VEST Her Podcast: Don't Leave Money On The Table
- 3 days ago
- 4 min read
Why How You Negotiate Matters More Than You Think
We don’t often think about negotiation as a defining factor in our careers, but it is. Not just in the obvious moments, salary conversations or business deals, but in the everyday decisions, conversations, and opportunities where we either advocate for our value.. or quietly leave something on the table. And over time, those moments add up.
In our latest VEST Her Podcast episode, we explore this idea with Jacqueline Twillie, negotiation expert and founder of Bend AI, in conversation with VEST Member Allison Anthony, CEO of Tulsa Area United Way.
The Hidden Cost of “Being Easy to Work With”
Many women have been socialized to prioritize likability, collaboration, and politeness, qualities that absolutely matter. But when those instincts show up in high-stakes moments without the balance of strategy and preparation, they can come at a cost.
We hesitate. We second-guess. We soften the ask, or avoid it altogether. And while each individual moment may feel small, the long-term impact is anything but.
The Real Work Happens Before the Conversation
One of the most important takeaways from this conversation is that negotiation success isn’t determined in the moment, it’s determined beforehand. How well you understand your value. How clearly you’ve defined the outcome you want. How prepared you are to navigate pushback, silence, or uncertainty.
When those pieces are in place, confidence becomes a byproduct, not something you have to force.
A Shift in How We Think About Negotiation
This episode challenges a few common assumptions:
That negotiation is a confrontation (it’s not, it’s a conversation)
That being prepared means scripting the perfect response (it doesn’t, it means thinking strategically)
That asking for more is risky (often, not asking is the bigger risk)
It also reinforces something many women don’t hear enough: advocating for yourself is not selfish, it’s essential.
About Jacqueline Twillie
Jacqueline V. Twillie is an author, leadership strategist, and founder of BNEDAi. She works with mid-career professionals and organizations on decision quality, negotiation, and high-stakes communication where clarity and judgment matter. She previously founded ZeroGap, a leadership development company that trained over 10,000 professionals. That work shaped her current focus on precision over scale and preparation over performance. Her approach centers on helping leaders slow thinking at the right moments, choose language with intention, and maintain credibility under pressure. BNEDAi reflects this evolution. The work integrates behavioral science, negotiation strategy, and applied AI to support leaders before critical conversations and decisions, not after them. It is designed for professionals who value discernment, structure, and clear thinking in complex environments. Jacqueline is the author of Navigating The Career Jungle, Don’t Leave Money on the Table, and Dear Resilient Leader, and is the creator of the L.A.T.T.E. Framework. Her work is grounded in lived experience, informed by years inside organizations, and focused on practical leadership behavior. She lives in New York and enjoys painting, sipping kombucha, and cooking Southern-inspired dishes. Connect with Jacqueline on LinkedIn
About Alison Anthony
Alison Anthony serves as the President and CEO of the Tulsa Area United Way. She joined TAUW in August 2017, after a long career at Williams, where she was President of the Williams Foundation and the company’s Director of Strategic Outreach. Alison found the perfect calling at United Way – uniting people and resources to improve lives and strengthen communities. Since 2017, she has led TAUW to raise more than $183 million.
A number of non-profit organizations are proud to name Alison as a member of their Board of Directors, including the Tulsa Community Foundation, the Tulsa Regional Chamber of Commerce, and more. To all her roles, Alison brings a passion for inclusion, justice, innovation, and a belief that we can join our talents together to make our community a place where we can all flourish and thrive. Alison earned her master’s and bachelor’s degrees from Oklahoma State University and has completed several leadership programs, including the Harvard Talent Pipeline Development Program. Alison has received many honors throughout her 35-year professional career, including induction into the Tulsa Hall of Fame, the Oklahoma State University Diversity Hall of Fame, and the 2025 recipient of the Leadership Oklahoma Distinguished Graduate award. She has five adult children, five grandchildren, and enjoys traveling, reading, walking with her dog, Jesse, and spending time with her lively and large extended family. Connect with Alison on LinkedIn
Book and Tool Recommendations
Don’t Leave Money on the Table by Jacqueline Twillie
Navigating the Career Jungle by Jacqueline Twillie
Dear Resilient Leader by Jacqueline Twillie
Research & insights from Margaret Neale (Stanford negotiation expert)
Growth mindset framework by Dr. Carol Dweck
Everything is Negotiable by Meg Myers Morgan
Hype Playlist for Women by Alison Anthony and Friends
If you’re looking for a space where women are having real conversations, sharing resources, and supporting one another in navigating careers, money, and life, we invite you to join us at VEST. Learn more and become a member at www.VESTHer.co.