Winning Season

Winning Season

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Winning Season episodes

  • Working Through Uncertainty - Turning Chaos Into Your Competitive Advantage w/ Jacqueline Twillie

    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 Takeaways

    • Leaders with structured self-regulation habits report 37% lower stress levels and 42% improved decision confidence
    • The most successful leaders aren't those who know the most, but those with habitual ways of processing new information
    • Elite performers don't reinvent their process with each new challenge—they build consistent mental models that create a foundation for agility

    ⚡ The Morning Momentum Method (5-Minute Daily Practice)

    1. Emotional Weather Check (1 min): Name your emotional state to improve cognitive function
    2. Contain Uncertainty (1 min): Write down one specific uncertainty you're facing
    3. Control Center (1 min): Identify one thing you can absolutely control today
    4. Purpose Alignment (1 min): Choose one micro-action that aligns with your core values
    5. Vocal Affirmation (1 min): Say your intention out loud to activate different neural pathways

    📚 Research Spotlight

    • American Psychological Association's 2023 Work and Wellbeing Survey: Leaders with consistent self-regulation habits show 37% reduction in stress and 42% improvement in decision confidence
    • McKinsey Study (Harvard Business Review, 2023): Leaders with continuous learning habits adapt 2.5 times faster to disruptive changes

    👉 Real Talk Resilience: Aaron's Story

    Follow how Aaron, a project lead in biotech and one of the only Black men in his division, navigated a massive company merger using his "Top Three Anchors" approach:

    • Gratitude focus: "What am I genuinely grateful for in this moment?"
    • Team-centered thinking: "What does my team actually need from me today?"
    • Progress mindset: "What progress can we make, even if it's small?"

    ❓ Ask Jacqueline

    Q: How do I lead my team when I don't have clear answers from senior leadership?A: Use the Known-Unknown-Next framework to be transparent without transferring anxiety

    Q: What's one habit that helps with executive presence during uncertainty?A: Continuous learning with strategic sharing using the 3-2-1 method

    ⏭️ Next Episode Preview

    Coming up next: How to take clear action when everything seems interconnected and chaotic. Jacqueline will share insights from the LATTE Framework that's helped hundreds of leaders cut through the noise.

    "Emulate excellence and eliminate excuses because this right here, it's your winning season."

    24 min
  • Volatility vs. Vision: Grounding Yourself When Everything Changes Fast

    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 when everything around you is changing rapidly.

    Introduction (0:00-2:45)

    • Introduction to the 4-part VUCA series using the AHA Framework

    • Today's focus: Volatility and transforming it from stressor to advantage


    Main Topic Discussion (3:15-11:30)

    • Definition of volatility beyond market fluctuations (3:15)

    • Research highlights (4:00):

      • American Management Association's 2023 "Leading Through Disruption" study surveying 1,200+ executives found 70% list "rapid change" as their top stressor

      • Harvard Business Review found leaders who regulate their response to volatility outperform peers by up to 45% in decision-making effectiveness

      • Key insight: Emotional regulation was a stronger predictor of success than technical expertise

    • Introduction to the Attitude component of AHA Framework (5:15)

    • Quote from Jacqueline's book "Dear Resilient Leader": "Resilience isn't about ignoring the storm—it's about learning how to dance in the rain."

    Leadership Lab (11:30-15:00)

    • Introduction of the "Reframe Ritual" practice

    • 7-day challenge with daily reflection component:

      1. Set a reminder for the same time each day

      2. Take 3 minutes to write down ONE volatile moment

      3. Complete: "This challenge is showing me..."

    • Example from Jacqueline's own experience (13:00)

    Real Talk Resilience (15:00-18:30)

    • Engineering manager case study using a "Volatility Protocol"

    • Three key questions in the protocol:

      1. What facts do we actually know today?

      2. What remains aligned with our team purpose?

      3. Where can we make progress despite the chaos?

    Ask Jacqueline (18:30-22:00)

    • Q1: Staying optimistic during volatility (18:30)

      • "Anchor Statement" Method:

        1. Write down the volatile situation

        2. List three previous times you've navigated significant change

        3. Identify one skill you used in each situation

        4. Craft your statement: "I've led through [similar challenge]. I have [specific skills]. I am not facing this alone."

      • Based on science-backed brain rewiring, not just positive thinking


  • Winning and Learning (22:00-24:00)

    • Success story from a Minneapolis listener in manufacturing

    • Applied the AHA Framework to successfully pitch a new initiative to C-suite using just 3 clear data points

  • Quote: "The clarity I got from the AHA structure made me feel like I deserved the seat at the table not like I was begging for one."


    Thank You to Our Sponsor

  • A special thanks to ZeroGap.co for sponsoring this episode! Your support enables us to continue providing valuable leadership insights and strategies to our Winning Season community. Visit ZeroGap.co to learn more about their commitment to helping professionals close the gap between where they are and where they want to be.

    Closing Remarks (24:00-25:30)

    • Key takeaways:

      • Volatility is inevitable. But your attitude is your anchor.

      • The Reframe Ritual turns chaos into clarity by creating a consistent response pattern.

      • Real leadership isn't about avoiding the storm—it's learning to move with purpose through it.

    • Next steps and resources:

      • Try the 7-day Leadership Lab Reframe Challenge


  • Power Phrases

  • 💪 "Resilience isn't about ignoring the storm—it's about learning how to dance in the rain." (7:00)

    💪 "I realized I couldn't control the change, but I could control how I showed up in it." (15:00)

    💪 "The clarity I got from the AHA structure made me feel like I deserved the seat at the table—not like I was begging for one." (22:00)

    💪 "Real leadership isn't about avoiding the storm—it's learning to move with purpose through it." (24:00)

    24 min
  • How to Lead Through VUCA Using the AHA Framework w/ Jacqueline Twillie

    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 explains it)

    • A breakdown of the VUCA framework—what each piece means and how it shows up

    • The philosophy behind Jacqueline’s AHA Framework (Attitude, Habits, Actions)

    • A preview of the full 4-part series and what you’ll learn in each episode

    • Why this content is especially relevant for mid-career professionals, team anchors, and unofficial leaders navigating complexity daily


    ⏱️ Timestamps:

    • 00:01 – Welcome + why work feels so unpredictable right now

    • 00:42 – What is VUCA and why it matters now more than ever

    • 01:04 – Breakdown of each part: Volatility, Uncertainty, Complexity, Ambiguity

    • 01:55 – Who this series is for and why it’s personal

    • 02:04 – What is the AHA Framework? (Attitude, Habits, Actions)

    • 02:50 – What you’ll get from each episode in the series

    • 03:50 – Leadership in the middle: honoring informal leaders

    • 04:10 – Final encouragement + what’s coming next


    💡 Key Quote:

  • “When the world around us is uncertain, we need internal certainty.”


    📚 Mentioned in This Episode:

    • Book: Dear Resilient Leader

    • Book: Don’t Leave Money on the Table
    • AHA Framework™ by Jacqueline V. Twillie


  • 📌 Connect with Jacqueline:

    • Website: ZeroGap.co

    • LinkedIn: linkedin.com/in/jacquelinetwillie

    • Podcast: Winning Season (Available on Apple + Spotify)

    • Threads: @jacquelinetwillie


    5 min
  • Stop Canceling Your One-on-Ones! Here's How to Make Them Count

    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

    1. What are you working on and what's going well?
    2. What challenges are you anticipating?
    3. What does success look like this month?
    4. Who do you need support from and how can I help?
    5. What have you learned recently and how can we apply it?
    6. What progress have you made on your goals since our last meeting?
    7. Is there anything else you'd like to discuss?


    Common Problems with One-on-Ones

    • Lack of structure
    • Too much focus on tasks rather than growth
    • Missed opportunities for coaching and development
    • Meetings getting canceled or postponed repeatedly
    • Turning into status updates that duplicate team meetings


    The LATTE Method Applied to One-on-Ones

    L - Look

    Question: What are you working on and what's going well?Purpose: Builds momentum, trust, and psychological safetySuggested phrasing: "Let's kick off with a win. What's something you're proud of this week?"Caution: Don't skip celebrating wins and jump straight to problems

    A - Anticipate

    Question: What challenges are you anticipating?Purpose: Encourages proactive thinking and builds coaching relationshipSuggested phrasing: "Is there anything that might create friction over the next week or so?"Focus: Help team members strengthen their ability to foresee potential issues

    T - Think

    Question: What does success look like this month?Purpose: Centers conversation on their goals, not just yoursSuggested phrasing: "Imagine it's the end of the month and you crushed it - what happened?"Tip: Be comfortable with pauses; don't define success for them

    T - Talk

    Question: Who do you need support from and how can I help?Purpose: Builds leadership voice, emotional intelligence, and a support mindsetSuggested phrasing: "Who else needs to be in the loop? How can I back you up?"Reminder: Empower your team member rather than taking on all responsibility

    E - Evaluate

    Question: What have you learned recently and how can we apply it?Purpose: Promotes reflection, celebrates growth, and improves decision-makingSuggested phrasing: "What's one lesson you've picked up recently? How can we use that?"Tip: Focus on insights, not just outputs

    Additional Resources

    • LinkedIn Lunch and Learn: Additional tools and dashboard for leveling up one-on-ones
    • Visit zerogap.co for details
    • Check out the Resilient Leaders Program by ZeroGap
    9 min
  • The Power of "Tell Me More" - A Simple Phrase That Changes Everything

    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 guidance on how to use this power phrase in various professional scenarios.

    Chapter

    • 00:00 - 01:30 Introduction and Episode Overview
    • 01:31 - 03:45 Host's Personal Check-in and Beverage of the Day
    • 03:46 - 06:20 Backstory: How "Tell Me More" Saved a Negotiation
    • 06:21 - 09:15 Three Key Ways to Use "Tell Me More" in Professional Settings
    • 09:16 - 12:30 Real Talk Resilience Segment: Additional Applications
    • 12:31 - 14:05 Listener Q&A on Using the Phrase Effectively
    • 14:06 - 15:45 Leadership Spotlight: Kelly Walton at Snipes USA
    • 15:46 - 16:20 Closing Thoughts and Call to Action

    Key Takeaways

    • The phrase "Tell Me More" can unlock clarity and help navigate difficult moments in professional settings
    • When used authentically, this power phrase can save relationships, negotiations, time, money, and prevent hurt feelings
    • Simple language shifts can lead to powerful breakthroughs in communication

    How to Use "Tell Me More" in Three Key Scenarios

    1. In Negotiations
    2. When Leading a Team
    3. When Facing Pushback


    Real Talk Resilience Segment

    • Resilience is about the words we choose, not just the actions we take
    • Additional ways to use "Tell Me More"

    Listener Q&A

      Q: "I've tried to use 'tell me more' in meetings, but sometimes people shut down or give vague answers. How do I navigate that without pushing too hard or seeming intrusive?"

      A:

      • Try rephrasing: "I'd love to understand more about your perspective"
      • Give people space and silence to gather their thoughts
      • Show appreciation for input already given
      • Be mindful of your tone to avoid seeming condescending

      • Leadership Spotlight
      • Celebrating Kelly Walton's appointment as Chief Marketing Officer at Snipes USA. Her career spans global giants like Amazon Music, NBA, Under Armour, and LVMH. In her new role, she will oversee all marketing activities and lead Snipes Serves, an initiative focused on community engagement.

        Remember: Small language shifts create powerful career moves. When you use "Tell Me More" intentionally, you'll deepen conversations, strengthen leadership, and open new doors.



    17 min
  • The Power of Strategic Female Networks: Building Your Inner Circle
    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 with strong female networks are 2.5x more likely to reach executive positions
    • Your inner circle provides insights on navigating workplace challenges unique to women
    • Male professionals' advancement isn't affected by the gender composition of their networks
    • Networking doesn't require money - meaningful connections can be built through simple actions
    The AHA Method
    • Attitude: Approach networking with a mindset of mutual growth, not clout
    • Habits: Consistently pour into your circle with small, meaningful actions
    • Actions: Share resources and create spaces for others to rise with you
    Leadership Lab Challenge
    1. Share the wealth: Pass on valuable articles and resources
    2. Go beyond the boardroom: Connect on personal interests and wellness
    3. Take action now: Share a resource, check in with a peer, introduce women who should know each other

    "When we lift each other up, we do not just rise, we thrive."

    Resources Mentioned

    Harvard Business Review • "Dear Resilient Leader" book • Resilient Leaders Program at Zero Gap

    Connect With Jacqueline

    Reach out on LinkedIn or Threads to share how you're expanding your table with intention.

    11 min
  • Meeting Leadership Secrets of Top Performers


    Episode SummaryIn 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 hours weekly, propelled finance leaders to promotions, and transformed team dynamics for startup founders.

    Learn how to transform draining meetings into platforms that showcase your leadership, amplify your team's brilliance, and accelerate your career.

    Key Power Phrases for MeetingsFor Setting Clear Meeting Goals (Risk):"Today we're specifically deciding [X] because it directly impacts our upcoming goals. Let's stay focused on actionable ideas in this meeting."For Handling Resistance (Resilience):"I understand it's different, but let's give this a try and evaluate its effectiveness afterwards. We all deserve more productive meetings.""Our goal is quality over quantity. If we stay focused, we'll free up more time for our actual work.""Let's touch base after this week to discuss how these changes are helping our productivity."For Recognizing Contributions (Rewards):"Thanks to Taylor's insights, we're saving significant production time.""Thanks to Christie's suggestions, our next steps are clarified and we can move forward quickly."The R4 Framework Explained1. Risk (00:06:35)Strategic disruption that signals authority. The first five minutes define the meeting's power dynamic. Take the risk to explicitly state meeting objectives and expected outcomes.2. Resilience (00:08:57)Staying firm when your new meeting approach faces resistance. Acknowledge concerns while gently reinforcing the benefits of structured meetings.3. Rewards (00:10:24)Strategic recognition to transform meeting culture. Intentionally highlight contributions that move the agenda forward and celebrate real outcomes.4. Reset (00:15:06)Create clear follow-up actions for lasting impact. Implement the 24-hour rule: summarize decisions in bullet points, assign clear ownership, and define actionable next steps.

    Resources MentionedHarvard Business Review article: "Stop the Meeting Madness" - Data source on meeting inefficiencyBook: "Dear Resilient Leader" by Jacqueline Twillie - Features detailed explanation of the R4 FrameworkBook: "Navigating the Career Jungle" by Jacqueline Twillie - Mentions the 24-48 hour networking rule adapted for meetingsResearch: Gallup study linking employee recognition to higher engagement and productivityWinning Season ChallengePick one R from the framework and implement it consistently this week. Start with one element, then gradually build to incorporate all four for maximum impact.

    Thank You to Our SponsorThis episode is sponsored by The Resilient Leaders Program by Zero Gap. They're starting a new 12-week group coaching cohort for mid-career professionals seeking clarity and strategic direction. Learn more at zerogap.co.

    Chapters00:01 Introduction to meeting challenges and statistics02:21 Welcome and introduction to the R4 Framework04:31 Jacqueline's personal experience with meeting overload06:35 Risk: Strategic disruption that signals authority08:57 Resilience: Protecting your meeting strategy10:24 Rewards: Strategic recognition to transform culture15:06 Reset: Clear follow-up for lasting impact19:32 Putting it all together: The complete R4 framework21:46 Winning Season challenge and sponsor acknowledgment

    21 min
  • Mini-Pod: Paris in Spring & Creative Writing

    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 the moment.


    Takeaways

    • Jacqueline feels she is in her personal winning season.
    • Traveling pushes her out of her cozy professional spaces.
    • Paris inspired her to explore her creative writing.
    • The writing class was about unlearning previous knowledge.
    • Experiencing Paris through all senses enhances her creativity.
    • Trying new things contributes to professional growth.
    • Jacqueline learns to embrace being a beginner again.
    • Connections with others enrich her experience.
    • Social media helps her reconnect with friends.
    • She plans to continue her creative writing journey online.


    Chapters

    00:00 Embracing the Winning Season

    02:31 Stepping Outside the Comfort Zone

    05:32 The Creative Writing Journey

    08:35 Exploring Paris and Its Inspirations

    11:15 Connections and Personal Growth

    13:55 Continuing the Creative Journey


    Keywords: personal growth, creative writing, Paris, comfort zone, sensory experiences, connections, professional development, storytelling, leadership, self-discovery

    15 min
  • The Art of Navigating Leadership Transitions with Confidence w/ Jacqueline Twillie

    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-doubt and imposter syndrome many face during transitions.

    Takeaways40% of new leaders fail within their first 18 months.Transitions are high risk, high reward situations that deserve serious preparation.Emotional intelligence is crucial for successful leadership transitions.Continuous learning is essential for adapting to new leadership roles.Building coalitions with key stakeholders can significantly impact success.Self-doubt is a common experience for leaders, but it can be reframed as a sign of growth.Effective communication and empathy are vital during transitions.Creating a structured 90-day transition plan can help establish credibility.Engaging in honest dialogue with team members fosters trust and collaboration.Leadership transitions are opportunities to step into your power and lead boldly.


    Chapters

    00:00 Navigating Leadership Transitions

    03:21 Recognizing the Stakes

    12:44 Strategies for Successful Transitions

    18:19 Leadership Lab Challenges

    28:25 Personal Reflections on Leadership

    33:26 Conclusion and Next Steps


    35 min
  • Unraveling Your Relationship with Money

    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 conversation emphasizes the need for women to own their financial power and to challenge societal norms that dictate their relationship with money.


    Takeaways

    • Most women feel there's never enough money, regardless of income.
    • Childhood experiences significantly shape our money mindset.
    • Negotiation is crucial for financial empowerment.
    • Women often struggle with feelings of guilt around money.
    • Scarcity mindset can lead to anxiety and stress.
    • It's important to set boundaries around financial giving.
    • Money is not inherently evil; it's a tool for empowerment.
    • Self-worth should not be tied to financial status.
    • Creating an abundance mindset takes time and effort.
    • Normalizing conversations about money can lead to greater financial literacy.


    Chapters

    00:00 Introduction to Money Mindset

    02:47 Childhood Influences on Money Perception

    05:54 The Impact of Gender on Financial Negotiation

    08:41 Scarcity vs. Abundance Mindset

    11:52 The Emotional Weight of Money

    14:57 Boundaries and Generosity in Financial Relationships

    17:35 The Importance of Negotiation for Women

    20:54 Challenging Money Myths

    23:41 Empowerment Through Financial Knowledge

    27:00 Conclusion and Call to Action




    37 min

About Winning Season

From the publisher's feed

Winning Season is the go-to podcast for mid-career professionals who want strategy, not just a pep talk. Every episode hands you something you can use Monday morning a way to negotiate, to be heard in the room, to reset when the plan falls apart.