“It’s okay to not know the answers, but it’s not okay to sit on that.”

In this episode, Craig P. Anderson speaks with Sean McDonald, President of MOR Associates, about navigating leadership in the face of autonomy, uncertainty, and change. Sean shares how his early experiences taught him to step into responsibility before he had a title - and why that mindset remains critical today. Sean and Craig explore the challenges leaders face when they don’t have all the answers, how to build trust during turbulent times, and why empathy requires action. Drawing on his own experiences and working with not-for-profit leaders, Sean offers a grounded, forward-looking perspective on leadership development.

After You Listen:

• Connect with Sean McDonald on LinkedIn: https://www.linkedin.com/in/mcdonaldsean/

• Check out MOR Associates: https://morassociates.com/

• Connect with Craig on LinkedIn: https://www.linkedin.com/in/craigpanderson/

• Sign up for Craig’s Monthly Business Leadership Webinars: https://us02web.zoom.us/meeting/register/3GDgSdp_RfGqegxIXIbAYg

Key Takeaways:

• Autonomy builds leadership muscles, especially when support is limited

• Listening creates trust, but action builds momentum

• In times of uncertainty, focus on what you can control

Things to listen for:

(00:00) Intro

(01:25) Recommended reading for leaders

(02:47) Lessons Sean learned from his father

(04:24) Leadership as choice, movement, and impact

(06:27) Navigating leadership in nonprofits

(09:02) Insights from Sean’s first leadership experience

(11:35) The impact of AI on leadership

(16:31) Sean’s professional leadership journey

(22:00) Challenges in leadership during change

(27:15) Advice for young leaders

“Enjoy the process and don't just focus on the future and the outcomes so much.”

In this episode of Executive Evolution, Craig Anderson sits down with Dan Fahrner, founder and CEO of Shake Up Cocktails and Hi & Mighty Distillery. From touring the country in a van with his band to leading a fast-growing canned cocktail brand, Dan shares how his leadership style evolved across wildly different stages of life. He reflects on lessons from working with creatives, managing part-time ambassadors across multiple states, and building a company around inspiration rather than control. He and Craig explore how casting a clear vision, pivoting with purpose, and aligning team incentives have been key to scaling with intention.

After You Listen:

• Connect with Dan Fahrner on LinkedIn: https://www.linkedin.com/in/danielfahrner/

• Check out Shake Up Cocktails: https://drinkshakeup.com/

• Check out Hi & Mighty Distillery: https://www.drinkhiandmighty.com/

• Connect with Craig on LinkedIn: https://www.linkedin.com/in/craigpanderson/

• Sign up for Craig’s Monthly Business Leadership Webinars: https://us02web.zoom.us/meeting/register/3GDgSdp_RfGqegxIXIbAYg

Key Takeaways:

• Lead with inspiration, not fear, to unlock your team's potential

• Align incentives to drive behavior and reinforce company values

• Stay open to pivoting when new information reveals a better path

Things to listen for:

(00:00) Intro

(00:21) Lessons from leadership in a call center

(01:55) Dan’s leadership insights

(06:56) The privileges and challenges of leadership

(14:30) Building Shake Up Cocktails

(19:36) Adapting and pivoting in business

(23:58) Managing a part-time workforce

(28:02) The importance of enjoying the process

“Leadership is influence with purpose and direction and service to others.”

In this episode, Craig P. Anderson speaks with Dr. Lani Jones, Owner and Founder of HBL Advisory Group, about the mindset shifts leaders must make when stepping into positions of influence, regardless of whether they hold the title. Dr. Jones reflects on her early leadership experience training interpreters in a clinical setting, where she learned to own her expertise and communicate with clarity and confidence. She and Craig explore how impostor syndrome can be reframed as a sign of growth, why feedback must be timely and constructive, and how leadership is as much about serving others as it is about direction and decision-making.

After You Listen:

• Connect with Dr. Lani Jones on LinkedIn

• Check out HBL Advisory Group

• Connect with Craig on LinkedIn

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

Key Takeaways

• Influence begins before the title—leadership is about showing up with agency

• Give and receive feedback in real-time to build trust and momentum

• Reframe imposter syndrome as part of the growth process, not a flaw

Things to listen for:

(00:00) Intro

(00:36) The importance of timely feedback

(02:17) Discussing 'Necessary Endings' by Dr. Henry Cloud

(06:09) Pursuing your leadership crush

(10:28) Keeping the human touch as a leader

(11:21) Early leadership role reflections

(25:55) A nuanced take on imposter syndrome

(32:36) A better way to receive feedback

“True leadership isn’t about doing it all yourself. It’s about helping others rise to the occasion.”

In this episode, Craig P. Anderson talks to Brian Wheeler, the President and Chief Visionary Officer of The Vertical Life, for an insightful conversation about leadership. Brian shares his leadership journey, from high school entrepreneurship to leading a faith-based nonprofit organization focused on developing young leaders. Brian’s story is a testament to the power of vision, humility, and influence in leadership. Brian reflects on key moments of his leadership evolution, including the lessons he learned as a teenager running a pressure washing business, and the ongoing work of leading with purpose in a mission-driven organization. He emphasizes the importance of self-discovery for young leaders and how developing a mindset of service, rather than self-centered ambition, has been crucial to his leadership style.

After You Listen:

• Connect with Brian Wheeler on LinkedIn

• Check out The Vertical Life

• Connect with Craig on LinkedIn

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

Key Takeaways:

• Leadership is about influence, not age, authority, or title

• Humility as a leader leads to better collaboration and growth

• Faith in your mission fuels motivation and commitment in your team

Things to listen for:

(00:00) Intro

(00:30) The importance of vision in leadership

(01:33) Brian’s leadership insights

(07:12) Brian’s early leadership journey

(11:24) Leadership in faith-based organizations

(16:36) The role of humility in leadership

“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

“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