
 Modern CTO
 Modern CTO His Worst Coach Made Him Into a Great Leader with Damon Lembi, CEO at LearnIt
 Sep 11, 2025 
 Damon Lembi, CEO at LearnIt and author of 'The Learn It All Leader', discusses how a negative coaching experience shaped his leadership style. He highlights the power of focusing on strengths over weaknesses and shares strategies for overcoming impostor syndrome. Lembi also dives into the balance of personal relationships and accountability in leadership, and introduces a four-step framework for personal growth. His insights on self-discipline and making tough decisions underline the transformative journey of becoming an effective leader. 
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Four-Step Roadmap To Overcome Imposter Syndrome
- Label your fear by imagining the worst outcome a year from now to shrink its power.
- Then prepare with hard work, deliberate practice, and finally perform and let go for growth.
Use Worst-Case Thinking To Make Better Decisions
- Purposeful awfulizing forces you to assess worst-case risks before big decisions.
- Use it to decide if an action is survivable or needs reevaluation.
Run A Team, Not A Family
- Treat your organization as a high-performance team, not a family; replace members who no longer contribute.
- Have compassionate, direct conversations and help people move to roles where they will thrive.





