Winning Season

A ZeroGap.co Production
  • 4.6 (36)
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Winning Season is the go-to podcast for mid-career professionals who want strategy, not just motivation. Host Jacqueline V. Twillie delivers actionable tools, negotiation frameworks, and candid conversations to help you lead with clarity, advocate for yourself, and find the win in every season. From navigating career transitions to thriving in challenging work environments, each episode is packed with insights you can use today. Powered by ZeroGap.co’s Resilient Leaders Program.

  1. 10/13/2025

    Pinpoint What Decision-Makers Actually Value

    This episode of Winning Season features a real lesson from Jacqueline V. Twillie, originally delivered live to a group of mid-career professionals. In it, Jacqueline unpacks the moment she cracked a high-stakes global project stalemate by identifying the single metric and timeline that mattered most to a senior leader. She walks listeners through her signature L.A.T.T.E. Framework—Look, Anticipate, Think, Talk, Evaluate—and shows how to use it to translate your solution into the language of decision makers. You’ll learn how to pinpoint priorities, anticipate objections, and present your ideas in a way that earns approvals faster. Whether you're preparing for a big pitch or navigating shifting priorities, this lesson gives you a repeatable playbook to get a clear yes. This podcast episode is an actual lesson taught by Jacqueline V. Twillie, founder of ZeroGap and creator of the L.A.T.T.E. Framework. You’ll hear her teaching in real time, not a scripted studio segment, so grab a notebook and get ready to apply these strategies immediately. 📌 Note

    29 min
  2. Marketing and Money Rules for Change Makers w/ Alair Castro

    08/05/2025

    Marketing and Money Rules for Change Makers w/ Alair Castro

    Summary In this episode of the Winning Season podcast, host Jacqueline Twillie interviews Alair Castro, a Director of Diversity and Inclusion Strategy and Marketing at Northwestern Mutual and founder of the AC Consultancy. Alair shares her journey and passion for addressing the racial wealth gap, advocating for Black women, and creating inclusive marketing strategies. The conversation explores the importance of building trust within communities, measuring success beyond traditional metrics, and the significance of maintaining authenticity in consultancy work. Alair emphasizes the need for multiple streams of income and the value of unplugged family time for personal and professional growth. Takeaways Alair Castro is a Director of Diversity and Inclusion Strategy and Marketing.Her career is dedicated to advocating for Black women.The racial wealth gap is a significant issue affecting the Black community.Building trust within the Black community is crucial for financial services.Inclusive marketing can drive business goals and community impact.Success indicators should go beyond clicks and impressions.Maintaining authenticity is key in consultancy work.Monetizing your skills can create additional income streams.Unplugged family time is essential for mental well-being.Effective communication of boundaries is vital in leadership.Chapters 00:00 Introduction to Alair Castro 01:40 Passion for Racial Wealth Gap 03:48 Understanding the Racial Wealth Gap 05:14 Building Buy-In for Inclusion 06:44 The Business Case for Inclusive Marketing 07:42 Cultural Insights in Marketing 09:23 Measuring Success Beyond Clicks 10:40 Overcoming Analysis Paralysis 12:15 Monetizing Your Genius 14:05 The Importance of Unplugged Time 16:00 Turning Conflict into Collaboration 17:56 Marketing and Money Rules for Change Makers 18:24 Fun and Personal Insights with Alair Castro Connect with Alair LinkedIn https://www.linkedin.com/in/alaircastro/ Instagram https://www.instagram.com/acoutoftheoffice/ Online https://www.theacconsultancy.com/

    22 min

  3. 08/01/2025

    Mini Episode - Career and Negotiation with Jacqueline Twillie - Resilient Leaders

    Winning Season Podcast - Mini Episode Show Notes Host: Jacqueline TwillieEpisode Type: Mini Episode - Career and Negotiation InspirationDuration: ~3 minutes Episode Overview A quick-hit episode sharing actionable career and negotiation tips from two of Jacqueline's current projects, designed to give listeners a boost in their professional journey. Main Tip: Highlight Your Unique Value Identify what makes you stand out from other candidatesLead confidently with your unique strengths in your job searchImplementation strategies:When: August 21stWhere: Maven.comCost: Free Core Concept: Going from "Almost" to "Absolutely" A 5-step method for building a negotiation strategy: L - LookA - AnticipateT - ThinkT - TalkE - EvaluateFramework Benefits: Preparation for challenges and questions from the other partyAddresses potential objections that typically arise early in negotiationsBuilds confidence and prevents being thrown off your gameLeads to faster, mutually beneficial agreementsSmall tweaks can create significant impact in career developmentPreparation is crucial for successful negotiationsConfidence comes from being ready to address challengesThe power to shape your career is in your handsThe Table: 30-day pop-up career strategy groupInstant Negotiation Strategy Class: Free class on Maven.com (August 21st)"The power to shape your career and own your negotiation - it only takes a few tweaks." Keep winning! Chapters 00:00 - 00:15 - Welcome & IntroductionHost introduction and episode overview 00:15 - 01:30 - The Table: Career Strategy for Black Women30-day pop-up group supporting those impacted by 2025 job market 01:30 - 02:45 - The LATTE Framework for Negotiation5-step method from the Instant Negotiation Strategy class 02:45 - 03:00 - Wrap-up & Closing Thoughts

    2 min

  4. 07/21/2025

    Building Bridges: Lexie Mendelson's Partnership Strategies

    Summary In this episode of the Winning Season podcast, Lexie Mendelson shares her extensive experience in building partnerships and launching innovative products like Google Pay. She emphasizes the importance of values such as truth and loyalty in partnerships, the need for adaptability in international rollouts, and the significance of aligning diverse stakeholders. Lexie also discusses the challenges of navigating regulatory environments, the importance of modeling realistic workloads, and the value of genuine relationships in professional networks. She offers valuable advice for emerging leaders on building authentic connections and understanding the needs of others. Takeaways Lexie's journey spans art history to tech and finance. Building infrastructure for new market categories is key. Truth and loyalty are essential in partnerships. Understanding success for all parties is crucial. Adapt products for different markets to succeed. Meetings enhance communication and stakeholder alignment. Leaders should model realistic workloads for teams. Genuine care for colleagues fosters strong relationships. Empathy is vital in professional conversations. Emerging leaders should focus on authentic connections. Chapters 00:00 Introduction to Lexi's Journey 02:16 Connecting Career Chapters 04:27 Values-Driven Leadership 07:45 Launching Google Pay Internationally 09:58 Aligning Stakeholders for Success 12:50 Navigating Regulations in Banking 15:10 Normalizing Workloads for Team Performance 19:54 Building Authentic Relationships 22:13 Foundational Skills for Emerging Leaders 24:03 Rapid Fire Fun Questions

    28 min

  5. 07/18/2025

    Navigating High-Stakes Negotiations with Confidence

    Summary In this episode, Jacqueline Twillie discusses the intricacies of navigating difficult conversations and negotiations. She introduces the Latte Framework, which consists of Look, Anticipate, Think, Talk, and Evaluate, providing practical strategies for each stage. The conversation covers how to observe tension, anticipate derailments, address bad behavior, maintain composure in power imbalances, know when to walk away, and reflect on negotiation outcomes. Jacqueline emphasizes the importance of preparation, emotional intelligence, and continuous evaluation in becoming a successful negotiator. Takeaways The real negotiation begins before the first word is even uttered.Successful negotiators expect derailments to happen.Observing the environment and your internal state is crucial.Address behavior, not character, to maintain psychological safety.Using power phrases can help redirect conversations effectively.Maintaining composure in high-stakes situations is essential.Knowing your walk-away points is critical for negotiation success.Reflection after negotiations helps in learning and improvement.Every difficult conversation is an opportunity for growth.Practice one technique at a time to build negotiation skills. Chapters 00:00 Introduction to Difficult Conversations 01:59 Understanding the Latte Framework 06:39 Navigating Tension in Conversations 09:56 Keeping Conversations on Track 10:47 Addressing Bad Behavior 13:46 Maintaining Composure Under Pressure 17:30 Knowing When to Walk Away 21:28 Reflecting on Negotiations

    27 min

  6. 07/08/2025

    Unlocking the Science of Confidence w/ Jacqueline Twillie ZeroGap.co

    Summary In this episode of the Confidence Rewired series, Jacqueline Twillie explores the science of self-trust and the mental skill of confidence. She emphasizes that confidence can be trained through neuroplasticity, which allows the brain to rewire itself based on experiences. Jacqueline introduces the 90-day confidence circuit plan, which includes identity anchors, micro actions, and reflection to build lasting confidence. The episode concludes with a final leadership lab challenge, encouraging listeners to map their next 90 days and commit to intentional actions that reinforce their values. Takeaways Confidence is a mental skill that can be trained.Neuroplasticity allows the brain to rewire itself based on experience.True change happens through intention and repetition.The 90-day confidence circuit plan combines identity, micro actions, and reflection.Choose one identity anchor to guide your actions.Set up weekly challenges to align with your values.Track your progress visibly to reinforce learning.Reflect on your actions with data, not drama.Confidence is built through consistent, intentional decisions.Your brain learns through repetition and visibility. Chapters 00:00 Introduction to Confidence Rewired 01:00 Understanding Neuroplasticity and Confidence 03:56 The 90-Day Confidence Circuit Plan 07:01 Final Leadership Lab Challenge and Conclusion Keywords: confidence, neuroplasticity, self-trust, leadership, mental skills, personal development, emotional regulation, identity anchors, micro actions, habit formation This podcast is for educational purposes only and is not a substitute for medical or mental health treatment.

    9 min

  7. 06/30/2025

    Breath Work: The Key to Confidence Rewired Part 5 w/ Jacqueline Twillie ZeroGap.co

    Summary In this episode of the Confidence Rewired series, host Jacqueline Twillie explores the intersection of breath work and confidence, emphasizing the importance of breath in high-stress situations. She introduces cyclic sighing as a powerful technique for reducing anxiety and enhancing leadership presence. The episode also outlines practical steps for incorporating breath work into daily routines, particularly through a 2 p.m. reset routine, and highlights the significance of building resilience and introspective awareness for effective leadership. Takeaways Confidence can be cultivated through breath work.Cyclic sighing is an effective anxiety-reduction technique.Breath work activates the parasympathetic nervous system.The vagus nerve plays a crucial role in stress regulation.Slowing your breath enhances decision-making under stress.Daily routines can help maintain confidence levels.Pairing breath with affirmations boosts self-trust.Introspective awareness is a superpower in leadership.One minute of breath work can shift your mood.Building resilience is essential for leading through challenges. Chapters 00:00 Introduction to Confidence and Breath Work 01:46 The Science of Breath and Anxiety Reduction 03:34 Implementing the 2 PM Reset Routine 06:02 Building Confidence Through Practice Keywords confidence, breath work, leadership, anxiety reduction, resilience, cyclic sighing, mindfulness, self-trust, neuroplasticity, personal development This podcast is for educational purposes only and is not a substitute for professional medical or mental health treatment.

    7 min

  8. 06/23/2025

    Unlocking Motivation with Dopamine w/ Jacqueline Twillie

    Summary In this episode of the Winning Season Podcast, the Confidence Rewired Series, host Jacqueline Twillie discusses the importance of dopamine in building confidence and motivation. She introduces the concept of the 'confidence comeback loop' and emphasizes the significance of tiny wins in stimulating dopamine release. Jacqueline provides a practical framework called the 'Tiny Win System' to help listeners identify small, achievable goals that can lead to greater emotional resilience and motivation. The episode concludes with encouragement to track progress and celebrate wins, reinforcing the idea that consistent, small achievements can lead to significant growth in confidence. Takeaways You need dopamine, not just any kind.Dopamine is the brain's reward chemical.Tiny intentional wins matter for motivation.Small achievements can stimulate dopamine release.Breaking down goals into smaller steps trains the brain.Create small, doable moments for dopamine hits.Big confidence comes from consistent wins.Celebrate wins out loud to reinforce the dopamine loop.Track your wins to build momentum.Tiny wins are powerful for personal development. Chapters 00:00 Introduction to Confidence Rewired 00:23 Understanding the Dopamine Comeback Loop 01:41 Implementing the Tiny Win System 04:35 Looking Ahead: Breath-Powered Reset

    5 min
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About

Winning Season is the go-to podcast for mid-career professionals who want strategy, not just motivation. Host Jacqueline V. Twillie delivers actionable tools, negotiation frameworks, and candid conversations to help you lead with clarity, advocate for yourself, and find the win in every season. From navigating career transitions to thriving in challenging work environments, each episode is packed with insights you can use today. Powered by ZeroGap.co’s Resilient Leaders Program.

Information

  • Creator
    A ZeroGap.co Production
  • Years Active
    2017 - 2025
  • Episodes
    303
  • Rating
    Clean
  • Copyright
    © A ZeroGap.co Production
  • Show Website
    Winning Season

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