102: Work on Your Game and Step Up, with Dre Baldwin

In this episode, I sit down with Dre Baldwin, CEO and founder of Work on Your Game, former professional basketball player, and four-time TEDx speaker. Dre shares his unique journey from sitting on the bench in high school basketball to a nine-year international pro career, and how the lessons he learned on the court translated into his impactful work with leaders and entrepreneurs.

Author of the book, “Work on Your Game”, Dre dives into his signature “four pillars” framework—discipline, confidence, mental toughness, and personal initiative—explaining how these core elements of mindset underpin professional performance and success in any industry. We explore practical strategies for building mental toughness without risking burnout, the crucial importance of understanding and connecting with individual team members, and the realities of leadership challenges at all levels, from new managers to experienced mid-level leaders.

Dre offers candid stories about his own missteps—especially around hiring and team management—and provides actionable advice for navigating common leadership pitfalls. We also discuss the dynamics of leading diverse teams, including the nuanced differences between male and female leaders, and why the ability to truly listen and communicate effectively is the most valuable skill for leaders in the modern workplace.

Key takeaways:

• Leadership is deeply rooted in mindset, with discipline, confidence, mental toughness, and initiative serving as critical pillars for success.
• Effective leaders invest time upfront to understand their people, recognizing that each team member requires a unique approach to motivation and feedback.
• Communication is more than what you say—it’s about listening, understanding non-verbal cues, and making others feel heard and valued.
• New leaders should seek real-world experience and mentorship, learning not just the “what” but the “why” behind effective leadership practices.
• Navigating middle management requires mastery of upward and downward communication, and a clear understanding of the “game” you’re playing within your organization.
• The best leaders proactively build trust and show genuine care for their teams, which unlocks higher engagement and performance.
• Replacing or motivating unengaged employees often comes down to connecting with them personally and aligning on shared goals, rather than relying solely on authority.
• Communication and people skills will continue to grow in importance as automation and technology accelerate, making human connection a powerful differentiator for leaders.

Tune in for an episode packed with practical wisdom and real-world advice you can bring to your leadership journey today.

Pick up Dre’s book