Deals with Heels
Deals with Heels is a leadership and business podcast for entrepreneurs, executives, and sales leaders who want clarity, confidence, and sustainable growth. Hosted by Debra Bowers, the show explores leadership decision-making, sales psychology, communication, and the human side of business through real conversations and practical insight. Each episode helps listeners lead better, sell with integrity, and build a business that works for real life.
Episodes
Description
Growth shouldn't feel this hard.
Yet business owners everywhere are saying the same things:
Sales are taking longer.
Buyers are more hesitant.
Teams are working harder than ever.
Marketing costs more.
Results feel smaller.
After decades in sales, marketing, demand generation, consulting, and more than 125 conversations with leaders and founders on Deals with Heels, Debra Bowers noticed a pattern she couldn't ign...
Description
Leadership is often measured by the decisions we make.
But what if the hardest part isn't making the decision?
What if it's living with it afterward?
In this episode of Deals with Heels, Debra Bowers sits down with leadership advocate, speaker, and author Carol Enneking to explore the emotional side of leadership that few people talk about.
Together they discuss burnout, people-pleasing, redefining success, setting healthy b...
Description
Growth doesn't create problems.
It reveals them.
As organizations grow, hidden challenges often become impossible to ignore. Communication breaks down. Departments become disconnected. Marketing gets blamed for slowing sales. Operations struggles to keep up with demand. Leaders are forced to confront issues that have often existed long before growth exposed them.
In this episode of Deals with Heels, Debra Bowers sits down w...
Description
Most organizations don't struggle because leaders lack intelligence.
They struggle because the conversations happening publicly are often different from the conversations happening privately. By the time culture issues, succession problems, declining performance, or strategic misalignment become visible, the warning signs have usually been there for much longer.
In this episode of Deals with Heels, Debra Bowers sits down w...
Description
Today's conversation explores what happens when leadership, ethics, and uncertainty collide.
It's easy to talk about values when business is thriving. The real test comes when pressure increases, budgets tighten, technology changes, and difficult decisions have to be made.
In this episode, Debra sits down with business strategist Jennifer Gligoric to discuss ethical leadership, AI adoption, transparency, trust, layoffs, an...
Episode Description
Growth is often portrayed as the goal.
More revenue. More customers. More opportunity.
But behind the scenes, growth can create something much heavier: more decisions, more pressure, more complexity, and more responsibility resting on the shoulders of leaders and founders.
In this episode of Deals with Heels, Debra Bowers sits down with fractional COO and revenue operations strategist Lauren Zaslansky Conner to expl...
Episode Description
Most business owners believe financial decisions are based on logic.
Look at the numbers. Work harder. Stay disciplined. Push through.
But beneath many financial decisions lies something far more powerful: fear.
In this episode of Deals with Heels, Debra Bowers sits down with business funding strategist Sue Schuster to explore the emotional relationship founders have with money, risk, growth, and responsibility.
Toge...
Description
Leadership isn't a choice between results and people.
The strongest leaders know how to build trust, accountability, and performance at the same time.
In this conversation, Debra Bowers sits down with leadership strategist Kathy Eastwood, creator of the E3 Leadership Code, to explore why so many organizations struggle with burnout, disengagement, and mistrust—and what leaders can do differently.
Drawing from decades o...
Episode Description:
Leadership pressure rarely arrives all at once. It builds quietly through growth, responsibility, constant decisions, and the weight of people depending on you.
In this deeply honest conversation, Debra Bowers sits down with leadership strategist and business consultant DeeAnn Palin to explore what really happens behind the scenes as organizations scale — and the emotional, operational, and relational costs...
SUMMARY
This episode dives into the often-overlooked emotional and practical aspects of women’s financial health, emphasizing the importance of awareness, communication, and proactive planning. Debra Bowers hosts Anna Felix, a financial strategist, to share insights on how women can step into financial ownership before crises strike.Main topics - key insights:
- The hidden vulnerabilities women face regarding finance, often d...
Summary
Join Debra Bowers, host of Deals with Heals, as she uncovers how Lauren Barker, CEO of Uresta, is transforming one of the most taboo health issues into a movement of trust, honesty, and humor. Discover the surprising strategies that break through shame, turning hesitant customers into loyal advocates without costly procedures or prescriptions.In this episode, Debra explores the critical role of community support in destigmat...
Summary
This episode explores the realities of building a sustainable online business, emphasizing the importance of simplicity, realistic expectations, and emotional resilience. Guest Sue Patz shares her inspiring journey of recovery and her strategies for solopreneurs to generate consistent income while maintaining well-being.
Key Topics
- The importance of simplicity in business systems
- Realistic expectations for revenue ...
SUMMARY
In this episode, Debra Bowers interviews leadership coach LaQuincia about the internal and external challenges high-achieving women face when speaking up, setting boundaries, and advocating for themselves. They explore practical strategies for overcoming fear, handling rejection, and building confidence in leadership and sales contexts.
KEY TOPICS
- Internal barriers to speaking up
- The cost of silence in business
- Strategies fo...
Summary
In this insightful interview, Renee Hastings shares her expertise on the emotional and practical aspects of delegation, trust, and creating space for growth in business. Discover how letting go can lead to increased capacity, better relationships, and a more sustainable business model.
Key Topics
• Emotional challenges of delegation
• Trust issues in leadership
• Creating space for growth and innovation
GUEST RESOURCES
Summary
Explore the human side of sales with Justine Beauregard, a sales coach and entrepreneur, as she shares her journey from robotic, manipulative sales tactics to a more natural, aligned approach. Learn how emotional resilience, curiosity, and authentic connection can transform your sales experience and results.
Key Topics
- Emotional Aspects of Sales: Exploring the emotional challenges and personal growth involved in sales rol...
Summary
Explore how scarcity mindset influences financial decisions and leadership, with insights from Linda Grisely, a financial wellness educator. Learn practical strategies to reframe money stories, boost confidence, and create a healthier relationship with money.
Key Topics
- Scarcity mindset in decision making
- Reframing negative money stories
- Impact of childhood money messages
- Strategies for financial c...
Summary
In this episode, Debra Bowers interviews Lori Rogers, a mindset expert and co-founder of Positive Activity, about building resilience through daily intentional action. They explore practical strategies for cultivating optimism, managing emotions, and taking inspired action to create a fulfilling life.
Key Topics
• Building resilience through daily habits
• The science of optimism and positivity
• Managing negative self-talk and...
Summary
Discover how Emily McSherry, CEO of Advize, shifted from early success to finding her true purpose and empowering others. This episode explores the importance of self-awareness, leadership, and building impact-driven careers beyond traditional achievement.
Key Topics
- The paradox of high achievement and feeling lost despite success
- How early accolades influence mindset in adulthood
- Practical steps for self-discovery and defin...
Summary
In this episode of Deals with Heals, host Debra Bowers engages in a profound conversation with Megan Mueller, President and CEO of the Oklahoma City Homeless Alliance. They discuss the complexities of leadership in addressing homelessness, the importance of curiosity and collaboration, and the transformative power of art in healing. Megan shares her journey from intern to CEO, emphasizing the need for sustainable systems and...
Summary
Discover how younger entrepreneurs like Sarah Ashley are redefining leadership, authenticity, and freedom in business and life. This episode explores the power of personal and brand voice, the role of AI as a thought partner, and living without limits to foster creativity and purpose.
Key Topics
- The significance of discovering and owning your authentic voice in personal and business contexts
- How brand promises shape percept...
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