221: Great Leadership Only Exists in Practice with CEO Caryn O'Sullivan

Leadership does not live in books, job titles, or good intentions. It's a daily practice. What does your daily leadership practice look like? Caryn O'Sullivan, CEO and founder of Drapery Street, joins me to share how she practices leadership, and what that means for you, your team, and your business. Caryn walks us through how she went from doing it all herself to empowering others with frameworks like Dare to Lead, EOS (Entrepreneurial Operating System), StoryBrand, and Working Genius. You'll hear how she's created a "leadership stack" at Drapery Street based on the frameworks used to operate the business. This conversation is about unlocking the daily habits and systems that make all the difference when leading your company during times of change and challenge. Your team needs your courage, your self-awareness, and your willingness to "rumble" with tough conversations. Caryn's journey shows how building systems and practicing vulnerability transform your business and your culture. By the end of this episode, you'll know how to move leadership from something you read about in books to something you live every day. You'll hear how self-awareness sets your business up for resilience, and how practicing healthy communication gives your team the confidence to support each other and your clients alike. This episode is about creating reliable, repeatable leadership habits to build a company where everyone thrives. Episode Highlights (00:00) What "leadership in practice" looks like—and why systems matter (02:23) Are leaders born or can leadership be learned? 03:00) The power of vulnerability and courageous conversations in business (07:00) How self-awareness builds trust and guides company culture (08:00) Building a "leadership" stack (11:43) How changing mindsets transforms your team, your business, and yourself (17:40) Creating a company where everyone works in their genius (22:10) Why self-awareness is now a top hiring priority (23:58) Defining your "why"—and what true success and fulfillment looks like (26:48) Compensating talent, recognizing blind spots, and growing leaders (28:57) What keeps leaders going on tough days—finding joy in learning (30:46) How to balance strengths, feedback, and leadership succession (34:24) Caryn's leadership advice for CEOs Connect with Caryn O'Sullivan https://www.draperystreet.com/ Caryn O'Sullivan on LinkedIn [email protected] About Andrea Butcher Andrea Butcher is a visionary business leader, executive coach, and keynote speaker—she empowers leaders to gain clarity through the chaos by being MORE of who they already are. Her experiences—serving as CEO, leading at an executive level, and working in and leading global teams—make her uniquely qualified to support leadership and business success. She hosts the popular leadership podcast, Being [at Work] with a global audience of over 600,000 listeners and is the author of The Power in the Pivot (Red Thread Publishing 2022) and HR Kit for Dummies (Wiley 2023). Connect with Andrea https://www.abundantempowerment.com/ Connect with Andrea Butcher on LinkedIn https://www.linkedin.com/in/leaderdevelopmentcoach/ Abundant Empowerment Upcoming Events https://www.abundantempowerment.com/events Subscribe to the Podcast Subscribe in Apple Podcasts Subscribe in Spotify