Episode 689 | How to Keep Your Remote Team Motivated and Engaged

Rob Walling:
Welcome to Startups For the Rest of Us. I’m Rob Walling, and today I sit down with Robert Cserti and we’d talk about how to keep your remote team motivated and engaged. This topic is based on a request that I received at MicroConf Europe, and Robert as the founder of SessionLab and a team of 13 has quite a bit of experience on this topic. He’s a founder, not a business coach or a consultant on how to keep your remote team motivated and engaged, but they have experimented a lot over the years with strategies and approaches for doing so. And I think it turned out to be a great conversation. 

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And with that, let’s dive into my conversation about keeping your remote team motivated and engaged. 

Robert, thanks so much for joining me.  

Robert Cserti:
Thank you. Excited to be here.  

Rob Walling:
Indeed, sir. So you are the co-founder of SessionLab. You are a TinySeed EMEA company, and the H1 of SessionLab is an easier way to design workshops, drag, drop, and reuse content, calculate time automatically, collaborate in real time. Create a workshop in minutes, not hours, with SessionLab. Can you give folks an idea, first of all, of the stage that SessionLab is at, whether it’s revenue or employee headcount?  

Robert Cserti:
We are 13 people growing profitably. And about SessionLab itself, we help facilitators, consultants, team leaders to design and deliver effective workshops. Typical use case, you would use our workshop agenda planner tool if you have a full-day strategy workshop or a two-day leadership retreat. Somebody plans these processes, what people do at what time of the day, and that’s the facilitator. And these are typically facilitators, agile coaches, org dev professionals, learning and development people. So we help them design better workshops. And next to that is also we have the biggest online library of workshop activities. So if you look for icebreakers, energizers, brainstorming techniques at the sessionlab.com/library and you can get inspiration for your next meeting or workshop.  

Rob Walling:
And in case folks are curious, where are you located in Europe?  

Robert Cserti:
We are a fully remote team. Our company’s officially Estonian. I live in Hungary. My co-founder’s in Sweden. We are Estonian e-residents and our company’s 10 different countries. That’s for our team members. Practically, we are remote since day zero. We happen to be in different countries and that’s how we started to grow the company.  

Rob Walling:
Well, that’s bootstrapped and mostly bootstrapped playbook almost, right?  

Robert Cserti:
Oh, yeah.  

Rob Walling:
That’s what we do. We don’t have the money to hire in these major cities and so we look around for the best people we can find. 

I want to set the stage for this episode. I actually was approached at MicroConf Europe in Lisbon just a month or two ago. And I didn’t get his permission to use his name so I won’t use his name. I’ll keep him anonymous, but he said, “You know what? I’d love to hear an episode about team engagement, specifically remote team engagement. How do you keep your employees, contractors, whoever you consider to be on your team, motivated, engaged?” Even just knowing one another, the more you know the other people on your team, the less likely there are to be, I don’t know, maybe conflicts. Or it’s easier to work together. 

I actually posted in the TinySeed Slack and I said, “I’m going to record an episode around this. Who has some thoughts on this?” And I got a bunch of really good responses, probably a dozen responses, from very knowledgeable founders, all running teams remotely. I think the first thing I was struck by was how many founders, including you, said, “I’m not an expert but here’s what we do.” So that’s the thing, you run this team. And how long has SessionLab been around?  

Robert Cserti:
Practically, we started the company 10 years ago. First five years was a hobby or side project. Then we realized, “Oh, we have customers. This is a business. Let’s build it.” Then we went full-time. A year later, we started hiring people as our revenue grew. So essentially, there’s two big distinct stages. And the interesting thing with remote engagement is it was definitely a process for us to realize that, well, building a team is a job itself and getting people engaged. Because initially as founders, we are into product and figuring out marketing and sales, and then realize, “Oh, we have now people on the team. It’s not only myself or two of us.” So we need to figure out what is our culture and how to keep people engaged. And that’s a very organic thing and it’s not the first thing that came to my mind. We also had our stage like, “Oh, we actually need to put more attention to how we engage people and what’s our culture.”  

Rob Walling:
Right. I think a lot of us who worked at other companies… I worked at a startup that was probably 40 people when it started or when I started there, and then it was several hundred by the time I left. And the company culture stuff always felt like just bull (beep) to me. It was like, “Let’s just come here and do the work.” But what I realized later as I started running teams as well, if you don’t introduce a culture, then the culture will happen on its own and you won’t be in control of it. And so that’s where mission, vision, values, I always thumbed my nose at them, these 50% companies. But a lot of that was because I didn’t feel like they were accurate or true versus my mission now. And I think MicroConf’s and TinySeed mission is to multiply the number of independent self-sustaining startups in the world. That’s a real mission and you see it, we’re actually doing that, most missions and values.  

Robert Cserti:
And you’re walking the talk, and that’s a big difference between a small and large company that you as the founder in a small team, you have an integral part in setting the culture.  

Rob Walling:
Right. We’re going to dive into your response along with some other points that were brought up by other folks. As I said, there were 12 different responses, but yours was good. It was long. It was detailed. It was thorough. And then your co-founder Filip even weighed in, and we’ll look at one of the points he raised. But in addition, there are some other TinySeed folks who weighed in, and certainly want to thank everybody who offered some points. 

Again, couching it with you’re not a company culture, neither am I, a company culture expert nor a consultant, but this is what’s working for you. And I’ve run remote teams. I would have to even count. It’s got to be four or five range. TinySeed is six people and MicroConf is five or six depending on how you count. And Drip was 10, half remote when we were running it. Anyway, I’ve just had a bunch of experience as well and I’ve seen what has worked and what has not. 

So let’s start with daily check-ins, and this is something that you mentioned that you do. You async daily check-ins specifically. A lot of people I know do not. We don’t do daily check-ins at TinySeed or MicroConf. We do have a weekly meeting where we get together and talk about stuff and then everyone, the introverted in our midst go separate ways and get work done. But specifically you said there are a bunch of tools for async daily check-ins. You are using Geekbot and usually when you start your day, if you’re working, it’s at SessionLab, you answer four questions, a combination of social and work-related. “How do you feel today? What did you do since yesterday? What will you do today? And what obstacles are impeding your process?” 

Talk me through this. Is this working? Did you try other things and weekly wasn’t enough? Why do a daily async check-in?  

Robert Cserti:
Yeah, absolutely. First of all, it’s a very iterative process to come up with what works for you and your team. We had different processes in place at a size of 3, 4, 5 people, and now at 13, and probably will have different as we grow. I think just to take a step back, one thing I would structure the thinking on various tools and processes, I see two big purpose. And we can break down to further subpurposes, but two big areas, both want to help with efficiency. So enable people to get their work done efficiently because everybody likes to do great work and be enabled to do that. And in the same time, also help people to feel valued, to feel appreciated, and to feel belonging. And most of the tools and structures are either for one or the other or a mix of both. 

For this part, the keeping aligned, we actually do weekly alignment calls as well. So every Monday, we have three bigger teams in the company, product, marketing, and customer success. We have a 30 to 45 minutes sync call where we align on the weekly priorities. And if there’s any questions, then we discuss those more in detail. And then these check-ins, then it’s a mix of keeping that alignment and also a social part, because essentially it feels good when we know that people are around. They are present. They’re available. And also it’s how we shape these things. I think important that, again, you’ve walked the talk, what you expect when you communicate with your colleagues. 

A fun thing that emerged over the years, we have people joining and they say, “When I was working in-person, I never knew that much about my colleagues.” And that’s because we share a lot of personal things in this first question, “How do we feel?” They don’t just say, “Yeah, I’m okay.” But what did I do yesterday, what I did the weekend with friends, with my kids, whatever. And it’s really up to the individual how much effort you put into it. But once you start opening up, you share more personal thing, you show some vulnerability, people get that and then they also join in that. So then it’s like a good, I think, water cooler. And just like when you enter a real office, people say hi to each other and they may have some short chat. Here as well. You can engage with it if you want a given day, or you can just not if you have other things to do on that day when you start. 

So that just evolved both with a social purpose of having this water cooler, and next to that, essentially helping each other know that what am I focusing on a given day. There was times when it just these slightly different question, it didn’t work as much. And then every once in a while, we reflect. Does this still work? Is this still giving value? If not, we tweak on it. If it’s good, then we keep doing it.  

Rob Walling:
And in addition to a daily check-in, it’s very common to have weekly, monthly. And there’s one-on-ones and there’s groups. And you specifically called out a few of these. You said these regular practices that some other folks mentioned were, I believe, do you have a week starting team alignment call?  

Robert Cserti:
Yep.  

Rob Walling:
45 to 60 minutes?  

Robert Cserti:
Yeah. Practically, with each Monday we have a team call with a subteam. So in our case, product, marketing, customer success where we align on the priorities, see where we are with our quarterly objectives projects, and that gives a focus for the team. And these daily check-ins are more like just what do I do on a given day, breaking it further down.  

Rob Walling:
The weekly get-on-the-same-page meetings, is that the entire company or is it team-based? So if there’s product and dev, that’s one. And then customer success and support maybe is another.  

Robert Cserti:
In our case, we now do it, team-based. But again as we evolved, I think when we were size of five, six, we had it together and then we broke it up. Then product was a bit bigger team and then customer success and marketing did together. It’s really like what type of projects and goals we have in a given quarter and just making sure that these alignments support achieving what you want to do in a given quarter.  

Rob Walling:
Got it. And then I believe, do you also have a biweekly all-hands that’s 45 minutes?  

Robert Cserti:
Yes. We just change it actually from weekly to biweekly because it’s a lot of meetings, and in product-  

Rob Walling:
Yeah, that’s the problem.  

Robert Cserti:
In a way, there is some meetings have a cost and so does working on a dead end path has cost. So there is a fine line between the two. And it really depends on your team as well, how much experienced people you have, what type of things you work on. We are trying to use for example the all-hands more for the purpose of some more inspiring presentations or things that everybody is useful to know about. Let’s say if you work on customer personas or have a big design project, that affects everybody. Those are good to be presented, while it’s less for aligning in terms of a practical operational way.  

Rob Walling:
Got it. And those are still work-focused, not a monthly hangout that I heard several folks talking about?  

Robert Cserti:
Yes, that’s right. So yeah, the all-hands are more for keeping us on the same page, what’s happening on a big picture or more on a strategy level. We also want to make sure that on the side of let’s have some more team bonding and team connection, we have every month, month and a half, some online team event, an hour of ideally something facilitated activity where we get to have some fun. I would say if we would work in-person in one city, we’ll probably go out in an evening or do some activity together. We don’t have that so we want to make space. 

On the grander picture, what really helps us is to have also team retreat. We try to have it twice a year. All of us get together for a week, and we use it both for a work purpose to workshop on a project that really benefit from that focused attention that you can have in live, and also have some leisure day when we have some organized activities and all the leisure time, all the unstructured time we have together. But in our case, there is half a year between them. So we want to make sure that next day, the everyday work, there is some activities where we both celebrate successes and also have some moments to build connections and build bonds, and again, just have opportunities where we can bring a bit more ourselves.  

Rob Walling:
Yeah. It’s a luxury that we have at MicroConf, TinySeed that we have so many in-person events that we don’t have to structure or we haven’t traditionally structured external team retreats where we just go to a place. Because we meet up at MicroConf, we meet up at TinySeed retreats.  

Robert Cserti:
Yeah, that’s an amazing opportunity.  

Rob Walling:
It’s really nice, and it’s an opportunity that SaaS companies don’t have because you’re located remotely and there’s just no reason for you all to be in a room. But the value of getting into a room, I know as companies get bigger, I believe Zapier went down to a once a year company retreat because it’s a quarter million dollars or something to throw their company retreat because it’s so many people. But it’s like I think three times a year would be ideal to get people together.  

Robert Cserti:
And it’s amazing how much those intense in-person meetings fuel collaboration. There’s a concept of a trust battery that you build with small human interaction and when you spend time together. And when that battery is high, then collaboration is happening at a higher quality during online work. So we definitely see after retreat, we communicate more, we shift things faster, we solve these agreements faster. It makes a difference. And then we need to also get by between two retreats to build up these trust batteries practically or maintain them to a high enough level that it doesn’t deeply do much before reach next one.  

Rob Walling:
Right, for sure. And so we were talking about an all-hands that you do every other week that is still focused on work stuff. Do you also, much like several of the folks who weighed in on the TinySeed thread, do you also do a monthly hangout where it’s still remote and it’s the team getting together just for happy hour-ish and more personal conversation?  

Robert Cserti:
Yeah. I would say that that’s more the team bonding focused events where we don’t have work agenda but it’s really to have an hour of time spent together ideally doing something which has some themes, some activity. One of our favorite activity that has been a big success whenever we played is an online board game called Cozy Juicy Real, which is again an activity which is somewhat facilitated and you open up about certain aspects of your life and you give appreciation to each other, you express gratitude to each other, and that just makes feel everybody happy. 

In the end, I think all these retreats and team activities definitely does have a cost in time and money, but people want to be part of a workplace where they are valued. If I reflect in my previous work experiences as well, whenever I feel that my bosses value me, I really put my best there because I don’t want to let people down who care about me. And that feels good to be at a place where you’re valued.  

Rob Walling:
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I want to read a couple of other responses around a monthly hangout that were in the Slack thread. These are from other folks who weighed in. One person said, “We have one monthly call with the entire team. We do a round of personal and work-related updates followed by a round of talking about a fun fact or playing a game on the call.” So it’s similar. It’s a good way to get to know everyone and learn a thing or two about them that usually doesn’t come up in normal work-related conversations. And then another founder weighed in. “We started doing a monthly happy hour for a social gathering of the entire team. We do social activities like trivia games, Guess the Desk,” I’m not sure what that is, “et cetera. People seem to love it.” So this does seem to be a relatively common theme with remote teams.  

Robert Cserti:
Absolutely. And I think it’s like you don’t have that intense human interaction as you would have in-person, so you need to make space for various ways for people to interact, both in a group setting, also if you can in a one-on-one setting. One of the useful things that we have seen that we are trying recently is people working in same teams, they interact often. But people who don’t work in the same teams don’t talk as much or don’t interact as often. And we introduce, for example, one activity where we have randomly assigned one-on-ones. So not for work purpose but just take half an hour from working time and just have a chat. And we use a Slack app called Donut for this, which essentially takes the scheduling or the randomization, which is also a nice small thing that it makes sure that between two retreats or between two such intense occasions, you actually get to speak with everybody on the team if you want. 

By the way, most of these things are also optional. The online team events, the extra one-on-one chats. So if people want, they can. They’re not forced to participate. But most people love it because it just builds human connections.  

Rob Walling:
I’ll be honest. You all do more than I typically do with my remote teams. And when I hear you describing the meetings, it feels to me like, “Wow, that’s a lot of meetings.” But maybe it isn’t that way. Maybe it doesn’t feel that way in your company. How do you think about that? At what point is it too many? And does the value decrease? Because each of these things you introduce can increase connection, but I think at a certain point, people will also glaze over at another Zoom meeting.  

Robert Cserti:
Yeah, that’s a good question. I think everybody need to evaluate it for themselves. What is the point where you feel it’s too much? In our case, that’s an average weekly two meetings for alignment and team purpose. Is that much or not> we feel when we have less, that we either have a gap in the team bonding side or we have a gap in the alignment side. And essentially, one of these is more for alignment, one of these is more for the team spirit. And very importantly if you have a team, I think one thing that we initially thought this all on us as founders to figure out, but people who are in our team, they have experiences themselves as well, what worked well in their previous jobs and not. So we try to reflect together what works well and what not. And there is a process. For example, we recently figured out that it’s not worth it to have every week in all-hands so we do it biweekly. And if it doesn’t give value biweekly, then we do it monthly.  

Rob Walling:
Right. So if you find you’re in too many meetings, you space it out further, as you said. You went from weekly to every other week to monthly. And I want to touch on two other points in this interview. Two things that you specifically called out that this first one I found interesting you put in the Slack thread. “Another interesting addition in the past half year in our workflow was part of our team using a sort of spatial video conferencing tool to hang out there during the day. The concept is it’s easy to move your avatar away. But if you want, then it’s very quick to start communication with other people just by moving next to them.” And you’re using spatial.chat for this.  

Robert Cserti:
Yeah, that was a fun experiment which is more in the work efficiency category, in that initial categorization that we realized that we had a couple of more context projects where it was important that we can align quickly when we have a problem. We had a major infrastructure change and we had series of bigger questions where it was just important that the key developers could interact quickly. And then it’s definitely not a tool we use company-wide, but there is opportunity for people who find it useful to do it. Essentially, you need to still have a chance to work focused and it gives that, but if you quickly need to regroup to discuss something, then you do that. 

And for our case, our dev team enjoys it so they going back there on a regular basis. And I think most days, one or two hours. It’s important to have the discipline though because you just don’t want to hang out because it’s definitely a need to have focused time to do deep work. But if you find what is the intersection then, and especially if you have a need for that, if you have a project where… Because sometimes work is simple and you have well-scoped projects to work on that everybody can take on individually and execute. Sometimes there is way more complexity and you need two people to be able to jam quickly on something. And when we recognize that case, then this is useful.  

Rob Walling:
One other tool you mentioned that I thought was pretty clever is you said, “It’s not so remote-specific, but one management tool I find really useful is sending a monthly reflection survey at the end of each month. It asks about accomplishments and challenges of the past month, asks how I can help, and asks for a rating on how happy, satisfied, they are and why.” And the results go directly to you the founder, not to the person’s manager. So talk us through the thought process of that and what information perhaps you’re learning that you wouldn’t if you didn’t have those.  

Robert Cserti:
This is a bit of a heat check on the team to get an impression of how everybody is doing individually. And first and foremost, which is even more important, that everybody has a mentor manager who takes care of one’s personal development and that one progresses. But this is more when we reached a stage that I was not anymore in a regular connection with each team member, then it was just a really practical way to… First the reflection part, that each month you actually have a moment when you look back, “This is what I achieved this month, and also what are my challenges?” And if everything is perfect, an ideal word, then this has no new information because the manager of the person already took care of that. 

But there’s always a couple of people who, for various reasons have various difficulties, more challenges, and they just essentially one outlet where you can voice that, “Well, I’m not that frustrated to proactively seek out support, but if I ask and I build the trust that whenever you say something that you need help, then I follow up.” Then people give that trust and they indicate, “Well, something is just not going the right direction,” and then they can help faster. So it helps to catch issues earlier on. And also it’s definitely have the element of not to go around once managerial line. It’s a complex word for a small company, but still give one more space to say if you feel that things are not in the right direction. 

And also what I found really useful is this essentially quantitative feedback of rate how you feel on a scale of 1 to 10 in the company, and it really is a quick feedback tool. If you give us lower than a certain rating, I know that I need to really follow up and pay attention. And not just me, but then we discussed with the manager there, “So what can we help? How can we support you? Whether you had a more difficult personal life in the past weeks or it’s work-related, what can we do to help?” So it just helps to catch these things.  

Rob Walling:
Well, thanks for talking us through all the tools that you’re using to grow SessionLab. I think before we wrap up, I wanted to offer one more comment that a TinySeed founder who I didn’t get their permission to mention him in the show so I’ll just keep them anonymous for now, but something they said that I think you and I probably both agree with but I’m curious to hear your take on it. They said, “I feel async remote requires different strategies versus purely remote where you can be synchronous.” 

This founder says, “We have very small overlaps of working day with the majority of our team, so we have to spend a lot of time on developing processes to ensure everyone is on the same page and working on the right goals. As much as we would love to do a big all-hands weekly catch-up to build team culture, it’s impossible for us to find a time that works for everyone. So we have to rely on Slack and ClickUp communication most of the time with varying levels of success.” 

So async remote different than remote, do you have experience with this? Do you have thoughts on it?  

Robert Cserti:
Well, only partially because we are in a lucky situation. We are roughly plus/minus one, two hours, same time zone. So we have the luxury to be able to meet each other. And I think it’s a sliding scale between almost having a full overlap versus having zero overlap. That’s a spectrum. 

In the end, I think the processes are very similar. It forces you to document effectively, to have the right processes. But also I think that’s a hard thing to start from. And I would definitely in this case make sure that it’s great to work with people remote if those people are experienced in remote and experienced in their specific job as well. So if I would not have overlapped with somebody who I worked together with, then I would be very cautious to handle somebody who just starts out. And one way is to just try to find people who are experienced both with remote work and with their specific field because that decreases the need of how close you need to communicate. 

And other than that, just take efficiency to a higher level. Yet you still, you need to build those async processes as well to have people feel valued and appreciated and part of that team if you want to build it for the long run. It’s easy to say and hard to do.  

Rob Walling:
I agree. I feel like in a perfect world, I would be in an office with my team maybe two days a week, two and a half days a week. That’s what we had when we were building Drip with most of the team, and it allowed us to collaborate, stand in front of our whiteboard, hang out, go to lunch. And then the other days we were at home and I was focused on getting work done. That was my ideal situation. That’s just not feasible really for the types of companies most of us are building. And the next hard, I’d say harder way to do it, it’s not hard mode per se but it is more difficult is to have a remote team and to have to try to get people together and get everyone to like each other and get people on the same page and build a culture. 

Then the next hard mode is async remote. It’s so hard when everything has to be a Slack response or a video recording or an audio recording or whatever it is. It really is a next-level challenge. And I would guess that most companies, whether bootstrapped or not, most companies around the world will have significant challenges doing async remote.  

Robert Cserti:
Yeah, that’s so true. It’s such a great opportunity if you can start at least with a team that is in roughly your time zones. That makes interaction easier. And also it just makes it easier to meet in live once a while because that’s a strong starting point. Also, to help defining your culture and align with those people.  

Rob Walling:
Right. And I know that’s what we’re talking about is just not feasible in every part of the world. You and I have this luxury of living in the US and in Europe and there’s a lot of talent within, as you said, plus or minus two, three hours of us. And some parts of the world, that’s just not the case. And so you certainly have your work cut out for you in that situation. 

Robert, thanks so much for joining me today. Folks want to keep up with what you’re building, sessionlab.com. And is there any social media that folks should follow?  

Robert Cserti:
Yeah on LinkedIn, Robert, C-S-E-R-T-I. Happy to connect there. And thanks so much, Rob. Pleasure to be here.  

Rob Walling:
Thanks for coming. Thanks again to Robert for joining me on the show, and thank you as always for listening to yet another episode of the show. This is Rob Walling signing off from episode 689.