When Your COO Takes A Hike

 When Your COO Takes A Hike


By Chris Taylor

Last year, our Chief Operating Officer, Elizabeth Schwartz, approached me with a once in a lifetime opportunity to hike the entire Pacific Crest Trail — an adventure that would have her out of office, and off the grid, for five months. My excitement for her was quickly overshadowed with reservations about how we could backfill such an integral person for an extended period of time without losing momentum and slowing growth.

Supporting Elizabeth’s journey was an embodiment of Square Root’s THRIVE value. It’s the idea that each member of the team has their own balance and varying interests, and celebrating those differences makes us stronger as an organization. Sometimes, flexible policies result in unexpected and unconventional requests, such as hiking 2,650 miles from Mexico to Canada. These requests are opportunities for growth of both individuals and company culture, and our goal is to figure out a way to say “yes” and celebrate the successful examples of our culture and policies in action.

When Elizabeth literally took a hike and went on a five month sabbatical, the team learned some invaluable lessons about our company, our culture and our leadership. For any CEO or business leaders exploring similar benefits and perks for their teams, here are a couple of things to consider.

Embrace Growth Opportunities

Sabbaticals, promotions and even turnover can be growth opportunities for individuals and the company. In the months leading up to her trip, the whole company came together to support Elizabeth, taking ownership of her tasks and responsibilities. I took over Elizabeth’s one-on-one meetings, seizing on a unique opportunity to engage more deeply and intentionally with her team and their departments. These sessions allowed me to get back into the details of our daily operations with a fixed end date, and helped me gain a new perspective on the way Square Root operates. Returning to day-to-day operations was a great reminder that regular, in-depth discussions with different departments and teams is crucial to ensuring every goal and business objective remains on track.

When Elizabeth returned, we adjusted the way we communicate cross-departmentally to keep us all better aligned as we grow. Perhaps most importantly, Elizabeth’s sabbatical gave her team a chance to step up into parts of her role. In an instance where there could have been many holes unplugged, we found several new opportunities to showcase individual strengths. Many of them ended up maintaining those responsibilities after her return, providing growth opportunities for both Elizabeth and her team.

Lead From The Front

Culture should not be theoretical. The best way to make it tangible is for the leadership team to be the first to embody the culture and values central to the organization. Leadership should consider the company mission and core values, and how these can be translated into unique policies and culture initiatives. When the executives and managers lead by example and utilize culturally reinforcing policies, it builds trust and empowerment within the organization. This way, everyone feels supported to take ownership over their professional and personal development.

An environment that cultivates individuals’ personal and professional lives, and is backed by programs and processes, brings culture to life. Not only does this create opportunities for everyone to grow, but it also helps with retention and recruiting. For example, during the interview process, prospective employees are generally skeptical of unlimited vacation policies, but we gladly greet that skepticism with real examples and celebrate experiences like Elizabeth’s. Demonstrating benefits in practice showcases the leadership’s commitment to development and enables everyone, no matter their title or tenure, to envision and appreciate how they can thrive at the company.

Culture is not something that is finished when the values are posted on the wall — it’s an eternal work in progress that takes constant thought, care and feeding. Having an executive take a five-month sabbatical is by no means the only way a company can create an opportunity to evaluate the culture and implement policies that create opportunities for growth. But however it manifests, the investment in culture is worth it — a strong culture builds upon itself, creating a virtuous cycle of reinforcement that will help the company thrive.

Chris Taylor is founder and CEO of Austin-based Square Root. He founded the company in 2006 with the goal of making business data accessible, understandable and actionable. A testament to Chris’ commitment to culture, Square Root was recognized as the 2015 2nd best small workplace in America by Fortune magazine.


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