Episode 20:
The Leadership Skill No One Teaches: Learning to Meet the Moment
with Courtney Pong, Speaker, Leadership Development Expert, and Owner + GM, CSZ Boston
What if the secret to better communication is actually learning improv skills?
In this episode, Lindsay sits down with Courtney Pong, owner of CSZ Boston + the Rozzie Square Theater, Boston’s only AAPI- and woman-owned improv theater, and a leadership trainer who teaches communication and collaboration to Fortune 500 companies.
Courtney shares how a career in Silicon Valley – combined with a life-changing medical event – led her to leave tech and build a leadership philosophy rooted in improv, community, and human connection.
Together, they explore how improv principles can transform the way we communicate, pitch ideas, handle failure, and lead with confidence. Courtney breaks down practical tools – from the “Yes, And” mindset to storytelling frameworks and the power of listening first – that can help anyone become a more compelling communicator.
If you’ve ever struggled with perfectionism, self-doubt, or speaking up in professional spaces, this conversation will show you how to trust your experience, meet the moment, and use your voice with more confidence.
LISTEN OR WATCH NOW:
Practice trusting your own confidence – stand with both feet planted and say, ‘I said what I said.’
Courtney Pong
What you learn in this episode:
- Why great communication starts with listening, not performing
- A simple storytelling framework to create compelling pitches and presentations
- How the principle “Yes, and” can help you navigate conflict and collaboration
- Practical ways to move through self-doubt and perfectionism by building a bias toward action
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About the Guest
Courtney Pong is a nationally recognized speaker, entrepreneur, and leader in applied improvisation with 24+ years of professional experience. As the Owner and General Manager of CSZ Boston, she has been teaching improv as an applied skill and performing improv comedy professionally for over 25 years. From the Bay Area to the Bay State, she has been trusted to design and lead team building workshops and communication trainings across a wide variety of industries and brands, from Ocean Spray, The Boston Red Sox, and Dana-Farber Cancer Institute to GE Aviation, Deloitte, and Harvard University.
She’s been recognized as a Boston Business Journal 40 under 40 Honoree, and featured in Boston Magazine and Inc. Magazine as an AAPI thought-leader in live entertainment and entrepreneurship.
Courtney hails from San Francisco, with 15 years of experience in Public Relations and Marketing.
She is a keynote speaker in the New England area.
Connect with Courtney:
Instagram (Courtney’s)
Instagram (CSZ)
About Urban Sandbox (featured at the end of the episode)
Urban Sandbox is a wellbeing-centered platform focused on preventive mental health support for children. Our mission is to close access gaps by connecting families directly to timely, individualized care—with the goal of providing 1:1, on-demand support for every student, regardless of background.
Built on the belief that mental well-being is foundational to a child’s ability to learn and thrive, Urban Sandbox supports children in two ways: encouraging creative expression to build confidence and resilience, and connecting families to trusted mental wellness resources early, before challenges escalate.
By linking families, schools, and care providers in one streamlined system, Urban Sandbox expands support capacity while combining play, psychology, and digital innovation in a privacy-first platform fully compliant with COPPA, FERPA, and HIPAA.
Connect with Urban Sandbox:
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