Underdog Leadership Podcast

Jenny Mitchell, Executive Coach for Women in Leadership
  • 5.0 (6)
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A podcast to help #2's become #1's in life and work. Meet your host, Jenny Mitchell, an executive coach, and professional fundraiser. Jenny believes in the power of the underdog - the person who has overcome hardship, stereotyping, typecasting, or debilitating self-doubt to step into the best version of themselves. Underdogs lead with compassion and kindness. These leaders are hard-wired to make the world a better place for everyone. Join Jenny in this podcast to grow your skills, step into who you were always meant to be, and expand into your best version of yourself. Because right now, the world needs more underdog leadership.

  1. 06/26/2025

    UNCUT - What DO You Want?

    In this punchy UNCUT mini-episode, Jenny Mitchell dives into one of the hardest questions many of us avoid: What do you want? Sounds simple, but if you're someone who identifies as a people-pleaser or is constantly tuned in to what others need, this question might leave you blank. Jenny explores how our desire to keep the peace, avoid discomfort, or live up to unrealistic expectations can cloud our own internal compass. Drawing from her own journey as a leader and coach, she offers a loving (but firm) reminder: You can't have it all, at least not all at once, and leadership means choosing what you want and accepting what comes with it. Listener Reflection: What do you really want and what are you willing (and not willing) to do to make it happen? Can you give yourself 10 quiet minutes to name it, write it down, and begin making a plan? Listen to Episode 6.8 here: https://chavender.com/underdog-leadership-podcast/stop-pleasing-others-and-start-reclaiming-your-leadership-power/  — ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/   Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09 Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27 Catch me on email: jenny@chavender.com Check out my website: chavender.com Hop on over to Instagram: @jennychavender Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA   "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw

    4 min

  2. 06/19/2025

    Stop Pleasing Others and Start Reclaiming Your Leadership Power

    Ever feel like you're leading a team, running a household, or juggling it all and still putting everyone else's needs ahead of your own? In this powerful solo episode, Jenny Mitchell dives headfirst into the messy truth about people-pleasing and how it quietly chips away at your leadership potential. With a mix of personal stories, hard-won insights, and "big girl pants" moments, Jenny challenges us to stop managing everyone else's emotions and start standing firm in our own decisions, even if it means someone might think a bad thought about us. Let them. This episode is a must-listen for recovering (or reluctant) people-pleasers, especially women leaders who are ready to get clear, get intentional, and reclaim their voice. If you've been feeling disconnected from what you want, this episode might just be the sign you've been waiting for.   Key Takeaways: People pleasing undermines leadership Self-awareness is the first step to change Resentment is a red flag Effective leadership requires tough choices Empowered leaders lead from intention   Chapters: 00:00 Understanding People Pleasing in Leadership 02:51 The Impact of People Pleasing on Leadership Effectiveness 06:12 Reactive vs. Creative Leadership Tendencies 09:05 Navigating Leadership Decisions and External Perceptions 11:56 Finding Clarity and Streamlining Leadership 14:42 Empowering Leadership Through Self-Awareness If you loved this episode, you'll also enjoy: Episode 6.5 - The ONE Thing All Leaders Must Do: https://chavender.com/underdog-leadership-podcast/the-one-thing-all-leaders-must-do/   Episode 6.4 - Compassionate Accountability for Leaders (ft. Nate Regier): https://chavender.com/underdog-leadership-podcast/compassionate-accountability-for-leaders/    Episode 4.1 - Giving Yourself Permission to Do The Big Thing: https://open.spotify.com/episode/715H358Nm9hgPnhgU5UqPO?si=MIvh8apBTeKLA1zPLeiaoA    — ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/ Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09 Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27 Catch me on email: jenny@chavender.com Check out my website: chavender.com Hop on over to Instagram: @jennychavender Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA   "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw

    21 min

  3. 06/12/2025

    UNCUT - A Leadership Fable about a Cat, an Electrical Cord, a Backpack

    This episode includes a dog, a cat who runs up a tree and gets stuck, an electrical cord, and a leadership lesson. There's a backyard rescue mission, a personal realization and a few more interesting plot twists.   But the real story? It's not about the cat. It's about what happens inside a people-pleaser's mind when something goes wrong, and the urge to fix, help, and over-function takes over. Jenny explores the discomfort of stepping back, resisting the urge to over-help, and learning to trust that other people are capable—even when it's hard to watch.   Listener Reflection: Have you ever helped without being asked? What would it have looked like to step back with compassion instead? Listen to Episode 6.7 here: https://chavender.com/underdog-leadership-podcast/how-successful-leaders-build-strong-communities-around-themselves/ — ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/   Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09 Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27 Catch me on email: jenny@chavender.com Check out my website: chavender.com Hop on over to Instagram: @jennychavender Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA   "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw

    9 min

  4. 06/05/2025

    How Successful Leaders Build Strong Communities Around Themselves (Secrets Revealed)

    Ever wonder how "that woman" does it? You know the one—she  knows everyone, is in the right room at the right time, and has the perfect connection for what you're looking for. This week, Jenny Mitchell pulls back the curtain on the not-so-secret, yet rarely talked about, art of building and maintaining a powerful leadership network. In this episode, Jenny shares the real reasons behind why strong leaders aren't just good at their jobs—they're connected, curated, and community-driven.  Whether you're an extrovert who thrives in a crowd or an introvert who excels one-on-one, community building is a skill you can learn. I'll share practical tips, the benefits of nurturing your network, and how to make time for new connections—even when your schedule feels full. This episode is for ambitious, compassionate women who want to lead with impact and build meaningful relationships along the way. Let's get started.   Key Takeaways: Strong communities are built with intention, not luck. Networking is essential for leadership and growth. Compassionate leadership includes accountability. Maintaining and celebrating relationships strengthens your network. Choose networking methods that align with your style—but do it consistently.   Chapters: 00:00 Building Strong Communities: The Foundation of Leadership 02:54 The Importance of Networking for Leaders 05:59 Masterminds and Collaborative Support 09:12 Digital Networking: Leveraging Online Platforms 12:11 Feeding Your Network: Maintaining Relationships 14:54 Strategic Connections: Future Networking 18:13 Creating Meaningful Communities and Retreats   If you loved this episode, you'll also enjoy: Episode 6.1 - Work Life Integration: Lessons Learned from a Workaholic Woman: https://chavender.com/underdog-leadership-podcast/work-life-integration-lessons-learned-from-a-workaholic-woman/  Episode 6.4 - Compassionate Accountability for Leaders (ft. Nate Regier): https://chavender.com/underdog-leadership-podcast/compassionate-accountability-for-leaders/    Episode 4.7 - How to Leverage the Enneagram for Crucial Conversations: https://open.spotify.com/episode/4ixwdvlzwy8whjr90r0S8Q?si=JN9P7OoiSxKkRg3X6gsYPw    — ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/   Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09 Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27 Catch me on email: jenny@chavender.com Check out my website: chavender.com Hop on over to Instagram: @jennychavender Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA   "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw

    24 min

  5. 05/29/2025

    UNCUT - From New Leader to Confident Boss: Key Messages for First-Time Woman Leaders

    In this week's Uncut episode, Jenny Mitchell takes us back to basics with a quick and practical set of "cue cards" — essential reminders for anyone stepping into leadership for the first time. This episode serves as a companion piece to last week's conversation with Katie McMillan about navigating the first year as a new executive director and the role coaching can play. Leadership is a marathon, not a sprint. Remember to embrace patience and persistence as key leadership traits. If you're stepping into a leadership role, this episode is packed with practical wisdom to help you stay grounded and purposeful in your first months and beyond. Listener Reflection: What is one area in your leadership where you might need to slow down and focus more on planning and pacing, rather than rushing to act?   Listen to Episode 6.6 here: https://chavender.com/underdog-leadership-podcast/navigating-leadership-as-a-new-executive-director/ — ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/   Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09 Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27 Catch me on email: jenny@chavender.com Check out my website: chavender.com Hop on over to Instagram: @jennychavender Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA   "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw

    5 min

  6. 05/22/2025

    Navigating Leadership as a New Executive Director: A Hospital Foundation Case Study with Katie McMillan

    Stepping into a new leadership role can feel like sailing into uncharted, rocky waters—exciting AND terrifying. Your inner critic is loud, your confidence shaken, and the pressure to lead feels overwhelming. In this episode, Jenny Mitchell chats with Katie McMillan, Executive Director of the Milton District Health Foundation, who shares real, raw lessons from her first year as a newly appointed leader. Katie opens up about the moment she knew it was time to move from a supporting role into leadership, the challenges of owning decisions, and how coaching became one of her secret weapon to thrive. Hear how Katie invited her board to invest in her growth, while embracing a leadership style that's about listening, learning, and empowering others—not having all the answers. Key Takeaways: Gain experience by trying new things and embracing challenges. Coaching builds confidence and supports leadership growth. Trust and compassionate listening are essential to effective leadership. Ask the right questions to resolve conflict and foster team ownership. Understand organizational dynamics and balance action with planning for success. Chapters: 00:00 Navigating Leadership Transitions 02:56 The Role of Coaching in Leadership 05:48 Building Trust and Vulnerability 08:52 Listening and Learning as a Leader 12:01 Conflict Resolution and Decision Making 15:01 Understanding Organizational Politics 18:05 Balancing Doing and Planning 21:02 Compassionate Leadership and Accountability   If you loved this episode, you'll also enjoy: Episode 2.1 - Transformational Leadership in Six Steps or Less: https://open.spotify.com/episode/1U4BkH5ru2TsKQ5cB7ggAG?si=ZSiW5ALiTJaUNcDqVWWxxQ   Episode 4.4 - How to Get (More) Comfortable Doing New Things: https://open.spotify.com/episode/0Z0fLQ0ciclFjUzQbnuuZY?si=DPSqYUCySUa0rrHzV12KNg   Episode 5.7 - Career Transitions and How to Navigate Them: https://open.spotify.com/episode/0aerfLW3l6EGYP69HFFTz1?si=eoMMiLe3QSiEOmEqS1JfJg   — ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/   Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09 Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27 Catch me on email: jenny@chavender.com Check out my website: chavender.com Hop on over to Instagram: @jennychavender Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA   "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw   Connect with Katie If you want to learn more or get in touch with Katie, here's how: LinkedIn: linkedin.com/in/katie-mcmillan-3683a84b Email: smalltownkate@gmail.com Feel free to reach out and connect with her!

    30 min

  7. 05/15/2025

    UNCUT - Use this exercise to ruthlessly prioritize your tasks for guaranteed success

    Feeling overwhelmed and pulled in a million directions? Take a load off, and have a listen! This episode is a lifeline to clarity. Jenny shares her go-to brain dump exercise—a powerful, simple practice she uses with clients, teams, even her partner—to cut through chaos and zero in on what really matters. Inspired by a Warren Buffett story about ruthless prioritization, this short session walks you through a process to clear mental clutter, sort your goals, and start taking aligned, strategic action. Jenny guides you to: - Brainstorm freely and get it all out of your head - Identify your "parking lot" ideas (hello, accordion!) - Circle your gut-level priorities - Map those priorities into your actual calendar - And stop moving the goalposts on yourself If you've been craving clarity, purpose, and some good practical wisdom, this episode delivers. Listen now and get focused on your next one thing.   Listener Reflection: What did your brain dump reveal about where you're spending your energy—and does it align with what truly matters to you right now?   Listen to Episode 6.5 here: https://chavender.com/underdog-leadership-podcast/the-one-thing-all-leaders-must-do/ — ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/ Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09 Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27 Catch me on email: jenny@chavender.com Check out my website: chavender.com Hop on over to Instagram: @jennychavender Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA   "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw

    8 min

  8. 05/08/2025

    The ONE Thing All Leaders Must Do

    In this solo episode, Jenny Mitchell takes listeners deep into one of the most critical skills every leader must master: the ability to prioritize with clarity and conviction. Drawing inspiration from Gary Keller's book The One Thing, Jenny explores how simplification is not a sign of weakness, but a strategic power move. She shares personal stories — like the shift from pedaling faster to pedaling smarter — and explains how true leadership begins when we train our attention on high-value tasks, streamline operations, and boldly say no to what no longer serves our purpose. Jenny also breaks down the common growth cycle leaders face: Grow → Plateau → Streamline → Reflect → Grow Again, emphasizing the need to pause and assess before scaling.   Key Takeaways: Focus on what matters most – Not everything is equal; prioritize high-impact tasks. Simplify and streamline – Reduce complexity to boost efficiency and clarity. Invest energy strategically – Choose where to focus your time and attention. Let go to grow – Release what no longer serves you to make space for progress. Stay adaptable and well – Embrace change and support productivity with habits like exercise and visualization.   Chapters: 00:00 Finding Your One Thing 02:50 The Importance of Simplification 06:02 Streamlining for Success 08:53 Prioritizing High-Value Tasks 12:01 The Power of Focus and Attention 14:50 Visualizing Success 18:14 Making Strategic Choices 21:09 Embracing Change and Growth   If you loved this episode, you'll also enjoy: Episode 6.1 - UNCUT: https://chavender.com/underdog-leadership-podcast/uncut-episode-6-1/  Episode 4.8 - Goodbye to Perfection, Hello to Flourishing with Homaira Kabir: https://open.spotify.com/episode/4RNZUB4GwYH1xQNRIRl8Ct?si=5FlTY5w0QoygLxqLGEXVlA  Episode 4.1 - Giving Yourself Permission to Do the Big Thing: https://open.spotify.com/episode/0Z8LsituOzOpjfcx1xDMTs?si=kbwU1zI6TQScmHYnVWWTEA  — ✨Buy the Embracing Ambition Book: https://chavender.com/embracing-ambition-the-book/   Book a discovery call: https://calendly.com/jennychavender/30min?back=1&month=2022-09 Lean into Meaningful Conversations with this complimentary 20 minute video all about the tools and techniques for moving conversations forward: https://youtu.be/zv1N_ZsDEAs Don't miss an episode by joining my Podcast VIP Email List: https://chavender.activehosted.com/f/27 Catch me on email: jenny@chavender.com Check out my website: chavender.com Hop on over to Instagram: @jennychavender Let's connect on LinkedIn: Jenny Mitchell, CFRE, CEC, DMA   "See" me on Youtube: https://www.youtube.com/channel/UC0Q97-c98aPUmfhzlpswfsw

    24 min
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About

A podcast to help #2's become #1's in life and work. Meet your host, Jenny Mitchell, an executive coach, and professional fundraiser. Jenny believes in the power of the underdog - the person who has overcome hardship, stereotyping, typecasting, or debilitating self-doubt to step into the best version of themselves. Underdogs lead with compassion and kindness. These leaders are hard-wired to make the world a better place for everyone. Join Jenny in this podcast to grow your skills, step into who you were always meant to be, and expand into your best version of yourself. Because right now, the world needs more underdog leadership.

Information

  • Creator
    Jenny Mitchell, Executive Coach for Women in Leadership
  • Years Active
    2022 - 2025
  • Episodes
    66
  • Rating
    Clean
  • Copyright
    © 2022
  • Show Website
    Underdog Leadership Podcast