Underdog Leadership Podcast

Hosted by Jenny Mitchell, Executive Coach for Women in Leadership

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Jun 2025

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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.

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June 26, 2025Episode 653 min

6.8: 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

June 19, 202521 min

6.8: 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

June 12, 2025Episode 639 min

6.7: 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

June 5, 2025Episode 6223 min

6.7: 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

May 29, 2025Episode 614 min

6.6: 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

May 22, 2025Episode 6030 min

6.6: Navigating Leadership as a New Executive Director 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!

May 15, 2025Episode 598 min

6.5: UNCUT - Use This Exercise to Prioritize Your Tasks for 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

May 8, 2025Episode 5823 min

6.5: 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

May 1, 2025Episode 576 min

6.4: UNCUT - Owning Your Emotions, Thoughts and Behaviours

This Uncut episode explores a powerful shift in leadership: letting others own their experiences. Building on last week's chat with Nate and inspired by Mel Robbins' Let Them, we unpack how women leaders overstep in the name of being helpful, offering unsolicited help that undermines others' confidence. Nate's insight around the importance of feeling valuable, capable, and responsible reframes how we support others without taking over. We dig into the importance of owning your own behaviour rather than trying to control others'. Simple language shifts—like saying "I want you to…" instead of "I need you to…"—create trust. This episode is a call to lead with self-responsibility, clarity, and compassion in today's evolving leadership landscape. Listener Reflection: What would it feel like to fully trust others to be valuable, capable, and responsible without stepping in? Listen to Episode 6.4 here: https://chavender.com/underdog-leadership-podcast/compassionate-accountability-for-leaders/ — ✨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

April 24, 2025Episode 5635 min

6.4: Compassionate Accountability for Leaders with Nate Regier

This episode will challenge everything you thought you knew about conflict, communication, and accountability. In this episode, Jenny Mitchell sits down with Dr. Nate Regier, founder of Next Element Consulting and author of Compassionate Accountability. Together, they dive into the often-misunderstood space between being nice and being firm—revealing that true leadership doesn't have to sacrifice kindness for results. Through candid stories and practical insights, Jenny and Nate explore how leaders can create cultures that honor people as capable, emotionally intelligent contributors, while still addressing behaviour that needs to change. Get ready to rethink the way you lead—with heart, honesty, and a healthy dose of compassionate accountability. Key Takeaways: Compassion and accountability go hand in hand Trust and communication are key Empowering others matters Women leaders need support Chapters: 00:00 The Intersection of Compassion and Accountability 03:00 Understanding Compassion in Leadership 05:51 The Value of Capability in Teams 08:59 Navigating Non-Consensual Helping 11:59 Setting Boundaries in Leadership 14:55 Addressing Gossip and Drama in the Workplace 17:51 Accountability vs. Responsibility 20:59 Empowering Women in Leadership 23:57 The Role of Language in Leadership 26:56 Owning Your Emotions 30:08 The Importance of Trust in Conflict If you loved this episode, you'll also enjoy: Compassionate Accountability Podcast with Nate Regier: https://open.spotify.com/show/1CpWMEjHNu2h64wIX94QvD?si=d2cd395713254879 Ep 5.4: Beware of Mothering Your Teams to Incompetence: https://open.spotify.com/episode/76ARiIZhy0Eceb2EELfV4w?si=TmPFN52QQAydNU3RpIV0AA — ✨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 Nate: Facebook:https://www.facebook.com/NextElement/# LinkedIn: https://www.linkedin.com/in/nateregier/ Next Element Consulting: https://www.next-element.com/ Buy Nate's Book here: https://a.co/d/faEuFmL Compassionate Accountability Podcast: https://open.spotify.com/show/1CpWMEjHNu2h64wIX94QvD?si=80844821d26d4bcf