Our firm recently had its fifth annual retreat, and it has caused me to reflect on the value that our team derives from taking two days per year to focus 100% on each other – not on our clients, not on the business, but on each other.
Company retreats have become increasingly popular in today’s workplace, offering teams a break from their usual environments and an opportunity to reconnect, reflect, and recharge. While they can be incredibly beneficial for company culture and communication, they aren’t without their drawbacks.
One of the greatest advantages of company retreats is the opportunity for authentic team bonding. Removed from daily responsibilities and distractions, people tend to open up more. Shared experiences—such as our annual hike to a waterfall, engagement in a discussion on a relevant topic with an outside facilitator, and a late-night conversation by the fire—foster trust and camaraderie. These relationships often carry over into the workplace, improving collaboration, morale, and communication. This in turn makes folks happier, and improves client outcomes.
In many companies, employees only interact with their immediate teams. Retreats create natural opportunities to meet colleagues from different departments or regions, breaking down silos that can form in larger organizations. We take part in silly games each year to promote this bonding. This cross-functional mingling can spark new ideas, uncover unexpected synergies, and promote a stronger sense of unity.
Stepping out of the office allows people to think more freely and reflect deeply. Retreats often create space for honest dialogue—about company direction, challenges, values, or personal goals. Whether structured through facilitated sessions or happening organically in downtime, these conversations can bring clarity, surface concerns, and generate meaningful insights that don’t always arise in day-to-day meetings. We try to create opportunities for both, so that each person can find a situation that suits their specific needs.
Of course, retreats require time, money, and planning. From travel and lodging to meals and facilitators, the costs can add up quickly—especially for remote or large teams. And while they’re intended to be productive, pulling people away from their normal work can cause delays or disrupt workflows. Thus, the planning process must be intentional and thoughtful, in order to make the investment worth it.
Further, group activities are not for everyone. While some thrive in social, immersive environments, others may find retreats draining or uncomfortable. The pressure to bond or share personal insights can be challenging for introverted or private individuals. Without thoughtful planning, a retreat can end up excluding rather than including. We strive to create different situations to suit different personalities, so that it’s not all large-group activities.
Finally, if poorly designed, retreats can feel more like forced fun than meaningful development. Without clear goals, follow-up, or integration into company culture, the retreat’s benefits may fade quickly once everyone returns to work.
When well-planned and inclusive, company retreats can be powerful tools for team bonding, deeper conversations, and breaking out of routine silos. The key lies in balancing purpose with play—and ensuring that what happens at the retreat doesn’t just stay there but helps shape a stronger, more connected workplace. Following our firm’s retreat last week, I feel recommitted to our values and to our people, and I know it will follow me throughout the year as we circle back to the provocative and thoughtful conversations we had.
