Offsite Insight

Ep. 2 - The "Identify, Discuss, Solve" Method for High-Impact Offsites

Andrew Bretton, founder of Mastermind Gym Solutions and CEO of Core Ventures, shares his battle-tested approach to running two distinct types of offsites: quarterly corporate retreats and mastermind summits for gym owners. He's refined a simple but powerful "identify, discuss, solve" methodology that ensures teams spend 90% of their time on the right problems before jumping to solutions. Hear why clear purpose and actionable follow-ups matter far more than any one team building activity or hosting it at a certain resport. 5 Actionable Insights 1. Require specific pre-work. Attendees need to know their numbers and come having identified their biggest challenges. 2. Use the "identify, discuss, solve" methodology - spend 90% of your time ensuring you're working on the right problem before jumping to solutions. 3. Create progressive engagement by having people think individually first, then discuss with a partner, then share key takeaways in small groups to accommodate both introverts and extroverts. 4. Don't leave without assigning specific action steps and owners, then hold weekly check-ins to ensure follow-through on offsite decisions. 5. Start small - think 1 day out of the office maybe at your house or a local library. Offsites are about getting away from daily distractions, not exotic locations or fancy hotels. Connect with Andrew: LinkedIn [https://www.linkedin.com/in/andrew-breton-3036b826/] Connect with Katherine: LinkedIn [https://www.linkedin.com/in/katherine-butler-dines/] | katherine@affinitytravel.co

Ep. 1 - Why This Remote Company Takes their team to Brazil Every Year (And How They Make It Work) | Leise & JJ of Superfiliate

Leise Trueblood, Chief of Staff and Jerônimo (JJ) Velasquez, Head of Design & Product Manager, at Superfiliate share how they planned 60-person, 6-day offsite in Brazil. Their team had doubled in size since their last offsite, including employees whose first day was at the retreat. They chose an all-inclusive resort in Florianópolis and balanced strategic business goals with relationship building. The result was so memorable that people posted about it equally on LinkedIn and Instagram—a sign of both professional and personal value. 5 Actionable Insights 1. For international destinations, start planning early (like 6mo +) and look for all-inclusive accommodations which can eliminate per diem headaches and reduce logistics complexity. 2. When your team is growing fast, create a "get to know you" deck with photos and fun facts for everyone to study during travel, then use it for a fun fact bingo icebreaker on day one. 3. Build in buffer - from extra rooms in case another hire joins to extra time between sessions because your team needs time to walk from venue to venue. 4. Design intentionally mixed cross-functional activities where groups are predetermined to create connections across departments. 5. Emails still need to be answered and sales call still need to get made so build in "work" time and "free" time, rather than packing the schedule with strategic sessions from dawn to dusk. Connect with the guests (they're happy to share planning templates and even more recommendations): Leise Trueblood: LinkedIn [https://www.linkedin.com/in/leisetrueblood/] | leise@superfiliate.com Jerônimo Velasquez: LinkedIn [https://www.linkedin.com/in/jeronimovelasquez/] Connect with Katherine: LinkedIn [https://www.linkedin.com/in/katherine-butler-dines/] | katherine@affinitytravel.co

Welcome to Offsite Insight

What makes a team offsite truly impactful, and what turns it into an expensive waste of time? How do today’s most thoughtful companies design gatherings that build connection and drive business results? Hosted by Katherine, founder of Affinity Travel Co., Offsite Insight brings you real conversations with the leaders behind high-performing team retreats. Each week, she sits down with CEOs, Chiefs of Staff, and People Ops executives to unpack the strategy behind their most recent offsites: what worked, what surprised them, what they’d never do again, and what they’d absolutely repeat. Come for the tactical takeaways; stay for the candid reflections. Whether you’re planning your first offsite or refining your tenth, you’ll walk away with clear frameworks, fresh ideas, and insider knowledge on how to combine camaraderie and commercial rigor. Subscribe to Offsite Insight on Apple, Spotify, or anywhere else you listen to podcasts.