“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

“Leadership is about authenticity, vulnerability, and building strong connections.”

In this episode, Craig Anderson talks with Dr. Debra Chromy, President and CEO of Trellis Company, about her evolution as a leader and the lessons she’s learned over her career. Debra shares her journey from early leadership roles to becoming a CEO, emphasizing the importance of being your authentic self and leading with vulnerability. She discusses how showing up as your true self fosters trust within teams, why curiosity is essential in leadership, and how making tough decisions for the organization, even at personal cost, defines strong leadership. Debra also reflects on the challenges of leading through change, the power of strategic planning, and how surrounding yourself with the right team can help drive success.

After You Listen:

• Connect with Dr. Debra Chromy on LinkedIn

• Check out Trellis Company

• Connect with Craig on LinkedIn

• Subscribe to Craig’s "The Evolving Leader" newsletter
  
  

Key Takeaways:

• Lead with authenticity to build trust and drive results

• Use vulnerability as a leadership tool to foster collaboration

• Surround yourself with the right people to enable success
  
  

Things to listen for:
(00:00) Intro
(01:00) The importance of authenticity in leadership
(03:15) How vulnerability builds trust within teams
(06:30) The role of curiosity in addressing leadership challenges
(09:00) Making tough decisions for the organization’s future
(12:45) The impact of strategic planning on organizational success
(15:30) Debra’s leadership lessons from past experiences
(18:00) Creating a culture of transparency and feedback within teams
(20:45) The leadership advice Debra would give her younger self

“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