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30: The High Price of Saying Yes
In this episode of Bad Boss Confessional, Beth talks with serial entrepreneur and coach Jill Salzman about the early mistakes that shape stronger leaders. From quick-start decisions to client-pleasing habits, Jill reflects on how saying yes too fast and avoiding boundaries can quietly erode confidence and clarity. The conversation expands into coaching, asking better questions, and resisting the urge to solve everything for others. The real lesson is not about one bad decision. It is about learning to trust experience over ego, service over approval, and patience over speed.
Timestamps
00:00 Introduction to Bad Boss Confessional
02:16 Meet Jill Salzman
05:05 Music and Personal Outlets
06:51 The Black Crows Concert Fiasco
12:15 Lessons from the Cancellation Fee
17:29 Influences and Coaching Philosophy
21:09 The Quick Start Challenge in Coaching
24:45 Human Connection vs. AI in Coaching
28:30 Detox from Social Media
32:57 The Big But Book
35:35 Tattoos and Final Thoughts
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
Jill Salzman isn’t your ordinary business coach. She’s a serial entrepreneur, a thinking partner, and a musician who rarely misses a beat. Jill brings humor, heart, and strategic clarity to every conversation. She thrives on collaboration, sparks creativity, and makes the hard parts of entrepreneurship feel a little lighter.
LinkedIn: https://www.linkedin.com/in/jillll
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.
View all episodes
By Speakeasy Podcast NetworkIn this episode of Bad Boss Confessional, Beth talks with serial entrepreneur and coach Jill Salzman about the early mistakes that shape stronger leaders. From quick-start decisions to client-pleasing habits, Jill reflects on how saying yes too fast and avoiding boundaries can quietly erode confidence and clarity. The conversation expands into coaching, asking better questions, and resisting the urge to solve everything for others. The real lesson is not about one bad decision. It is about learning to trust experience over ego, service over approval, and patience over speed.
Timestamps
00:00 Introduction to Bad Boss Confessional
02:16 Meet Jill Salzman
05:05 Music and Personal Outlets
06:51 The Black Crows Concert Fiasco
12:15 Lessons from the Cancellation Fee
17:29 Influences and Coaching Philosophy
21:09 The Quick Start Challenge in Coaching
24:45 Human Connection vs. AI in Coaching
28:30 Detox from Social Media
32:57 The Big But Book
35:35 Tattoos and Final Thoughts
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
Jill Salzman isn’t your ordinary business coach. She’s a serial entrepreneur, a thinking partner, and a musician who rarely misses a beat. Jill brings humor, heart, and strategic clarity to every conversation. She thrives on collaboration, sparks creativity, and makes the hard parts of entrepreneurship feel a little lighter.
LinkedIn: https://www.linkedin.com/in/jillll
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.