The Leadership Podcast
Sibley Bacon is an applied researcher and functional artist, and shares how she blends creativity with structure to build more human-centered teams. Sibely describes what it means to be a "functional artist"—a leader who truly sees the big picture, connects deeply, and inspires through presence, not position. She reflects on lessons from her time at Google, where she worked on improving team dynamics and navigating the gap between theory and business reality. Sibley offers a new take on employee engagement: when people see their work as art, not just tasks, their connection to the purpose...
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Linda Ugelow is the author of “Delight in the Limelight: Overcome Your Fear of Being Seen and Realize Your Dreams.” In this episode, Linda shares how fear often stems from past experiences, and how leaders can reframe internal narratives to demonstrate more confidence. She dives into the power of self-acceptance and how it shapes leadership presence, especially in high-stakes situations. Linda shares how leaders can embrace strategic vulnerability—being open without oversharing—to build trust and credibility. If you’ve ever doubted your voice, this conversation will...
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In this episode, Jim and Jan dive into the critical aspects of leadership and talent development in today’s fast-changing work environment. They discuss how companies often seek “unicorn” candidates with unrealistic expectations—and why focusing on core traits like emotional intelligence, curiosity, and continuous learning is essential. Jim and Jan explore how hybrid work is reshaping the workplace and why relationship-building, trust, and clear expectations are key to fostering strong teams. They also examine how job seekers and employers often set themselves up for failure by chasing...
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Susan Kelsey has authored four historical books and produced the award-winning documentary, “The Negotiator: Billy Caldwell.” In this episode, Susan shares her journey of discovering Billy Caldwell, the "Great Negotiator" of early Chicago. She reflects on the leadership lessons she learned from both Caldwell and Native American leaders, focusing on values like moral courage, tenacity, and the importance of handling success and failure with grace. Through her work with Native American tribes, Susan has gained a deeper understanding of leadership—one rooted in respect,...
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Adam Contos is a former SWAT leader turned CEO, leadership advisor, and author of “Start With a Win: Tools and Lessons to Create Personal and Business Success.” In this episode, Adam begins by defining a "win" in leadership not as just hitting KPIs or completing projects, but as creating momentum through small, daily victories. Adam stresses the importance of fostering a culture of accountability within teams, but without micromanaging. He explains that accountability is about creating an environment where people can succeed, rather than policing behavior. When discussing...
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Pippa Begg, is the co-founder and CEO of Board Intelligence and co-author of “Collective Intelligence: How to Build a Business that’s Smarter than You.” In this episode, Pippa discusses the mindset shifts required for leaders to let go of control and empower others, emphasizing the dangers of hubris and the importance of questioning one's own authority. She also addresses the common struggle with delegation, advising leaders to trust their teams and ask powerful questions that drive innovation and collaboration. Pippa dives deep into the topic of communication, sharing a powerful...
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Giles Watkins—coach, speaker, and author of “Positive Sleep: A Holistic Approach to Resolve Sleep Issues and Transform your Life (Positive Wellbeing).” In this episode, he explores why quality sleep is essential for high performance, decision-making, and long-term success. He dives into sleep’s role in workplace culture—how it affects performance, decision-making, and even global business operations. Giles discusses how different cultures view sleep, how leaders can help their teams without overstepping personal boundaries, and why some companies are incorporating naps into the...
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Jamie Beaton is CEO of Crimson Education, helping students gain admission to top universities. A Harvard, Stanford, Yale, and Princeton graduate, he also founded Crimson Global Academy and authored “ACCEPTED! Secrets to Gaining Admission to the World's Top Universities.” In this episode, Jamie reveals the mentors who shaped his leadership, including legendary investor Julian Robertson, and explains how to accelerate growth as an emerging leader. He discusses the challenges of leading a global company, how cultural differences impact leadership, and what truly defines top talent beyond...
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Kasey D’Amato’s experience goes from launching a dermatology division and founding a global skincare brand to building a multi-seven-figure real estate portfolio. In this episode, Kasey shares her insights on how leaders can avoid burnout, overcome stagnation, and create a life that aligns with their true purpose. She introduces her Holistic Leadership Mastery™ Framework, which breaks leadership into four essential quadrants and explains why so many leaders feel overwhelmed despite their achievements. We discuss why leaders should periodically disconnect, how to recalibrate every...
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Dr. Hope Zoeller is the Founder and President of HOPE (Helping Other People Excel), LLC, a consultancy dedicated to helping organizations cultivate effective and impactful leaders. In this episode, Hope shares why so many leadership programs fail and what companies must do to see real results. Drawing from her experience in corporate leadership, academia, and executive coaching, she unpacks the critical gaps between theory and practice, the hidden power of institutional memory, and why most organizations struggle with succession planning. Hope also challenges leaders to rethink how they...
info_outlineKasey D’Amato’s experience goes from launching a dermatology division and founding a global skincare brand to building a multi-seven-figure real estate portfolio. In this episode, Kasey shares her insights on how leaders can avoid burnout, overcome stagnation, and create a life that aligns with their true purpose.
She introduces her Holistic Leadership Mastery™ Framework, which breaks leadership into four essential quadrants and explains why so many leaders feel overwhelmed despite their achievements. We discuss why leaders should periodically disconnect, how to recalibrate every 90 days, and the importance of surrounding yourself with the right people.
She also shares her personal story of career reinvention, going from a physician assistant to a business leader and leadership coach. Kasey emphasizes that many successful professionals eventually feel stuck, questioning, "What’s the point?" even when they have achieved financial success. She explains how leaders can overcome this by focusing on emotional intelligence, resilience, and self-awareness.
Kasey also talks about how leaders can break free from self-imposed limitations. She also discusses the importance of regularly evaluating time and energy allocation, challenging leaders to reassess 20% of their calendars every 90 days.
Whether you’re thinking about a career pivot or struggling with burnout, this episode provides actionable insights to help you lead a fulfilling life.
Key Takeaways
[02:12] Kasey and her husband rescue and rehabilitate large dogs with difficult pasts. She finds that this requires calm, confident leadership, much like business leadership.
[04:20] Many leaders neglect their personal well-being, relationships, and joy. Kasey’s framework breaks leadership into four quadrants: business acumen, self-leadership, team leadership, and industry leadership. A strong leader balances all four.
[06:58] Kasey agrees that leaders often misallocate time and energy. Most spend too much time on tasks that don’t drive results. She recommends reviewing time allocation every 90 days to ensure alignment with goals.
[08:24] Leaders often focus solely on strengths but may ignore personal weaknesses that could limit them in the long run. Kasey believes that while focusing on strengths is good, leaders should also be aware of what they are neglecting and consciously decide how to balance priorities.
[14:15] She felt she had mastered her previous roles and began asking, “Is this all there is?” She realized she wanted to impact others in a broader way, leading her to reinvention.
[19:21] Kasey advises completely disconnecting from routine for at least a week (ideally out of the country) to gain clarity. It takes about five days for the mind to stop focusing on daily work and start thinking about bigger questions like “Am I happy?”
[24:35] Leaders often avoid tough decisions or self-improvement. Kasey recommends surrounding yourself with three types of accountability partners: mentors, peers, and direct reports.
[28:34] Kasey plays the “What If” game with clients. If they say they don’t have time or money, she asks, “What if you did? What would you do differently?” This helps reverse engineer solutions and uncover creative options.
[35:59] And remember, “When you have balance in your life, work becomes an entirely different experience. There is a passion that moves you to a whole new level of fulfillment and gratitude, and that's when you can do your best for yourself and for others.” - Cara Delevingne
Quotable Quotes
“Am I happy? Is this the life I dreamed of?”
“We are our own problem. Look in the mirror.”
“If you don’t believe in yourself, no one else will.”
“You need to recalibrate your time and energy every 90 days.”
“The first step to resilience is awareness. Just being aware changes everything.”
“What if you did have time? What would you do differently?”
“I’m the queen of reinvention.”
“Confidence is critical. If you don’t believe in yourself, nobody else will.”
Resources Mentioned
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The Leadership Podcast | theleadershippodcast.com
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Sponsored by | www.darley.com
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Rafti Advisors. LLC | www.raftiadvisors.com
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Self-Reliant Leadership. LLC | selfreliantleadership.com
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Kasey D’Amato Website | www.kaseydamato.com
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Kasey D’Amato Facebook | www.facebook.com/kasey.damato
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Kasey D’Amato LinkedIn | www.linkedin.com/in/kaseydamato
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Kasey D’Amato Instagram | @kaseydamato