Deals with Heels

SUMMARY You've hired marketing experts. You've invested in advertising, social media, SEO, or a new website. Maybe you've even changed agencies. But your business still isn't growing the way you expected. What if the problem isn't that your marketing experts aren't good at what they do? What if you've hired them to solve a problem their expertise was never designed to s...

SUMMARY Being indispensable sounds like a compliment. You're the person everyone depends on, the one who knows how everything works, and the one everyone calls when something goes wrong. But what happens when being indispensable becomes the very thing preventing you—or your organization—from growing? And as AI and automation change how work gets done, what happens when sharing your knowledge c...

SUMMARY What if some of your most valuable leadership credentials never appeared on your résumé? We tend to measure leadership experience through job titles, degrees, promotions, and positions of authority. But many of the capabilities that make us effective leaders develop long before we receive formal recognition for them. In this episode of Deals with Heels, Debra Bowers welcomes Dr. Mickey Fit...

SUMMARY What happens when the resilience that helped you survive, succeed, and build an extraordinary career starts getting in your way? Victoria Pelletier became a COO at 24, a president by 35, and a CEO at 41. She's a corporate executive, board director, bestselling author, and speaker whose TEDx talk on healthy resilience has reached nearly two million views. But behind those achievements i...

SUMMARY What can more than 3,000 marriage proposals teach you about love, trust, and creating a moment someone will remember for the rest of their life? Ash Fox never planned to become a marriage proposal expert. She was a fine artist and photographer in New York City when a client asked her to photograph his proposal in Central Park. Then another request came. And another. Before long, Ash realiz...

Summary Being exceptional at what you do and knowing how to build a business around it are two very different things. Sometimes the very thing that makes a business extraordinary is also what makes it difficult to explain, systematize, and scale. In this episode of Deals with Heels, Debra Bowers talks with intuitive abstract artist Tammy Conover about the Soul Painting experience, Tammy’s own heal...

Summary When we experience something extraordinary, we naturally notice the person standing in front of us—the performer, the leader, the person taking the bow. What we rarely see are all the people behind the scenes whose work made that moment possible. For more than 25 years on Broadway, Teri Pruitt has worked in an environment where hundreds of people have to trust one another, adapt when somet...

Summary Have you ever known exactly what you needed to do—and still couldn't make yourself do it? You know the boundary you need to set. The habit you need to change. The role you've outgrown. You may even understand why you keep repeating the same pattern, yet somehow you continue making choices from the person you've learned to be rather than the person you're trying to become. I...

Summary We make decisions with more than logic. Our experiences, fears, conditioning, bodies, expectations—and sometimes something we can only describe as intuition—are all giving us information. But what happens when those signals disagree? When logic says go but something inside you says stop, is that resistance fear you need to move through—or information you need to pay attention to? In this e...

Most people don't struggle because they have nothing to say. They struggle because they're not yet convinced anyone needs to hear it. We wait until we feel more experienced, more qualified, more confident, or more certain. But what if confidence doesn't have to come before contribution? What if confidence grows because we choose to contribute? In this episode of Deals with Heels , Debr...

Description Every leader eventually reaches a moment when they can see what needs to change. The harder part is helping everyone else see it too. Organizations, teams, and communities rarely resist change simply because the idea is bad. Change asks people to give up something familiar, accept uncertainty, learn something new, invest time and energy—and trust that they can handle whatever happens n...

Description When someone betrays our trust, we expect it to change how we see them. What we may not expect is how deeply it can change the way we see ourselves . If I trusted someone and I was wrong, can I trust my own judgment? My intuition? My decisions? And what happens when those questions quietly follow us into our leadership, relationships, work, and willingness to connect with other people?...

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 event...

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 o...

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-...

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 conversa...

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 no...

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, peopl...

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 Dea...

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...

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,...

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 str...

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...

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 d...

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, op...