The Enduring Importance of Retreats for Remote Companies: A 6-Year Update

Six years ago, when remote work was not yet cool, I shared our experiences and insights on the importance of company retreats for remote teams. Back then, our team at PSPDFKit had grown to about 26 full-time employees, and we were just beginning to understand the transformative power of retreats. Fast forward to today, and we’ve scaled to a robust team of 122 people, from 4 different companies, located in 27 different countries. You might wonder, do the benefits of retreats still hold true for a company of our size? The answer is a resounding yes, and here’s why.
The Journey from 26 to 122
Scaling from a small team to a medium-sized scale-up enterprise brings its own set of challenges, especially in a remote setting. As the team grows, maintaining a cohesive culture and ensuring effective communication become increasingly complex tasks. This is where the magic of retreats comes into play.
Why Retreats Still Matter

Building a Unified Culture
As we’ve grown through organic hiring and inorganic mergers and acquisitions, the need for a unified culture has only intensified. Retreats offer a unique setting for team members to interact, share experiences, and build those necessary relationships to ensure daily work can progress seamlessly. This is especially crucial for new hires or people who just joined the company through acquisition who may feel disconnected from the broader community or unsure about this new company they find themselves a part of now.
Facilitating Cross-Team Collaboration
As a company grows, the risk of departmental silos forming also rises, amplifying the necessity for cross-team collaboration. Company retreats serve as an ideal platform for such interactions, dismantling barriers and fostering a collaborative spirit that endures long after the retreat is over. This is especially crucial for us as we expand our range of products, integrate acquired companies, and increasingly rely on interdepartmental cooperation to solve work that once was expected to be handled by one person or team.
Employee Retention
We know through feedback and surveys that retreats contribute significantly to employee satisfaction and, by extension, retention. The sense of belonging and community fostered during these events are irreplaceable and can be a powerful motivator for team members to grow with the company.

Innovation and Problem-Solving
Our retreats have always been a hotbed for innovation. The relaxed atmosphere encourages open dialogue and cross-polination of thoughts and ideas allowing us to tackle challenges head-on and brainstorm new offerings we might have not thought of while separated and siloed in our functional departments. For example in Budapest, we spent a good bit of time in randomized breakout groups brainstorming what the future of documents could look like.
Why Retreats Are Invaluable for Leadership
One aspect of company retreats that often goes underemphasized is the unique opportunity they present for the CEO and the executive team to spend quality time with employees. In a remote work environment, much of the interaction between leadership and staff happens through digital channels, which, while efficient, can sometimes lack the nuance and depth of face-to-face communication. Everyone knows the difference between a zoom call and an in-person meeting: you can actually tell the height of the individual you are communicating with. Jokes aside, hxere’s why these in-person interactions during retreats are invaluable from a leadership perspective.
Direct Feedback Loop
Retreats offer an unfiltered channel for employees to share their thoughts, concerns, and suggestions directly with the leadership team. This direct feedback is gold for executives, as it provides insights that may not come through in regular surveys or virtual meetings. It’s an opportunity to understand the pulse of the organization and make informed decisions.

Building Trust and Transparency
When the CEO and executives are approachable and actively participate in retreat activities, it fosters an environment of trust and transparency. This is particularly important in a remote setting where building relationships can be challenging. An open dialogue during retreats can go a long way in making employees feel valued and heard, which in turn strengthens their commitment to the company.
Gaining Diverse Perspectives
As our company has grown to include members from different companies and countries, the range of perspectives has broadened significantly. For the leadership team, retreats offer a chance to tap into this diversity. Whether it’s a unique approach to problem-solving or a cultural insight that could benefit the company, these perspectives are most vividly captured in the relaxed, open setting of a retreat.
Strategic Alignment
Retreats are not just about relaxation and team-building; they are also strategic events. The informal setting is conducive to brainstorming sessions and deep dives into the company’s goals and strategies. This time spent with employees helps the executive team ensure that everyone is aligned with the company’s vision and objectives.

Employee Empowerment
When employees see that their leaders are taking the time to listen and engage with them, it empowers them to take more initiative and ownership of their roles. This empowerment is a powerful motivator that can drive performance and innovation long after the retreat is over.
Lessons Reaffirmed
-
Transparency is Key: Our “Ask Me Anything” sessions continue to be a hit, fostering an environment of trust and openness.
-
Balance is Crucial: Striking the right balance between work and leisure activities remains essential for a successful retreat.
-
Feedback Loop: Continual feedback helps us adapt and improve, ensuring that our retreats meet the evolving needs of our growing team.
Conclusion
Six years and nearly a hundred more team members later, the core benefits of company retreats remain unchanged. They are essential for building a unified culture, facilitating collaboration, and fostering innovation. As we continue to scale, the role of retreats in maintaining the health and happiness of our team only becomes more critical. To echo the sentiment of one of our team members, “that’s the power of the retreat.”
So, whether you’re a startup or a growing enterprise, don’t underestimate the transformative power of a well-planned retreat. It could very well be the glue that holds your remote team together.