The highs, lows, and lessons of leadership aren’t just found in conference rooms—they’re lived every day in unexpected moments and hard conversations.

In this episode, Damon Lembi walks listeners through three unforgettable leadership stories: the good, the bad, and the ugly. From a surprise party text mishap to the transformation of a struggling salesperson, a cautionary tale about hiring toxic talent, and an executive’s all-too-public coaching call blunder—each vignette offers practical takeaways, frank advice, and actionable strategies for becoming a more coachable, courageous, and intentional leader. Whether you’re managing the pressures of performance reviews, navigating interview pitfalls, or worried about digital privacy, Damon’s stories will help you avoid the biggest mistakes and seize growth opportunities.

Packed with real-world examples, memorable anecdotes, and tangible challenges, this episode will give you the tools to have the tough conversations, foster coachability, and protect your culture. Plus, listeners get a special gift in the show notes, a free download of Damon’s bestselling book.

In this episode, you’ll learn:

• Why having direct, honest conversations is critical for leaders—and how it can transform an employee’s career.
• The essential mindset shift every employee needs to make when struggling: let go and become coachable.
• The hidden dangers of hiring toxic high-performers, and why they’re never worth the risk to your team culture.
• Interview etiquette mistakes that kill trust—and how to avoid sabotaging your own reputation.
• How multitasking and digital mistakes can destroy privacy, and the steps you must take when sharing sensitive information.
• Simple challenges and intentional steps to help you grow as a leader or team member, starting today.

00:00 – Intro: Why nobody fully prepares you for being a CEO

00:35 – The movie-inspired theme: The Good, The Bad, and The Ugly

01:05 – The Good: Freedom, impact, and designing your ideal week

01:40 – Damon’s personal favorite: Building culture from the top down

02:30 – The privilege of hiring, promoting, and celebrating people

03:15 – The Bad: Constant context-switching and decision fatigue

03:55 – Loneliness at the top—why fewer people tell you the truth

04:30 – Damon’s go-to strategies for staying grounded

05:10 – The Ugly: Letting people go—and how it never gets easier

06:00 – Firing a friend: Damon’s personal story

06:45 – How he’s learned to lead through pain without avoiding it

07:20 – What helps: A learning mindset, trusted advisors, and staying human

08:00 – Advice for aspiring CEOs: It’s worth it—but not easy

08:45 – Challenge to listeners: Ask your CEO one honest question

09:15 – Damon’s parting thought: Stay human, stay humble

09:45 – Free Book Giveaway

About Damon Lembi

Damon Lembi is a 3x 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.

Resources & Mentions

• Damon Lembi LinkedIn
• Learnit
• Learn It All Leader (Book by Damon Lembi)
• The Learn-It-All Leader for Kids (Kids Book by Damon Lembi
• Ruben Gonzalez’s TED Talk on letting go: Watch here
• Damon Lembi’s free book download: https://BookHip.com/FTZRCJB
• Learnit: www.learnit.com

Website: www.learnit.com

Email: [email protected]

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