5 Takeaways from Our First Leadership Retreat
5 Takeaways from Our First Leadership Retreat
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5 Takeaways from Our First Leadership Retreat

🕒︎ 2025-10-28

Copyright Inc. Magazine

5 Takeaways from Our First Leadership Retreat

For the first time in the history of our marketing agency, our senior leadership team gathered in person rather than on Zoom to discuss the growth of our company. We carefully mapped out discussion points in advance, planned the agenda, booked a space where we could comfortably speak with one another, and then simply showed up. We were a bit hesitant going in; some of the topics were tough, and we weren’t sure how candid conversations would unfold. Could we be open with each other without breaking bonds? Would we be able to talk honestly about the pitfalls of our respective departments? It turns out, yes. The experience was both enlightening and incredibly helpful. We left feeling inspired for the year ahead and with a renewed appreciation for the unique perspectives and strengths each of us brings to the table. While our entire company meets annually, dedicating time for the senior leadership team to focus on a structured agenda proved to be a valuable experiment. Without the usual distractions of running a 30-person retreat, we were able to dig deep. We hope to continue the exercise of setting aside time to review the big picture, dream big, and say the tough things to each other that move us forward into greater balance and success as a marketing agency. Featured Video An Inc.com Featured Presentation Through our time together, these five takeaways stood out as lessons to carry us throughout the year ahead. #1: There is immense value in hearing what troubles your colleagues. We dedicated a portion of the agenda to discussing the issues that bother us most. Initially, we anticipated this conversation would be uncomfortable and were unsure whether it would help or hurt. Instead, it proved invaluable. Hearing directly from our peers about the challenges they face gave us a better understanding of one another and highlighted areas where we can make decisions that alleviate pain points. It reinforced that we are all invested in supporting each other and committed to making our shared work environment better. #2: We value the same A-level players. One enlightening moment was realizing how much we share an appreciation for certain key team members. Hearing each other’s perspectives confirmed who is essential to our team and highlighted the contributions that make a real difference. This alignment strengthens our understanding of team dynamics and helps us prioritize the people and resources that drive our company forward. #3: Less structured activities, more focused work. Our agenda included planned team-bonding activities, but when discussions hit a high level of productivity, we chose to continue working instead of pausing. In hindsight, the optional evening activities ended up being more effective than the daytime team-building exercises. This reinforced that sometimes, giving space for uninterrupted, meaningful conversation is far more valuable than following a rigid schedule. #4: Our strengths are obvious when we step back. It’s easy, in the day-to-day grind, to focus on what could be improved. During the retreat, we intentionally outlined our company’s strengths. Seeing them all in one place highlighted who we are as a company and what we truly value. It was a moment of pride that reminded us how far we’ve come and the foundation on which we continue to grow. #5: Old-school paper and pen work best. We took notes with markers and paper, and we turned off all technology to eliminate distractions. There was something almost nostalgic about the experience. Being fully present allowed us to engage deeply with the conversation, and it’s a method we plan to continue using in future leadership sessions. Sometimes presence drives progress, and we’re here for it In today’s era of Zoom and remote work, it’s natural to want to hold important conversations online. But meeting in person allowed us to be more candid, more forward, and more connected with each other. For a leadership team responsible for the company’s growth and stability, the insights we gained from these face-to-face discussions were invaluable. Peter Boyd is the founder and president of Paperstreet.

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