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December 23, 2025 32 mins

In this episode of The Impostor Syndrome Files, we explore what it really means to lead with authenticity in a world that doesn’t always welcome it. My guest this week is Judy Hoberman, a trailblazing executive coach, speaker and author who built her career in male-dominated industries like commercial roofing and financial services. Judy shares stories from her early days climbing ladders in skirts, navigating bias and building unexpected alliances, and how those experiences shaped her belief that relationships are at the heart of everything.

Together, we talk about how the leadership landscape has changed and how it hasn’t. Judy and I explore the loneliness of leadership, the complicated dynamics among women in the workplace and the ongoing tension between showing confidence and being labeled as too much. Judy also offers practical, encouraging advice on how to build a network (even as an introvert), how to start authentic conversations and how to lead from a place of generosity instead of fear.

About My Guest
Judy Hoberman is President of Judy Hoberman and Associates, a company focused on empowering professional women. She is an award-winning international speaker, best-selling author, trainer, and leading authority on women in leadership and sales. She is also a Certified High Performance Coach™ where changing your habits can change your life. Her focus is on Executive Coaching and Trailblazer Masterminds for women. This direction is where her true passion is and gives her the time and attention to work with these incredible women, primarily in financial services and healthcare, which has always been part of her mission and vision.

Judy’s 30 years in business along with her experience in sales and leadership has helped her clients realize the importance of building relationships, standing out and being the authority in their market. She is often described as “transformational.” 

She is a best-selling author, a TEDx speaker and the host of The Trailblazer Chronicles podcast.

Judy’s mission…to help one woman a day by following an important philosophy- "Women Want To Be Treated Equally...Not Identically"®

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Connect with Judy:
LinkedIn: https://www.linkedin.com/in/judyhoberman/
Website: https://sellinginaskirt.com/
Instagram: https://www.instagram.com/sellinginaskirt/
Facebook: https://www.facebook.com/sellinginaskirt

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Connect with Kim and The Impostor Syndrome Files:

Join the free Impostor Syndrome Challenge:
https://www.kimmeninger.com/challenge

Learn more about the Leading Humans discussion group:
https://www.kimmeninger.com/leadinghumansgroup

Join the Slack channel to learn from, connect with and support other professionals: https://forms.gle/Ts4Vg4Nx4HDnTVUC6

Join the Facebook group:
https://www.facebook.com/groups/leadinghumans

Schedule time to speak with Kim Meninger directly about your questions/challenges: https://bookme.name/ExecCareer/strategy-session

Connect on LinkedIn:
https://www.linkedin.com/in/kimmeninger/

Website:
https://kimmeninger.com

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