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

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 growth. Erika explains how many leaders unintentionally overlook talented women because they communicate differently from more outspoken employees.
• She also shares how some employees naturally focus on details while leaders are often focused on outcomes. When communication styles do not align, high performers can easily be misunderstood or overlooked.

Treat Your Career Like A Business

• Erika shares advice on how women can become more intentional about career growth by treating their career like a business.
• Set goals, build relationships with mentors and stakeholders, and develop a strategy for long-term advancement instead of waiting to be noticed.

“Success doesn’t come by copying somebody else. Success comes when you know who you are.” — Erika Chestnut

Resources

• Connect with Erika Chestnut on LinkedIn or visit her website to learn more about leadership development, career strategy, and building confidence as you grow into your next role.
• Keep track of your sales activity and boost your results with the Prospect Pro sales tool.
• Step up your sales game with Sales Mastermind. Get accountability, stay motivated, and tackle the blockers keeping you from hitting your goals.
• Visit Blue Mango Studios for help in creating podcast production content.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.