Winning Season

Episode Summary In this episode, Jacqueline Twillie shares a simple yet powerful three-word phrase that can transform your leadership, elevate your negotiation skills, and help you navigate workplace dynamics with greater confidence: "Tell Me More." Jacqueline reveals how this simple language shift led to a breakthrough in a challenging negotiation situation and provides practical guidan...

The Power of Strategic Female Networks The Power of Strategic Female Networks: Building Your Inner Circle Episode Summary In this mini-episode, Jacqueline shares insights about building a strong inner circle of female peers for professional success. Harvard Business Review found women with strong female-dominated inner circles are 2.5x more likely to land executive positions. Key Takeaways Women w...

Episode Summary In this power-packed episode, Jacqueline Twillie tackles the universal workplace challenge of ineffective meetings. Drawing from research showing professionals spend over 20 hours weekly in meetings with half feeling wasted Jacqueline shares her exclusive R4 Framework typically reserved for private coaching clients. This actionable framework has helped tech executives reclaim 10 ho...

In this episode, Jacqueline shares her transformative experience in Paris, where she stepped outside her comfort zone to take a creative writing class. She reflects on the importance of embracing new challenges, her surroundings' sensory richness, and her connections with others. Through her journey, she emphasizes the value of personal growth, storytelling, and the impact of being present in...

In this episode, Jacqueline Twillie discusses the challenges and strategies for confidently navigating leadership transitions. She emphasizes the importance of mindset shifts, emotional intelligence, stakeholder engagement, and continuous learning. Jacqueline shares personal experiences and practical tips to help leaders succeed in their new roles while addressing the familiar feelings of self-dou...

Summary In this episode, Shannah and Jacqueline delve into the complex relationship women have with money, exploring how childhood experiences shape financial mindsets, the pervasive feelings of scarcity, and the importance of negotiating self-worth. They discuss the emotional weight of money, the myths surrounding wealth, and the necessity of creating boundaries in financial giving. The conversat...

Summary In this episode, Jacqueline Twillie discusses the concept of managing up, emphasizing the importance of effective communication, proactive problem-solving, and self-advocacy in leadership. Through the story of a fictional character named Jordan, she illustrates key lessons learned in navigating workplace dynamics and building trust with managers. The episode also addresses handling vague f...

Summary In this episode of Winning Season, host Jacqueline V. Twillie discusses the importance of reclaiming personal value amidst chaos and overwhelming circumstances. She introduces the AHA framework (Attitude, Habits, Actions) as a method for leaders to navigate challenges effectively. Jacqueline emphasizes the need for healthy habits, setting boundaries, and taking intentional actions to maint...

Episode Summary In this episode, Jacqueline Twillie discusses the crucial shift from reactive to responsive leadership using her R4 framework. She addresses how leaders can transform chaos into clarity and move from survival mode to strategic control. The episode provides practical tools for managing overwhelming situations and building resilience in male-dominated industries. Key Points Reacting...

Summary In this episode of Winning Season, Jacqueline discusses the importance of resilience in leadership, especially in male-dominated industries. She shares three proven strategies to build resilience: celebrating small wins, pausing to reset, and connecting tasks to a larger purpose. Jacqueline emphasizes that resilience is not about perfection but about adaptability and intentional action. Sh...

Summary In this episode of Winning Season, host Jacqueline Twillie delves into the complexities of imposter syndrome, particularly as it affects women and marginalized groups in leadership roles. She emphasizes that imposter syndrome is not a personal failing but a reflection of systemic issues such as racism and sexism. Jacqueline shares 12 empowering phrases to help listeners combat self-doubt a...

Summary In this episode of the Winning Season podcast, Jacqueline Twillie discusses the concept of imposter syndrome, particularly how it affects underrepresented leaders in male-dominated industries. She emphasizes the importance of transforming feelings of doubt into impactful leadership and provides practical strategies for overcoming imposter syndrome. The episode introduces the AHA method (At...

Summary In this episode, Jacqueline Twillie discusses the challenges and opportunities of being the only one in the room, particularly in leadership roles. She emphasizes the importance of resilience, authenticity, and building influence while navigating the complexities of representation. Jacqueline shares personal anecdotes and practical strategies for turning feelings of isolation into empowerm...

Summary In this episode, Jacqueline explores the evolving landscape of leadership and workplace trends for 2025. She discusses the integration of AI, the evolution of hybrid work, the importance of employee well-being, and the necessity of diversity and inclusion. Jacqueline emphasizes the need for personalized employee experiences, sustainable practices, and the critical role of trust in leadersh...

Summary In this episode, Jacqueline discusses the importance of resilience in the workplace, drawing from her book 'Dear Resilient Leader.' She introduces the R4 framework (Risk, Resilience, Reward, Reset) as a practical tool for navigating challenges and emphasizes the AHA method (Attitude, Habits, Actions) for fostering resilience in teams. Through real-life scenarios and listener questions, Jac...

Summary In this episode, Jacqueline Twillie recaps the Women in AI Summit held in New York City, sharing her experiences and insights from the event. She discusses the importance of education adapting to AI, the need for diversity and representation in tech, and how AI can empower underserved communities. Jacqueline emphasizes the collaborative nature of AI in creative fields and the rapid evoluti...

Summary In this episode, Jacqueline Twillie discusses how to level up your career while maintaining your peace of mind. She emphasizes the importance of prioritizing skill development over hustle culture, optimizing productivity, and balancing work demands with personal time. Jacqueline shares practical strategies for enhancing productivity and highlights the significance of treating personal time...

Summary In this episode, Jacqueline Twillie discusses the importance of finding gratitude even during tough times, emphasizing that it's possible to hold both gratitude and grief simultaneously. She explores the connection between gratitude and resilience, offering practical strategies for cultivating gratitude in daily life. The conversation also addresses workplace challenges and how to navigate...

Summary In this episode of Winning Season, host Jacqueline Twillie shares her journey of writing her first book, 'Navigating the Career Jungle.' She discusses her challenges, the importance of resilience, and the lessons learned along the way. Jacqueline emphasizes the value of mentorship, networking, and the need to embrace authenticity in professional settings. The episode inspires underrepresen...

Summary In this episode, Jacqueline Twilley discusses the impact of microaggressions in the workplace and offers strategies for resilience and leadership. She defines microaggressions, shares personal experiences, and emphasizes the importance of recognizing and addressing these subtle forms of discrimination. The conversation highlights coping strategies, the role of leaders in fostering inclusiv...

Summary In this keynote speech, Jacqueline discusses the importance of resilience in leadership, introducing the Latte method as a framework for aligning values and actions. She emphasizes the need for leaders to anticipate challenges, cultivate a growth mindset, and maintain open communication with their teams. The AHA framework is presented as a tool for self-reflection on attitude, habits, and...

Summary In this engaging conversation, Dr. Jacqueline Ashley shares her journey in leadership studies, emphasizing the importance of resilience, the distinction between leadership and management, and the need for self-awareness in effective leadership. She discusses practical strategies for building trust in male-dominated fields, the significance of aligning personal values with leadership practi...

Summary This episode of Winning Season focuses on executive presence and how to cultivate it. The host, Jacqueline Twillie, breaks down executive presence as a blend of confidence, communication skills, and the ability to project authority and authenticity. She shares personal stories and provides tips on developing executive presence, such as being aware of body language and practicing emotional...

Summary In this episode, the host, Jacqueline Twillie discusses the concept of leadership stagnation and provides insights and tips on how to break free from it. Leadership stagnation is when leaders stick to outdated management styles, resist change, and maintain the status quo. The host highlights four signs of leadership stagnation: being too comfortable, lack of team growth, resistance to chan...

In this episode of Winning Season , we tackle the tough topic of burnout and its impact on leaders at every level. If you’re feeling overwhelmed and stretched too thin, this episode is for you. We’ll dive into actionable strategies to help you reset, recharge, and realign your focus, so you can get back to leading with renewed energy and clarity. We’ll explore the importance of taking meaningful b...