speaker B: Mhm.

Speaker A: We don't look though, just at one specific country. So when we're hiring we might look at multiple countries that we hire from or multiple locations. And we're open to people wherever they are in the world and we're just looking at the talent, the best possible talent that we can get. M so I also like to use tests where possible. There's some roles that doesn't work for, but for some roles, if you can give people a test that really exactly matches the work that they're going to do in the job.

Speaker B: Mhm.

Speaker A: Especially for roles where you're getting a thousand applicants and you give them a test, it's hard to do hundreds of interviews. It really takes up your day. And so having some kind of streamlined process where you're filtering applicants and you're trying to figure out who the best person is is really important.

Speaker B: Yes. Now in my previous company, we kind of hired because it was a curated freelancer platform. So we processed like hundreds of thousands of applications and uh, also went through that learning then. And we also ended up, you know, we had these automated tests for the early stages, filtering and we had test task. Test task is, you know, wonderful if you can nail the test task. It's so predictive. But uh, that sounds like a good system. When did you start using LinkedIn, by the way? It works well.

Speaker A: Yeah, LinkedIn, we've been using it for a while. Obviously it's the number one hiring platform. But it changed during the pandemic where you couldn't set remote as a location.

Speaker B: Mhm.

Speaker A: So you had to put a specific city, which is kind of annoying because you're saying, I want to hire remotely. Why do I have to put a city? And they did change that, but you still have to put a country. So you can't just say I want to hire from the whole world. They haven't got their head around that concept yet.

Speaker B: Yes, LinkedIn, if you're listening, next, productivity, you know, maybe that's something you're thinking about a lot with time, doctor and your service. Maybe you also want to explain just a couple of sentences about your service and who is it for and what do you think about productivity in remote teams and how do you ensure that?

Speaker A: Yeah, so our service is at the moment it's primarily targeted to BPOs. Like we have some uh, large business process outsourcing companies, whether they're in an office or working from home in a lot of cases. So they do have concerns about productivity. When their team are working remotely from home, maybe they're getting distracted. Like they want to know the hours of work, they want to have some accountability around that attendance, they want to know time in and time out. So that's some of the things that we're doing in the software. I think productivity for me, I look at it in a multifaceted way. There's no one answer to, to is someone productive. Like you could have a salesperson who produces a lot of sales and another salesperson who didn't sell anything. But actually the person who didn't sell anything was a better, uh, more productive person because they were working on an enterprise deal that's $2 million about to close next week.

Speaker B: Right.

Speaker A: The other person had an easy territory. There's no simple formula, but I think you need to meld together multiple factors. What are the outputs of their work, what are the inputs to their work? So what kind of activities is the person doing as well? Like in sales, you Always measure activities as well as outputs. Very important in other areas of work, people don't tend to do that. They tend to just try and only measure the outputs. But I think it's quite hard to do that. So I think it's good to measure the inputs and the outputs as well as the time worked as well is a measurement that we put into it. So I think when you amalgamate everything together, you don't focus on one thing. You can come up with a synthesized answer, is this person productive or not? And it varies a lot for the type of work. So if someone is doing knowledge work that's very, very high level, then really the output and the result is what you're going to judge on primarily. But if someone is doing at a lower level of sales, maybe you're going to judge more on the inputs as well as the outputs as well as the attitude. You want to also evaluate in terms of the values that you have as a company and how the person is matching those values as well. So all of those things.

Speaker B: I also wanted to get into Culture in a Remote Team, which you have talked about in the past and maybe a little bit about the book. And there's like two aspects to this as I think about it. It's culture in the regions people are from and of course the culture in the company. There is this universal culture developing on the Internet. And indeed that is why it's not, you know, like when an Egyptian and a person from the Philippines met in the 1800s, you know, there is a shared cultural lattice that is broadly downloaded from the Internet. But nevertheless there is still a, uh, you know, a significant cultural component which is not shared or which is not universal, but which is kind of place bound. And when you have a remote team like Time doctor or many of the other remote companies you've had on your conference, the importance of that shared cultural lattice in the company becomes more important. Right. To have predictable ways of addressing each other and treating each other and stuff like that. So what do you think about that understanding? Like what's your understanding about culture and cultural differences in a remote team?

Speaker A: I definitely think that you want to. We try to have a culture which is based on more of a universal culture of business, which is, if you want to call it a U.S. culture, it's basically, it is, it's like a U.S. business culture, um, getting down to business, getting things done. Um, and uh, there's a few other aspects to it as well. There are some key things that you'll notice when you have a team in different countries, especially in Asia, you'll find that people will be less often speaking up or voicing their opinion or objecting or saying something contrary to the boss. So they're just going along with what the boss is saying. So often would say to people, look, it's your obligation. You must disagree with me at certain times, otherwise you're not doing your job properly. Which kind of fries their brains a little because they're thinking, well, I'm not supposed to disagree with the boss, but now you're telling me that as the boss, you have to disagree with me. So you need to do that to break that existing culture, which is a, uh, huge deference to the boss and what their opinion is. And there's definitely a wide variety out there. Another aspect would be in cultures like in France or other European cultures where they're a lot more direct about negatives. So, for example, you know, you didn't do a great job. What were you thinking? Now, that would be considered extremely rude in the US because the US Is more like making sure that you're being very careful about what you say so that you're not saying something offensive. Whereas in Scandinavian cultures, in Russia, Ukraine, and also in France, they would give more direct feedback. No, did that wrong. What are you talking about? And the person in the US Might find that offensive because it's so direct and so confrontational. So actually, the US Is less confrontational. It's less hierarchical as well. But the US Definitely has that deference to the boss's opinion is the one that's going to go. So there's all of these different flavors and just noticing what they are. And I think creating what your culture is as your company and trying to make that a little bit unique, getting people to understand that and to adapt to that and understanding where they're coming from as well is important.

Speaker B: No, it is definitely important and necessary. And, you know, in safe doing. We have definitely a big flavor of Norwegian, probably a flavor of Silicon Valley, ish, you know, sort of by combination vibe of companies. And then we have a bit of our own. And, you know, that cultural stew there is definitely some that is hardest to onboard people on. You know, the one you mentioned is one of them that we have to kind of reiterate over and over again and talk about expressively. Another that is quite related is autonomy. This is like something you have in, like, did you get for free in Norway? And we kind of learned the hard way when people were doing it, and we're like, wait, in Norway, it's A very non hierarchical work culture. People will basically act quite autonomously and take responsibility for that area. You know, if something seems unreasonable in application, they won't do it. Like uh, you know, even, you know, you will be at a situation where you know someone at the border or like anywhere else you would expect them to just follow the rules kind of like a bit kind of cold heartedly. And in Norway you will have this thing and they're like. And you say like oh no, that's unreasonable because such and such and the border guard might say like oh yeah you're right and then they'll change it which is because they see that as their responsibility in their little area. Okay. So that's the thing that in the beginning we just took for granted and were very frustrated with when other people weren't doing it. And as we've been trying to onboard people onto this, I understand that this particular norm, it's quite deep. They're like, it has roots in other norms. It's a bit of a hard one to tune.

Speaker A: Yeah. The negative of what you're saying could be that well you just don't even listen to the boss at all. And like basically you just do whatever you want to do and ignore the boss what they say, even if they have an opinion that might have a good perspective. So that can happen. I've actually been in the situation where people are not voicing their opinions that like in the Philippines they might not voice their opinions but I've been in the opposite situation where ah, have someone in the US who is voicing their opinion very strongly and totally ignoring mine even though I'm the boss, I'm the CEO, uh, but they're basically ignoring me and disagreeing with me, not explaining why they're correct in a very comprehensive way. And I think the US culture in general is that uh, yes, you'll have discussion but the boss wins out at the end and they make the decision. So other cultures like in Japan and I think the Scandinavian countries also, there's a lot more collaborative decision making. So it's actually not always the case that the boss is making the decision. Certainly in Japan and I think the case as well.

Speaker B: Right, Yeah, I think that is pretty accurate. Certainly there is this, you say deference, there is this like deference to closeness. In Norway I had the experience on my first summer job where it was like this problem with the paper machine and this person I worked with, it was kind of like general level. Went up to basically the CEO's office in a larger organization and Kind of like told him off. And that was like normal. That was not like a story that was like, oh, yeah, it's completely reasonable thing to do. Uh, you got to address this problem because he's basically seen as a bit of an authority on the paper machines, right? Being close to them, that's not exactly the same as collaborative, but that is kind of underlying some of these things. I'm just trying to put kind of like the Norwegian framework into practice. What are the most difficult cultural differences you've come across? You mentioned one. Are there some others? And how do you solve them?

Speaker A: I think the most difficult one is getting people to speak up. In the Philippines and in Asia, I found that they will be unhappy and they just won't tell you. And you'd ask them, how are you going? Yeah, are you happy in your job? Yes, they'll say yes. But actually they're not, or anything like that. Where there's not a complete truthfulness. You have to really dig in to get the truth behind what's going on. So I find that tricky. Uh, India as well. Like, people will, if they're saying, is the job going well? Is it on track? And they would say yes, but actually they have no idea it means. What they're actually saying is yes. The boss wants me to say yes, so I'm saying yes. That kind of attitude is hard to deal with. Uh, and something that you need to kind of correct for, basically, and try to figure out how to train people to be more honest, accurate in what they're saying.

Speaker B: What are some mechanisms you found useful in reinforcing the company chosen cultural norms?

Speaker A: So we have our vision document which has our values and we're constantly going over them in our all hands meeting. So I think that helps. We hire, uh, with the values in mind. So I think if you're hiring someone and they don't match the values, it's already a bit too late. It's hard to change people in that aspect. So you kind of want to make sure that you get the right people in the beginning and you also fire people based on that as well. So one of our values is being generous and another is remote work. We love remote work. So if somebody in a company is saying, you know what, I really don't like working remotely, that's an absolute no. It doesn't normally happen. We have had a couple of cases where people have been very unhappy remotely because they're working from home and they don't have any family. And so they're by themselves and they're not going out socially. So it's very rare. But we have had that happen where it's not a fit for them to be remote. And so, yeah, those kind of values, just making sure really that the person is the right fit. I don't know how much you can mould people to it. I think you can to an extent, but it's more important to select the person.

Speaker B: How do you monitor that your culture is healthy and not going haywire?

Speaker A: We do employee NPS and we got a really good school. We got over uh, 60, I think for employee NPS, which is fantastic. So people are generally really happy. So we start with that and then we have a people ops team that talks to people and tries to gauge what's going on and make sure that score is really actually accurate. They're not just saying what they think they should say, but they're not covering, uh, other issues. So that's pretty much how we do it.

Speaker B: Are there any other kind of big takeaways from writing the book and doing the conferences and building a remote team that you've found that could be helpful for founders listening who maybe are just getting started or who are struggling? Struggling, you know, with the remote team?

Speaker A: I think one thing I think everyone needs to get familiar with is the multiple modes of communication. So not just getting fixated on one. I think what happens is people tend to just chat on Slack or something and that's their way of communicating. But instead of that, uh, being more intentional about this is why I'm using this modality. Slack now has ah, video recording which is fantastic. So you can send a video message which is more personal. You can also do audio recording very, very quick to record it and send it recording your screen as you explain something. Also really great way to do things. So making sure that you mix up these modalities and use things intentionally is something that you need to do, especially if you're not familiar with remote work. A lot of companies will only M do meetings and Slack and text chat, which is not enough to get that breadth of communication that you need.

Speaker B: How did you get started to do that and what's important with how it's implemented in the company for it to be an effective additional tool when you

Speaker A: see one person doing it and then it kind of spreads. So once you get familiar with something, you've tried it, you'll understand that it's a better way of communicating. You'll start to see the nuances like, okay, we've been going back and forth for 10 different charts here. Uh, this is time to have a meeting. Another thing that I learned is actually just reading a bit of how Amazon does things. I really love their process. They go into a meeting with a document which is really well thought out, written down with a lot of detail. So there's a lot of preparation into the document. Um, we don't do exactly that way, but we do some elements of it. And by having that document, you make sure that you're not wasting people's time in the meeting. You're doing this combination of Async and synchronous. So you're doing all the Async first, you're getting complete familiarity and then you're coming into a meeting to discuss the final details and things that are harder to discuss on, like too much back and forth chatting. That kind of combination, where you do a bit of both is also really good.

Speaker B: Well, it's been wonderful. I can highly recommend everyone I know as well who's been to Running Remote. Love it. I look forward to reading the book for people who want to read it or try out time. Doctor, what are the URLs you send them to?

Speaker A: So you can go to Amazon to check out Running Remote. The search for Running Remote.

Speaker B: Mhm.

Speaker A: And then the conference is runningremote.com as well. And you can also check out our softwaretimedoctor.com wonderful.

Speaker B: Well, uh, I'm very glad you were an early pioneer in developing all that knowledge for the now many companies like Safetywing, who are building remotely. So thank you very much for doing that and thanks for coming on the podcast.

Speaker A: Thank you. It's great to chat.

Speaker B: You can also get more insights from other remote leaders on Building remotely dot com. Here you'll find the first chapters of the Building Remotely book as well as articles and events relating to remote work. See you next time.