How to Avoid Retreat Planning Mistakes
Annual offsites can be transformative—but only if they’re designed with balance in mind.
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The Culture Impact of Night One
Not every retreat activity turns into a lasting tradition, but karaoke night at metalab has become a highlight of their annual retreat at the Westin in Whistler, Canada. In this episode, Freya Rozzano, People & Culture Manager, shares how this lighthearted event sets the tone for the summit each year. From unexpected Spice Girls performances to bold power ballads, karaoke night encourages people to let their guard down, cheer one another on, and create shared memories that last long after the retreat ends. It’s a perfect example of how small, joyful traditions can become cornerstones of team culture.
Cross-Team AI Collaboration
Retreats often create space for reflection but at Pacaso, they also spark innovation. In this episode, Rasika Rajagopalan, VP of People and Talent, describes how her team turned their annual retreat at the Intercontinental San Diego into a hands-on AI sprint that engaged every function of the company. Product and engineering teams led workshops where cross-functional groups prototyped solutions to real challenges: legal explored faster contract review, sales built a lead prioritization model, and HR developed AI-driven manager support tools. The result was not just ideas but working prototypes, and a renewed sense of empowerment among non-technical teams. Rasika shares how this retreat became a powerful moment of alignment, creativity, and collaboration.
Designing Corporate Day Retreats
When planning a retreat, understanding your team’s unique profiles can make the difference between a good event and a transformative one. In this episode, Belén Suárez, Culture and Internal Communications Lead at Nacar Designs, shares why aligning retreat activities with team expectations—and involving employees in the process—creates a deeper sense of purpose and connection. Belén reflects on lessons from hosting biannual retreats, including how thoughtful planning and open communication help translate leadership goals into meaningful experiences for everyone. Her insights provide a framework for organizers seeking to create retreats that feel inclusive, intentional, and impactful from start to finish.
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