“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