Leadership Rooted in Values

Episode 31

144 seconds

For Glide, retreats are more than a getaway—they are an essential part of how the team lives its core value of building meaningful relationships.

With Guest

June 18, 2025

Retreat location: Country of retreat

For Glide, retreats are more than a getaway—they are an essential part of how the team lives its core value of building meaningful relationships. In this episode, Travis McAshan, founder and CEO, shares how annual in-person retreats became a cornerstone of their culture, even as a small company navigating remote work. Travis reflects on the unique energy that emerges from being together face-to-face: late-night conversations, shared experiences, and the trust that forms beyond daily tasks. He also touches on the subtle metrics that reveal the impact of these gatherings, from improved mental health to reduced burnout and stronger team communication. This conversation is perfect for leaders wondering how retreats can support team trust, culture building, and long-term performance in remote or hybrid settings.

Making the Case for Getting Away

With Sharath AbrahamJun 26th, 2025Retreat location:

Convincing leadership to fund company retreats can be a challenge, especially when the return on investment is hard to quantify. In this episode, Sharath Abraham, Global Strategy Manager at Jabra, explains why retreats are worth the investment and how they create value beyond traditional metrics. Sharath shares his perspective on designing offsites that encourage vulnerability and authentic connection. By taking teams out of familiar office settings and into environments where guards naturally come down—whether that’s a pool, a cabin, or even a teepee—retreats can spark conversations and relationships that simply don’t happen in day-to-day work. His advice offers a practical lens for leaders seeking to justify and maximize the impact of team gatherings.

Episode 33

Culture-Driven Retreat Moments

With Amanda SimmsSimms & Associates Jun 24th, 2025Retreat location: Barcelona, Spain

When Simms & Associates gathered for their annual retreat at Montsaint-Benet in Barcelona, Spain, one activity quickly became a highlight. Amanda Simms, Founder and CEO, recalls how their education manager introduced an exercise exploring words from different languages that appear similar but have completely different meanings. The discussion sparked laughter and curiosity, encouraging team members from across the globe to share cultural insights and connect on a deeper level. Amanda explains why these lighthearted yet meaningful moments often leave the most lasting impact and why simple, inclusive activities can be just as powerful as formal programming.

Episode 32

Building Hype on Retreats

With Lauren SatnickHiroJun 19th, 2025Retreat location: Cancun, Mexico

Retreats are often remembered for their venues or agendas, but at Hiro Systems, surprise is the secret ingredient. In this episode, Lauren Satnick, Executive Operations Manager, shares why she builds unexpected elements—both big and small—into every retreat she plans, from location reveals to surprise team challenges. One standout example was a survivor-style challenge on a private island during their retreat at the Fairmont Mayakoba in Cancun, Mexico. The team expected a boat ride and ended up with a full-day adventure that’s still talked about long after the event. Lauren’s approach shows how creative twists can heighten excitement, foster deeper connections, and leave lasting memories long after the retreat ends.