“A true challenge in leadership is learning when to step back and let others find their own path from A to Z.”

In this episode of Executive Evolution, Craig Anderson talks with Adam Hayes, owner of Hayes Group Marketing, about the journey of leading and scaling a small business. Adam shares how he transitioned from a hands-on approach to a visionary role, focusing on empowering his team through trust, clear communication, and structured systems.

Drawing on over 20 years of experience, Adam emphasizes the importance of balancing guidance with autonomy, building a solid organizational framework, and using regular check-ins to maintain alignment with the company’s vision.

After You Listen:

• Connect with Adam on LinkedIn
• Check out Hayes Group Marketing
• 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:

• Define a clear vision. Make sure your team understands it, so they can align their actions with your business goals
• Encourage team ownership. Let them be part of the solution, which drives engagement and accountability
• Learn to balance empathy with tough conversations. Compassionate leadership fosters trust and better outcomes

Things to listen for:

(00:00) Intro

(02:01) Leadership influences and favorite books

(06:29) First experiences in leadership and early lessons

(09:18) Balancing guidance and independence

(12:35) The importance of structured communication

(17:30) Scaling a small business with a vision-driven approach

(20:01) Goals for the future and stepping into a full-time visionary role

"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

"Instead of protecting their feelings for them, I’ve learned that it’s their job to protect their feelings. It’s my job to give them the truth, and you can do it in an empathic way.”

In this episode, Craig Anderson speaks with Peter Dunn, CEO of Your Money Line, about the leadership lessons that come from embracing empathy and self-awareness. Peter recounts his early experiences where he focused on achieving his personal goals, only to realize that true leadership means helping others grow. He shares how this shift in perspective transformed his approach and led to better team outcomes.

After You Listen:

• Get your copy of Give and Take by Adam Grant

• Connect with Peter Dunn on LinkedIn

• Check out Your Money Line

• 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:

• Leadership is about providing resources and removing obstacles to help your team succeed

• Empathy in communication, especially during difficult conversations, is crucial for effective leadership

• Nurturing potential in team members who may not see it in themselves promotes internal growth and leadership development

Things to listen for:

(00:00) Intro

(02:32) Lightning round with Peter Dunn

(04:05) Setting up a “talent bomb”

(11:09) How self-awareness shapes leadership growth

(15:35) Leadership is a privilege

(16:37) The power of empathy in leadership

(21:57) Maturity means being comfortable with difficult conversations

"Leadership is about more than directing, it's about inspiring your team and guiding them towards a shared goal.”

In this episode of Executive Evolution, Craig Anderson interviews his son, Daniel Anderson, discussing various aspects of leadership experienced throughout Daniel’s naval career.

Daniel reflects on his initial leadership role as a Combat Electronics and Main Propulsion Division Officer upon joining the Navy. He shares his insights into the balance between hands-on leadership and administrative duties, the evolution of his leadership strategies, and the application of the "good dude" theory of leadership.

After You Listen:

• Connect with Craig on LinkedIn
• Check out Craig’s monthly free training on holding difficult conversations
  
  

Key Takeaways:

• Identify individual motivations to inspire and effectively lead your team
• Delegate tasks according to team strengths to maintain efficiency
• Trust your team but verify their work to ensure accountability and foster growth

Things to listen for:

(00:00) Intro
(02:10) Lightning round
(05:55) Navigating team dynamics in the Navy
(08:16) How to balance leadership and learning
(14:43) Lessons on delegation and micromanagement
(19:45) The ‘good dude’ theory in leadership
(22:50) How to improve time management in leadership

"Make sure your intent and the impact are aligned, right? Because even if it's not necessarily a positive situation, if you do your job well, then it should be articulated objectively and with the right tone and outcome.”

In this episode of Executive Evolution, Craig Anderson chats with Caroline Abeleda, Co-Founder of Exploradoor. Caroline discusses why treating your team with dignity is essential, even in difficult situations like layoffs. She explains how embracing vulnerability helped her address the challenges of transitioning from peer to leader and how this openness fostered trust within her team. Caroline also talks about the realities of leading a company that’s always in growth mode, and where time management and resource allocation play a crucial role.

After You Listen:

• Get your copy of Leaders Eat Last by Simon Sinek
• Connect with Caroline on LinkedIn
• Check out Exploradoor
  
• Connect with Craig on LinkedIn
• Check out Craig’s monthly free training on holding difficult conversations

Key Takeaways:

• Show your team honesty in one-on-one conversations to build trust and strengthen relationships.
• Ensure your leadership actions match your business goals to achieve desired outcomes
• Handle tough decisions with compassion, preserving the dignity of your team members
  
  

Things to listen for:

(00:00) The lightning round

(07:22) Defining leadership beyond the title

(10:38) Becoming a leader among your peers

(15:07) Challenges of leading a company that’s always in growth mode

(19:13) The Importance of self-awareness in leadership

“Leadership is getting in the trenches with those you serve and leading by example.”

In this episode of Executive Evolution, Craig Anderson chats with Cassie Mecklenburg, Executive Director of Sheltering Wings, about how emotional intelligence and empathy play a big role in leadership.

Cassie shares her story, starting from her leadership roles in college all the way to running a successful non-profit, and how she leads at Sheltering Wings today. She talks about how she balances big-picture thinking with the day-to-day stuff, and why having a team with different strengths makes all the difference.

After You Listen:

• Connect with Cassie on LinkedIn
• Connect with Craig on LinkedIn
• Check out Craig’s monthly free training on holding difficult conversations

Key Takeaways:

• Practice empathy by understanding your team’s challenges
• Surround yourself with diverse perspectives to enrich decision-making
• Lead by example by getting in the trenches and showing you're willing to do the hard work alongside them

Things to listen for:

(00:37) The importance of emotional intelligence

(01:54) How to navigate tough topics with people-first leadership

(03:49) Knowing when to compromise or stand firm

(15:03) The importance of curiosity in leadership

(17:31) From daily tasks to community-focused leadership

(20:07) How to be a coach and not just a problem solver

(24:25) Why leaders should build friendships with their teams

"Be confident in yourself to pour into other people what they need.”

In this episode, our host, Craig Anderson, is joined by Steve Rupp, a seasoned real estate coach and passionate leader. Steve shares how managing from a place of confidence and generosity can break the negative cycle of threatened leadership and drive real team success.

Listen in as Steve recounts his journey from his first leadership role as a Boy Scout patrol leader to his impactful career in real estate coaching. He discusses the critical lessons learned along the way, emphasizing the importance of building trust and improving communication through creative team-building exercises.

You'll also hear about the transformative power of mentorship and effective delegation. Steve offers actionable insights on how young leaders can motivate their teams from within and the art of asking the right questions to inspire self-reliance and ongoing improvement.

After You Listen:

• Get your copy of Leadership Promises for Every Day by John Maxwell

• Connect with Steve on LinkedIn

• Connect with Craig on LinkedIn

• Check out Craig’s monthly free training on holding difficult conversations

Key Takeaways:

• Be confident and provide your team with the right tools—don't feel threatened. It’s essential for positive leadership.

• Stay positive and maintain confidence for your team, even during challenging times. Positivity is contagious.

• Embrace the power of questioning. Encourage self-discovery instead of providing all the answers.

Things to listen for:

(00:00) The lightning round

(02:23) Defining leadership

(07:09) Leadership lessons from the Boy Scouts

(11:07) Challenges of young leadership

(15:19) Scarcity vs. contribution in leadership

(17:45) The importance of creativity in leadership

(23:31) The role of curiosity in effective leadership

(27:14) Steve’s advice to his younger self

"Leadership isn't just about steering the ship. It's about making sure every crew member knows they're on the right journey.”

In this episode of Executive Evolution, our host Craig Anderson sits down with Evan Huck, CEO of UserEvidence, to discuss the highs and lows of leading through uncertainty, building a thriving remote culture, and inspiring a mission-driven team.

Join us to discover how Evan leads with empathy and insight, even when facing the hard truths of executive life.


After You Listen:

• Get your copy of Let My People Go Surfing: The Education of a Reluctant Businessman by Yvon Chouinard

• Connect with Evan on LinkedIn

• Check out UserEvidence

• Connect with Craig on LinkedIn

• Check out Craig’s monthly free training on holding difficult conversations

Key Takeaways:

1. Sharing your company's story openly fosters trust and keeps your team motivated, especially during tough times

2. Documenting priorities and progress helps everyone to be aligned and focused

3. Curiosity and humility: these qualities drive growth and problem-solving within the company
   
   

Things to listen for:

01:22 Evan's Leadership Journey

01:52 Lightning Round: Leadership book

03:48 Leadership Influence

08:23 Defining Leadership

10:31 Early Leadership Roles

16:30 Lessons in Leadership

22:56 Final Thoughts and Takeaways