

462: My Biggest Leadership Mistakes + Regrets
May 8, 2025
Leadership isn't always as glamorous as it seems. Discover the pitfalls of hiring too fast and the importance of trusting your gut in decision-making. Dive into the hidden costs of avoiding tough conversations and how people-pleasing can lead to an identity crisis. Learn about the breakthroughs that emerge from breakdowns and gain insights into what healthy leadership looks like today. The conversation offers raw and honest reflections aimed at helping leaders grow with integrity.
AI Snips
Chapters
Transcript
Episode notes
Leadership vs Business Building
- Leading a team requires a different skill set than building a business.
- Without leadership skills, teams become bottlenecks instead of sources of freedom.
Promote Based on Proven Readiness
- Promote team members only after testing leadership abilities with stretch projects.
- Tie raises to performance milestones and clearly define success at the new level.
Address Issues Early
- Have hard conversations early to prevent problems from growing.
- Lead with honesty, care, and specific examples to build trust and clarity.