From Teen Dreamer to Fashion Powerhouse – Colleen Callander

In an exclusive conversation with CEO World, Colleen Callander—award-winning former CEO of Sportsgirl, entrepreneur, bestselling author, keynote speaker, founder of Mentor Me Women, business strategist, and board advisor—shares her extraordinary journey, leadership philosophy, and insights from a career spanning more than three decades at the helm of some of Australia’s most iconic fashion brands.

At just 16, Colleen made the courageous decision to step into the world of fashion, choosing passion over a conventional academic path. That early leap laid the foundation for a remarkable leadership journey defined by authenticity, resilience, and people-first leadership. Over the years, she has learned that true leadership isn’t about having all the answers—it’s about courage, self-belief, and empowering others to thrive.

Through moments of self-doubt, bold decisions, and transformational leadership roles, Colleen discovered that confidence is built through action and belief. Her upcoming book, The Power of Confidence (Wiley Publishing, 2026), reflects these lessons, offering practical strategies, personal stories, and a 30-day framework designed to help individuals overcome self-doubt and lead with conviction.

Join CEO World as we explore Colleen Callander’s leadership journey, defining career moments, and the experiences that continue to shape her impact on business and beyond.

1. You began your retail career at just 16, choosing fashion over completing your education. What inspired that bold decision so early in life?

At 16, I reached a crossroads. While many of my peers were preparing for university, I felt a strong pull toward fashion. Retail, for me, wasn’t just about clothing—it was about people, relationships, and creating meaningful experiences.

My parents instilled strong values of integrity, hard work, and self-belief, which gave me the confidence to pursue a path that felt right, even if it seemed unconventional. From my first day in retail, I knew I had found my place. That leap of faith ultimately became the foundation of a three-decade career leading two of Australia’s most iconic fashion brands. Looking back, it wasn’t just a career choice—it was a decision to trust myself and build a future on my own terms.

2. Looking back on your 30-year career, what defining moment set you on the path to becoming a CEO?

A pivotal moment came early in my career when I was offered a leadership role I didn’t feel fully prepared for. On paper, I didn’t tick every box, but something inside me said, take the leap. That decision changed everything.

It taught me that leadership isn’t about having all the answers—it’s about willingness to learn, adapt, and back yourself. From that point forward, I approached leadership through a people-first lens, focusing on culture, connection, and courage. That moment shaped my entire leadership philosophy and ultimately paved the way to the CEO role.

3. Having led iconic fashion brands, what lessons did you learn about building and sustaining a strong brand identity?

A brand is far more than its products—it’s an emotional connection. Authenticity is critical because today’s consumers instantly recognize what’s genuine. Building a brand identity means standing for something bigger than commercial success.

For me, it was about inspiring confidence, fostering community, and championing purpose—especially empowering women. Strong brands are built daily through culture, storytelling, and customer experience. When teams genuinely connect with the brand’s vision and values, that energy creates lasting trust and loyalty.

4. You often speak about building “winning cultures.” How did you create this at Sportsgirl and Sussan?

Culture doesn’t happen by chance—it’s intentional. My guiding principle has always been People + Purpose + Passion = Profit. I focused on creating environments where people felt heard, valued, and inspired.

Open communication, celebrating wins, encouraging collaboration, and aligning teams with purpose were key. We also built initiatives that supported mentoring and community engagement. When people feel proud of where they work and connected to a shared mission, performance follows naturally.

5. What distinguishes good leaders from truly great leaders in today’s fast-changing business world?

Great leaders inspire belief. In an evolving business environment, emotional intelligence, adaptability, and authenticity are critical. Great leaders listen deeply, embrace vulnerability, and lead with courage and kindness.

They understand that culture drives performance and that leadership is about empowerment, not authority. The most impactful leaders create space for diverse voices and leave people feeling confident, capable, and valued.

6. Did you experience moments of self-doubt, and how did you overcome them?

Absolutely. I’ve experienced imposter syndrome—walking into boardrooms and questioning whether I truly belonged. What helped was understanding that confidence isn’t about knowing everything; it’s about trusting yourself to take the next step anyway.

Mentors and trusted supporters played a crucial role, reminding me of my strengths during moments of doubt. Those experiences taught me that courage isn’t the absence of fear—it’s moving forward despite it.

7. Leader by Design is often described as the guidebook you wish you had at 16. What core principles should aspiring leaders embrace?

Self-awareness, purpose, and confidence are essential. Knowing who you are and what you stand for guides better decisions. Purpose fuels motivation, while confidence grows through action.

Leadership isn’t a title—it’s a daily choice. Setting boundaries, practicing resilience, and leading with kindness are as important as strategy. When leaders show up authentically, they unlock their own potential and that of others.

8. What advice would you give young women aspiring to leadership roles but struggling with confidence or mentorship?

Don’t wait until you feel ready—confidence grows through action. Say yes to opportunities, learn as you go, and surround yourself with people who uplift you.

Leadership isn’t about being the loudest voice; it’s about being authentic, consistent, and courageous. Your perspective matters, and when you believe in yourself, you inspire others to do the same.

9. Your new book The Power of Confidence releases in 2026. What can readers expect?

The Power of Confidence is deeply personal and practical. It reflects my life journey and the lessons I’ve learned about leadership, self-belief, and purpose.

Confidence isn’t something you’re born with—it’s something you build daily. The book includes real-life stories, actionable strategies, and a 30-day transformation program to help people overcome self-doubt and step into their power. My goal is to encourage readers to stop waiting for the “perfect moment” and start taking small, courageous steps toward lasting confidence—because when you change your confidence, you truly change your life ✨