In this episode of Leadership Matters by The Bailey Group, host Kaylee Thomsen sits down with Founder Leigh Bailey to unpack one of the most challenging transitions in leadership: moving from being a trusted technical expert to becoming a strategic people leader. They explore why this shift can feel so uncomfortable - loss of control, a new definition of success, and the identity work required when you’re no longer “the doer” but the developer of others. Kaylee and Leigh break down the limiting beliefs that hold leaders back, share practical ways to rethink how you spend your time, and discuss why self-awareness, relationship-building, and emotional intelligence matter more than ever in an AI-driven world. They also reference a reel from @kelsewhatelse that perfectly illustrates this mindset shift.

Reel Mentioned in This Episode:

Instagram: https://www.instagram.com/reel/DPCTlkZgUZ0/?hl=en

YouTube: https://www.youtube.com/shorts/nywIeE-0-Cc

In this episode of Leadership Matters by The Bailey Group, host Kaylee Thomsen sits down with Kris Fortman, CEO of Minneapolis Heart Institute Foundation, to explore what it truly means to lead with heart, clarity, and courage over the long haul. Kris shares her journey from growing up with a professor father at the University of Minnesota, to conducting healthcare research at HealthPartners, to global work at Medtronic, and ultimately stepping into a mission-driven CEO role in cardiovascular health. She reflects on the early mentors and strong female leaders who shaped her leadership style, why kindness and accountability must work together, and what it was like to inherit a broken culture and quietly turn it around by focusing on people, listening deeply, and building an executive team that can think big while staying grounded in the mission. Kris also talks candidly about hiring lessons, the hard but deeply kind work of helping people find the right role, her passion for women’s heart health and education, and how coaching from The Bailey Group has strengthened both her leadership and her team. If you are a purpose-driven leader looking for honest, practical insight on culture, confidence, and sustainable impact, this conversation delivers grounded wisdom you can use right away.

In this episode of Leadership Matters by The Bailey Group, Kaylee Thompson talks with Libby Doran, Founder of Doran Leadership Partners, about what it truly means to lead with courage, humanity, and clarity. Libby traces her journey from international development work with USAID in the Horn of Africa to boutique management consulting and ultimately building her own executive search firm. Along the way, she shares how early experiences in global aid shaped her beliefs about privilege, education, and economic mobility - and how those lessons now inform the way she advises leaders and organizations. Libby reflects on the power of values-based decision-making, why having hard conversations is an act of care, and how to navigate seasons of uncertainty as a business owner without burning out. She also offers a candid look into executive search: why so many leadership hires fail, what organizations overlook when they focus only on experience, and how to create the right “habitat” for new leaders to thrive. If you’re looking for thoughtful, grounded leadership wisdom that meets the moment we’re in today, this episode delivers powerful insights you won’t want to miss.

In this episode of Leadership Matters by The Bailey Group, Kaylee Thomsen talks with Mary Nutting, co-founder of Strategic Talent Partners, about what it really takes to grow as a leader. Mary shares how early imposter syndrome shaped her leadership journey and how leading 30 developers in her twenties taught her the power of vision, service, and humility. Drawing on her experience as an entrepreneur and talent strategist, Mary reflects on why leadership is rarely linear, how to navigate major career pivots, and why surrounding yourself with the right people makes all the difference. She also offers an honest look into the world of executive search and the realities of building - and rebuilding - a business. If you’re a leader, business owner, or aspiring entrepreneur seeking grounded, practical insight into becoming a more confident and authentic leader, this episode is filled with takeaways you can use right away.

In this episode of Leadership Matters by The Bailey Group, Kaylee Thomsen talks with Mike Braun, founder of Pivotal Advisors, about what great leaders actually do. Mike shares how strong leaders shift from being the “answer man” to a coach who asks better questions, builds clarity, encourages feedback, and redefines accountability. Drawing on experience with 4,000+ companies, he explains why promoting top performers doesn’t always create great managers and why transparency matters most during tough moments. They also discuss how to scale teams, define success realistically, and move from daily operations to true leadership. If you’re a founder, sales leader, or manager who wants to build healthier teams and drive stronger results, this episode is packed with practical lessons you can apply right away.

In this episode of Leadership Matters by The Bailey Group, host Kaylee Thomsen brings together a panel of The Bailey Group’s executive coaches for an honest, heartfelt conversation about what truly shapes great leaders. They explore the power of the right conversation at the right time, the pivotal decisions that changed their trajectories, and the mistakes that became turning points. Through stories of executive presence, conflict, vulnerability, and growth, the panel pulls back the curtain on what really happens in executive coaching—and how meaningful reflection creates healthier workplaces, stronger teams, and better humans.If you care about leading with purpose and growing as both a professional and a person, this conversation is for you.

In this episode of Leadership Matters, we sit down with Craig Warren, CEO of Washburn Center for Children, for a powerful conversation about what it means to lead with courage, curiosity, and care, especially when the environment feels chaotic.

Craig’s leadership journey has been anything but linear. From his formative experiences in the U.S. military to his work in nonprofit leadership, he’s learned that no book or training fully prepares you for the moments when things don’t go your way. Drawing from both the battlefield and the boardroom, Craig shares how those early lessons taught him to “keep moving” through uncertainty and to cultivate resilience rooted in purpose.

Together, we explore how he’s navigated what he calls “crisis stacking,” why he believes in energy management over time management, and how curiosity fuels his ability to stay grounded and forward-looking as a leader. Craig also brings his passion for mental health advocacy to the conversation, offering insights into early interventions that build healthier children, and, ultimately, a healthier society and workforce.

If you care about leading through complexity without losing your humanity, this conversation will remind you that the most courageous leaders are the ones who stay curious, keep moving, and lead with heart.

In this episode of Leadership Matters, Sals Mondelli joins us for a candid conversation about what it means to lead with heart, resilience, and a relentless commitment to growth. Drawing from his diverse leadership journey, Sals shares how authenticity, trust, and clear vision shape strong teams and lasting impact.

Tune in to hear practical leadership wisdom, personal stories, and strategies for creating meaningful change in any organization.