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.

Deals with Heels is a business podcast hosted by Debra Bowers, with 136 episodes on record and a Required Pod Score of 80.

Debra Bowers hosts Deals with Heels, a business show with 136 episodes published.

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  Episode #136

  What Broadway Can Teach Us About Trust, Teamwork, and Extraordinary Performance with Teri Pruitt

  Sep 29, 202638 minS6

  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 something goes wrong, and consistently create excellence most of the audience will never see. And organizations aren't really that different. In this episode of Deals with Heels, Debra Bowers sits down with Teri, founder of Open the Aperture, to explore what the theatrical process can teach us about leadership, teamwork, communication, trust, recognition, and creating an extraordinary experience. Teri takes us backstage to explain how Broadway productions move from development through technical rehearsals and previews, where teams continuously rehearse, test, adjust, and learn before opening night. Debra and Teri also explore what corporate teams can learn from theatrical improvisation, including using “yes, and” to break down silos, invite ideas, and help people step outside their own perspective. They discuss what happens when a great team's work doesn't produce the expected outcome, why timing and audience readiness matter, and how strong professional communities create relationships that extend far beyond a single production. Because extraordinary performance is rarely created by the person everyone sees. It is built through trust, alignment, respect, empowered teams, and the work happening backstage long before the customer experiences the result. Key Topics & Main Ideas - What Broadway can teach organizations about teamwork and trust - Why extraordinary performance depends on work the audience never sees - How backstage teams experience recognition without standing in the spotlight - Why respect for someone's competence creates a foundation for trust - How a shared goal helps teams work through conflict - What technical rehearsals and Broadway previews can teach businesses about testing and iteration - Using “yes, and” to move teams beyond silos and defensiveness - How changing perspectives can help teams solve difficult problems - Why outrageous ideas sometimes lead to the best practical solutions - The difference between internal competition and collective success - Why a strong performance can still fail when the audience isn't ready - How teams respond to decisions made far above their level of authority - Why professional relationships and community matter over an entire career - How team empowerment affects the experience customers ultimately receive - Why leaders have to build the backstage before customers experience the performance RESOURCES Connect with Teri Pruitt Website: https://www.teripruitt.world LinkedIn: https://www.linkedin.com/in/teri-pruitt-a2b341101/ Teri also invites listeners interested in her personal work and theater life to connect with her on Facebook and Instagram. Connect with Debra Bowers our Host 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/ Human Sales Playbook: https://thegrowthvanguard.com/free-ebook Hexagon Media: https://hexagonmedia.net/ Stay Connected with Deals with Heels Follow Deals with Heels on your favorite podcast platform so you never miss an episode. Join the conversation by connecting with Debra on LinkedIn and sharing what resonated with you. ⭐ Leave a rating or review to help more people discover Deals with Heels and the conversations that can help them grow. Until next time, stand strong in your power—especially when it gets uncomfortable.

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  Episode #135

  Why Knowing What to Do Isn't Enough to Change with Janylène Turcotte

  Sep 22, 202642 minS6

  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. In this episode of Deals with Heels, Debra Bowers sits down with executive coach and clinical hypnotherapist Janylène Turcotte, founder of Hypnocoach, to explore the gap between knowing and becoming. Janylène explains why we can remain attached to what is familiar even when it is uncomfortable, how subconscious beliefs influence our choices, and why getting clear about the “why beneath the why” can change the decisions we make. She also introduces a provocative question: What benefit might we be receiving from staying exactly where we are? Debra shares her own experience of mistaking functional freeze for procrastination, learning to regulate herself in real time, rebuilding the capacity to make decisions, and recognizing how scarcity once led her to give away the very strategy and creativity she was trying to sell. Their conversation expands into confidence, value, people-pleasing, relationships, identity, deliberate action, and what happens when the people around us have grown comfortable with an older version of who we were. Together, they explore something at the heart of real transformation: insight can show us what needs to change, but becoming someone new requires us to create new experiences, new evidence, and eventually a new version of what feels familiar. Key Topics & Main Ideas - Why knowing what to do doesn't necessarily create change - Why the familiar can feel safer even when it is unhealthy or uncomfortable - Finding the “why beneath the why” before making major decisions - How subconscious thoughts and beliefs influence behavior - Functional freeze, procrastination, and emotional regulation - Accessible ways to become curious about subconscious thoughts - Why the meaning we attach to an experience may matter more than the experience itself - Capacity, confidence, and trusting ourselves to handle uncertainty - Why we sometimes give away our expertise instead of standing in its value - The hidden benefit behind staying stuck or maintaining the status quo - Scarcity, validation, and the urge to prove our value - Why action can help us discover what we actually want - How deliberate action creates new evidence about who we are becoming - Why old patterns can eventually become less familiar than new ones - What happens to relationships when one person changes - People-pleasing, fawning, and the people who benefited from the old version of us - Why human implementation—not strategy—is often the hardest part of growth Resources: Connect with Janylène Website: https://hypnocoach.ca/ LinkedIn: https://www.linkedin.com/in/janylene/ Instagram: https://www.instagram.com/hypnocoach_janylene_aka_jt/ Facebook: https://www.facebook.com/janylene.turcotte.2025 Janylène offers a complimentary 30-minute call through her website and publishes a weekly newsletter with reflections and client stories. Connect with Debra 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/ Human Sales Playbook: https://thegrowthvanguard.com/free-ebook Hexagon Media: https://hexagonmedia.net/ Stay Connected with Deals with Heels Follow Deals with Heels on your favorite podcast platform so you never miss an episode. Join the conversation by connecting with Debra on LinkedIn and sharing what resonated with you. ⭐ Leave a rating or review to help more people discover Deals with Heels and the conversations that can help them grow. Until next time, stand strong in your power—especially when it gets uncomfortable.

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  Episode #134

  When Fear, Logic, and Intuition Disagree: How Do You Know What to Trust - with Stephanie Peirolo

  Sep 15, 202640 minS6

  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 episode of Deals with Heels, Debra Bowers talks with board-certified executive coach and author Stephanie Peirolo about discernment, self-trust, resistance, grief, leadership, and the different ways we learn to make consequential decisions. They explore why many high achievers become exceptionally good at pushing through discomfort, but not necessarily at recognizing when discomfort deserves their attention. Stephanie explains why discernment is a practice we can develop before the difficult decision arrives—and why understanding our own decision-making style matters in leadership, relationships, and even sales. The conversation also explores the stories we mistake for facts, how grief affects our ability to make decisions, why leaders need to accept influence, and how learning to trust ourselves can change the way we navigate uncertainty. Key Topics & Main Ideas - Logic, intuition and somatic wisdom in decision-making - Why we may learn to distrust our own internal signals - How conditioning shapes what we believe we're allowed to trust - Building a discernment practice before the difficult decision arrives - The difference between emotional reactivity and intuition - Why self-trust increases our capacity to navigate uncertainty - The stories and inherited narratives we mistake for facts - How grief affects decision-making - Why grief doesn't follow a prescribed timeline - Knowing when resistance deserves curiosity instead of force - Why high achievers may be especially likely to override resistance - Accepting influence as a leadership skill - Why leaders need information from the people closest to the problem - Understanding your personal decision-making style - How decision-making styles become buying behaviors - Why resistance to organizational change may actually be fear about personal capacity - Why different leadership styles are valid - How to make a decision when you don't have unlimited time - Movement, meditation, creativity and community as tools for discernment - Why fear of making the wrong decision can become paralyzing Resources Stephanie Peirolo Author of The Saint and the Drunk: A Guide to Making the Big Decisions in Your Life Website: https://speirolo.com Substack: Fierce Grace Stephanie is also active on Instagram and TikTok under @SPeirolo. Connect with Debra Bowers LinkedIn: https://www.linkedin.com/in/debra-bowers/ The Growth Vanguard: https://thegrowthvanguard.com/ Human Sales Playbook: https://thegrowthvanguard.com/free-ebook Hexagon Media: https://hexagonmedia.net/ Stay Connected with Deals with Heels Follow Deals with Heels on your favorite podcast platform so you never miss an episode. Join the conversation by connecting with Debra on LinkedIn and sharing what resonated with you. ⭐ Leave a rating or review to help more people discover Deals with Heels and the conversations that can help them grow. Until next time, stand strong in your power—especially when it gets uncomfortable.

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  Episode #133

  Someone needs what you know. Will you risk saying it? with Wiebke Tasch

  Sep 8, 202648 minS6

  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 , Debra Bowers sits down with Wiebke Tasch , founder and CEO of Digital Authors, to explore what happens when we finally begin trusting our own voice—and allow other people to benefit from what we've learned. Wiebke shares how writing her first book began not with confidence or a publishing strategy, but with a personal need to put her experiences into words. That book eventually became a bestseller and helped launch the publishing career she has today. Debra and Wiebke also explore why capable people—particularly women—can struggle to claim their expertise, how years of expectations and people-pleasing can teach us to water ourselves down, and why sharing what we know can change us as much as the people who receive it. Because sometimes the experience you dismiss as “just my life” contains exactly the insight someone else needs. And sometimes confidence doesn't arrive before we speak. It develops because we finally do. Key Topics - Why capable people struggle to stand behind what they know - Trusting your own voice before you feel completely confident - Why our lived experience can feel ordinary to us - The fear of being judged, misunderstood, or disliked - How people-pleasing can cause us to water down our ideas - Women, authority, and permission to claim expertise - Separating other people's reactions from our responsibility - Why sharing our ideas changes us - Writing as a way to process and understand experience - How articulating your ideas reveals connections between them - Why confidence can follow contribution instead of preceding it - Recognizing the value of your own story - Turning lived experience into something that helps others - Why one meaningful impact can matter more than thousands of passive views - Writing a book as a transformative process for the author - Using your story to create frameworks that help other people - Listening when an idea continues calling you forward - Why market research should happen before writing and positioning a book - Matching expertise with existing market demand Resources Connect with Wiebke Tasch Wiebke shares resources for prospective authors through her website, including a free course based on the Hero's Journey and a market-analysis resource for people considering a book. She is also active on LinkedIn and invites listeners to connect with her there. Website https://www.digital-authors.com LinkedIn https://www.linkedin.com/in/wiebke-tasch-%F0%9F%93%9A-43731b164/?locale=en Connect with Debra Bowers LinkedIn https://www.linkedin.com/in/debra-bowers/ The Human Sales Playbook https://thegrowthvanguard.com/free-ebook The Growth Vanguard https://thegrowthvanguard.com/ 5 Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ Hexagon Media https://hexagonmedia.net/ Stay Connected with Deals with Heels Deals with Heels explores the human side of leadership, growth, sales, decision-making, and the moments that shape who we become as leaders. If this conversation made you think of someone who has something valuable to say but hasn't quite trusted themselves enough to say it yet, share this episode with them. Follow Deals with Heels on your favorite podcast platform so you never miss an episode. Join the conversation by connecting with Debra on LinkedIn and sharing what resonated with you. ⭐ Leave a rating or review to help more people discover Deals with Heels and the conversations that can help them grow. Until next time, stand strong in your power—especially when it gets uncomfortable.

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  Episode #132

  When Everyone Resists Your Idea: Leadership, Trust, and the Courage to Listen with Tina Larsson

  Sep 1, 202637 minS6

  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 next. In this episode of Deals with Heels , Debra Bowers sits down with Tina Larsson , co-founder of The Folson Group, to explore leadership, governance, resistance to change, and what HOA and co-op boards can teach us about leading people through difficult decisions. Drawing from Tina's experience advising condominium and co-op boards—and her own experience helping transform her building's board—Debra and Tina discuss why volunteer boards can become reactive, how competing priorities derail long-term planning, why the loudest complainer may still have something important to say, and why outside perspective can sometimes break through problems insiders have been raising for years. They also explore an uncomfortable leadership question: What if people aren't resisting your idea because they're afraid of change? What if they're resisting because your idea isn't actually the best one? Because leading change requires more than conviction. It requires trust, listening, discernment, communication, and enough confidence to reconsider your own thinking when the evidence tells you to. Key Topics - Why people resist necessary change - Fear of change versus fear of our capacity to handle change - Why familiarity can feel easier than intentional change - How HOA and co-op boards make complex decisions - The challenges of volunteer leadership - Why organizations become trapped in reactive problem-solving - Proactive versus reactive leadership - Building trust before asking people to follow - Listening as a leadership skill - How leaders build demand for change - Why credibility and consistency matter - The value of outside perspective - When complainers stop being heard - How emotional history creates listening blind spots - Using data to build support for change - How to tell whether resistance is fear—or your idea is wrong - Separating personal investment from good decision-making - Prioritizing infrastructure over appearances - Creating long-term plans that survive leadership turnover - Starting with the end in mind Resources Connect with Tina Larsson The Folson Group https://thefolsongroup.com/ Living the High Life Tina Larsson's book about helping co-op and condominium boards move from reactive management toward proactive governance. The first chapter and additional free resources are available through The Folson Group website. Connect with Debra Bowers LinkedIn https://www.linkedin.com/in/debra-bowers/ 5 Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ The Human Sales Playbook https://thegrowthvanguard.com/free-ebook 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, board member, 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 .

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