There comes a point in your career when you stop wondering whether you belong in the room—and start realizing that your experience, perspective, and decisions have real value.

In Part 2 of their Behind the Thread conversation, Anna Kenney, Co-Founder and Managing Partner of Thread Advisory Group, welcomes back Dani Bentley of Ulta Beauty for a candid discussion about growing up in retail, finding your confidence as a leader, and the lessons that shape a career.

With experience spanning Bon-Ton, Kohl's, and Ulta Beauty, Dani reflects on how her perspective has changed as she's moved through the merchandising profession—from the early days of feeling like she needed to know every answer to recognizing that real success is about making an impact, building relationships, and helping others grow.

Anna and Dani discuss the moments that build confidence, the challenge of knowing when to stay in a role versus pursuing something new, and why even difficult leadership experiences can teach valuable lessons.

They also talk about the importance of mentorship, the power of trusting and empowering your team, and how their definitions of success have evolved over time.

For Dani, one of the most important leadership lessons has been learning to extend trust from the beginning. As she explains, "You can lose my trust, but you don't have to gain it."

It's a philosophy shaped by leaders who gave her the freedom to make decisions, take ownership, and learn through experience—and one she now brings to the people she leads.

In This Episode

• The moment you realize you're no longer the junior person in the room
• How confidence develops through experience and making decisions
• Why career success becomes less about knowing every answer and more about making an impact
• Knowing when to stay in a role, keep learning, or pursue a new challenge
• Finding value in career experiences that didn't go as planned
• The mentors and relationships that shape your career
• Why trusting and empowering employees creates stronger leaders
• Lessons learned from both great and difficult managers
• How the definition of career success changes over time
• The advice Dani would give her 25-year-old self
• A fun, personality-themed round of "This or That"

Missed Part 1? Catch Anna and Dani's conversation about The Art & Science of Merchandising: Why Instinct Still Matters, available now on Behind the Thread.

Carrie Habel, host of Behind the Thread, is a dynamic leader operating at the intersection of retail, leadership, and wellness. As the owner of multiple ventures—including Thread Advisory Group and the Scottsdale chapter of Collective Women’s Leadership—she brings deep expertise in operational transformation, change management, and business growth. With a career that started on the frontlines of retail and expanded into consulting for major brands like Estée Lauder, Nordstrom, and T-Mobile, Carrie is known for helping organizations bridge the gap between strategy and execution.

DISCLAIMER:
The information shared on this podcast is intended for general informational and educational purposes only and should not be considered medical, legal, or other professional advice. The views and opinions expressed by the host and guests are their own and do not necessarily reflect those of Behind the Thread, Thread Advisory Group, or Collective Women’s Leadership. This podcast is not a substitute for professional guidance, diagnosis, or treatment. Listening does not establish any professional, client, or advisory relationship. Always seek the advice of a qualified professional regarding any questions you may have related to your health, wellness, business, or other specialized matters.