When a Leader Takes a Hike

Editor’s Note: This post was contributed by Chris Taylor, Founder and CEO of Square Root. Chris has spent his career developing strategic partnerships in the automotive and technology sectors. His fundamental understanding of these industries helps us develop easy-to-use, problem-solving technology.


Last year, my Chief Operating Officer, Elizabeth, took a sabbatical to hike the Pacific Crest Trail — a trip that would render her offline and unreachable for nearly five months. As her friend and colleague (and avid hiker), my initial reaction was excitement — this is a once in a lifetime opportunity! But as the CEO of a growing company, I had reservations about how we could backfill such an integral person for an extended period of time without sacrificing momentum in our culture and growth.

Supporting Elizabeth’s journey was also an embodiment of our THRIVE value. It’s the idea that everyone has their own balance and varying interests, and celebrating those differences makes us stronger as an organization. We empower each of our Radicals (our math-geeky name for the Square Root team) to pursue development opportunities, interests, and experiences that will help them not only feel successful professionally, but also feel fulfilled personally — even when they choose to hike 2,650 miles from Mexico to Canada.

As COO, Elizabeth plays a critical role in keeping both the company — and our culture — thriving. So, what happens when one of the most valuable members of your leadership team takes an extended leave? Elizabeth’s adventure was an opportunity to learn some invaluable lessons about our company, our culture, and about myself as a leader.

Lesson #1: Lead from the front

Culture shouldn’t be theoretical and the best way to make it tangible is for the leadership to embody the culture everyday. Our goal is to say “yes” to requests from our team and celebrate the successful examples of our culture and policies in action. This encourages our team to take advantage of our more unique benefits and truly thrive. For example, prospective employees are generally skeptical of unlimited vacation policies, but we gladly greet that skepticism with real examples, like Elizabeth’s.

Lesson #2: Culture takes constant nurturing

Culture isn’t done when you post your values on the wall. Creating a strong, positive, and scalable culture requires constant monitoring and adjustment, especially at a growing organization. While she was away, I took over Elizabeth’s weekly 1:1s which gave me a chance to better understand each team’s specific areas of concern and delight. When Elizabeth returned, we adjusted the way we communicate cross-departmentally in order to keep us all better aligned as we grow..

Lesson #3: Culture is a virtuous cycle

Establishing a strong culture can also be one of the most beneficial ways to foster leadership in your organization — at every level. An environment that cultivates individuals’ personal and professional lives that is backed up by programs and processes that really bring it to life gives opportunities for the team to grow. One of the other benefits of Elizabeth’s sabbatical was that it gave her team a chance to step up into parts of her role. Many of them ended up maintaining those responsibilities after her return — providing growth opportunities for both Elizabeth and her team.

Having your COO take a five-month sabbatical is by no means the only way a company can make the connection and drive changes between culture and leadership, but it was fortuitous for us. While it was challenging at times, the re-immersion allowed me to more fully understand the impact leadership and growth has on our culture. The experience also reminded me how important Elizabeth and each of the Radicals are to the success of Square Root. If nothing else, we could all use a reminder to be more grateful for the team that is building the company, and the culture, with us.