EP 104 – Katie O'Malley, Founder and Leadership Coach at Encourage Coaching, on self-awareness and why great leaders master listening
03/13/25 • 45 min
In this episode of Business Leader Breakthroughs, Ryan Castle sit down with leadership coach Katie O'Malley to explore the essential qualities of great leadership—self-awareness, psychological safety, and listening skills. Katie shares her personal career journey, from pursuing political science and nonprofit work to discovering her true passion for coaching. She reveals how a misalignment between values and career choices can lead to burnout and dissatisfaction, and why developing self-awareness is the foundation of effective leadership.
Ryan and Katie also discuss how leaders can create psychologically safe workplaces where employees feel heard and empowered. Katie explains why listening is the most underrated leadership skill, how different communication styles impact team trust, and practical strategies leaders can use to foster open, productive conversations. Whether you’re looking to enhance your leadership skills or rethink how you engage with your team, this episode is packed with actionable insights.
Useful links:
Katie O'Malley’s Coaching Practice – Encourage CoachingDr. Amy Edmondson on Psychological Safety – Harvard Business Review article
The Five-Factor Model of Personality – The psychological framework behind Hogan Assessments
Armchair Expert Podcast – One of Katie’s favorite podcasts on psychology and leadership
Where else you can find us
Website: https://thebreakthrough.co
LinkedIn: http://www.linkedin.com/company/the-breakthrough-company
Podcast: https://thebreakthrough.co/podcast/
In this episode of Business Leader Breakthroughs, Ryan Castle sit down with leadership coach Katie O'Malley to explore the essential qualities of great leadership—self-awareness, psychological safety, and listening skills. Katie shares her personal career journey, from pursuing political science and nonprofit work to discovering her true passion for coaching. She reveals how a misalignment between values and career choices can lead to burnout and dissatisfaction, and why developing self-awareness is the foundation of effective leadership.
Ryan and Katie also discuss how leaders can create psychologically safe workplaces where employees feel heard and empowered. Katie explains why listening is the most underrated leadership skill, how different communication styles impact team trust, and practical strategies leaders can use to foster open, productive conversations. Whether you’re looking to enhance your leadership skills or rethink how you engage with your team, this episode is packed with actionable insights.
Useful links:
Katie O'Malley’s Coaching Practice – Encourage CoachingDr. Amy Edmondson on Psychological Safety – Harvard Business Review article
The Five-Factor Model of Personality – The psychological framework behind Hogan Assessments
Armchair Expert Podcast – One of Katie’s favorite podcasts on psychology and leadership
Where else you can find us
Website: https://thebreakthrough.co
LinkedIn: http://www.linkedin.com/company/the-breakthrough-company
Podcast: https://thebreakthrough.co/podcast/
Previous Episode
Ep 103 – The office debate: is remote work over?
In this episode of Business Leader Breakthroughs, Ryan Castle and Dr. Mike Ashby dive into the heated debate on returning to the office. With major corporations and governments pushing for in-office mandates, they explore the real drivers behind these decisions—productivity, company culture, and even cost-cutting disguised as policy shifts. They break down how different industries are approaching hybrid work and why a one-size-fits-all policy is often ineffective.
Ryan and Mike also discuss the critical role of leadership in setting fair and practical workplace expectations. They examine why some leaders push office attendance while choosing to work remotely themselves, how hybrid policies impact team dynamics, and why great management—not location—is the key to high performance. If you're a leader navigating the return-to-office landscape, this episode offers practical insights to help you make decisions that drive both engagement and results.
Where else you can find us
Website: https://thebreakthrough.co
LinkedIn: http://www.linkedin.com/company/the-breakthrough-company
Podcast: https://thebreakthrough.co/podcast/
Next Episode
Ep 105 – How to build high-performing teams with IQ, EQ and adaptability with Jennifer Aubin
In this episode of Business Leader Breakthroughs, Ryan Castle chats with early-stage tech leader and HR expert Jennifer Aubin about what it really takes to lead teams in high-growth, high-stress environments. With 20+ years in startup leadership, Jennifer brings real-world insight into how great teams stay aligned, adaptable, and emotionally intelligent—without burning out.
Jennifer introduces her “three-pronged” leadership model: IQ, EQ, and AQ (Adaptability Quotient)—a simple but powerful way to assess talent and build capable, well-balanced teams. She unpacks why smart people alone won’t get you across the line, and how adaptability is the trait that separates average teams from high performers.
Useful links:
Connect with Jennifer Aubin - LinkedInSurrounded by Idiots by Thomas Erikson - Amazon (Note: We are not affiliated with this link; it’s shared for reference only.)
Grit by Angela Duckworth - Amazon (Note: We are not affiliated with this link; it’s shared for reference only.)
Entrepreneurial Operating System (EOS)
Where else you can find us
Website: https://thebreakthrough.co
LinkedIn: http://www.linkedin.com/company/the-breakthrough-company
Podcast: https://thebreakthrough.co/podcast/
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