24. The Shift from Peer to Boss with Jessenia Flores-Gayle

On this episode of Bad Boss Confessional, Beth Fahey sits down with marketing executive and general manager Jessenia Flores-Gayle to explore what happens when you suddenly become the boss of people who used to be your peers. Jessenia describes the emotional and practical challenges of stepping into an integrator role inside a close-knit, all-female leadership team. She talks about the pressure to be liked, the discomfort of holding friends accountable, and the self-doubt that surfaces when you feel caught between belonging and leading.
Jessenia shares how her background in dance shaped her natural ability to bring people together and build strong relationships that support collective goals. She and Beth discuss boundaries, decision making, and the importance of vulnerability when the demands of leadership feel heavy. Jessenia stays grounded with a personal mantra that guides her work: forgive, learn, and move forward with intention.

Timestamps
00:00 Introduction to Bad Boss Confessional
01:56 Jessenia’s Career Journey and Integrator Role
06:36 Challenges of Leading Friends
12:12 The Skill of Relationship Building
15:35 Vulnerability and Saying No
20:18 Influences and Decision-Making
24:08 Tattoos and Leadership Lessons

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
Jessenia Flores-Gayle is a marketing executive and General Manager with over 13 years of experience in the haircare industry, recognized for building impactful brands and leading philanthropic campaigns, including a Shorty Award for her work with nonprofit partners. Throughout her career, she has championed culture, language, and representation, creating inclusive experiences that resonate with diverse audiences. She is also the co-creator of Mighty Big Love, a bilingual children’s brand designed to celebrate identity and heritage from an early age.

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.