"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

"Leadership isn't just about making decisions and giving orders. It's about building resilience, mental strength, and guiding your team through adversity.” In this episode of Executive Evolution, host Craig Anderson sits down with leadership speaker and author, Scott Mautz, to discuss the essentials of becoming a mentally strong leader. Join us as Scott shares invaluable insights from his extensive research and new book, The Mentally Strong Leader. You’ll learn how to stop chasing approval, start chasing authenticity, and develop the mental strength you need to lead effectively. Tune in to learn practical tools for building resilience, making smart decisions, and maintaining a positive presence.

After You Listen:

Get your copy of Good to Great by Jim Collins

Connect with Scott on LinkedIn

Get Scott’s book, The Mentally Strong Leader

Check out Scott’s website

Connect with Craig on LinkedIn

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

Key Takeaways:

1. Quit chasing approval and embrace your authenticity and trust you were chosen for a reason
2. Build mental strength by regulating emotions, thoughts, and behaviors even in tough situations
3. Prepare for difficult conversations by imagining sitting next to the person, not across

Things to listen for:

[02:40] Lightning round with Scott

[06:55] The importance of mental strength in leadership

[11:12] The balance between confidence and vulnerability

[21:31] Advice Scott would give to his younger self

[24:08] Craigs takeaways

Leadership isn't just about telling people what to do. It's about inspiring them to achieve their full potential and creating a sense of belonging and trust within your team.

In this episode of Executive Evolution, our host, Craig Anderson, is joined by Grant Calder, CEO and founder of Flyt Coaching. Grant discusses the importance of emotional connections in the workplace, how they strengthen business success, and the transformative power of asking the right questions.

Discover why building close relationships with your team matters and how coaching can lead to success.

After You Listen:

Get your copy of Coaching for Performance by John Whitmore

Connect with Grant on LinkedIn

Check out Flyt Coaching

Connect with Craig on LinkedIn

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

Key Takeaways:

1. Building emotional connections with employees and colleagues is crucial for business success
2. Leaders should embrace diverse communication styles and personalities within their teams to enhance decision-making
3. Consistently showing care, support, and presence for team members can foster loyalty and a sense of belonging

Things to listen for:

[01:33] Lightning round with Grant

[11:57] Leaders empower others

[15:04] Everything gets done through people

[21:02] Establish a sense of trust and safety in your leader

[23:36] Every leader is different, and that’s okay

[29:16] Advice Grant would give to his younger self

[34:23] Craigs takeaways

Leadership often requires stepping out of your comfort zone. And once you do this, you’ll find growth.

In this episode of Executive Evolution, our host Craig Anderson is joined by Jason Barnaby, Founder and President of Fire Starters Inc., to dive deep into a candid conversation that peels back layers of personal and professional growth, focusing on the role of discomfort in leadership.

Join us as Jason discusses his most challenging leadership moments and why he believes being uncomfortable is not just inevitable but essential for growth.

After You Listen:

Get your copy of Tribes: We Need You to Lead Us by Seth Godin

Connect with Jason on LinkedIn

Check out Fire Starters Inc.

Connect with Craig on LinkedIn

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

Key Takeaways:

1. Prioritize mental health and seek help early to prevent burnout and maintain leadership effectiveness
2. Foster collaboration by valuing team input and allow collective ideas to shape big initiatives
3. Admit when you're unsure and encourage your team to do the same

Things to listen for:

[02:15] Lightning round with Jason

[06:14] Embrace discomfort for personal and business growth

[18:36] Disc profiles impact leadership

[21:20] Exceed expectations, learn, adapt, become subject

[24:11] Assess sales meetings and hold one-on-ones for accountability

[27:59] Mental health and well-being matters

[29:14] Checking in on others is important

[37:31] Advice Jason would give to his younger self

[40:18] Craigs takeaways

"Leadership isn't just about directing people on what to do. It's about inspiring them to see what they could achieve and helping them unlock that potential.”

In this episode of Executive Evolution, our host Craig Anderson is joined by Chad Schultenover, GM and COO at Meridian Hills Country Club, to share the critical importance of mentorship, strategic patience, and emotional intelligence in successful leadership.

Join us as Chad shares how leadership roles require not only understanding organizational culture but also effective communication, relationship building, and the ability to inspire and empower others.

After You Listen:

Get your copy of Leading Change by John P. Kotter

Connect with Chad on LinkedIn

Check out Meridian Hills Country Club

Connect with Craig on LinkedIn

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

Key Takeaways:

• Whether you're climbing the leadership ladder or already at the top, find a mentor to provide you with guidance and a different perspective that is crucial for personal and professional growth
• Understand your team's and stakeholders' needs to help craft more inclusive and effective strategies
• Embrace change and strategic patience for gradual and accepted improvements without alienating the team

Things to listen for:

[02:03] Lightning round with Chad

[07:48] Leadership means recognizing potential in others

[11:53] Mentorship, promotion, and transition in leadership roles is key

[18:55] New leaders should cautiously implement changes

[24:03] Emotional intelligence increases hospitality

[22:11] Advice Chad would give to his younger self

[24:00] Craigs takeaways