Connecting Across Borders: A Guide To Remote Work With Andrew Swiler

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TBT Andrew Swiler | Remote Work


Remote work is not just a location change. It is a revolution of the workplace that redefines leadership and makes global talent more accessible. In this episode, Penny Zenker talks to Andrew Swiler about the right way to manage and lead remote teams today. They discuss how this setup gives leaders flexibility in hiring people not just within their local area but across the world. Andrew explains why remote work is a great fit for those who have kids and families, as well as those who require many hours of commute just to reach the office. He also underlines the need for intentional communication to keep messages clear and ease tensions even when the team is not meeting face-to-face.

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Connecting Across Borders: A Guide To Remote Work With Andrew Swiler

We’re going to talk about leading remote teams. I know that there’s a lot of talk about that going on. I feel like you can’t talk enough about it because everybody’s got some tips and tricks that might be right for you and your team. I’m excited to have Andrew Swiler with me. He is an expert in this space. He has an amazing team around the world. He lives it firsthand. He’s an entrepreneur with several years of experience starting and acquiring software companies. He’s built up a portfolio of small HR SaaS companies. That’s why he’s working with people around the world. Without further ado, Andrew, welcome to the show.

Thanks, Penny. It’s awesome to be here. I’m excited to share what we do with our team and hopefully impart some wisdom that helps some people out there to do a better job managing remote teams.

I’m going to dive into the nitty gritty if that’s okay. A lot of people feel that there are managers who want to get people back to the office because they feel that people aren’t working when they’re remote. What do you have to say about that mentality and, in general, about that statement?

First and foremost, there’s a type of company and a type of job for everyone. There are people who are made for remote jobs. There are people that have a lot of agency and ownership. They take a lot of pride in what they do. That type of personality lends itself to remote work. It’s valid. There are a lot of people who like to build relationships with people at work. They use work as a socializing event. That’s where they build up a lot of their day-to-day contact with people. I don’t think there’s one right way or the other way. I only run remote companies, but I’m not a maximalist in any way to say, “I can’t believe these companies are taking people back to their offices.” There are people for each type of job.

There are some people that perform better when they’re in the office. That’s where they like to be. The fact is that there are not many companies that can be all in the present. You’re going to have a little bit of hybrid. There are a lot of people out there who are able to work efficiently at home. As a matter of fact, they might be able to work even more efficiently because there’s not somebody stopping by their desk to have a chat with them.

That’s why they hire you.

I helped them get rid of Slack, which might also be as much of a productivity tool. It is a huge stress. How do you do it? How do you create a social connection? That is important, no matter whether you’re hybrid or in person. How do you do that with your team to create that social connection so that you feel connected? I can reach out for help. We build a relationship even though we’re never going to see each other in person.

One of the top five most challenging things that we have is building a relationship with people. A big portion of our company is based in Ukraine. We acquired our company from two Ukrainian founders. We have almost ten people based in Ukraine. They can’t leave the country. The typical remote workforce is we’re going to get together every quarter or every six months. We’re going to do an offsite. We’re all going to get together. The company is going to spend all the money they would’ve spent on the office on this one offsite, and we’re going to build this bonding moment. Unfortunately, our team is in a situation where we can’t do that.

What we try to do from a bonding perspective is go a little against the grain and do a lot of synchronous meetings. We do quick fifteen-minute standups. Even my partners, the guys that I work with, like our CTO, will do a quick standup. It’s not like, “Let’s hit the numbers. Let’s go through everything. Let’s do the high level.” It’s, “Let’s connect. Find out what’s going on.”

Our CTO’s daughter was sick. I talked to her on Zoom to connect for a few minutes. That’s what’s critical about one-on-ones. There are people who are anti-one-on-ones. I’ve heard the arguments for and against it. In a remote setting, you need to over-communicate all the time and over-accentuate these interactions that are intimate. Getting together with the people who report to you, letting them talk about what’s going on in their life, and understanding them as a person is critical that the original theory of one-on-ones is much more important when you put yourself in a remote setting.

In a remote setting, you need to over-communicate all the time. Over-accentuate your interactions with the team to make them more intimate. Click To Tweet

Do you think that it’s better to have a loosely structured standup connection or something more structured? Something that is like, “We’re going to go around and answer this question.” It is a structured game or way to connect. Is it better to leave it loose, have a happy hour, and the people just chat?

The happy hour of the whole team together, at least in our team, has always failed. It’s big. There are many voices and things going on. Usually, I end up talking most of the time. I’ll ask people things, and nobody answers. You’re sitting there with crickets, and you’re uncomfortable. Personally, it always comes from the top. What does the leadership feel comfortable with? What fits their personality?

Even if we didn’t offsite, I’m not going to be doing trust falls. I’m not going to be doing games with people. I would rather sit down with them, have a beer or whatever if they don’t drink, and chat about what they’re doing, what they feel about the company, understanding them, letting them feel heard in those situations.

In remote settings, one of the keys is to feel like you have a voice and you’re not getting these orders from on high that are telling you, “Do this.” It’s like, “I sent this feedback to you a few weeks ago.” That became an actionable thing that happened, which in any company is an important thing to have. In remote companies, it’s even more because people want to see that there are real people doing real things. People can disappear for days into Slack where you don’t hear from them. They might show up for the weekly meeting and say, “I did this.” You’re like, “How are you doing? I haven’t seen or heard from you for a few days.” They give you an update. You’re like, “Cool.”

It’s a great fit for certain people, especially people that have kids and families. Remote work is a fantastic way. You eliminate those two hours of commute. Those two hours can be dedicated to bringing their kids to school, picking them up at school, and spending some more time with their families. People who prioritize that. It’s a great way of life. They have to have some ownership in what they do. Otherwise, it’s easy to disappear into the ether. We had a sales guy who was working two jobs at one point. We had to fire him. Things like that pop up in remote work. The over-employed movement pops up.

How do you mature ownership and accountability with remote? How do you do it so that it’s the right mix that it’s not too much micromanagement and it’s not hands-off that you don’t know somebody’s working two jobs?

The two jobs thing was hard to tell. It was the other employer who noticed it more than us because the other employer called me. They were like, “Does this guy work for you? I saw it on LinkedIn. He works for me.” I was like, “He works for me.” He’s like, “He started with us. He’s not doing anything.” I was like, “He’s doing an okay job for us.” The lie was you can’t let that stand.

We run a model of OKRs. A lot of times, people use OKRs. They’re structured like, “Do this. I’m going to do this.” It can work for certain companies. I try to keep an overall goal of marketing and sales. “We need X amount of MQLs this month. How are we going to get there?” At the beginning of the quarter, we sit down and come up with ideas. Some of those don’t work. We throw them over to the side. We sit down again. We come up with new ideas.

Our marketing team feels like they’re iterating with me or with leadership inside of there. They also know the overall role. It’s like, “We got to get to X amount of leads. We’re not there.” They own that. We acquired this company. It took us a while to get them because the previous owners were like, “Whatever comes in, comes in.” It took a while to get them to own that. We did have to make some changes.

Sometimes, there are people who are not fit for remote work. It doesn’t work for them. They can’t feel that ownership of the things they’re doing. If you give people clear goals and expectations on a week-to-week basis, communicate, make changes, and iterate, they see that their feedback and what they are doing matters to the company. If you say, “We need 50 leads a month,” they disappear. You’re like, “Why didn’t we get 50 leads?” They’re like, “I don’t know. It didn’t work. What do you want me to do?”

There has to be that structure and communication. I’m a believer in that. Even when we’re in the office, we need to communicate. It’s not like these aren’t fundamentals that make teams and companies work. They become even more important or emphasized in communication that you can’t take for granted when you’re next to somebody that you might be able to stop by and have a chat. You have to schedule it and be purposeful about those communication efforts.

That in-person communication isn’t viewed as negative as it is in a remote setting. A lot of times, someone pings you on Slack or wants to have a huddle. If they showed up at your desk, it would be more of an informal thing where if someone pings you on Slack, you’re like, “I was working on something else.” That shift, for some reason, when you’re in a remote setting, is a harder shift.

From a structural perspective, I’m a big fan of Level 10 meetings. It’s from the guys who created EOS and who wrote the book Traction. Level 10 meetings are awesome structures. At the beginning of the meeting, we’re going to go over the KPIs and the high-level stuff. The rest of the meeting is focused on solving big problems. What’s the biggest problem in our team and the specific team, whether it’s the leadership team, marketing, or tech team? Let’s go deep into that problem and see if we can solve it in these 45 minutes.

That type of structure is not too structured because you are loosely going to discuss something where I know other people hammer the KPIs, go over what they did, and everyone talks about their tasks. What am I doing? What am I doing next week? That works in certain areas in certain ways. I love Level 10 meetings because they give people a chance to own big problems and discuss them. It helps.

TBT Andrew Swiler | Remote Work

Remote Work: Level 10 meetings are great because they give people a chance to serve their own big problems and discuss them.

I haven’t heard of that, but that makes a lot of sense. What brings up for me is the theory of constraints. It is constantly looking for the bottlenecks and issues. The way I think is to look for the biggest obstacle. Once you find and solve that, you’ll find the next one.

The water always flows. It always hits a wall somewhere.

It seems logical to me. You can beat your head against the wall with what you’re doing every day, but people don’t need to know what you’re doing every day. You need to come together to solve problems. I like that model.

The biggest issue is when things aren’t getting done. When you do hit a wall, people aren’t hitting their KPIs consistently, you don’t know why, and you don’t have an explanation for that, they don’t know why, either. They can’t explain it. They don’t know what to do. You run into these situations where that personal relationship that is built up in an in-office situation might overcome that. In remote, it can create a lot of tension where it’s like, “Why are we not doing that? What is going on? Why can’t you push us forward on this?” There are some tensions that get created more than in-person where the relationship overcomes that.

The biggest business issues happen when things are not getting done. Be on the lookout when people aren’t hitting their KPIs consistently and you don’t know why. Click To Tweet

Why wouldn’t that be the same online? You have a relationship, and you can hear the person’s tone if you jump on to say, “Let’s discuss this.” Isn’t it a matter of the quality of the questions that you ask, whether you’re in person or not? I’m pushing you because maybe you came up with something that I didn’t think about.

I’m thinking of a specific issue I’m dealing with. We’ve been consistently dealing with not hitting certain numbers in our sales team. As it continues, it’s almost like a snowball. It compounds into something bigger. You can’t sit down on the whiteboard or get together and hash out what’s going on outside of sitting down for a couple of hours and working through some of these bigger problems.

When that consistently isn’t getting overcome and you don’t know what the next step is, at least in my feeling compared to other in-person situations, I feel like the tensions grow faster because there isn’t that in-person, “Let’s sit down. Let’s have lunch. Let’s discuss this.” It’s like, “You have a blocked-off time. We’re going to talk about this blocked-off time. We’re going to try and figure it out. We didn’t figure it out. Let’s block it.”

Because it’s formal, it creates that tension. You know this. There are tools like Miro or different types of dashboard tools where you can do a whiteboard or brainstorm. I’ve been in situations where I was in the office, and that happened. Quarter after quarter, nobody is taking ownership.

I find that it’s because we ask the same questions. We get stuck in this pattern of asking the same questions and thinking about things the same way. I find that whether you’re in person or online, it’s finding some new questions, perspectives, and ways of looking at the problem and seeing that you agree with what the problem is. Maybe you and the other party are seeing it as a different problem.

I’m going to turn it back on you. I know this is your show, but I’m going to ask you a question. If they see the same problem, but when the questions are being asked, and they’re saying, “That is something that we should try.” It doesn’t get executed, or it’s not pushed through. This is normal in any company that’s growing. There are people who aren’t the right fit for the role that they’re in. They were in a role, and now they’re not in the right role. That happens a lot.

You can ask all the questions in the world. That’s not going to overcome that if they’re not the right fit for the position because they’re floundering. They don’t know how to execute. They don’t have the skillset they need. Usually, you bounce that off to say, “What resources do you need to make this happen?” You hit the resource side and the different areas. There comes a time when you say, “It’s not a fit.”

I’ve hit a few different sides in this situation. It’s something I’ve been reflecting on a lot. What stands out in my mind is this situation. In other situations, it has been solved. A lot of times, I’m bringing someone new. On the technical side, I’ve seen that solved a lot of times. I was bringing on somebody that’s the next level that does take the technical team, ramps them up, and motivates them. Replacement is oftentimes the solution.

It depends on the circumstance. It sounds like you’re doing everything that you can, and that does happen. Let’s go there. If you have to let somebody go because it’s not the right fit, how do you do that when you’re remote? How do you communicate that? How does that maybe differ from when you’re in person?

It has its positives and negatives. My dad hates having employees. He always stayed as a solopreneur. He’s like, “I hate dealing with the employees.” Whenever he had employees, he was like, “It must be so much easier remote. You fire people. They’re over there on the other side of the planet. Who cares?” I’m like, “No, you know their life. You talk to them every day. You’re working with them.”

The way I’ve tried to do things is not cutting them off. I try and say, “Here’s the situation.” Usually, they know it’s coming. I don’t fire people for no reason. Usually, there is consistent feedback given. I try to communicate it to them. I made a Loom video for the rest of the team explaining the decision and reason. I give the person’s personal contact to everyone. They can reach out to them. I try and say, “If anyone has any questions and you’re worried about your job and why this is going on, feel free to reach out to me.” Some people do. Many people are like, “Am I next? I have a big salary.”

I find that the only thing is over-communication with everyone. You are making sure you’re transparent about it and always telling the truth. Never try to gloss over anything and make it sound better or worse. Always tell the truth because you know they’re going to talk to that person. In a remote setting, it’s quick that things can go into Slack DMs, and things can turn toxic quickly.

You want to be as open as possible all the time, which is in any setting. In remote, it’s key to use all the tools that are available to you and communicate quickly with people. They know right away. It’s not like this person told this person. It has to be the person who made the decision right away, sending out the communication.

Is there anything that I didn’t ask you that you want to make sure that you mentioned before we sign off?

Remote has its positives and negatives. One of the things I love about being able to work remotely is we do a lot of recruiting. We have maybe a marketing job. I’ll go on LinkedIn and post it in 20 different cities and 30 different countries. I run a post every single day and collect 50 people a day. You get an amazing collection of people that apply for these jobs.

If you are trying to hire them in Denver and you’re stuck with that pool of candidates, I’m sure you can find a great candidate. The flexibility of finding these people that have these different backgrounds working at different companies. You can find people who work for a competitor of yours who is working in a different country and has the exact skillset you need. That flexibility is incredible if people harness it.

You have many more people available to you, and people want to do that. They want to move to different places and be able to work from wherever. That’s an advantage for them and you.

It’s not the cost savings. A lot of people view it as cost savings, but it’s availability. You have more people and capacity available to you than ever before and more perspectives. People from different countries have different perspectives. They bring that to the table. It’s interesting.

One last question because this came up. You’re in different time zones. Is there any trick to dealing with the different time zones?

As the leader of the company, I keep an open calendar. That comes with the job. Anyone who’s in leadership keeps a big range because we go from India to California. It’s a big change. I live a normal life. We try and push asynchronous ways of doing things when people are off. We try and say, “If you need something for someone that you know that’s going to be up before you, make sure you ask them before you sign off because otherwise, you lose 24 hours if that communication doesn’t take place at the right moment.

We always try to tell people, “If something is going on, make sure you communicate it before the end of your day. Somebody can maybe pick up that task or problem when they wake up.” That’s one of the key things for me to be responsive. If people reach out to you in a DM in Slack or send you an email, make sure you don’t take 48 hours to respond to them. If it’s someone on the team, try and get back to them. Make them feel like they matter and their voice is being heard.

I don’t know if you do this, but a way to also help is to have different channels for different types of urgencies and communication. You also are clear. With this one, I need to be responsive, but with these other ones, I don’t. If you have your hands and are listening on five different channels, you’ll never get any work done.

We try and have some protocols around if you @ someone or mention them, that’s something urgent, and the person should respond within an X amount of time, but it doesn’t always get followed. Sometimes, people put their things on mute, especially developers. They tend to disappear for eight hours at a time and code, which is fine, but we try to keep some protocol.

Tell us where people can reach you and find out more about you and your company.

You can find me on LinkedIn and Twitter. Those are the two places I’m active. On Twitter, @SwilerA is my handle. You can visit our company if you are an HR professional on Take a look if you’re looking to optimize your HR processes.

Thank you so much for being here. I appreciate it.

Thank you, Penny. I appreciate it. It was great to talk to you.

It’s my pleasure. Thank you all for reading. This is an important topic. We did get a nice different nuance here from Andrew and thinking about how you are working with your people remotely. Are you communicating as much as you need to? Are you over-communicating? Listening to your people, making sure that they feel heard and valued, and making sure that you’re creating that social connection even if you’re not physically present. Thanks for being here. We’ll see you in the next episode.


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About Andrew Swiler

TBT Andrew Swiler | Remote WorkEntrepreneur, investor, and HR innovator. Andrew, with his wealth of knowledge and experience in the HR tech and investment sectors




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