From Law to Leadership: A Journey of Self-Reflection and Vision

My journey into the world of leadership coaching might seem a little unconventional as my career path began in law. Prior to attending law school, I had always imagined I would focus on environmental law. But in my second year at Osgoode Hall Law School, I had an “aha moment”: How on earth (no pun intended) could we treat the inanimate world with respect if we can’t even treat each other, as humans, with respect? Thus began my focus on human rights.

This worldview became particularly locked in immediately after law school. Early in my career, I took some time off to travel through East and South Asia. During that trip, I encountered various aspects of Buddhist philosophy again and again. In particular, the notion of unity (that we are all connected) was a recurrent theme during those six months of travel.

Career Challenges and Lessons in Values

This philosophical approach stayed with me as I returned to “real life” and resumed my career. Over the course of the next decade, I had many great experiences working at various human rights organizations. But there were also challenges. For example, when returning from travels in Asia, I experienced a nine-month period of unemployment. This taught me a great deal about humility: We have control over our actions, but not the outcome of those actions. Meaning, I can do the best I can to get hired, but I can’t actually hire myself.

Another challenge occurred when working at a non-profit with an Executive Director whose values were unaligned with mine. It was more important to him that the organization we both worked for got credit for its work than whether the communities we served would most benefit from the approach we adopted. This experience taught me to prioritize values alignment with the next role I took (rather than to focus on salary, title or even subject matter).

Values-Driven Work: Working in Alignment

With that changed orientation, I moved to New York City to work for a global philanthropy where I truly flourished. Surrounded by people that shared my values, and who helped nurture my curiosity, I developed an approach to leadership rooted in active listening and self-reflection.

After eight great years with that organization, I decided to take a leap in January 2020: I started my own consultancy that offered professional coaching and other kinds of services to non-profits. Though it wasn’t the greatest time to start a new business (Covid!), I was still able to connect with clients who shared a conviction I have: People do their best work when they feel heard and seen, and creating such conditions requires intention (it doesn’t happen by accident).

The Leader’s Mindset: Uncovering Vision

But for leaders to truly embody this point, it does require them to be interested in self-reflection. To truly influence and inspire others, leaders need to understand the “why” for the things they do. This directly relates to a foundational component of one of the tools we use here at The Humphrey Group: The Leader’s Mindset. In particular, its focus on vision.

When a leader has vision, they can see the future they want and are committed to creating it. They’re also able to rally others and guide them toward this vision. When I work with a leader who is hoping to uncover their vision, I advise them to start with these two steps:

• First, they need to acknowledge the benefit of uncovering a deeper part of their motivation. That may sound obvious, but like most things in life, a vision won’t feel right if it’s created under false pretence. I talk to leaders about sincerely seeing the value in making these inquiries into the self, and understanding how this connects to the larger picture of them as a leader.
• Second, I recommend exploring this question with a coach, mentor, supervisor – whatever feels right. The point is to find someone who can help you, and to create a space where your path can be explored together.

Conclusion: Embracing Vision for Impactful Leadership

In my journey from lawyer to leadership coach, the importance of self-reflection has been paramount in defining effective leadership. Understanding one's 'why' through thoughtful introspection is crucial for any leader seeking to communicate a clear and compelling vision.

Our teachings at The Humphrey Group emphasize vision as a foundational pillar to leadership, and my background and experience has shown me how critical personal growth is to being able to form a meaningful vision.

By embracing their core motivations, leaders can inspire trust and drive meaningful action, ultimately creating a more engaged and motivated team. Recognizing and reflecting on these personal drivers is essential for anyone looking to lead with impact.

Curious to explore how self-reflection and vision can transform your leadership? Check out our Authentic Leadership™ program, designed to help leaders uncover their purpose and inspire others with clarity and confidence. Learn how intentional leadership can drive meaningful impact.