Why So Many Talented Women Never Make It to Leadership | Erika Chestnut - 2003

Why So Many Talented Women Never Make It to Leadership | Erika Chestnut - 2003

From The Sales Evangelist by Donald C. Kelly

May 18, 2026 · 32 min · Episode 2003

About this episode

The episode discusses the challenges women face in pursuing leadership roles and how they can be better supported by sales leaders.

Many women in sales struggle with feeling like they’re not fully qualified for leadership roles, even when they’re already doing the work. That self-doubt can make it harder to pursue promotions and career growth. To help break this down, I invited leadership coach and tech executive Erika Chestnut to share the challenges women face when advancing their careers and how sales leaders can better support them. Meet Erika Chestnut Erika Chestnut is a transformational leader with more than 25 years of experience in the tech industry. She is passionate about helping individuals and teams rethink leadership, communication, and workplace culture to create stronger performance and long-term success. Through coaching, leadership development, and strategic guidance, Erika equips professionals with practical tools to build confidence, strengthen relationships, and lead more effectively. The Confidence Gap Holding Women Back Erika shares how often women underestimate their readiness for leadership opportunities. She explains that many women feel like they need to accomplish every requirement before applying for a promotion, while others are comfortable taking the leap much earlier. Erika also…

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