Remote Work Interviews

Conversations with leaders and innovators about how industries and organizations think about the future of remote work.
How HubSpot Is Building Remote Work Into Its Company Culture
Katie Burke: Chief People Officer at HubSpot
How to Lead a Remote-Friendly Startup
Hiten Shah: Co-Founder of FYI, Product Habits, and Crazy Egg
February 13, 2019
Interview by Sophia Bernazzani
Photography by Hiten Shah
Hiten Shah is the co-founder of numerous successful SaaS companies, including FYI, Crazy Egg, Product Habits, KISSmetrics, and others. He's also an angel investor and startup advisor to companies like Buffer and Automattic.

We're Owl Labs, and we build amazing collaborative experiences with our intelligent video conferencing hardware. Remote Work Interviews is a series of conversations with different leaders about how remote work fits into the future of work, featuring leaders from companies like HubSpot, Basecamp, Buffer, and many more. Subscribe to get notified whenever we publish a new conversation.

Hiten Shah has founded several successful SaaS companies over the course of his career, including FYI, Crazy Egg, Product Habits, KISSmetrics, and others. He's an advisor and angel investor with a lot of career experience working on, and building, remote-friendly and remote-only teams. In this interview, Hiten shares with us lessons learned for startup founders and leaders on how to make remote work, work.

Owl Labs (OL): What are your thoughts on what makes remote work actually work?

Hiten Shah (HS): Ultimately, the reason there are so many different types of remote work is because the ways that we work as humans are usually in-person, and it's been that way for a long time. Truthfully, it's the very early days of remote work, and we're all just trying to figure it out. The amount of people who are talking about and doing remote work has increased probably by 1,000-fold, maybe even more, since I started working on internet businesses 16 years ago. All of the companies I've started have been remote.

OL: As a leader who has built a number of remote-friendly or remote-only companies, what are some of the things that you wish you could've done differently with people who have worked remotely on one of your teams in the past?

HS: The processes of doing remote work, the ways of doing it, and the ways I think about it continually evolve as I continue in my career. So, today if you were to ask me, "How do you do it?" or,  "What have you learned?" the biggest thing is that when you have an office where your team works together in-person, you can get away with a lot of things that you're unable to get away with when you're remote.

One thing you can get away with in the office is less documentation, fewer processes, and more informal in-person conversations in the hallway. When you're remote, these conversations don't happen. We have tools like Zoom, Slack, and Telegram, along with a bunch of different ways to communicate with each other, but still, that doesn't really solve the problem or the feeling of a spontaneous drive-by meeting where you're just walking by someone's desk and you stop to chat and build rapport.

We're getting better at communicating remotely as remote work becomes more and more commonplace. At my companies, we make sure that there's a lot more process and documentation. We make sure to share that information via Zoom, Slack, email, or whatever tools we're using to communicate with our remote team members.

Sharing information like this helps everybody stay on the same page. When you're working remotely, it's easy to feel like you're not in the loop, and like you don't know what's going on. Spending more time doing things that help you get that feeling of knowing what's going on  or, being able to find out what's going on if you need to  is where documentation including meeting notes and recordings come in handy. This way, you're spending more time on developing processes that make it easier to feel like you're all in the same "room"  in-person or virtually.

One thing you can get away with in the office is less documentation, fewer processes, and more informal in-person conversations in the hallway. When you're remote, these conversations don't happen.

OL: Can you walk me through all of the companies you've started, the size they eventually reached when you were done working on them, and what percentage of those teams were remote?

HS: At one of my companies, KISSmetrics, we were about 50% remote and reached about 70 employees. Another team I'm on is about 25 people, all of whom work remote. Another team is a lot smaller  only about 12 people, all of whom work remote. Additionally, I advise a couple of companies that are much larger  Buffer and Automattic  and are remote-only. I've seen how they've evolved over time, and how they've improved the way they work together on remote teams.

The commonality between all remote-friendly or remote-only teams is how much more writing you have to do. You're communicating via text more frequently than you are in-person, and you also have this requirement of making sure your processes are documented and written down for the rest of your team. And, if you're trying to improve those processes, a lot of it has to do with making sure they're written down for everyone to access and iterate on.

For example, at my companies, we have a Slack channel called "Daily Updates" and it's actually named "A_DailyUpdates" on purpose so that it's always at the top of people's channels. Everybody sends an update every weekday or every day they're working that lists out what they did yesterday, and what they're working on today, to make sure everyone is in the loop on each others' day-to-day work.

OL: When comparing a Slack channel for updates and a weekly stand-up, do you think that one is more effective than the other? Or are they just different?

HS: The Slack channel doesn't replace stand-ups for us. Our teams will still do their weekly meetings and their daily stand-ups, in addition to using the Slack channel to keep the rest of the larger team in the loop.

One tool isn't to replace the other, and that's intentional. We're not doing things to replace what you would do in-person  we're actually doing more things to make sure everyone knows what everyone else is working on and feels like they're in the loop.

Regardless of what part of the company you work in or level you're at or what you're doing, you want to make sure you know what you need to know  and you want to make sure each team member does as well. These kinds of practices are designed around making sure people know what's going on as much as possible.

OL: How do you think the remote companies you've built would be different  as far as growth and outcomes  if everybody worked in an office instead of remotely? What do you think would change?

HS: In our case, with our latest company, I think we would probably be spending more time talking to each other verbally and wouldn't be writing as much. There would be some time saved, technically, by not writing, but I could also see that leading to problems because we wouldn't have as much documentation. We wouldn't be so specific about improving processes because we could get away with chatting about it in-person on the fly, or in another team meeting.

I wouldn't say that the outcomes or the business would grow faster or slower or anything like that, but the way we run the company would be quite a bit different. It takes a lot more effort to get process down, and the way workflows and processes are improved is simply different when leadership relies more on documented meeting notes versus in-person conversations and meetings.

OL: Do you think that there's a certain type of person that works well remotely? And, if so, what does that person look like, and how do they work?

HS: I'm not sure it takes a certain type of person, just because I've worked with many different people remotely. It's more of a "what do you have to know how to do?" if you're working on a remote team, you need to want to learn how to deal with any feelings of isolation you might have. Some people on our team know how they work best, so instead of working from home every day, they'll go work at a coffee shop or at a co-working place because they want the energy of other people around them. Your awareness of where you derive your energy from is one big consideration of how well you can work remotely.

It's also important that remote workers learn how to be a little more self-directed  or maybe a lot more self-directed. The reason for that is, again, because you're not always motivated by other people working around you.

You're not going to get motivation from your team working on the same thing and being all around you like you would in an office environment. You're getting motivated by something else intrinsically, so self-motivation and that ability to do work on your own and get it all done is a really critical part of success when you're working remotely. It takes discipline, because the thing is, it's so easy to go watch Netflix or YouTube if you're working from home because no one else is around.

It all hinges upon your own motivation to get work done that causes you to make stuff happen when you're remote. This type of motivation isn't a skill that most people naturally gravitate towards or have, so I wouldn't want to say that certain people are bad at remote or certain people are good at it. I would just say that, if you want to work remotely, you need to have a lot of self-motivation and self-direction.

OL: As a leader of lots of companies where big portions if not the whole team works remote, what do you think it takes to continue being an effective leader and producing the same feeling of rapport and trust that someone would have in a room with you?

HS: I don't think anything gets taken away when your team is distributed. As a leader or a manager of a remote team, you have to learn different skills than you might not be used to if you've always worked in an environment where everybody's in-person. For example, your communication skills via Slack and email will need to level up. You have to communicate very clearly, you have to check your own emotions at the door before you communicate something tough to an employee so your communication isn't too abrupt or misunderstood.

Thinking before you communicate with someone else is of huge importance when it comes to remote work. You have to get good at having voice calls with somebody, where you're actively listening and responding. The skills to be an effective manager are similar whether you're in-person or remote, but the way you're communicating needs to be fine-tuned.

As we're moving to a world where there are more hybrid or more all-remote companies, this is not a choice. As leaders, we have to figure it out to help our teams adapt.

Thinking before you communicate with someone else is of huge importance when it comes to remote work. You have to get good at having voice calls with somebody, where you're actively listening and responding. The skills to be an effective manager are similar whether you're in-person or remote, but the way you're communicating needs to be fine-tuned.

OL: What do you think is the biggest misconception about the way people are thinking and talking about remote work now?

HS: People tend to overemphasize the fact that it's different, and then all of their conversations start by focusing on the difference. So then remote work gets treated as something completely different by everyone. We're still all working together. We're still one company. Everyone's still getting a paycheck. The whole conversation is about how remote work is different, instead of being about the amazing tools we have at our disposal that remote teams and non-remote teams are able to use at any time. We have this opportunity to have a lot more freedom in our environment compared to when we had to be in an office, or even in school, 40 hours per week.

People are spending too much time thinking about the downsides instead of the upsides, but there's been some progress. Sixteen years ago, I didn't talk about working remotely because I didn't think anyone cared to understand it. Now, people are actually trying to understand it now. But we're spending too much time thinking remote work is different. Instead, we should spend our time focusing on how productive we're being at creating things and getting the results we need to grow and improve our business.

Our personal environment and the concept of it at work has drastically changed because now, so many people work remotely. We're even seeing more new tools and software being built to help us work together effectively with greater freedom and flexibility.

OL: Is there a benefit to a company having a headquarters of some sort, where employees can meet and work in-person when they wish to?

HS: I've seen companies go both ways on that. One of the advantages of being remote-only is not needing one single place that the company is located. I personally feel like it can be a crutch to have a headquarters. I honestly think that because we're so unfamiliar with remote work today, by having a centralized location of any kind, you're actually creating more friction and might be making remote folks feel isolated from the team that works in the same office. Then, you'll be doing a lot of work for both groups of team members to make sure that everyone feels great.

It's never the intention, but sometimes having a headquarters manifests in causing even more isolation for remote team members. Then you end up with a bigger problem where it feels like there are two "classes" of people at the company  with the lower class being remote workers. I'm rarely opinionated about these topics, but because we're so focused on remote work right now, I truly think it's important to make sure that, if you're going to have a hybrid team, you're highly conscious of what that looks like  and how it can go wrong Even companies that have multiple offices on different coasts or different countries end up setting up cameras and monitors to create portals between the offices.

I think we're going to see a lot more remote work practices permeate the in-office workplace. There are more and more companies with more and more people working remotely  even if an office already exists  and I think that's a trend we'll continue to see.

My prediction is that work is going to fundamentally change, and remote-first companies, more remote workers, and the way remote work is done now is going to just become the way work is done. All companies are going to start implementing practices inspired by companies that are remote-only.

OL: When you think about remote work 20 years from now, how do you think it will affect the way we think about work, period?

HS: In my opinion, people will feel happier. We'll get more flexibility in our lives. If you want to go pick up your kids from school at 3:00 p.m., you can do that. At all of my companies, you can do that, and nobody's stopping you  except maybe yourself, and your perception of your workload. If you have a doctor's appointment in the middle of the day, nobody is going to watch you leave the office and wonder where you're going. Maybe in your daily update, you'll mention that you'll be offline at the doctor's for a couple of hours. Ultimately, being on a remote team makes you stop caring about each other in ways that are meaningless or that encourage gossip and micromanagement.

"Are they getting their work done?" That will be the only question we ask about our coworkers. It's the only question that matters. In the future, responsibility will shift from everyone worrying about everyone else, to people starting to worry about the work. That's an exciting future to me.

Work is going to fundamentally change, and remote-first companies and the way remote work is done today is going to just become the way work is done in the future.

OL: From a cost perspective, if you're advising a company that is thinking about remote work and they're on a growth trajectory that looks like at some point in the future they'll be a bigger team, do you have any thoughts on cost considerations of being remote-only vs. remote-friendly?

HS: I would say that do whatever works for your culture and your team, and that's the start and the end of it for me. There's no one-size-fits-all policy for how often your remote team meets in-person, or why you meet or when you meet. The biggest priority should be making sure you don't let your team down. If you start out saying, "We're going to fly you all out once a quarter," and then you stop doing it, that's not cool. When people meet in person, they like it and want to keep doing it, so it's important to make sure you don't backpedal on a policy your remote team really loves. Clear communication and messaging around remote-only company policies for spending time together in-person are critical.

OL: Are there any specific things leaders should consider implementing to help remote teams work more effectively and productively?

HS: I believe that we will start seeing more remote practices implemented within remote friendly or in-office companies, so my biggest tip is to really think through how you want to be as a company, and what you want to facilitate and encourage on your team. So, if you really want to have hybrid team, or if you know folks are going to be working from home more, or you're going fully remote and you're not remote right now, then start thinking through what are the processes you can implement that will help people feel comfortable and included when they're working remotely.

If you're already remote, I would challenge you to ask if you're documenting enough. Are you iterating on your processes enough? Do you know how people feel about the work they're doing? Does the team have enough information about what's going on in meetings and within the rest of the company? Or do you need to do more there and be more deliberate about keeping employees in the loop? People can always benefit from more context and insight into company growth and what other people are working on. This type of context helps improve collaboration, performance, and encourages the happiness and flexibility remote workplaces allow.

Key Takeaways

1. Remote work will lead to a happier team and leaders in the future.

The self-motivation and discipline that make for successful remote employees will make people happier in the future, Hiten predicts, because work will be about results and deliverables instead of face time spent sitting at a desk in the office.

2. Effective documentation is critical to having a productive remote team.

If you think you're documenting already, start documenting more. Hiten calls for documenting all processes, meetings, and other communications via shared documents, email, or Slack to supplement live video conferencing so remote employees have context and feel included in decision-making and collaboration.

3. Use technology to supplement remote team meetings, not to replace them.

Slack rooms shouldn't replace Zoom stand-up meetings. Hiten suggests using synchronous and asynchronous technologies so remote employees can collaborate and socialize in real-time with their teams while keeping up-to-date through regular updates via Slack with the rest of the organization.

To learn more, read our state of remote work report.

Subscribe to see more stories

Explore the art and technology behind the Meeting Owl.
Tech Specs & Product Comparison