BL&T No. 164: Hosting Our Second Annual Barrel Retreat

Agency Leadership

This post originally appeared in my newsletter, Borrowed, Learned, & Thought. BL&T is sent weekly on Mondays. In every edition, I share lessons learned in agency leadership, life, and e-commerce. This post does not include all the details shared in the newsletter sent via email. Subscribe here.


"Long-term relationships (in families and at work) that cultivate our growth, rather than ending because of our growth, are precious, and they’re necessary for the continuity and wholeness of our lives."

From "An Everyone Culture" by Robert Kegan, Lisa Laskow Lahey [Book]

Learned & Thought

Last week, I had the opportunity to escape to the Catskills with the Barrel team for our second annual team retreat. We stayed at the Wylder Hotel, a scenic resort where all our activities were conveniently on-site. Thanks to the incredible Allison, our Team Experience Coordinator, who orchestrated the retreat, especially coordinating the smooth arrival of team members from all over the world.

Spending time together in the calm of upstate New York was a nice change of pace from our time together last year in the hustle and bustle of New York City. On my long drive home, I was thinking back on my thoughts coming out of our first retreat (read: BL&T No. 111). While it was a blast, we learned what worked and could improve and applied many of those learnings to our second go-round.

Me and the Barrel partners trying to act like we're not being photographed.

We applied those lessons to this year's retreat, and I'd say our evolution was a success, resulting in a fantastic few days as a team. So, here are my reflections on our second retreat:

1) One Location, All-Inclusive

A takeaway from last year was that doing the retreat in a city, especially NYC, made it more difficult than we would have liked to coordinate activities with the team.

This time around, we were curious to see how the overall vibe of the retreat might change if we were to do it in a single location. This decision proved to be a great one. While it was more challenging to get folks out to the Catskills, once everyone arrived, there was nothing else to worry about.

The Wylder Hotel offered a comprehensive on-site experience, including meals, activities, and amenities, allowing us to maintain a tight schedule with only brief breaks. With everything within walking distance, we maximized our time together, with no time needed for travel. Overall, the location created the perfect laid-back feel we were going for.

2) Office vs. Remote Work: A Non-Issue

Folks from Client Services team.

Whenever we gather as a team, I can't help but wonder how it might be if we were still working from a physical office. However, this is less about a desire to return to the office and more of a fleeting thought.

What I realized this time is that we wouldn't have the same awesome group of people if we hadn't embraced our current distributed work culture. Rather than pondering an alternative, we should focus on nurturing deeper relationships, meeting in person, and continuing to shape a company culture that people take pride in.

3) Embrace the Outdoors

Hiking selfie with the crew.

Just like last year, we carved out time for the team to enjoy activities together. The difference this time was that we took it all outdoors, and for those who were up for it, we broke a sweat. I must say, I thoroughly enjoyed it.

Before the official schedule began on Wednesday morning, I joined our CEO, Peter, and CTO, Wes, for a bracing outdoor exercise. The grass was chilly and damp, but it didn't deter us. Meanwhile, many other team members gathered for morning yoga at the lodge.

Following our team session, we embarked on various outdoor activities, from hiking to biking to pool and sauna sessions to lawn games. I ended up hiking, playing badminton, and tossing a football around.

Being active, especially outdoors, is a great way to clear the mind and unwind. As a distributed team, our goal is to connect and get to know one another better, and being active outdoors was an excellent way to achieve that. I look forward to seeing what other activities we can incorporate in future events. Beyond these activities, I also loved ending the nights with some s'mores and karaoke.

4) Deepening Connections with an Expert

To change up our team-building sessions, we enlisted the expertise of Alex Auerbach, a performance psychologist currently working within the NBA.

Alex's workshop on Wednesday focused on helping the team learn more about their colleagues, including insights into personality types, working styles, and values. It was not only fun but also eye-opening to discover new facets of our team members. We found ourselves spanning various personality types yet aligning on many shared values.

On Thursday, we participated in an exercise where each team member had to draw or paint three of the most impactful moments in their lives. It was moving to witness everyone's vulnerability as they shared the experiences that had shaped them.

Having Alex with us had a powerful impact on the event. His presence and expertise facilitated a deeper connection among us, one that would have been challenging to achieve without his guidance.

5) Learning from Planning Challenges

While immersed in the planning phase, there were moments when it felt like we were encountering one challenge after another. In retrospect, it was our doing. We sought feedback and perspective from the team, and at times, we got frustrated when everyone's opinions didn't align. However, it all turned out wonderfully in the end.

In the future, I think we can be more prescriptive about certain aspects of the retreat, knowing that once the event begins, everyone will be happy to come together, create memories, and enjoy each other's company.

My last photo of the trip with the one and only Allison

We also hired a photographer this year to remove the stress of capturing content during the event. Very much looking forward to seeing those photos!

Based on our team's feedback thus far, it sounds like everyone had a great time. I'm excited to continue experimenting with how we spend our in-person time together and improving the experience from one retreat to the next.


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