In this episode of the Breaking Through Series, host Michael Rom speaks with bestselling author, entrepreneur, and digital transformation expert Charlene Li about her book Winning with AI: The 90-Day Blueprint for Success. Together, they explore why successful AI adoption is not simply a technology challenge, but a leadership, strategy, and people challenge. Charlene shares a practical roadmap for leaders who want to move beyond small AI experiments and efficiency gains toward meaningful enterprise value. She explains why AI must be connected directly to business strategy, why responsible governance and clear ownership matter, and how organizations can avoid the “efficiency trap” by using AI to expand human capability rather than simply reduce headcount. The conversation also examines the human side of AI transformation, including employee skepticism and fear, the importance of transparency and fairness, the evolving role of managers, and the mindset shift required for people to see AI as a tool for agency, growth, and unlocking potential. Charlene emphasizes that the organizations most likely to win with AI will be those that break down silos, build AI fluency across the workforce, and lead with purpose, values, empathy, and realistic optimism. Key themes: AI strategy, leadership, digital transformation, responsible AI, workforce change, human potential, AI fluency, organizational culture, and the future of work.