387: Why Managers Should Embrace a Learn-It-All Mindset With Damon Lembi

December 09, 20253 min read

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Ever feel like you should know more, be more confident, or have everything figured out by now?

You’re not alone, and more importantly, you don’t need to be a “know-it-all” to be an exceptional leader.

In fact, the strongest leaders today share one trait:

They are learn-it-alls, people who grow through challenges instead of shrinking from them.

Fortunately, this week’s guest brings a powerful, actionable framework that helps managers move from self-doubt into genuine capability.

Damon Lembi is a 2x bestselling author, the host of The Learn-It-All Podcast, and CEO of Learnit, a live learning platform that has upskilled over 2 million people. Drawing from his prior baseball career, Damon brings an athlete’s perspective to leadership. Through his journey, he has gained invaluable insights into what helps organizations grow, how great leaders learn, and why learn-it-all companies outpace their competitors every time.

We explore why action transforms confidence faster than motivation ever could, how to stop perfectionism from stalling your growth, and how “possibility spotting” turns obstacles into opportunities for advancement. If you’ve ever felt like you’re not ready, not experienced enough, or not “the right fit,” this conversation will help you step forward as the leader you truly are.

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Conversation Topics

  • (00:00) Introduction: Why imposter syndrome spikes when stepping into leadership

  • (01:12) What imposter syndrome really is (and why nearly everyone experiences it)

  • (05:42) Why we undervalue ourselves when taking on bigger roles

  • (08:30) Confidence through action, not waiting to feel ready

  • (11:18) Building leadership skills through mentors, reps, and learning

  • (13:44) Why difficult conversations trigger self-doubt for new managers

  • (15:56) Owning your gaps to build credibility

  • (18:03) Asking for help and advocating for your development

  • (22:58) Finding opportunities inside constraints

  • (25:57) [Extended Only] Why everyone has imposter syndrome

  • (26:45) [Extended Only] Damon’s 4-step framework for overcoming imposter syndrome

  • (34:05) [Extended Only] Turning obstacles into an advantage

Additional Resources

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✨Read the full transcript here

Keep up with Damon Lembi

Guest Bonus (available to members of Podcast+): FREE Digital Version of Learn-It-All Leader

In The Learn-It-All Leader, Learnit CEO Damon Lembi shares:

  • How being a "Learn-it-All" vs "Know-it-All will set you up for success and get you invited to more happy hours!

  • A three-step approach to overcoming imposter syndrome

  • How to use Purposeful Awfulizing to overcome fear and build resilience

  • Discover why treating your employees as a team rather than as family can lead to greater success

  • Why you should choose potential over experience in the hiring process

  • What the “Trust Tax” is and why it’s worth paying

  • How a leader's personal model of integrity is crucial to creating trust and a thriving workplace

  • A proven model for building great teams

  • How implementing a culture of continuous learning & professional development helps attract & retain talent

  • Why you should focus on elevating strengths over improving weaknesses


With entertaining anecdotes and inspirational examples, The Learn-It-All Leader is a compelling guide to being your best and playing to win every time.

👉 To get this guest bonus and many other member benefits, become a member of The Modern Manager Podcast+ Community: https://themodernmanager.com/more 


The Modern Manager is a leadership podcast for rockstar managers who want to create a working environment where people thrive and great work gets done.

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