Executive coaching plays a pivotal role in driving innovation, especially when technological change demands a cultural shift, as illustrated by the transformation behind Nissan’s nationwide “Nissan Way” initiative. In guiding Retail Operations Managers through the transition from paper-bound practices to a fully digital performance system, coaching became the bridge between long-established habits and new expectations in a rapidly evolving industry. From navigating unforeseen challenges—like a Mardi Gras-timed coaching trip in New Orleans—to conducting hands-on “ride along” sessions in rural Louisiana dealerships, the work revealed that the greatest barriers were not technical, but human. By addressing skill gaps, resistance to change, and the discomfort of seasoned professionals facing unfamiliar tools, executive coaching created the foundation for sustainable innovation and ultimately helped reshape Nissan’s field operations across the country.