In The Da Vinci Coach, seasoned executive leadership coach Keith B. Cupp draws from the life and work of Leonardo da Vinci to guide business coaches and leaders toward Maestro status—where art, science, and mastery converge.

Even accomplished executive coaches hit career plateaus when they over-rely on rigid techniques, frameworks, certifications, or their own experience without developing the deeper judgment, character, and versatility needed to lead at the C-suite level. Grounded in more than two decades of coaching CEOs and studying accomplished coaches across six continents, Cupp demonstrates that true leadership mastery develops across five interconnected areas: Experience, Character, Skills, Roles, and Results.

Just as da Vinci moved fluidly among roles as a learner, teacher, and problem solver, spending a lifetime honing his craft, a modern Maestro cultivates the human depth required to create extraordinary value for the leaders they serve. This story-driven roadmap provides a proven developmental model, teaching practitioners how to recognize when to ask a question, when to teach, and when to deliver an uncomfortable truth. While this framework draws deeply from Cupp’s coaching background, experience as a CEO, and da Vinci’s genius, its principles will equip anyone seeking Maestro status in their chosen field to break through their own career stagnation.

In this executive guide, you will learn how to:

• Navigate the developmental journey from established coach, to business advisor, to trusted C-suite advisor, and ultimately, for a select few, to Maestro.

• Cultivate vital character traits—including curiosity, humility, trust, and courageous honesty—that drive deep client value.

• Develop strategic versatility to move seamlessly among the roles of coach, advisor, teacher, confidant, and strategic co-architect.

• Build a high-caliber peer community and mentorship relationships required to sharpen your high-level thinking.

• Translate lived executive experience into a distinctive coaching practice.

Whether you are an established executive coach seeking your next summit or a transitioning CEO entering advisory work, The Da Vinci Coach will help you see the next part of the mountain. It is not a shortcut to instant success, but a legacy guide for those who want to serve leaders deeply and remain humble enough to keep climbing.