Cover image of show Deals with Heels

Deals with Heels

Podcast by Debra Bowers

English

Business

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About 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.

All episodes

127 episodes

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

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 Website https://carolenneking.com [https://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 LinkedIn https://www.linkedin.com/in/debra-bowers/ [https://www.linkedin.com/in/debra-bowers/] Free Resource – 5 Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ [https://5signs.thegrowthvanguard.com/] The Human Sales Playbook https://thegrowthvanguard.com/free-ebook [https://thegrowthvanguard.com/free-ebook] The Growth Vanguard https://thegrowthvanguard.com/ [https://thegrowthvanguard.com/] Hexagon Media https://hexagonmedia.net/ [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.

Yesterday - 41 min
episode What Growth Reveals About Leaders, Teams, and the Businesses They Build with Kathie Feng artwork

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/ [https://www.linkedin.com/in/kathiefeng/] Signal Growth website Fractional CMO Collective | Signal Growth [https://signalgrowth.webflow.io/] Growth strategy and founder advisory services for small and mid-sized businesses Connect with Debra Bowers LinkedIn https://www.linkedin.com/in/debra-bowers/ [https://www.linkedin.com/in/debra-bowers/] Free Resource – The Human Sales Playbook https://thegrowthvanguard.com/free-ebook [https://thegrowthvanguard.com/free-ebook] Free Resource – 5 Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ [https://5signs.thegrowthvanguard.com/] The Growth Vanguard https://thegrowthvanguard.com/ [https://thegrowthvanguard.com/] Hexagon Media https://hexagonmedia.net/ [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.

7 Jul 2026 - 39 min
episode What Great Leaders See Before Everyone Else Does with Liz Weber artwork

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/ [https://www.wbsllc.com/] LinkedIn https://www.linkedin.com/in/lizwebercmc/ [https://www.linkedin.com/in/lizwebercmc/] Executive leadership consulting, board advisory, strategic planning, and organizational development. Connect with Debra Bowers LinkedIn https://www.linkedin.com/in/debra-bowers/ [https://www.linkedin.com/in/debra-bowers/] Free Resource – 5 Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ [https://5signs.thegrowthvanguard.com/] Free Resource - The Human Sales Playbook https://thegrowthvanguard.com/free-ebook [https://thegrowthvanguard.com/free-ebook] The Growth Vanguard https://thegrowthvanguard.com/ [https://thegrowthvanguard.com/] Hexagon Media https://hexagonmedia.net/ [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.

30 Jun 2026 - 42 min
episode Ethical Leadership in Uncertain Times: What Happens When Values Are Tested with Jennifer Gligoric artwork

Ethical Leadership in Uncertain Times: What Happens When Values Are Tested with Jennifer Gligoric

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, and the responsibility leaders have to the people they serve. Together they explore: * Why ethics matter most during uncertainty * The difference between automation and expertise * The hidden risks of over-relying on AI * How leaders can maintain trust during difficult transitions * What transparency really looks like * Why culture is shaped by leadership decisions * How to navigate change without abandoning your values This conversation is ultimately about leadership, responsibility, and what it means to remain human in an increasingly automated world. Key Topics * Leadership under pressure * Ethical decision-making * AI and business leadership * Trust and transparency * Company culture * Leadership communication * Economic uncertainty * Technology and human expertise * Workplace trust * Leadership accountability * Business ethics * Organizational change Connect with Jennifer Gligoric Super Clinic Project https://superclinicproject.com [https://superclinicproject.com] Hyperwave Medical https://hyperwavemedical.com [https://hyperwavemedical.com] Business coaching, clinic growth strategy, and operational support for healthcare and wellness business owners. Connect with Debra Bowers our host LinkedIn https://www.linkedin.com/in/debra-bowers/ [https://www.linkedin.com/in/debra-bowers/] Free Resource – 5 Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ [https://5signs.thegrowthvanguard.com/] The Human Sales Playbook https://thegrowthvanguard.com/free-ebook [https://thegrowthvanguard.com/free-ebook] The Growth Vanguard https://thegrowthvanguard.com/ [https://thegrowthvanguard.com/] Hexagon Media https://hexagonmedia.net/ [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.

23 Jun 2026 - 40 min
episode Growth Is Supposed to Feel Good. So Why Does It Feel So Heavy with Lauren Zaslansky Conner artwork

Growth Is Supposed to Feel Good. So Why Does It Feel So Heavy with Lauren Zaslansky Conner

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 explore what really happens during the messy middle of growth. Together they discuss founder bottlenecks, decision fatigue, operational complexity, change management, team empowerment, customer experience, burnout, and why many organizations struggle not because of a lack of opportunity, but because their systems, processes, and leadership capacity haven't evolved alongside their growth. Lauren shares practical insights from years of helping growing organizations create structure, improve communication, and navigate change without sacrificing their people in the process. If you've ever felt overwhelmed by growth, stuck in constant decision-making, or frustrated by organizational friction, this conversation offers a thoughtful look at what sustainable growth actually requires. Key Topics * The hidden weight of growth and leadership * The messy middle of business growth * Why founders become organizational bottlenecks * Decision fatigue and leadership overwhelm * Growth versus operational readiness * The connection between sales, operations, and customer experience * Why organizations struggle with change management * Empowering employees without creating confusion * The role of systems, documentation, and process clarity * Why retention is often more valuable than acquisition * Communication breakdowns during growth * The dangers of burnout by example * Leadership modeling and workplace culture * Unlimited PTO, vacation culture, and employee well-being * Why businesses aren't families—and why that distinction matters * Building sustainable growth through clarity and intentional leadership Resources Connect with Our Guest, Lauren Zaslansky Conner ZAZ Business Solutions Helping growing organizations navigate the messy middle of growth through operational clarity, strategic planning, revenue operations, and sustainable systems. Website: https://zazbusinesssolutions.com [https://zazbusinesssolutions.com/] LinkedIn: https://www.linkedin.com/in/laurenzaslanskyconner [https://www.linkedin.com/in/laurenzaslanskyconner] Interested in exploring what's creating friction in your growth or operations? Lauren welcomes conversations with founders and leaders navigating periods of change, scale, and organizational complexity. Connect with Debra Bowers & Stay Connected with Deals with HeelsLinkedIn: https://www.linkedin.com/in/debra-bowers/ [https://www.linkedin.com/in/debra-bowers/] Free Resource – 5 Signs Your Growth Is Breaking: https://5signs.thegrowthvanguard.com/ [https://5signs.thegrowthvanguard.com/] The Human Sales Playbook: https://thegrowthvanguard.com/free-ebook [https://thegrowthvanguard.com/free-ebook] The Growth Vanguard: https://thegrowthvanguard.com/ [https://thegrowthvanguard.com/] Hexagon Media: https://hexagonmedia.net/ [https://hexagonmedia.net/] 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.

16 Jun 2026 - 46 min
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