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What We Learned As We Transitioned To A Remote-Friendly Team

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Luke Ryan

We have always believed that rigid rules are unnecessary when you build a team of highly engaged, passionate and committed people. Like many in this not-so-new paradigm of remote work, we value results over having people clock in and out at the same time and place every day.

Our deeply held core value to Embrace Freedom and Flexibility, allowed us to have a globally distributed team from day one. Today, employees continue to contribute to our success from as far away as Poland and Ukraine. 

Remote work can be incredibly fun and satisfying. What could be better than working for a few hours from some tropical paradise, and taking a break by learning how to surf? But it also requires certain techniques and rituals in order to be effective. Below is a review of the pros and cons of telecommuting, as well as our recipe for creating a productive and fulfilled remote-friendly team.

Distributed vs. Remote

In our early days we were completely distributed, and we discovered that aligning a team of 5 across three different time-zones was manageable enough. Everybody was remote, but stayed on the same wavelength through the power of communication technology.

As we grew to a team of twenty spread across 5 time-zones, the challenges of remote work began to surface. So we reigned it in a bit and brought people closer to one of our two main offices.

You may choose to be 100% distributed with no centralized office. Buffer and Zapier have done this quite successfully. Or you may choose to deliberately have a portion of the team in one office and the rest scattered in remote locations. (This has worked well for Batchbook.)

The latter style is what we have experimented with as our team has grown to 20 employees. Half the team (leadership, sales, marketing and customer success) work out of one central location in San Francisco, and most of our developers are in our New York office. Several support roles are spread across the US and in Europe. 

Through all of this we have learned that self-directed people can perform at a higher level and simultaneously take better care of their lives when they’re able to design for themselves how, when and where they work.

The Pros & Cons of Remote Work

We recently asked our team a question via our own weekly 15Fives: 

What do you like about working virtually/ partially distributed? What do you not like about working virtually?


– access to a global talent pool

– developers in different time zones means we don’t have to sacrifice sleep for vigilance

– no office space rent to pay

– no soul-sucking commute

– fewer distractions at home which leads to higher productivity and creativity


– even with technological improvements, it is harder to communicate

– lack of team camaraderie

– can lead to actually overworking by not separating office and home

– prohibits cultural growth because people don’t engage each other on a regular basis

– productivity can suffer without the group setting the tone for focus

15Five’s Recipe for Remote-Friendly Success

Remote work is not right for every team and presents unique challenges. Communication, company culture, and team momentum can all take a hit when people regularly report in or collaborate from far away. Here are the 5 key practices that we have implemented to support a successful remote-friendly team:

1. Video conferencing.  Every team member joins a Zoom video meeting for 15 minutes each morning (or afternoon/evening depending on the time zone). On this “Daily Boost”, we share recent triumphs and the day’s priorities. We also create connection by sharing gratitude for some facet of life on Mondays, and by answering personal questions on Fridays.

2. Vision & values first. Providing the space for people to do their best work on their terms requires that they have a clear idea of the company vision and values. Remote employees must be empowered to autonomously make important decisions every day, otherwise remote managers will be on email constantly. The company’s core values are the principles that help guide those decisions.

Free Guide: The Ultimate Guide for Making OKRs Work At Your Company. Learn how to fit OKRs into your vision and values. Download Now.

3. An app for that. Slack, Trello, Github, and an entire slew of collaboration tools help employees share calendars and vital information, and work together on projects. (And yes, we also use our own software so that managers and employees can briefly connect and have the most important conversations every week).

4. Leaders meet across time zones. Our leadership team meets every Monday to review and discuss the numbers, performance, objectives and key results (OKRs). We check in on team and customer headlines and areas of tension — all to ensure that we are on track from a high level. These meetings set the tone for each week and keep us cohesive and accountable.

5. Facetime from time to time. We schedule quarterly leadership retreats and an all-team retreat every January. When the team comes together in-person they organically swap personal stories with others. This deepens bonds and trust between one another, creating the foundation for exceptional teamwork.

Despite our systems and philosophies, we are far from utopian. Disagreements arise and are most welcome. A culture of transparency, support, and knowledge-sharing transforms conflict into creative growth opportunities.

Given our value of embracing freedom and flexibility we will always have an appreciation for remote work of some form or another.  While our values are absolute, their interpretation sometimes needs to be adapted to the company’s trajectory.

Learn more about how companies are leveraging remote work. See our 2016 remote teams survey results on Slideshare

Discuss this on Hacker News.

Luke Ryan is the Director of Growth at 15Five, employee performance software that helps managers celebrate wins, remove roadblocks and discover great ideas in just minutes each week. Follow Luke’s tweets about growth marketing and workplace culture @iamlukeryan.

Image Credit: NASA