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Deals with Heels

Deals with Heels

Von: Debra Bowers
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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.Debra Bowers Management & Leadership Ökonomie
  • The Surprising Power of Follow-Up That Builds Trust and Closes Deals with Wanda Allen
    Feb 17 2026

    Summary -

    In this episode, we dive deep into the art of follow-up with sales expert Wanda Allen. Follow-up is often seen as a daunting task, but Wanda reveals how it can be transformed into a powerful tool for building trust and closing deals. Through engaging stories and practical advice, she uncovers the emotional barriers that hold us back, such as the fear of rejection and the misconception of being pushy.

    Wanda shares her journey from struggling in sales to mastering the follow-up process, emphasizing the importance of confidence and professionalism. She explains how effective communication, whether through phone calls or voice messages, can create authentic connections that lead to lasting relationships and referrals.

    Key Topics:

    • The true purpose of follow-up: service, relationship, trust, and demand building
    • Common misconceptions about follow-up and how fear sabotages efforts
    • Emotional barriers: fear of rejection, pushiness, and how to reframe mindset
    • The importance of confidence and professionalism in follow-up communication
    • Effective strategies: phone calls vs emails, using voice messages, and multi-channel approaches
    • The role of systems and CRM tools to stay consistent and avoid burnout
    • Building and maintaining relationships post-sale to encourage repeat business and referrals
    • Practical tips for clear messaging, setting purpose, and asking for specific next steps
    • The importance of persistence: contact frequency and managing prospect response expectations
    • Personal stories: lessons learned from neglecting follow-up and turning failure into success

    Chapters -

    • 00:00 - Why follow-up is the most misunderstood part of sales
    • 00:42 - The real purpose of follow-up: service, trust, and demand building
    • 01:46 - Common misconceptions: follow-up as pressure or pushiness
    • 02:47 - How follow-up develops relationship and trust
    • 03:13 - Building demand and preparation through consistent follow-up
    • 04:43 - Emotional friction in follow-up: fear of rejection and pushiness
    • 05:12 - Overcoming the mindset barriers: reframing follow-up as opportunity
    • 06:27 - Why follow-up feels uncomfortable and how to shift perspective
    • 07:30 - The importance of accepting rejection and valuing referrals
    • 08:42 - Stories we tell ourselves that justify avoiding follow-up
    • 09:43 - The power of persistence even after a "no"
    • 10:52 - How building genuine relationships leads to future opportunities
    • 12:35 - The act of professional follow-up as a mark of integrity
    • 13:00 - Effective follow-up communication: the power of voice calls
    • 14:35 - Using voice messages and the pitfalls of over-automating
    • 16:32 - Multi-channel communication: respecting preferences and human connection
    • 18:21 - Keeping messages concise and impactful
    • 19:30 - Clarity in purpose: what to communicate in each follow-up
    • 21:34 - Building trust by asking for help and creating human touchpoints
    • 23:36 - The statistic: most sales occur after multiple contact attempts
    • 24:04 - The danger of quitting too early and losing pipeline momentum
    • 25:21 - The importance of relaunching relationships with warm contacts
    • 28:25 - How leadership perspectives shape follow-up strategies
    • 29:58 - Common mindset mistakes: neglecting follow-up as a priority
    • 32:09 - Balancing automation with genuine relationship-building
    • 33:12 - The value of relationship management beyond closing
    • 34:36 - Maintaining connections with past clients and referral sources
    • 37:19 - Resources and tools for mastering follow-up, including a free assessment and challenge
    • 37:48 - How to connect with Wanda for ongoing support and coaching
    • 38:29 - Free resource: The Human Sales Playbook to boost confidence and trust

    You can connect with Wanda and book a free follow-up assessment at https://www.followupsalesstrategies.com/

    And From Debra, our host: Selling doesn’t have to feel uncomfortable, scripted, or “salesy.” Download her free resource The Human Sales Playbook here: https://thegrowthvanguard.com/free-ebook

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    39 Min.
  • Why Chasing Visibility Is Dead—Focus on Demand and Trust Instead- with Debra Bowers
    Feb 10 2026

    Summary


    In this conversation, Debra Bowers discusses the critical role of trust in sales and marketing, emphasizing that demand building is essential for creating genuine connections with potential clients. She explores the concept of the trust gap, where visibility does not equate to demand, and outlines practical steps for building trust and demand through consistent messaging, resonating with the audience, and demonstrating care. Bowers also highlights the importance of patience in the sales process, as trust takes time to develop.


    Takeaways

    • Trust is essential for effective sales.
    • Demand building is about preparation, not just promotion.
    • Different buying personalities require different approaches to trust.
    • Visibility does not equal demand; real connections are necessary.
    • Sales is a transfer of trust, not just enthusiasm.
    • Consistency in messaging builds trust over time.
    • Resonating with your audience is crucial for demand building.
    • Proof of care is necessary to demonstrate genuine interest.
    • Stop chasing virality; focus on building familiarity.
    • Trust compounds over time; be patient in the sales process.


    Chapters

    00:00 - Why trust is the true currency in content marketing
    00:32 - Demand as preparation, not just promotion
    01:09 - The farming analogy for demand building
    02:11 - How to nurture relationships with prospects
    03:09 - The importance of patience and timing in demand building
    04:20 - Recognizing different buyer personality types and trust levels
    07:11 - The concept of the trust gap: attention vs. trust
    07:40 - Why visibility doesn’t equal demand
    09:07 - Listening for signs of the trust gap in your content performance
    10:33 - Symptoms of being in the trust gap and how to identify them
    12:01 - Building demand through trust: creating human connection
    13:00 - Transfer of enthusiasm and the role of genuine engagement
    14:50 - The three pillars of trust: consistency, resonance, proof of care
    18:47 - The importance of demonstrating care authentically
    19:19 - Actionable tips: shift from chasing virality to building familiarity
    20:17 - Speaking to the moments before the sale for better demand
    21:16 - Patience as a key factor in trust development

    Resources & Links:

    Find out More about Debra's work with Demand Building on Hexagon Media's website https://www.hexagonmedia.net

    If you’ve ever struggled to talk about what you do, avoided selling altogether, or felt anxious when money enters the conversation, this playbook will help you approach sales in a way that actually feels like you.

    Download the Human Sales Playbook https://www.thegrowthvanguard.com/free-ebookConnect with Debra Bowers:https://www.linkedin.com/in/debra-bowers/

    https://www.instagram.com/debra444bowers/


    If you enjoyed our show, please leave us a review!


    We would love to hear from you! email us at Deals@dealswithheels.com


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    21 Min.
  • How Inner Freedom Is the Key to Unlocking True Leadership Potential-with Regina Huber
    Feb 3 2026

    Summary


    In this conversation, Debra Bowers and Regina Huber explore the intricate relationship between freedom and leadership. They discuss the costs associated with leadership, the illusion of freedom in entrepreneurship, and the importance of self-awareness and emotional intelligence. The dialogue emphasizes the need for vulnerability, the impact of childhood conditioning, and the significance of creating a supportive team environment. Ultimately, they highlight the role of energy and humanity in effective leadership.


    Takeaways


    • Many leaders appear successful but feel constrained inside.
    • Entrepreneurship can lead to new forms of imprisonment.
    • True freedom is an internal state, not just external circumstances.
    • Right and wrong are subjective; perspectives vary.
    • Self-awareness is crucial for effective leadership.
    • Vulnerability can empower leaders and teams.
    • Emotional regulation is key to personal growth.
    • Childhood conditioning affects adult emotional responses.
    • Creating a supportive team environment fosters collaboration.
    • Energy and authenticity are vital in leadership.


    Chapters


    00:00 The Cost of Freedom in Leadership

    02:44 Success Without Freedom: The Entrepreneurial Trap

    05:40 Inner Freedom vs. External Constraints

    08:32 The Illusion of Right and Wrong

    11:16 The Power of Perspective in Leadership

    13:58 Authenticity and Self-Awareness in Leadership

    16:34 Emotional Regulation and Leadership

    19:35 Freedom vs. Avoidance: Understanding Emotions

    22:15 The Impact of Childhood Experiences on Leadership

    25:03 Creating a Trusting Environment in Teams

    28:07 The Role of Energy in Leadership

    30:42 Humanity in Leadership: Embracing Imperfection

    33:31 Conclusion and Resources


    As the CEO of TRANSFORM YOUR PERFORMANCE, Transformational Leadership & Freedom Coach, Speaker and Author Regina Huber drives bold, heart-centered leadership. She helps her clients become THRIVING LEADERS with THRIVING TEAMS by leveling up their leadership of themselves and their teams, while keeping stress levels low and energy high.

    With eclectic experience on 5 continents, she guides her clients to recognize their own genius and potential, and to create the work and overall life that's right for them – while experiencing true freedom & power - in 4 languages.


    Get Regina's CREATE YOUR FREAKIN' AMAZING LIFE Template: https://transformyourperformance.com/freakinamazinglife

    Contact Regina https://transformyourperformance.com/sociallinks


    Learn more about our show on our website ⁠https://www.dealswithheels.com⁠Our Amazing host, Debra Bowers, offers strategy and media through her agency Hexagon Media. Find out more at ⁠https://www.hexagonmedia.net⁠Download the Human Sales PlaybookSelling doesn’t have to feel uncomfortable, scripted, or “salesy.” The Human Sales Playbook is a practical, human-centered guide for professionals, entrepreneurs, and thought leaders who want to communicate their value with confidence and integrity—without pressure or manipulation.Inside the playbook, you’ll learn how to:•Build confidence before sales conversations•Understand different buying personalities•Communicate your value clearly and simply•Create trust and connection that leads to natural yeses•Sell ideas, services, or expertise without feeling pushyDownload the playbook here:⁠ https://www.thegrowthvanguard.com/free-ebook⁠
    Thank you for Listening! Did you enjoy this episode? If so, please leave us a review!

    Please Like, Share and Subscribe! Your Support is Important to us!


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    38 Min.
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