Deals with Heels

Debra Bowers
  • 4.6 (9)
  • Management
  • Updated Weekly

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.

  1. 1d ago

    When Survival Becomes a Superpower: Turning Adversity Into Leadership Strength with Allie Grack

    Description Some of the skills that make people exceptional leaders aren't learned in classrooms, boardrooms, or leadership programs. They're learned much earlier. Through adversity. Adaptation. Reading the room. Solving problems quickly. Navigating uncertainty. Learning how to keep going when no one is coming to rescue you. But the same survival strategies that once protected us can eventually become the patterns that hold us back. In this episode of Deals with Heels, Debra Bowers sits down with entrepreneur and Workhorse Marketing founder Allie Grack for a candid conversation about childhood adversity, resilience, creativity, self-trust, leadership, and learning to work with the mind and experiences you've been given rather than constantly fighting against them. Allie shares how adoption, foster care, becoming a teen mother, and growing up without consistent stability shaped her fierce independence and belief that there is always another step forward. She also explores what she's had to learn as a leader: understanding her own weaknesses, developing emotional intelligence, creating a workplace where people can thrive, and recognizing that success doesn't have to mean sacrificing everything else. Together, Debra and Allie explore a deeper question: How do we know when we're responding to today's reality with wisdom—and when we're still reacting from the survival patterns that got us here? Because growth isn't about erasing where we've been. It's about understanding what our experiences taught us, deciding what still serves us, and learning to trust ourselves enough to write what comes next. Key Topics - Childhood adversity and leadership - How survival strategies become leadership strengths - Hyper-independence and self-trust - Processing experience instead of avoiding it - Compound Confidence and accumulated evidence - Creativity and the “messy mind” - Pattern recognition as a leadership strength - Knowing what you know—and what you don't - Emotional intelligence and communication - Creating psychologically safer workplaces - Modeling the culture you say you value - Redefining success beyond money - Separating your identity from other people's judgments - Choosing what your story means Resources Connect with Allie Grack Workhorse Marketinghttps://teamworkhorse.com/ LinkedIn — Allie Grack Workhorse Marketing is a women-founded, women-run marketing agency working with “good people doing good things.” Connect with Debra Bowers LinkedInhttps://www.linkedin.com/in/debra-bowers/ The Human Sales Playbookhttps://thegrowthvanguard.com/free-ebook 5 Signs Your Growth Is Breakinghttps://5signs.thegrowthvanguard.com/ The Growth Vanguardhttps://thegrowthvanguard.com/ Hexagon Mediahttps://hexagonmedia.net/ Stay Connected with Deals with Heels If this conversation resonated with you, share it with a leader, founder, or colleague who needs to hear it. Deals with Heels is where we explore the human side of leadership, growth, sales, decision-making, and the moments that shape who we become as leaders. Follow the show so you never miss an episode, and if you're enjoying these conversations, please leave a review. Your reviews help more listeners discover the show and support our ability to bring thoughtful, meaningful conversations to a wider audience. 🎙 Follow Deals with Heels on your favorite podcast platform⭐ Leave a review and help us grow📢 Share this episode with someone who could benefit from the conversation Until next time, stand strong in your power—especially when it gets uncomfortable.

    When Survival Becomes a Superpower: Turning Adversity Into Leadership Strength with Allie Grack

  2. Aug 11

    Compound Confidence: Why Trust in Yourself Is Built One Experience at a Time with Debra Bowers

    Description We're often told to "be more confident" as though confidence is something we can simply decide to have. But what if confidence isn't something we create? What if it's something we accumulate? Every success, failure, difficult conversation, disappointment, risk, recovery, and uncertain moment becomes evidence. Over time, that evidence shapes what we believe about our competence, our capacity, and our ability to handle whatever comes next. In this solo episode of Deals with Heels, Debra Bowers introduces the concept of Compound Confidence and explores why confidence isn't certainty or optimism. It's the trust that develops when you've accumulated enough evidence to believe you can navigate uncertainty, recover from setbacks, learn, adapt, and keep moving forward. Debra also shares the deeply personal story of her mother, Juanita, who survived nearly five years after being diagnosed with Stage 3B lung cancer despite initially being given less than a 10% chance of surviving one year. Her experience became a powerful example of how confidence can compound—not only within ourselves, but through the evidence other people accumulate about us. Key Topics - Because the experiences we have matter. - But so does the story we decide those experiences mean. - What Compound Confidence means - Why confidence isn't the same as certainty - How we accumulate evidence about ourselves - Why recovery can build more confidence than success - The relationship between competence, capacity, confidence, and trust - How uncertainty helps us learn to trust ourselves - Why two people can experience the same setback and carry forward completely different evidence - How emotional reactions affect the stories we tell ourselves - Building confidence as we move into higher levels of leadership - How leaders contribute to the confidence of other people - Why other people are constantly accumulating evidence about us - The relationship between confidence and Compound Credibility - How one person's confidence can become evidence for an entire community Resources Connect with Debra Bowers LinkedInhttps://www.linkedin.com/in/debra-bowers/ The Human Sales Playbookhttps://thegrowthvanguard.com/free-ebook 5 Signs Your Growth Is Breakinghttps://5signs.thegrowthvanguard.com/ The Growth Vanguardhttps://thegrowthvanguard.com/ Hexagon Mediahttps://hexagonmedia.net/ Stay Connected with Deals with Heels If this conversation resonated with you, share it with a leader, founder, or colleague who needs to hear it. Deals with Heels is where we explore the human side of leadership, growth, sales, decision-making, and the moments that shape who we become as leaders. Follow the show so you never miss an episode, and if you're enjoying these conversations, please leave a review. Your reviews help more listeners discover the show and support our ability to bring thoughtful, meaningful conversations to a wider audience. 🎙 Follow Deals with Heels on your favorite podcast platform ⭐ Leave a review and help us grow 📢 Share this episode with someone who could benefit from the conversation Until next time, stand strong in your power—especially when it gets uncomfortable.

    Compound Confidence: Why Trust in Yourself Is Built One Experience at a Time with Debra Bowers

  3. Aug 4

    The Biology of Capacity: Leadership, Pressure, and the Limits We Ignore with Hannah Curman

    Description Leadership isn't just about competence. It's about capacity. In a world filled with uncertainty, many leaders assume they need better strategies, more discipline, or stronger leadership skills. But what if the real limitation isn't competence at all? What if it's biology? In this episode of Deals with Heels, Debra Bowers sits down with executive coach and neuroscience-based leadership expert Hanna Curman to explore how our nervous systems influence leadership, decision-making, resilience, communication, and our ability to navigate uncertainty. Drawing from both neuroscience and deeply personal experiences, Debra and Hanna discuss grief, burnout, emotional regulation, work-life integration, corporate pressure, leadership expectations, and why sustainable growth requires building the capacity to hold it. Whether you're leading a company, rebuilding after a difficult season, or simply trying to grow without sacrificing your health, this conversation offers a new perspective on what leadership really demands. Key Topics - The biology of leadership - Capacity versus competence - How uncertainty affects the nervous system - Burnout and sustainable performance - Emotional regulation under pressure - Leadership and life balance - The curse of being capable - Why capable leaders often struggle to ask for help - Building the capacity to hold growth - Creating healthier leadership habits Resources Connect with Hanna Curman Website https://hannacurman.se LinkedIn https://www.linkedin.com/in/hannacurman/ BrainShift Executive coaching, neuroscience-based leadership development, and organizational transformation. Connect with Debra Bowers LinkedIn https://www.linkedin.com/in/debra-bowers/ Free Resource – 5 Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ The Human Sales Playbook https://thegrowthvanguard.com/free-ebook The Growth Vanguard Website https://thegrowthvanguard.com/ Hexagon Media Website https://hexagonmedia.net/ Stay Connected with Deals with Heels If this conversation resonated with you, share it with a leader, founder, or colleague who needs to hear it. Deals with Heels is where we explore the human side of leadership, growth, sales, decision-making, and the moments that shape who we become as leaders. Follow the show so you never miss an episode, and if you're enjoying these conversations, please leave a review. Your reviews help more listeners discover the show and support our ability to bring thoughtful, meaningful conversations to a wider audience. 🎙 Follow Deals with Heels on your favorite podcast platform ⭐ Leave a review and help us grow 📢 Share this episode with someone who could benefit from the conversation Until next time, stand strong in your power—especially when it gets uncomfortable.

    The Biology of Capacity: Leadership, Pressure, and the Limits We Ignore with Hannah Curman

  4. Jul 28

    What Freedom Costs: A Conversation with Iranian Human Rights Leader Zolal Habibi

    Description As the world continues watching events unfold in Iran, it's easy to lose sight of the people whose lives have been shaped by decades of oppression, sacrifice, and hope. In this episode of Deals with Heels, Debra Bowers sits down with Iranian human rights activist and National Council of Resistance of Iran Foreign Affairs Committee member Zolal Habibi for a deeply personal conversation about courage, leadership, and the price of freedom. After losing her father to the Iranian regime at just seven years old, Zolal made a life-changing decision to dedicate her future to the fight for democracy and human rights in Iran. More than two decades later, she continues that work as an international advocate for freedom and women's leadership. Rather than focusing on politics alone, this conversation explores the human side of leadership—what it means to live for a cause greater than yourself, to continue when the outcome isn't guaranteed, and to choose hope in the face of extraordinary adversity. Whether you follow world events closely or simply want to better understand the courage required to stand for what matters, this is a conversation you won't soon forget. Key Topics - Leadership when freedom is at stake - What freedom really costs - The human side of the Iranian resistance - Living for a cause greater than yourself - Women's leadership and courage - Purpose, sacrifice, and resilience - Hope as an act of resistance - Building democratic movements - Leadership without certainty - The responsibility that comes with freedom Resources Learn More About Zolal Habibi and the Iranian Resistance National Council of Resistance of Iran https://www.ncr-iran.org/ Maryam Rajavi https://www.maryam-rajavi.com/ Maryam Rajavi – Ten Point Plan https://www.maryamrajavi4change.com/ Organization of Iranian American Communities https://oiac.org/ Iran Freedom https://iranfreedom.org/ Connect with Zolal Habibi on LinkedIn, and Instagram. LinkedIn https://www.linkedin.com/in/zolalhabibi/ Instagram https://www.instagram.com/ashrafi4ever/ Connect with Debra Bowers LinkedIn https://www.linkedin.com/in/debra-bowers/ The Growth Vanguard https://thegrowthvanguard.com/ Free Resource: 5 Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ Hexagon Media https://hexagonmedia.net/ Stay Connected with Deals with Heels If this conversation resonated with you, share it with someone who believes leadership is about more than titles—it's about courage, conviction, and choosing to move forward even when the outcome isn't guaranteed. Deals with Heels explores the human side of leadership, growth, resilience, and the decisions that shape who we become. Follow the show so you never miss an episode, and if you're enjoying these conversations, please leave a review. Your support helps more listeners discover thoughtful conversations that challenge us to lead with greater courage and humanity. 🎙 Follow Deals with Heels on your favorite podcast platform ⭐ Leave a review and help others discover the show 📢 Share this episode with someone who believes freedom—and leadership—are worth fighting for. Until next time, stand strong in your power—especially when it gets uncomfortable.

    What Freedom Costs: A Conversation with Iranian Human Rights Leader Zolal Habibi

  5. Jul 21

    Why Growth Feels Harder Than It Should with Debra Bowers

    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 ignore. Organizations don't experience growth one department at a time. They experience growth as a complete system. In this special Season 6 opening episode, Debra introduces two original frameworks—the Architecture of Demand and the Enterprise Growth Cycle—to explain why so many organizations continue solving the wrong problems and why sustainable growth requires looking beyond sales alone. If you've ever wondered why your organization is working harder while growth feels more difficult, this episode offers a completely different way to think about demand, leadership, customer experience, trust, and organizational alignment. Key Topics - Why growth feels harder than it should - The Architecture of Demand - The Enterprise Growth Cycle - Why organizations experience growth as systems but manage it in departments - The difference between demand building and lead generation - Why sales often carries the weight of organizational problems - How customer experience creates sustainable demand - Trust as the foundation of growth - Leadership, alignment, and organizational friction - Why growth breaks in the connections between systems Resources Connect with Debra Bowers LinkedIn https://www.linkedin.com/in/debra-bowers/ Free Resource – 5 Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ The Human Sales Playbook https://thegrowthvanguard.com/free-ebook The Growth Vanguard Website https://thegrowthvanguard.com/ Hexagon Media Website https://hexagonmedia.net/ Stay Connected with Deals with Heels If this conversation resonated with you, share it with a leader, founder, or colleague who needs to hear it. Deals with Heels is where we explore the human side of leadership, growth, sales, decision-making, and the moments that shape who we become as leaders. Follow the show so you never miss an episode, and if you're enjoying these conversations, please leave a review. Your reviews help more listeners discover the show and support our ability to bring thoughtful, meaningful conversations to a wider audience. 🎙 Follow Deals with Heels on your favorite podcast platform ⭐ Leave a review and help us grow 📢 Share this episode with someone who could benefit from the conversation Until next time, stand strong in your power—especially when it gets uncomfortable.

    Why Growth Feels Harder Than It Should with Debra Bowers

  6. Jul 14

    The Cost of Being the One Everyone Depends On with Carol Enneking

    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 boundaries, difficult personal decisions, and why sustainable leadership requires more than working harder. Drawing from both of their personal journeys—including divorce, caregiving, rebuilding careers, and learning to redefine success—they explore how our personal patterns often become our leadership patterns. Whether you're leading a company, managing a team, or simply trying to build a life that aligns with your values, this conversation is a reminder that leadership isn't just about carrying responsibility—it's about learning what you're no longer willing to carry alone. Key Topics - The emotional weight leaders carry after difficult decisions - Burnout and the hidden cost of high achievement - Why people-pleasing follows us into leadership - Redefining success before it defines you - Creating sustainable leadership habits - The importance of margin and healthy boundaries - Helping employees connect to organizational purpose - Why strategy must connect emotionally—not just intellectually - How personal growth shapes professional leadership - Growth, responsibility, and self-trust Resources Connect with Carol Enneking Websitehttps://carolenneking.com Book: The Rebalancing Act: Wisdom from Working Women for Success That Matters Available through Amazon, Barnes & Noble, and major booksellers. Leadership resources and speaking information are available on Carol's website. Connect with Debra Bowers LinkedInhttps://www.linkedin.com/in/debra-bowers/ Free Resource – 5 Signs Your Growth Is Breakinghttps://5signs.thegrowthvanguard.com/ The Human Sales Playbookhttps://thegrowthvanguard.com/free-ebook The Growth Vanguardhttps://thegrowthvanguard.com/ Hexagon Mediahttps://hexagonmedia.net/ Stay Connected with Deals with Heels If this conversation resonated with you, share it with a leader, founder, or colleague who needs to hear it. Deals with Heels is where we explore the human side of leadership, growth, sales, decision-making, and the moments that shape who we become as leaders. Follow the show so you never miss an episode, and if you're enjoying these conversations, please leave a review. Your reviews help more listeners discover the show and support our ability to bring thoughtful, meaningful conversations to a wider audience. 🎙 Follow Deals with Heels on your favorite podcast platform ⭐ Leave a review and help us grow 📢 Share this episode with someone who could benefit from the conversation Until next time, stand strong in your power—especially when it gets uncomfortable.

    The Cost of Being the One Everyone Depends On with Carol Enneking

  7. Jul 7

    What Growth Reveals About Leaders, Teams, and the Businesses They Build with Kathie Feng

    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 with global growth strategist and founder Kathie Feng to explore what scaling a business really reveals about leadership, organizational culture, customer behavior, and the people behind the business. Drawing from her experience leading growth initiatives across Fortune 500 companies, startups, and international markets, Kathie shares how relationships, trust, data, and cross-functional collaboration create sustainable growth—and why the strongest organizations recognize that growth is never just a marketing problem. If you're leading a business, managing a team, or trying to scale without breaking what you've already built, this conversation offers practical insights into the human side of growth. Key Topics - Why growth reveals existing organizational problems - Leadership across cultures and generations - Building trust within diverse teams - The relationship between confidence, competence, and accountability - Why marketing often feels the weight of organizational problems - Cross-functional collaboration and breaking down silos - Data-driven decision making versus reactive leadership - Building customer trust across cultures - Scaling without sacrificing customer experience - Why relationships remain the foundation of sustainable growth Resources Connect with Kathie Feng LinkedIn https://www.linkedin.com/in/kathiefeng/ Signal Growth website Fractional CMO Collective | Signal Growth Growth strategy and founder advisory services for small and mid-sized businesses Connect with Debra Bowers LinkedIn https://www.linkedin.com/in/debra-bowers/ Free Resource – The Human Sales Playbook https://thegrowthvanguard.com/free-ebook Free Resource – 5 Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ The Growth Vanguard https://thegrowthvanguard.com/ Hexagon Media https://hexagonmedia.net/ Stay Connected with Deals with Heels If this conversation resonated with you, share it with a leader, founder, or colleague who needs to hear it. Deals with Heels is where we explore the human side of leadership, growth, sales, decision-making, and the moments that shape who we become as leaders. Follow the show so you never miss an episode, and if you're enjoying these conversations, please leave a review. Your reviews help more listeners discover the show and support our ability to bring thoughtful, meaningful conversations to a wider audience. 🎙 Follow Deals with Heels on your favorite podcast platform ⭐ Leave a review and help us grow 📢 Share this episode with someone who could benefit from the conversation Until next time, stand strong in your power—especially when it gets uncomfortable.

    What Growth Reveals About Leaders, Teams, and the Businesses They Build with Kathie Feng

  8. Jun 30

    What Great Leaders See Before Everyone Else Does with Liz Weber

    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 with internationally recognized executive advisor, leadership strategist, and board consultant Liz Weber to explore what experienced leaders notice beneath the surface—and why the hardest leadership conversations are often the ones that matter most. Together they discuss accountability, organizational culture, communication, difficult decisions, leadership clarity, and why so many organizations mistake symptoms for the real problem. Whether you're leading a business, managing a team, or preparing for your next level of leadership, this conversation will challenge how you think about performance, trust, and sustainable growth. Key Topics - What experienced leaders notice before problems become visible - The hidden conversations shaping organizational culture - Leadership accountability versus being "mean" - Why organizations often solve symptoms instead of root causes - The connection between communication and organizational trust - Sales culture is bigger than the sales department - Helping employees understand how their role contributes to growth - Why leaders avoid difficult conversations - Cross-functional collaboration and breaking down departmental silos - How culture, leadership, and strategy work together Resources Connect with Liz Weber Website https://www.wbsllc.com/ LinkedIn https://www.linkedin.com/in/lizwebercmc/ Executive leadership consulting, board advisory, strategic planning, and organizational development. Connect with Debra Bowers LinkedInhttps://www.linkedin.com/in/debra-bowers/ Free Resource – 5 Signs Your Growth Is Breakinghttps://5signs.thegrowthvanguard.com/ Free Resource - The Human Sales Playbookhttps://thegrowthvanguard.com/free-ebook The Growth Vanguardhttps://thegrowthvanguard.com/ Hexagon Mediahttps://hexagonmedia.net/ Stay Connected with Deals with Heels If this conversation resonated with you, share it with a leader, founder, or colleague who needs to hear it. Deals with Heels is where we explore the human side of leadership, growth, sales, decision-making, and the moments that shape who we become as leaders. Follow the show so you never miss an episode, and if you're enjoying these conversations, please leave a review. Your reviews help more listeners discover the show and support our ability to bring thoughtful, meaningful conversations to a wider audience. 🎙 Follow Deals with Heels on your favorite podcast platform ⭐ Leave a review and help us grow 📢 Share this episode with someone who could benefit from the conversation Until next time, stand strong in your power—especially when it gets uncomfortable.

    What Great Leaders See Before Everyone Else Does with Liz Weber
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About

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.

Information

  • Creator
    Debra Bowers
  • Years Active
    2023 - 2026
  • Episodes
    132
  • Rating
    Explicit
  • Copyright
    © Debra Bowers
  • Show Website
    Deals with Heels