The Danger of Optimism: CEO Jim Schleckser on His Biggest Leadership Mistake

My Favorite Mistake: Business Lessons from Failures and Success

My guest for Episode #316 of the My Favorite Mistake podcast is Jim Schleckser, founder and CEO of The CEO Project.

Episode page with video, transcript, and more

Jim is a seasoned business leader, bestselling author, and trusted advisor to CEOs around the world. With experience spanning 42 countries and multiple industries, Jim has spent decades helping leaders grow their companies and think more strategically. He’s also the author of Great CEOs Are Lazy and Professional Drinking, and he’s a certified sommelier—something we get to at the end of the episode!

In our conversation, Jim shares a formative early-career mistake—being too optimistic as a leader. His enthusiasm led to overpromising revenue, under-delivering on results, and ultimately damaging his credibility to the point where he had to leave the organization. Jim reflects on how he’s since learned to balance positivity with realism, buffer commitments, and truly listen to skeptics on his team. His story is a powerful reminder that leadership isn’t just about vision—it’s also about judgment, humility, and learning from painful experiences.

We also dive into what it means to be an effective CEO, including why Jim says great CEOs are lazy. He shares how high-performing executives focus their time on removing bottlenecks, not micromanaging, and why a trusted CEO peer group can be a game-changing support system. Plus, for fellow wine lovers, we cap off the episode with a fun bonus: wine mistakes, how to order like a pro, and Jim’s best tip for getting the most out of a wine list.

Questions and Topics:

• What’s your favorite mistake, and what did you learn from it?
• Can you share specific examples of how your optimism led to overcommitment or missed expectations?
• How did that mistake affect your credibility and position in the company?
• How have you learned to balance optimism with realism in leadership?
• What’s your approach to setting stretch goals versus achievable targets?
• How can unrealistic goals create dysfunction or unethical behavior in organizations?
• What’s the best way to avoid data manipulation and maintain integrity in performance reporting?
• What is The CEO Project, and how does a CEO peer group provide value to its members?
• You say “great CEOs are lazy”—what does that really mean, and how does it work in practice?
• How can CEOs identify the biggest constraint or bottleneck in their business?
• Why do some CEOs struggle to admit mistakes, and how does that affect their leadership credibility?
• How do peer groups foster psychological safety for leaders?
• What inspired you to become a certified sommelier?
• What are some common mistakes people make when ordering wine?
• What’s your best tip for confidently ordering wine at a restaurant?
• If someone only drinks Napa Cabernets, what’s a good way to branch out?
• Have you observed gender bias in how sommeliers treat guests at the table?