“Leadership starts with clarity—and the courage to act on it.”

In this episode, Craig Anderson takes the mic solo to share the three leadership mistakes he sees time and again: outsourcing your vision, waiting for certainty, and over-indexing on empathy. Drawing from decades of experience and recent coaching conversations, Craig reflects on why leaders must stop looking for consensus and start setting direction. He opens up about times he made the wrong call, how he course-corrected, and why taking imperfect action is better than standing still. Craig also unpacks how empathy without accountability can stall a team—and what it really looks like to lead with both compassion and conviction.

Whether you're navigating your first strategic plan or struggling to have hard conversations, Craig’s insights will help you evolve with confidence and purpose.

After You Listen:

• Connect with Craig on LinkedIn
• Subscribe to Craig’s "The Evolving Leader" newsletter
• Download Craig’s “10 Tips to Level Up Your Leadership” guide

Key Takeaways:

• Vision starts at the top—not in a group vote
• Leaders grow by acting, adjusting, and learning
• Empathy means being honest, not avoiding discomfort

Things to listen for:
(00:00) Intro
(01:18) Stop crowdsourcing your vision
(02:38) The cost of indecision
(05:44) A real story about making the wrong call
(08:52) When empathy becomes avoidance
(11:31) Building empathy into your leadership style
(12:41) How to hold high standards with kindness
(13:41) The most empathetic thing might be a hard truth
(14:38) A call to action for evolving leaders

“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