"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

"Leadership is about more than making decisions. It's about being curious, courageous, and continuously learning from those around you."

In this episode of Executive Evolution, host Craig Anderson welcomes Dr. Jackie Freiberg, co-founder of Epic Work, Epic Life, to discuss building brave leaders who embrace risks and seek better ways to lead.

Jackie shares invaluable insights on creating a support network, addressing problems quickly, and surrounding yourself with advisors who challenge your decisions. She emphasizes the transformational power of asking questions and avoiding "I know" statements, drawing on her rich experience with iconic leaders. Tune in and learn about practical wisdom from a seasoned leadership expert.


After You Listen:

• Get your copy of Nuts!: Southwest Airlines’ Crazy Recipe for Business and Personal Success
• Connect with Jackie on LinkedIn
  
• Check out Epic Work, Epic Life
  
• Connect with Craig on LinkedIn
  
• Check out Craig’s monthly free training on holding difficult conversations

Key Takeaways:

1. Emerging leaders must cultivate a mindset of curiosity and courage to ask questions and seek better ways of doing things

2. It's important for leaders to build a strong support system of trusted advisors and to develop superior public speaking skills

3. Effective leadership requires avoiding toxic work environments and fostering an atmosphere of feedback, empathy, and grace
   
   

Things to listen for:
02:14 Lightning Round with Jackie
02:21 Discussing Leadership Books
05:22 Leadership Crushes
10:26 Defining Leadership
12:50 Challenges for New Leaders
18:03 Dealing with Bad Bosses
21:50 Key Lessons for Successful CEOs
28:35 Final Advice for New Leaders
33:12 Conclusion and Key Takeaways

"True leadership isn't just about making decisions. It's about being authentic, serving your team, and building real connections.”

In this episode of Executive Evolution, host Craig Anderson sits down with Matt Tait, CEO of Decimal, to have a conversation about the transformative power of authentic leadership.

Matt shares how transparency and authenticity have steered him through challenging times, including scaling a company and navigating the uncertainties of the pandemic. He

also jumps into the importance of leading with core values, managing both up and down within your organization, and the necessity of self-care for sustainable leadership while opening up about his reliance on family support, executive coaching, and peer groups.

After You Listen:

Get your copy of The Great CEO Within by Matt Mochary

Get your copy of I'm Proud of You: Life Lessons from My Friend Fred Rogers

Connect with Matt on LinkedIn

Follow Matt’s podcast, After the First Million

Check out Decimal

Connect with Craig on LinkedIn

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

Key Takeaways:

1. Position your office to engage with your team. Align furniture for eye contact and spontaneous conversations to build relationships
2. Embrace transparency. Openly share challenges and plans to gain trust and validate your team’s feelings
3. Stay healthy for better leadership. Prioritize daily workouts, even if it means waking up early for "me" time

Things to listen for:

[02:05] Lightning round with Matt

[19:34] Advice Matt would give to his younger self

[21:23] Craigs takeaways