When it comes to your AI initiatives, is your company playing chess, or checkers? Recent reports share that only 5% of AI initiatives are successful. Why is that? According to Brian Evergreen, most companies don’t yet have a playbook for leadership in the AI era. This week on AI Heroes & Headaches, I sit down with Brian Evergreen, President of the Future Solving Club. Brian went from being an internationally competitive chess player to advising Fortune 500 CEOs on AI strategy. He has been recognized on the @Thinkers50 Radar list. His discipline and systems thinking show up in the way he frames the AI leadership challenge. In this full episode, we break down: Why incrementalism kills AI strategy The systems thinking that Brian took from chess into his professional career What an AI-first vision is, and how leaders can build it to rally their teams If you’re a leader navigating AI adoption, this conversation is full of practical lessons and bold insights.