Question 1

What does your remote-friendly company do?

Accepted Answer

Tortuga helps people live on their terms by making luggage for city travel.

Question 2

Did you switch to remote or start out that way?

Accepted Answer

Jeremy and I started working remotely out of necessity. When we decided to grow the team, we saw no reason to change what was working for us. Plus, neither of us wanted to have to report to an office every day, even if it was our own office.

Question 3

How important is remote work to your business model?

Accepted Answer

Essential. “Working on our terms,” which includes being remote, is one of our core values and an important part of our mission. For most companies, being remote is a perk. For us, it’s what we do and what many of our products are used for. Working remotely has been part of our DNA since day one.

Question 4

What do you consider the biggest benefits of a remote workforce?

Accepted Answer

We’re able to hire the best people, regardless of where they are, and help them to work (and live) on their terms. Luckily for us, people who want to work remotely are likely to share our values and mission, which makes hiring remotely much easier.

Question 5

What were the main reasons to integrate remote work into your workforce?

Accepted Answer

When we started the company, Jeremy (my co-founder) and I were living in different cities and working on other things. Jeremy was in film school in Los Angeles, and I was working for Google in San Francisco. We didn’t immediately quit either to work on Tortuga, so we started by working remotely. We’ve known each other for years and have a bit of a mind meld, so working remotely was easy for us. As we grew and started to hire, we stayed remote even before it was a trend that everyone was talking about. Now, being remote is a more popular choice with a strong community talking about it.

Question 6

What traits do you look for in candidates for a remote job?

Accepted Answer

Every company is looking for “self-starters,” but this is essential for remote workers. Without anyone looking over your shoulder, will you still take initiative? Will you still have the drive?

Question 7

How do you conduct interviews for remote jobs?

Accepted Answer

We ask questions related to the job in the application process. Then we do phone screens for promising candidates. The finalists then move on to a role-based interview and a values-based interview. We do all of our interviews via Skype. If someone can’t communicate well by text or video call, they won’t work well in a remote team. So we don’t feel any pressure to fly someone out to meet in person. The book Who is an excellent resource for structuring your interview and hiring processes. It&#8217;s helpful in formulating questions and interviews for consistency to reduce bias in hiring.

Question 8

How do you convey your remote culture in the recruiting process?

Accepted Answer

The good candidates have already read about our culture on our website or blog. I’m often trying to convince them that this is really how we work, rather than conveying the details. Working remotely and having autonomy seem like common sense to me but are vastly different from the autocratic way that most companies operate. I like to say that remote is only the first step. What we really want to build are more human companies. Remote companies can do more than just let people work from home. We can build 21st century companies designed around how people work best and how they find fulfillment in their work.

Question 9

Do you organize remote team retreats?

Accepted Answer

Yes, in-person time is important. For us, the most important part of the retreat is all of the non-work time. We plan a fun activity, volunteering, and lots of team dinners for our retreats. This is our top priority. Please don’t spend your retreats sitting around a table looking at your laptops. You can do that the rest of the year. Our work sessions on the retreat are meant to be inclusive of the whole team and focused on the future. We talk big picture ideas, brainstorm new products, and push our thinking. Being in a new location is helpful for getting outside of your mental boxes.

Question 10

How do you measure the productivity of remote workers?

Accepted Answer

We focus more on priorities than on numeric goals. We set then frequently adjust those priorities. Productivity is measured by how much progress we make on those priorities in a given time frame.

Question 11

What is the hardest part about managing a remote workforce?

Accepted Answer

The hardest part of management is keeping everyone on the same page. As I mentioned above, we try to do this weekly, monthly, and quarterly. As CEO, the highest leverage thing I can do is focus the team’s efforts on a single problem or area of opportunity. My job is to get everyone in the boat and rowing in the same direction.

Question 12

How do you keep remote employees engaged and feeling part of the bigger picture?

Accepted Answer

Most importantly, we have a mission that everyone believes in and is working towards. Each quarter, we set a “theme” for the company that everyone uses to set their individual quarterly priorities. Each month, we send out team-level recaps discussing what each team is working on and the results. Each week, we send individual check ins by email with what we accomplished that week, what we’re prioritizing for next week, and where we need help.

Question 13

What is your time off policy for remote workers?

Accepted Answer

We offer unlimited vacation. I know that some companies have changed policies to minimum vacations, required vacations, or something else. As a travel company, our team has been pretty responsible about taking time off. If that ever changed, we may change course as other companies have. I try to set a good example by taking time off myself and by reminding people to take breaks, especially between big projects, to recharge.

Question 14

What were your biggest fears in managing remote workers?

Accepted Answer

I’m a first-time people manager and first-time CEO. My fears were (and still are) around leading a team of people. Being remote was never part of the concern. I didn’t consider myself a leader before Tortuga, so I’m trying to develop those skills, lead by example, and always put helping the team first.

Question 15

How did you implement a remote work policy?

Accepted Answer

Being remote happened organically for us, but we formalized it into our core values. We wanted our team to know that we were going to work this way even when it got difficult. That’s what makes it a core value.

Question 16

What advice would you give to a team considering to go remote?

Accepted Answer

If you’re going to do it, go all in. Remote doesn’t work well as an option or as a partial solution. Working remotely is a challenge. You have to design all of your communication and project management systems around being remote. If remote employees are the exception, not the rule, you will likely fail.

Question 17

What are the most effective tools for remote team communication?

Accepted Answer

Slack chat, for casual conversations, and Slack video calls for one-on-ones and team meetings. Chat is good for more frequent but less important discussions. Video calls are for the more important meetings and for staying better connected.

Question 18

What has changed about how your remote team operates?

Accepted Answer

As we grow, we build out more processes and planning. Done wrong, this could equal bureaucracy. Done right, these systems help us function despite not being colocated. Working remotely can lead to even more communication problems than working in an office. We use Asana and Instagantt to plan big projects like product development, product launches, and website redesigns. Having one tool “of record” lets us all share the same view and see the same plan, regardless of where we are.

Question 19

What is your personal remote work environment?

Accepted Answer

I moved from San Francisco to Oakland a few years ago for more space. Now, I work primarily from my home office (second bedroom) and from a standing desk. When I become too much of a hermit, I’ll vary my environment by working from cafes and coworking spaces.

Question 20

What are the biggest benefits of being a remote worker?

Accepted Answer

Freedom to manage my schedule based on what works for me. Even companies with flexible hours end up conforming to a schedule because of peer pressure at the office. Instead, I work the times when I’m productive. In the mornings, I do my high priority, focused work. Then I have lunch and go to the gym for a break. Then, in the afternoon, I do admin work like email.

Question 21

What tips do you have to disconnect when working remotely?

Accepted Answer

Set rules and boundaries for yourself. Have a way to signal that you’re taking a break or done for the day. I have a separate room for my office, so it’s easier to have some physical distance between myself and my computer. I can close the door to the office as a signal to myself. I recommend building some signals or routines into your work that remind you when you’re “done.”

Question 22

What is your favorite business book?

Accepted Answer

I read too much to pick just one. Here’s an entire list of my favorite business books.

Question 23

Do you have a favorite quote or bit of business wisdom?

Accepted Answer

I’m always quoting people, even when I only half remember the quote itself. Mostly, I have some mantras that I come back to. Perhaps the most important is “Play the long-game.” For me, that means do what’s best in the long-term, not just for today.

Question 24

Where is the best or worst place you’ve worked remotely?

Accepted Answer

China because of the Great Firewall. I never realized how often I use Google and social media. The best places have always been about who is there (then the Wi-Fi speeds). I enjoyed working from the Hive in Bangkok because of the great people I met there. We’ve also had great times on our retreats in San Sebastian, Montreal, Lisbon, and New Orleans.

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