In-person sales kickoffs provide the most value when focused on activities that can't be done remotely, like role-playing, interactive workshops, and building team energy. Reserve "stand and deliver" content for virtual pre-work sessions to maximize the impact of face-to-face time.

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.

Forced, one-time onboarding flows are brittle; users forget information or want to revisit it later. A more resilient approach is to structure help content as a library of on-demand, replayable chunks. This allows users to learn what they need, when they need it, improving long-term retention.

To overcome resistance and drive genuine enthusiasm for AI, position internal training not as a mandatory requirement, but as a promotional campaign. Focus on showcasing exciting, impactful use cases ("look at the cool things I can do") to create a pull-effect and foster a positive learning culture.

To overcome employee time constraints, Pendo implemented both scheduled, interactive workshops to create dedicated learning time and a Slack channel for asynchronous, "many-to-many" sharing. This dual approach ensures both focused learning and continuous, organic knowledge exchange across the organization.

Standalone training often fails to translate into practice. Coaching acts as a powerful accelerator when paired with a specific learning experience, driving up the implementation of new skills and behaviors by 400% and accelerating adoption up to four times faster.

Traditional sales training fails because reps quickly forget most information. The "teach-back" method flips the model by requiring reps to actively teach concepts to others. This active learning process dramatically increases retention to 90%, builds confidence, and fosters a coaching culture.

A key leading indicator of a successful kickoff is the team's motivation to learn more. Instead of just satisfaction surveys, measure success by tracking metrics like immediate requests for transcripts and content, and the speed of adoption for follow-up training modules.

To ensure executive workshop insights aren't forgotten, facilitators can implement a peer accountability system. Attendees are paired up and tasked with contacting their partner in 30 days to check in on progress. This simple social contract dramatically increases the likelihood of applying new knowledge.