Welcome to The Leadership Side
I am Caroline DeStefano, a certified coach dedicated to investing in the human side of leadership. Through coaching and facilitation, I help individuals tap into the leader and learner within. Whether you are seeking personal growth, professional development, or a little bit of both, we will explore what matters most so you can lead with greater clarity, connection, and purpose—in your life, your work, and your community. Welcome along the journey.
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Leadership Coaching
One-on-one coaching for individuals looking to grow with more intention, confidence, and clarity in both life and work.
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Emerging Leaders Coaching
Personalized coaching for young adults navigating what's next. Build self-awareness, direction, and a sense of purpose.
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Customized Workshops
Interactive sessions tailored to your team and organization’s needs. Builds engagement, collaboration, and shared learning.
Growth Across Industries
I’ve had the honor of partnering with individuals and teams from a wide range of sectors, including:
Marketing & Communications
Startups & Entrepreneurship
Biotechnology & Life Sciences
K–12 & Higher Education
Non-Profit Leadership
Government Leaders & Changemakers
Professionals in Career Transition (including retirees)
Emerging Leaders & Young Professionals
No matter the field, coaching offers a space to grow, reflect, and move forward with greater clarity and confidence.
“This experience is amazing for one who may be grappling with challenges or needing some clarity and would benefit by having someone to listen and tease out what the underlying concerns and challenges are while guiding one on a path forward.”
— Professional in Career Transition
“Before working with Caroline, I had spent months losing sleep over a complex organizational problem. In just three sessions with her, I was able to get at the heart of the matter, take clear actions steps to move forward, and see results!”
— Non-Profit Executive
