Known for seizing “big, scary opportunities,” Bryan Power has defined his career by embracing risk, adapting to change, and staying focused under pressure. After turning down a promotion at Google for a new challenge at Square, he quickly realized he was in over his head. But it was in facing that discomfort head-on, that he experienced his most significant growth moments. In this episode, Bryan joins Ilana to discuss the importance of tackling challenging opportunities, the practices that lead to career growth, and his unique approach to leadership.

Bryan Power is a certified executive coach with over 20 years of experience in human resources management. Having worked with top companies like Google, Yahoo!, Square, and Nextdoor, he specializes in guiding leaders through growth, high-stakes transitions, and fast-paced environments.

In this episode, Ilana and Bryan will discuss:

(00:00) Introduction

(00:22) His Journey to Silicon Valley

(01:31) Big, Scary Opportunities that Drove His Growth

(03:45) Bryan’s Annual Growth Reflection Ritual

(05:29) Transitioning from Google to Square

(08:40) The Weight of Leadership in Today’s World

(10:18) How COVID-19 Impacted the Way We Work

(12:37) The Pros and Cons of Remote Work

(16:52) Why Adversity Makes the Best Leaders

(20:05) How Bryan’s Background Influenced His Success

(22:46) Bryan’s Secret to Landing Your Dream Job

(25:57) Key Skills Every New Leader Must Master

(29:54) Building Trust in Your First 90 Days at a New Job

(34:41) Nextdoor’s Success in Digital Community Building

(39:37) Career Lessons Bryan Wishes He Had Learned Sooner

Bryan Power is a certified executive coach with over 20 years of experience in human resources management. Having worked with top companies like Google, Yahoo!, Square, and Nextdoor, he specializes in guiding leaders through growth, high-stakes transitions, and fast-paced environments. Bryan has a proven track record of building and leading high-performing teams across North and South America, Europe, the Middle East, Australia, and Asia. His expertise extends to board-level work, where he has developed executive compensation strategies, company-wide cash/equity incentives, and benefits programs.

Connect with Bryan:

Bryan’s LinkedIn: www.linkedin.com/in/bryanpower

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Nextdoor’s Bryan Power: Turning Big, Scary Opportunities into Career-Defining Success | E59