To maximize the value of bringing teams together physically, focus on one of three goals. "Doing" involves collaborative work on a key project. "Learning" focuses on gaining business context. "Planning" aligns the team on strategy and roadmaps. This framework ensures gatherings are purposeful and effective.

Differentiate marketing channels by their purpose. Use online platforms for broad reach and repeated touchpoints. Reserve offline, in-person events for fostering the genuine, vulnerable connections that are difficult to replicate digitally and are critical for building strong relationships.

In-person meetings are fundamentally more effective for building trust than any amount of digital communication. This trust is the foundation for significant business decisions, as people buy from individuals and brands with whom they've had a positive, tangible experience.

SKOs often fail with high-level corporate presentations. A better approach is to put top-performing reps on stage to share specific, tactical "how-to's" for key sales activities like cold calling, email outreach, and champion building, fostering peer-to-peer learning.

The most valued parts of the event were not the keynotes, but breakout groups and off-site excursions like pickleball. These activities create a "third space"—separate from work and home—where attendees can form genuine human connections, which is often the ultimate, unstated goal of attending.

The third week of the year is the ideal time for an SKO. This allows the team to decompress after year-end, gives enablement time to prepare pre-work, and sets the tone for the business before the quarter gets too hectic. It avoids being too rushed or too late.

While online platforms excel at one-to-many content delivery, the unique value of offline events lies in creating psychological safety for vulnerability. Small, in-person group settings allow participants to share business fears and struggles, forging much deeper bonds than a scaled online format allows.

While remote work is efficient, it lacks opportunities for spontaneous chemistry-building. The speaker prioritizes in-person time for his remote team, noting that camaraderie is built not in meetings but during "the little moments in an Uber" or over lunch. These informal interactions are critical for effective remote collaboration.

To make workshops memorable, design them around active participation rather than passive listening. Facilitate live exercises, group problem-solving, or hands-on coaching. When attendees 'do' something and walk away with a tangible result, the lesson sticks far longer than a simple presentation.