Are your top performers consistently getting passed over for senior leadership roles despite their excellent work? The problem might not be their capabilities but how they show up in workplace relationships. 

In this compelling episode, former Amazon executive Reagan Cannon shares insights from her research on why talented women often struggle to break into senior leadership and what it really takes to advance. Drawing from her journey from crying in an In-N-Out parking lot to leading 10,000 people at Amazon, Cannon explains how "relational courage,"  the willingness to show up authentically and challenge others respectfully can transform careers. She offers practical strategies for scaling leadership, building strategic relationships, and communicating with impact, whether you're leading five people or 5,000. 

 This Episode Covers: 

• Why doing great work alone won't get you promoted to senior leadership 
• How to transition from informal to intentional communication as your organization scales 
• The critical importance of building peer relationships that your team can leverage 
• Why women need to stop trying to be "good" and start being strategic thought partners 
• What it really means to delegate effectively as your organization grows 
• The power of combining data-driven arguments with authentic passion 
• How to handle team members who can't scale with the organization 
• Why relationships and politics are fundamental to senior leadership success

 Chapters: 

(00:00) Introduction to Reagan Cannon – Damon introduces Reagan Cannon, leadership expert and author, to explore the concept of relational courage. 

(02:00) Defining Relational Courage – Reagan explains how her research revealed the importance of courage in workplace relationships, especially for women in leadership. 

(05:30) Overcoming Fear of Failure – Reagan shares personal stories of how embracing failure helped her succeed in challenging environments. 

(09:00) Building Trust Through Feedback – Reagan discusses how feedback and trust can transform relationships and open doors for growth. 

(12:33) Leading Large Teams with Intention – Reagan reflects on lessons learned while leading teams of up to 10,000 people and creating scalable communication strategies. 

(17:00) Transitioning to Entrepreneurship – Reagan talks about the challenges and rewards of leaving corporate leadership to start her own business. 

(21:30) Developing Future Leaders – Reagan provides insights into coaching and mentoring aspiring leaders, with a focus on women breaking into senior roles. 

(33:18) Final Thoughts on Leadership – Reagan emphasizes the importance of balancing courage, connection, and authenticity in leadership. 

About Reagan: 

Drawing from over two decades of executive leadership at Fortune 15 companies including Amazon and AT&T, Reagan Cannon is a globally recognized leadership authority who has coached and developed thousands of leaders across six continents. As the former global head of Amazon's Executive Development and architect of their work-from-home strategy, she led organizations of up to 10,000 people while achieving record-breaking results. In her book The Cure for Career Quicksand and through her coaching practice, Reagan shares her proven "Reagan's Rules" framework that helped her ascend from entry-level manager to executive leadership by age 33, empowering today's leaders to excel both professionally and personally. 

Resources Referenced: 

 Reagan Cannon's Website 

Reagan Cannon on LinkedIn 

The Cure for Career Quicksand: Advancing Your Career One Slice at a Time by Reagan Cannon  

 Reagan’s TEDx Talk (2022) 

INSEAD Research on Women and TED Talks 

Podcast Contact Information: 

Website: www.learnit.com 

Email: podcast@learnit.com 

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