This week on Bad Boss Confessional, Beth Fahey welcomes Dominic Sergi, CEO of Clear Height Properties, for a conversation about how unchecked empathy almost held his company back. Dominic shares the hard lesson he learned from keeping the wrong people in the wrong seats for too long, all because he cared too much.

What began as a culture built on patience and compassion evolved into one grounded in clarity, accountability, and authentic care. Dominic reveals how a mindset shift from fear to candor transformed his leadership, accelerated growth, and created a workplace where radical honesty builds trust, not resentment. It's a story about letting go, leaning in, and learning to say “yes, and…” instead of “yes, but.”

Chapters

00:00 Empathy: Superpower or Kryptonite?

05:09 Learning from a Mentor

09:00 Empathy’s Double-Edged Sword

12:35 Right People, Right Seats

17:29 Mastering the EOS Journey

20:49 Building an Authentic Culture

26:52 The ‘Yes And’ Mindset

About: 

Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.

 

Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.

 

Show Links

For more information about Beth Fahey follow the links below.

Website: www.eosworldwide.com/beth-fahey 

Facebook: www.facebook.com/BethFaheyEOS

Instagram: www.instagram.com/bethfaheyeos/

TikTok: www.tiktok.com/@bethfaheyeos

LinkedIn: www.linkedin.com/in/bethfahey/

Bad Boss Confessional YouTube: 

https://www.youtube.com/@badbossconfessional 

Beth's Youtube: 

https://www.youtube.com/@bethfaheyeos 

Guest Links

Dominic Sergi is an entrepreneur and investor with a passion for building enduring companies. As CEO of Clear Height Properties, he’s led over $1 billion in industrial real estate transactions, co-founded Cresco Labs, one of the nation’s leading cannabis companies, and launched Westshore Capital Group, his family office built on the belief that patient capital can outperform the market while leaving a lasting legacy.

Clear Height Properties: https://www.clearheight.com/

LinkedIn: https://www.linkedin.com/in/dominic-sergi-8b5ba24

Sponsor Links

Thanks to our Sponsors

A big thank you to our amazing sponsors for making this episode possible:

Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies.

Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.