Winning Season

A room full of women builders at MIT asked ChatGPT to draw them based on everything it knew. It drew the same white man over and over. That moment sparked Erica Rooney's new book, The AI Gap, and this conversation. Erica joins Jacqueline as the first AI expert on Winning Season to break down the four gaps quietly widening between who AI was built on and who gets left behind, and the surprising...

Hermence Matsotsa, a global leadership expert, author, and advocate for community-centered health and transformation joins Jacqueline Twillie in Conversation. In this episode, Hermence shares her multicultural background, her journey through global health, and the profound lessons she's learned about service, vulnerability, and interconnectedness. This conversation reveals how embracing humili...

Join us as we dive into Traci Saulsberry's inspiring journey of self-discovery, leadership, and radical self-love. Traci shares powerful insights from her debut book, revealing how vulnerability, curiosity, and authenticity can transform our lives and careers. In this episode: Traci's experience breaking barriers as one of the youngest Black executives at NBC and leading at Peacock The mea...

Summary In this inspiring interview, Alison Anthony shares her journey from corporate leadership to nonprofit impact, emphasizing the power of preparation, authentic communication, and strategic use of AI in advancing community goals. Discover how to leverage your strengths, build trust, and make impactful asks to create lasting change. Key Topics Preparation and strategic planning in negotiation...

Standing in Your Power: A Conversation with Denise Foss on Self-Leadership and Transformation Discover how Denise’s journey from dance to leadership led her to create a powerful deck focused on helping individuals reclaim their strength and authenticity. In this episode, we explore the nuances of standing in your power, navigating unexpected challenges, and cultivating resilience within yourself a...

Discover how authentic leadership, community, and self-awareness can transform your career and life. Suezette shares practical insights, personal stories, and strategies to help you lead fearlessly beyond titles. In this episode: Suezette’s journey from education reform to tech leadership The true meaning of authenticity in leadership How to uncover and eliminate self-imposed dissonance The impact...

Unlock the powerful leadership principles grounded in Black church traditions and culture. In this episode, L.Michelle Smith shares her insights on how call and response, faith, community, and resilience can transform your leadership approach and drive authentic connections. L.Michelle's inspiration behind writing  Call and Response  and how her church experiences shape her leadership philosop...

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, Anticipa...

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...

Winning Season Podcast - Mini Episode Show Notes Host: Jacqueline Twillie Episode Type: Mini Episode - Career and Negotiation Inspiration Duration: ~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 Identi...

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 chall...

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 imbala...

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 reflectio...

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 rout...

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 h...

Summary In this episode of the Confidence Rewired Series of the Winning Season Podcast, host Jacqueline Twillie explores the concept of the 'messy middle' where life and work pressures collide, leading to a dip in confidence. She discusses the neuroscience behind confidence, emphasizing how chronic stress affects the brain's ability to function effectively. Jacqueline introduces the BL...

Summary In this series of Confidence Rewired, Winning Season Podcast host Jacqueline Twillie delves into the intricacies of confidence, particularly how it can be affected by setbacks and stress. She introduces the concept of the brain's confidence center, the ventral medial prefrontal cortex, and discusses the importance of an identity anchor in maintaining self-assurance. Through personal an...

Winning Season Podcast: Confidence Rewired Series Episode 1: The Neuroscience of Confidence Crashers Host: Jacqueline Twillie In this episode of Winning Season, Jacqueline Twillie explores the science behind confidence crashes and provides practical tools to rewire your response to setbacks. Drawing from her personal experience with imposter syndrome during Zero Gap's first enterprise rollout,...

Episode Summary: In this episode of Winning Season, host Jacqueline welcomes talent executive and inclusion strategist Fadjanie Cadet to discuss revolutionary approaches to performance management, talent development, and creating psychologically safe workplaces. Fadjanie shares insights from her career, including practical frameworks for identifying high-potential talent, building effective feedba...

In This Episode In this revamped episode of The Winning Season Podcast, host Jacqueline Twillie introduces a new "professional girlfriend" format, offering candid advice on navigating VUCA (Volatility, Uncertainty, Complexity, Ambiguity) environments when the chaos feels overwhelming including when we're contributing to it ourselves. Drawing from personal experience, Jacqueline shares actionable s...

In this episode, Jacqueline Twillie breaks down how to navigate Volatile, Uncertain, Complex, and Ambiguous (VUCA) situations using the science-backed AHA framework—Attitude, Habits, and Actions. Key Topics: Understanding VUCA: Volatility, Uncertainty, Complexity, and Ambiguity defined The neuroscience behind uncertainty and decision-making The AHA Method: Attitude, Habits, and Actions explained P...

Episode 2 in the VUCA Series: Understanding Uncertainty & Building Powerful Habits In this powerful episode, Jacqueline Swilley breaks down why uncertainty isn't your weakness—it's potentially your greatest competitive advantage. Discover how consistency trumps certainty in leadership and learn practical habits that create clarity during wildly unpredictable times. 🎙️ Episode Highlights 🔑 Key...

In this first episode of a 4-part series on leading through VUCA (Volatility, Uncertainty, Complexity, and Ambiguity), Jacqueline explores how to transform volatility from your biggest stressor into your competitive advantage using her AHA Framework: Attitude, Habits, and Actions. This episode specifically focuses on the "Attitude" component and provides practical strategies for staying grounded w...

In this episode, Jacqueline V. Twillie introduces what VUCA really means Volatility, Uncertainty, Complexity, and Ambiguity and why it’s showing up in your work life more than ever. Whether you have a formal leadership title or not, this series will give you practical tools to stay grounded, clear, and confident. 🧭 What You’ll Hear in This Episode: Why work feels so chaotic lately (and how VUCA e...

Episode Summary In this mini-pod episode, Jacqueline shares a practical seven-question framework to transform your one-on-one meetings from basic check-ins into meaningful growth opportunities. She explains how to apply her LATTE method (Look, Anticipate, Think, Talk, Evaluate) to create more intentional and empowering conversations with your team members. The Seven Question Framework What are you...