Lessons in Leadership: Reflections from a Small Business Entrepreneur

Lessons in Leadership: Reflections from a Small Business Entrepreneur
By: Kirsten Anderson

In honour of Small Business Week, I was asked to reflect on the lessons I have learned as a life-long entrepreneur that continue to influence my work as a leadership coach and consultant with The Humphrey Group. My decades as a business owner have profoundly shaped me and greatly inform my perspective on what effective leadership requires, no matter what the size of the organization.


Key Leadership Qualities Developed Through Experience

While still a teenager, I first stepped into a leadership role as a manager of a team of sixty at a multiplex movie theatre. Given the large age gap between some of the long-term employees, I had to figure out how to build trust quickly. I discovered that communicating with storytelling over the popcorn counter built those bridges of connection. A trial by fire, this experience provided me with valuable insights into what qualities I wanted to embody to be an effective leader.

It was through this firsthand experience that I learned the importance of the following key areas, which I still focus on today when working with leaders:

  • Clear communication, that enables leaders to articulate their vision and goals, fostering alignment and collaboration.
  • Empathy, that cultivates a supportive work culture where individuals feel valued and motivated to contribute.
  • Trust, that builds the foundation of strong professional relationships.

At The Humphrey Group, we emphasize these core leadership qualities in our training programs, recognizing how vital they are across all levels of management.


The Entrepreneurial Journey: From Toy Store to Leadership Coaching

When I was invited to transition into a buyer and manager role for my family's toy store, I saw it as a chance to step into something new. Little did I know, this decision would eventually lead me down the path of entrepreneurship. When a decade later the opportunity arose to open my own toy store in a new city, I embraced the uncertainty and change. I have found that the challenges that are both exciting and terrifying create greatest growth and reward.

Opening my own store gave me free rein to unleash my creativity and innovate in ways that captured the imagination of the public beyond my community to reach across the country. With my sales team donning white lab coats as “Toyologists” and prescribing “Prescriptions for Play”, I created an immersive experience that set the store apart in the industry and even earned me a regular spot as an expert guest on the news for over a decade. 

This pivotal moment in my career highlights the importance of adaptability, a confidence to take on risks with continuous changes, and an optimistic creative vision of possibility. In this VUCA (Volatile, Uncertain, Complex, Ambiguous) world these skills are more essential to leaders than ever.  Taking inspiration from the entrepreneurial journey, those leading within organizations who adopt an intrapreneurial skill set are more proactive, creative, and resilient cultivating these innovative problem-solving qualities with their teams.


Embracing Change and Leading with Impact

Entrepreneurship has continued to be a catalyst for lessons in leadership. Specifically, I realized the significance of taking initiative and sharing my voice. This led me to sell my store and move into professional speaking, facilitation and leadership coaching.

At every stage of this small business journey, I have consistently learned that fostering meaningful connections, embracing change as we take risks together, and communicating with clarity and storytelling are the most effective ways to create the greatest impact. These essentials continue to guide me in my work as a leadership coach at The Humphrey Group today. By embodying these principles, leaders can create thriving workplaces where employees feel valued, motivated, and inspired to achieve their full potential.



Interested in learning more? Explore Leadership Coaching and Leadership Training at The Humphrey Group.