Episode
Why So Many Talented Women Never Make It to Leadership | Erika Chestnut - 2003
- Podcast
- The Sales Evangelist
- Published
- May 18, 2026
- Duration seconds
- 1893
- Processing state
not_requested- Canonical source
- https://thesalesevangelist.com
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Summary
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 shares an exercise she uses with clients where they compare their current responsibilities to the role above them. In most cases, women are already doing 50% to 75% of the next position without realizing it. Many women feel pressure to constantly prove themselves through performance while still struggling to advocate for their own advancement. Erika explains how this mindset can keep high performers stuck, even when they are already operating at the next level in their careers. Why Leaders Need to Better Understand Communication Styles Communication styles also play a major role in career grow…