Deals with Heels

Debra Bowers
  • 4.5 (8)
  • 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. What Great Leaders See Before Everyone Else Does with Liz Weber

    2d ago

    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.

    42 min
  2. Ethical Leadership in Uncertain Times: What Happens When Values Are Tested with Jennifer Gligoric

    Jun 23

    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 uncertaintyThe difference between automation and expertiseThe hidden risks of over-relying on AIHow leaders can maintain trust during difficult transitionsWhat transparency really looks likeWhy culture is shaped by leadership decisionsHow to navigate change without abandoning your valuesThis conversation is ultimately about leadership, responsibility, and what it means to remain human in an increasingly automated world. Key Topics Leadership under pressureEthical decision-makingAI and business leadershipTrust and transparencyCompany cultureLeadership communicationEconomic uncertaintyTechnology and human expertiseWorkplace trustLeadership accountabilityBusiness ethicsOrganizational changeConnect with Jennifer Gligoric Super Clinic Projecthttps://superclinicproject.com Hyperwave Medicalhttps://hyperwavemedical.com Business coaching, clinic growth strategy, and operational support for healthcare and wellness business owners. Connect with Debra Bowers our host 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.

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

    Jun 16

    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 leadershipThe messy middle of business growthWhy founders become organizational bottlenecksDecision fatigue and leadership overwhelmGrowth versus operational readinessThe connection between sales, operations, and customer experienceWhy organizations struggle with change managementEmpowering employees without creating confusionThe role of systems, documentation, and process clarityWhy retention is often more valuable than acquisitionCommunication breakdowns during growthThe dangers of burnout by exampleLeadership modeling and workplace cultureUnlimited PTO, vacation culture, and employee well-beingWhy businesses aren't families—and why that distinction mattersBuilding sustainable growth through clarity and intentional leadershipResources Connect with Our Guest, Lauren Zaslansky Conner ZAZ Business SolutionsHelping growing organizations navigate the messy middle of growth through operational clarity, strategic planning, revenue operations, and sustainable systems. Website:https://zazbusinesssolutions.com LinkedIn: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/ Free Resource – 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/ 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.

    47 min
  4. When Financial Pressure Stops Being About Money with Sue Schuster

    Jun 9

    When Financial Pressure Stops Being About Money with Sue Schuster

    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. Together they discuss why so many entrepreneurs rely on personal credit, wait too long to seek funding, struggle to price their services confidently, and carry financial pressure alone. Sue shares lessons from her own entrepreneurial journey and explains how founders can begin making funding decisions from strategy rather than survival. Whether you're scaling a business, navigating financial uncertainty, or questioning your next growth move, this conversation offers practical insights into the mindset and financial habits that shape long-term success. Key Topics Fear-driven vs. strategy-driven financial decisionsWhy founders often wait too long to seek fundingThe emotional relationship entrepreneurs have with moneyPersonal credit vs. business creditThe hidden risks of bootstrapping everything yourselfHow financial pressure impacts decision-makingUnderstanding business funding optionsThe dangers of merchant cash advances (MCAs)Why many business owners underprice their servicesStanding confidently in your value and pricingThe role of financial advisors, CFOs, and strategic partnersBreaking financial decisions down into manageable numbersBuilding a business that supports sustainable growthResources Connect with our Guest Sue Schuster Biz-fi.io Business funding and capital strategy resources Website https://biz-fi.io/sue-schuster email sue@biz-fi.io Connect with Debra Bowers Our Amazing Host 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 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.

    39 min
  5. How Great Leaders Build Trust Without Sacrificing Results with Kathy Eastwood

    Jun 2

    How Great Leaders Build Trust Without Sacrificing Results with Kathy Eastwood

    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 of executive leadership experience with organizations including EY, Hewlett Packard, startups, and private equity-backed companies, Kathy shares practical insights on navigating difficult decisions, creating psychological safety, building accountability, and leading through pressure without sacrificing humanity. Whether you're leading a team, growing a business, or trying to create a healthier culture inside your organization, this episode offers a powerful reminder that trust isn't the opposite of performance—it's the foundation of it. Key Topics & Main Ideas Human-centered leadership in high-pressure environmentsWhy leadership is often confused with controlBuilding trust before difficult decisions ariseThe hidden emotional burden leaders carryHow to handle layoffs and organizational change with dignityThe importance of psychological safety at workWhy employees need purpose, belonging, and clarityFear-based leadership vs. trust-based leadershipHow communication failures create organizational disconnectCreating alignment during periods of uncertaintyThe role of accountability without blameWhy expectations must be clearly definedThe connection between leadership and sales psychologyUnderstanding what motivates different peopleSelf-awareness as the foundation of effective leadershipEmotional regulation and leadership under pressureHow curiosity strengthens leadership relationshipsCreating sustainable performance without burnoutResources Kathy Eastwood - Guest Website: https://kathyeastwood.com LinkedIn: https://www.linkedin.com/in/kathyeastwood/ Instagram: @kathyeastwoodleadership Debra Bowers - host - The Growth Vanguard https://thegrowthvanguard.com Free Resources: The Human Sales Playbook https://thegrowthvanguard.com/free-ebook Five Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ Debra's LinkedIn https://www.linkedin.com/in/debra-bowers/ If today's conversation resonated with you, if it challenged how you think about leadership, growth, or the pressures organizations face beneath the surface, then Deals with Heels is where those conversations continue, and I am happy you are here. Every week, I sit down with leaders, founders, experts, and change-makers to explore what actually drives sustainable growth—from trust and leadership to sales, culture, customer experience, and the human realities behind performance. Follow and subscribe so you never miss an episode. And if you found value here today, I'd be grateful if you'd share the show with someone who could benefit from the conversation. It's one of the most meaningful ways to support the show. Until next week, Stand strong in your power- especially when it gets uncomfortable. Debra

    36 min
  6. When Growth Starts Breaking Leaders: Trust, Burnout & the Hidden Cost of Carrying Too Much with DeeAnn Palin

    May 26

    When Growth Starts Breaking Leaders: Trust, Burnout & the Hidden Cost of Carrying Too Much with DeeAnn Palin

    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 leaders often carry silently. After leading major teams inside organizations like Target, Motorola, and the Phoenix Suns, DeeAnn now works with founder-led CEOs navigating rapid growth, leadership breakdowns, burnout, trust issues, and decision fatigue. Together, Debra and DeeAnn unpack why what built a company often won’t sustain it, why middle management is one of the hardest roles in business, and how organizations quietly begin breaking when trust, alignment, and communication fall behind growth. This episode goes far beyond traditional leadership advice. It explores emotional exhaustion, organizational pressure, sales culture, customer experience, founder identity, and why many leaders lose themselves while trying to hold everything together. If you’re a founder, executive, manager, entrepreneur, or someone carrying more than people realize, this conversation will hit home. Key Topics & Main Ideas The emotional cost of leadership and growthWhat breaks down when companies scale too quicklyWhy CEOs silently carry overwhelming pressureTrust, alignment, and communication inside organizationsLeadership loneliness and executive burnoutWhy middle management is often the hardest role in businessSales culture vs. enterprise growth cultureCustomer experience as part of the growth cycleDecision fatigue and organizational misalignmentBuilding loyalty and trust in modern workplacesThe shift away from “clock-in culture”Why high performers leave organizationsCreating healthy company culture and accountabilityFounder identity and leadership evolutionHow leaders reconnect with clarity and intuitionPractical strategies for avoiding burnout and overwhelmResources & Links 🌐 DeeAnn Palin – OnPoint Business Solutionshttps://www.onpointbiz.com 🌐 Learn more about Debra Bowers & The Growth Vanguardhttps://thegrowthvanguard.com 📘 Download Resources from The Growth Vanguard The Human Sales Playbook https://thegrowthvanguard.com/free-ebook Five Signs Your Growth Is Breaking https://5signs.thegrowthvanguard.com/ 🎙️ Follow & Subscribe to Deals with Heels so You Don't Miss Out Future Episodes and ConversationsAvailable on Spotify, Apple Podcasts, YouTube, and all major podcast platforms.

    41 min
  7. Breaking the Silence: Women, Money, and Hidden Vulnerabilities with Anna Felix

    May 19

    Breaking the Silence: Women, Money, and Hidden Vulnerabilities with Anna Felix

    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 due to conditioning and societal normsThe emotional impact of unexpected life changes like death or divorce on financial stabilityHow to start and sustain conversations about money with partners, family, and in business settingsRecognizing red flags in financial situations, including hesitancy and misinformationPractical steps for women to gather and organize their financial documents and informationOvercoming cultural, religious, or personal barriers to financial involvementThe importance of regular financial check-ins and transparency in relationshipsEncouragement to view financial planning as a love letter to loved ones and a gift of securityResources & Links: https://annafelix.com/https://www.thegrowthvanguard.comThe Human Sales Playbook https://thegrowthvanguard.com/free-ebook5 Signs Your Growth is Breaking https://5signs.thegrowthvanguard.com/Anna Felix LinkedIn https://www.linkedin.com/in/annafelix-smartmoney/ or reach out to Anna here 209 613 9445 anna.felix@strongholdpartners.com Our Host Debra Bowers' LinkedIn https://www.linkedin.com/in/debra-bowers/Final notes:This conversation emphasizes that financial awareness and dialogue are vital tools for women to foster security and confidence, and not just for their own benefit, but as a gift to those they love. Starting the conversation can feel daunting, but it’s an investment in a more secure future, and it all begins with just one step—making that list, having that talk, and staying engaged. If you enjoyed this conversation, if it changed how you think about leadership, decision making or how you grow your business, please follow Deals with Heels so you don't miss out of future conversations! Please Like, Share and Subscribe to Help our Show!

    37 min
  8. The Surprising Power of Community Support in Destigmatizing Women's Health Issues - with Lauren Barker

    May 12

    The Surprising Power of Community Support in Destigmatizing Women's Health Issues - with Lauren Barker

    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 destigmatizing bladder leakage, and how genuine stories and social proof accelerate demand for solutions that truly improve lives. Lauren shares the power of humor, education, and real customer experiences in building trust in a private, sensitive space—proving that vulnerability can be your loudest marketing voice. You'll discover the importance of tapping into authentic customer feedback, creating accessible products that fill a market gap, and leveraging social proof to overcome societal conditioning about women’s health. Lauren also emphasizes the unique challenge of communicating complex medical solutions visually and how understanding your audience’s emotional journey leads to more impactful marketing. If you're a business builder working in a sensitive or taboo niche, this episode is your playbook for turning hesitation into action, building community, and transforming perception from shame to empowerment. Perfect for entrepreneurs, health innovators, and marketers ready to challenge societal taboos—this is the episode that will inspire you to lead with honesty, humor, and heart. Lauren Barker is the CEO and co-founder of Uresta, an FDA-cleared bladder support device designed to help women live leak-free. Her journey from finance into Femtech has made her a powerful advocate for women’s health, leveraging community, education, and innovative product solutions to change millions of lives. Get ready to unlock the secrets behind building trust in taboo markets and turning shy customers into outspoken champions. This episode is your guide to making authentic connections that drive demand and create lasting impact. Learn more about Uresta and Lauren's mission at urusta.com and join the conversation through their active social channels. This is more than a product—it's a movement to normalize women's health and turn silence into strength. Main Topics: Transition from finance to Femtech and the importance of authentic storytellingBuilding trust with women on stigmatized health issues using humor, education, and real storiesCreating a supportive community through Facebook groups and social proofSelf-managed, FDA-cleared solutions that fill a critical gap in women’s healthThe role of social proof and influencer marketing in taboo topicsEmphasizing customer feedback and continuous product evolutionAddressing emotional and lifestyle impacts of bladder health issuesDemystifying market barriers with accessible, over-the-counter solutionsResources & Links: The Growth Vanguard https://www.thegrowthvanguard.comUresta Website: https://urusta.comUresta Instagram: https://www.instagram.com/myuresta/Facebook Community - Uresta Insiders: https://www.facebook.com/groups/urestainsiderHuman Sales Playbook (Free Resource): https://thegrowthvanguard.com/free-ebookBook Suggestion: "Building a StoryBrand" by Donald Miller: https://www.amazon.com/Building-StoryBrand-Donald-Miller/dp/0718033329Connect with Lauren Barker: LinkedIn:https://www.linkedin.com/in/lauren-barker/Twitter: https://twitter.com/lauren_barkerJoin us on Deals with Heals as we dive into transformative conversations that challenge the status quo and empower you to lead with authenticity and courage. Subscribe now to never miss an episode and connect with us on social media to join our growing community of change-makers. Your journey to impactful growth starts here! Stand Strong in your Power, Especially When it Gets Uncomfortable Like, Share & Tell Your Friends

    35 min
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4.5
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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
    125
  • Rating
    Explicit
  • Copyright
    © Debra Bowers
  • Show Website
    Deals with Heels