Executive Evolution

"Leadership is about building others up while getting out of their way." In this episode, Craig Anderson talks with Peter Dunn, founder and CEO of Your Money Line, about what it really takes to grow into a leadership role. Pete shares candid reflections on how he went from a self-focused leader to someone committed to empowering others through trust, transparency, and support. He opens up about past missteps, the guilt he carries over early leadership choices, and the ongoing work of becoming someone worth following. Pete also explores why feedback is an act of care, how empathy and performance go hand in hand, and why the mission behind Your Money Line is so deeply personal. Whether you're a new leader or a seasoned executive, Pete's story is a reminder that leadership is less about having the answers—and more about asking the right questions. After You Listen: Connect with Peter Dunn on LinkedIn Check out Your Money Line Connect with Craig on LinkedIn Subscribe to Craig's "The Evolving Leader" newsletter Key Takeaways: Feedback is an investment in someone's growth Empathy makes hard conversations more effective Leadership is about helping others shine, not just hitting goals Things to listen for:(00:00) Intro (01:11) Seeing leadership potential in others (02:15) Pete's book for HR leaders (03:00) The difference between givers and takers in leadership (04:06) What it means to truly empower your team (05:39) Creating a coaching tree inside your business (07:00) Pete's leadership role model (08:11) Learning from a strong executive team (09:56) Valuing teammates' career journeys (11:22) Pete's first leadership experiences (13:25) Recognizing privilege and using it for good (15:10) Identifying and developing high-potential team members (17:11) Leadership lessons from unexpected places (18:34) Telling the truth with empathy (20:07) Leading with curiosity and compassion (21:17) The impact of mission-driven leadership (26:11) How culture reinforces the mission (27:18) The advice Pete would give his younger self (28:53) The role of self-awareness in leadership growth

"Great leaders know when they're wrong." In this episode, Craig Anderson talks with Ben Pippenger, Co-Founder and Staff Product Manager of Zylo, about the evolution of leadership and the lessons learned from building and scaling a company. Ben shares his journey from an individual contributor to a leader, emphasizing the importance of understanding what truly motivates a team. He discusses how recognition—not just money—keeps employees engaged, why leaders must carve out time for their people, and how making mistakes can be a powerful learning tool. Ben also reflects on lessons from his time at Salesforce, the challenges of maintaining company culture at scale, and why leadership isn't just about getting things done—it's about bringing people along with you. After You Listen: Connect with Ben Pippenger on LinkedIn Check out Zylo Connect with Craig on LinkedIn Subscribe to Craig's "The Evolving Leader" newsletter Key Takeaways: Understand what motivates your team to drive engagement and performance Prioritize recognition over money to build lasting team appreciation Embrace mistakes as learning opportunities to grow as a leader Things to listen for:(00:00) Intro (01:30) Ben's transition from contributor to leader (04:12) The role of motivation in building a high-performance team (07:28) How Salesforce's leadership principles influenced Ben's approach (10:18) Why leadership isn't just about more productivity (14:23) The importance of career paths for non-managers (18:30) Creating a culture of recognition and peer feedback (22:45) The one leadership lesson Ben would tell his younger self

"What you put out as a leader will be heard and will affect every level of the organization." In this episode, Craig Anderson talks with Ian McCoog, Assistant Professor of Medical Education at Geisinger Commonwealth School of Medicine and author of Leadership Bites. Ian explores the challenges healthcare professionals face when transitioning from clinical expertise to leadership roles. Drawing from his book and personal experience, Ian shares how leadership theories can guide decision-making and foster team collaboration. He also emphasizes the importance of self-care for maintaining balance in high-pressure environments and discusses how storytelling can make leadership lessons stick. After You Listen: Visit Ian's website at ianmccoog.com Connect with Ian McCoog on LinkedIn Get a copy of Ian's book, Leadership Bites Connect with Craig on LinkedIn Subscribe to Craig's "The Evolving Leader" newsletter Key Takeaways: Build confidence by understanding that everything you say or do as a leader has an impact on your team and organization Develop competence by leveraging leadership frameworks and reflecting on lessons learned from experience Maintain calm by finding moments for self-care, even during hectic and demanding days Things to listen for: (00:00) Intro (01:38) Ian's early leadership journey (02:38) Lightning round: leadership insights (07:51) Challenges in medical leadership (16:01) Leadership theories and applications (18:24) Maintaining equilibrium in medicine(20:17) Resident leadership as a paradigm

"Oftentimes, positive reinforcement training ability translates well to humans too." In this episode, Craig Anderson talks with Mandy Stetzel and Kathleen Schonsheck, Co-owners of Uptown Pup, about how they built a successful pet care business by prioritizing transparency, trust, and a strong team culture. Mandy and Kathleen share their journey from passionate dog lovers to business owners despite having no formal business or leadership training. They discuss how they learned to lead, the importance of hiring and mentoring the right people, and how staying true to their values has helped them grow a business that serves both people and pets. They also explore how positive reinforcement—used in training dogs—can apply to leadership, the role of financial transparency in building team trust, and why leading by example is the best way to create a thriving workplace. After You Listen: Visit Uptown Pup's website at uptownpupindy.com Follow Uptown Pup on Instagram: @uptownpupindy Like Uptown Pup on Facebook: Uptown Pup Follow Mandy & Kathleen on BlueSky: The Uptown Girls Connect with Craig on LinkedIn Subscribe to Craig's "The Evolving Leader" newsletter Key Takeaways: Trust your instincts and learn from experience—even when you make mistakes Invest in leadership books, mentorship, and financial transparency with your team Know yourself, recognize your triggers, and prioritize self-care to be a better leader Things to listen for: (00:00) Intro (01:02) Meet the owners of Uptown Pup (01:52) Lightning round: leadership books (05:01) Lightning round: leadership crushes (09:11) The early days of building Uptown Pup (12:47) Hiring and team building strategies (16:29) Growing into leadership roles (22:36) Maintaining culture and vision

"You can't build trust without relatability and authenticity—when your team knows you're genuine, trust naturally follows." In this episode, Craig Anderson sits down with Kyle McDowell, author of Begin With We and founder of Kyle McDowell Inc., to discuss his evolution as a leader and the principles that have shaped his leadership philosophy. Kyle shares how his transformative journey led to the creation of his "10 We's"—a set of principles designed to foster trust, authenticity, and collaboration within teams. Reflecting on the highs and lows of his corporate career, Kyle opens up about the mistakes that shaped his leadership style, the challenges of stepping away from the corporate world, and the lessons he learned about relatability and building a culture of excellence. After You Listen: Connect with Kyle McDowell on LinkedIn Connect with Craig on LinkedIn Subscribe to Craig's "The Evolving Leader" newsletter Key Takeaways: Earn trust by leading with authenticity and relatability Inspire teams by removing barriers and empowering them to excel Foster a culture of excellence through shared principles and accountability Things to listen for: (00:00) Intro (02:10) Leadership lightning round (07:30) Lessons from leadership mistakes (13:40) The power of self-reflection in leadership (18:15) The "10 We's" and their impact on team culture (23:10) Overcoming skepticism and earning trust (30:00) Balancing empathy and accountability as a leader (37:00) Advice for new and experienced leaders alike

"You're setting the direction. But how you get from Point A to Point B is really up to that person." In this episode, Craig Anderson sits down with Chrystal Struben, President and CEO at AYS Inc, to share her journey as a leader navigating the complexities of nonprofit organizations. Chrystal reflects on her experience following a 34-year founder, sharing how she developed her unique leadership style while building trust and driving organizational growth. Chrystal shares the challenges of balancing compassion with accountability and emphasizes the importance of clear communication and empowering teams. With her leadership philosophy, "Be the compass, not the map," and inspiration from thought leaders like Gino Wickman, she offers practical insights on building trust, managing change, and communicating vision effectively. After You Listen: Connect with Chrystal Struben on LinkedIn Connect with Craig on LinkedIn Subscribe to Craig's "The Evolving Leader" newsletter Key Takeaways: Set the big vision for your team. Guide, and don't micromanage Embrace structure. Consistency builds trust and clarity, reduces chaos, and aids in smoother operations Learn from mentors. Their insights can provide invaluable support and perspective on your leadership journey Things to listen for: (00:00) Intro (02:36) Lightning round with leadership insights (07:13) Be the compass, not the map (08:28) Building structure to guide your team (12:39) Why vision must come first in leadership (16:04) Balancing compassion with leadership authority (19:51) Leading in mission-driven organizations

"Leaders are meant to serve. It's not an ego trip. It's how you serve your team." When Kyle Lacy, now CMO of Jellyfish, took on his first leadership role, it was all about him and his performance. But over time, he's learned to check his ego at the door and focus on pouring into his people instead to achieve more success than he ever thought possible. In this episode, Kyle shares his insights on investing in team members' career growth, managing stress, and understanding how to effectively lead and motivate people. Listen in for a deeper understanding of what servant leadership looks like and how to put it into practice. After You Listen: Check out "Do Better Work by Max Yoder" and "How to Stop Worrying and Start Living by Dale Carnegie" Connect with Kyle on LinkedIn Connect with Craig on LinkedIn Subscribe to Craig's "The Evolving Leader" newsletter Key Takeaways: Take the ego out of leadership and focus on serving your teams Work to understand how your team members work best and what motivates them Go big picture: to best support your people think about their careers, not just their daily tasks Things to listen for: (00:00) Intro (02:35) Lightning round with Kyle (05:30) Mentoring your team for their career growth (12:04) Understanding the weight of leadership (15:55) Navigating constant change without getting burnt out (18:23) Kyle's advice for his younger self (19:07) Craig's takeaways

"A really powerful lesson is knowing that it is okay to admit when you've made a mistake. That shows people that your ego isn't getting in the way of you showing up as a good human." In this episode of Executive Evolution, Craig Anderson sits down with Susan Baroncini-Moe, Executive Coach and CEO at Baroncini-Moe Executive Coaching, about leadership grounded in empathy, self-awareness, and authenticity. Susan shares the importance of vulnerability in building team trust and explains why candid feedback, rather than anonymous reviews, strengthens teams. Susan reflects on her early career managing her father's medical practice and shares the leadership lessons she learned firsthand through these experiences. She also advises fostering a safe, open culture that promotes honesty, growth, and authenticity, which is essential for today's executives. After You Listen: Get your copy of Fierce Leadership by Susan Scott Connect with Susan Baroncini-Moe on LinkedIn Check out Baroncini-Moe Executive Coaching Connect with Craig on LinkedIn Subscribe to Craig's "The Evolving Leader" newsletter Check out Craig's monthly free training on holding difficult conversations Key Takeaways: Develop emotional intelligence and self-awareness to inspire authentic connections Build a legacy of integrity and growth through honest, open communication Approach difficult conversations with empathy and listening first Things to listen for: (00:00) Intro (02:26) Lightning round (17:46) Mastering self-awareness (18:29) Evolving leadership philosophy (19:00) The power of vulnerability (20:01) Handling mistakes with grace (20:52) The weight of leadership (27:30) The role of a coach (31:31) The pitfalls of Performance Improvement Plans