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Simulating the Water Cooler: Help Scout’s Tips for Building a Great Remote Team

“While growth is important, team and values are paramount.”

This is the foundation upon which Nick Francis co-founded Help Scout. Since launching in April 2011, they’ve helped over 9,000 businesses across 150 countries by humanizing customer service software.

Right from the get-go, Nick wanted to prioritize talent and find the best people for the roles Help Scout needed. It’s this ambition that prompted Help Scout to be a remote-first company, using that approach to shape the company culture from day one. With no constraints on location, Nick was able to intentionally select individuals based on what really mattered, not based on whether they could commute to the nearest city or not.

This approach has allowed them to hire talented people from many different places. Help Scout’s team of 75 people is stretched across 50 different cities throughout the world: a truly international organization.

So, is setting up a remote-first company really that beneficial? There are bound to be a few pitfalls, right? Nick shared his thoughts on the trade-offs associated with a remote culture, the things you can do early on to ensure that your remote employees feel “in-the-loop,” and the habits you should build.

Addressing the Trade-offs of Being a Remote Company

It’s common to compare office-based organizations with remote cultures. You’ve probably seen reports or articles with titles like “What are the benefits of having a remote-based team?” or “Is a remote working business better than location based?” Often these types of articles or reports will take a stance and state that either or works best. However, as Nick points out:

“It’s not which is a better way of working: office or remote? Both have their pros and cons. As long as you’re aware of the challenges that exist on either side, you can make either one scale in the long-run.”

There’s no right answer, but one or the other might suit your business better, based on your goals and aspirations. For example, going back to what Nick said at the start of the interview, Help Scout wanted to make sure they got the best people possible for the jobs to be done, and they didn’t want to be restricted by location. In that case, they can benefit greatly from one of the pros of remote work: accessibility to talent.

If you’re starting a company and are considering which option best fits your needs, consider writing down your priorities. Articulate how you want to hire, how you intend to shape your culture, and what you want the day-to-day work to look like. Let these priorities guide your decision to be co-located, remote, or some combination of the two.

The Cornerstones of a Successful Remote Organization

If you do opt for a remote team, start by clarifying the cornerstones of your company’s “operating system”. These are the beliefs, values, and processes that guide how you do business. Nick shares two cornerstones that guide their team: information and relationships.

Making sure everyone has access to the same information

When people feel out of the loop in a remote company, it’s incredibly difficult for them to get involved and do their best work. Every employee must have access to the same information; when they don’t, it creates huge problems.

“Transparency in a remote company is not a luxury, it’s something that you absolutely have to have.”

This problem can be especially prevalent in companies that aren’t remote-first, but rather, have just a few remote employees. The company isn’t used to sharing information outside of their office and doesn’t have the infrastructure or processes in place to do so. As a result, there is a lack of transparency, and remote employees don’t receive the same feed of information. Even when just a fraction of the company is remote, it’s critical to invest time and thought into making sure all team members have equal access to information.

Simulating the “water cooler”

The second cornerstone that Nick mentions is the need for an organization to help people build relationships in an environment where it won’t happen naturally. There’s no mutual water cooler or lounge area when you have employees in 50+ cities.

This is tough, and it’s going to take some work. The way in which you achieve the “water cooler” effect will depend on your company and the types of people you employ, e.g., their interests, hobbies, and traits. Help Scout uses techniques such as:

  • Company retreats
  • Fika (a random one-on-one with someone in the company each month)
  • An introduction week with team members in Boston to meet colleagues

All of these routines play a role in connecting remote employees with one another; they also encourage new team members to actively engage when they’re remotely located.

Information: what, where, when, why, how

If you’ve predominantly worked on traditional, co-located teams, you might be wondering how Help Scout and other remote organizations manage to share information with every employee in a secure and effective way.

Help Scout is bullish on good documentation. They store all company information in Dropbox, including everything from designs to metrics to office leases. The only information they don’t share relates to personal employee information, such as salaries, which is securely stored away in a separate folder.

A key tenet of this approach is collaboration. Each employee can contribute to the Dropbox repository, sharing information about their current projects or work. They take an “open by default” approach in most situations.

In terms of daily communication, Help Scout uses Slack. Interestingly, Nick revealed that they also use Slack to post a monthly update on each team and how they’re performing.

In terms of recurring meetings, they opt for a fortnightly “town hall” meeting and every quarter they hold an “all-hands” meeting. All of which are recorded so that people located in different time zones can watch the meetings at their own convenience.

Building Habits and Investing in Success

The success of your remote team often depends on the habits you’ve built during the early days. Help Scout benefitted from an early commenting habit: their team often left written comments about how a meeting went and what happened. When they reached a team size of 50-70 people these habits held strong, maintaining the processes and structure the first ten employees had leveraged.

Nonetheless, it can be hard to form new habits, not to mention sticking with them. One way to do this is by hiring for culture fit. When you bring on the right people, it’s easier to uphold the habits and processes you’ve put in place.

This is one reason that Help Scout invested in people operations early on. They knew that by leaning into people ops, they’d have a better chance of building good habits and an easier time hiring people who would engage with these habits. Nick shares that they had three people working in people operations when the entire company was only 20 employees. That might seem disproportionate, but as Nick explains, it helped them focus on getting the culture to where it needed to be at that point:

“We were really, really focused on getting the team, the culture, and the way that we work together, right… We didn’t have to grow the people ops team after that point.”

Clearly Articulated Values

The systems and processes that Help Scout put in place have helped shape their culture. They document the things they value most and then use that information to ensure that each new hire fits those criteria.

Even now, when they arguably have an already strong company culture, the thing that Nick and his team put at the top of their mandate for 2018 was, you guessed it, make their culture even stronger.

“I love the business I’ve built, and I want to always make it better… To this day we’re really intentional about the things we value. We try to vocalize those as much as possible, both internally and externally, and the rest takes care of itself.”

Building a Team of Coaches and Players

One of the things that Nick wished he had known sooner relates to the way in which he perceived and referred to managers and employees. He has written about the idea of calling managers “coaches” and individual people “players” and the philosophy around that concept.

In short, it’s much harder to be a “coach” in a remote culture. It’s a full-time job that is incredibly time-consuming. Plus, you lose out on key opportunities to participate in face-to-face meetings and conversations with the “players” that you’re coaching.

For example, in a typical office-based company, you might have a daily standup. You’ll know what each of your players is working on and what challenges they’re facing. A lot is, though, beyond what’s actually said. Tones of voice, body language, attitude…all of these things help a coach understand how the players are performing. It takes 15 minutes of a coach’s time, but it sets up the players and coach for the day ahead.

At Help Scout, those standups happen in a Slack room. Not only are the “unspoken data points” lost in this way, but coaches also need to navigate the fact that players are in many different time zones. You might have an Australian player who has sent through work overnight that requires your approval. You have players on the East Coast of the US, getting up and starting their day. And you have West Coast players who will need to be filled in on what has happened so far and what they need to do. It can be hard to feel in sync with so many people who may have different needs because of differing time zones.

One-on-ones become increasingly important when you’re limited in your ability to have synchronous conversations. The best coaches consistently show up and make the most of one-to-one meetings. Their importance is amplified in a remote culture. This is the one chance each month to interact with your players on an interpersonal level, and generally, it cannot be replaced by Slack messages and documentation.

Using your Team and Values to Shape your Remote Culture

We opened this article with a line directly from Help Scout’s “About Us” page: “While growth is important, team and values are paramount.” That principle is at the heart of their ethos as a company, and as Nick highlighted, it’s crucial to focus on what you value and find people who fit the culture.

To wrap up the interview, we’ve summarized the key points that Nick made below:

  • There’s no right answer to whether you should base your company in an office (central location) or remotely. Both have their pros and cons
  • If you do run a remote organization, make sure that everyone in your team has access to all the same information
  • Give people, both new and old, the chance to build relationships. You have to facilitate this or it won’t happen
  • Build habits from the early days (less than 10 employees) and they’ll stick with you as you scale. Fail to build habits and you’ll struggle to manage a remote culture once you reach 50+ people
  • Build a team of coaches and players rather than managers and employees. The “coaches”, coach, and the “players”, play.

If you want even more guidance, Nick recently wrote an excellent post about their remote culture, which you can read here.

CRO at Tettra. Reader, long-walker, Sloanie, beer brewer and drinker, 'villan, parent, spouse, friend, human. Previously at Ovia Health, Wistia, and Transparent Language