Acknowledging the Challenges while Staying Positive with Steve Rupp

Executive Evolution

"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