Elements of Leadership

Watershed’s Will Galloway: ‘Show Up and Participate as Informed Citizens’

Posted:  Wednesday, March 20, 2019 - 10:30am
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The Penobscot Bay Pilot’s series, “Elements of Leadership,” features leaders in local communities who reflect on the motivations and challenges faced by those in leadership roles. For the fifth installment of the series, Watershed School Head of School Will Galloway responded to six questions, in his own voice.

What do you wish you knew about Leadership in high school and college?

I wish that I had a greater appreciation for the fact that real change takes time, and usually more time than you expect. In my role as President of the Senior Class in high school, as editor of a college newspaper at Bowdoin College, and as a Peace Corps volunteer in Thailand, I have committed myself to making positive change in the world through expanding student voice in education, cultivating participatory democracy as informed citizens, and by helping people help themselves. These experiences have taught me that effective leadership demands patience and quiet determination.

What are the keys to developing the next generation of leaders?

Most importantly, the key to developing the next generation of leaders depends on cultivating resilience. The belief that it is good to do hard things and that there is great satisfaction derived from overcoming difficult challenges represent the enduring values at the heart of leadership for the next generation. Carol Dweck’s research on a Growth mindset sets the stage for moving out of our comfort zone into a learning zone that leaders must embrace. Challenging experiences bring into focus the idea that we still have work to do — that we are not there yet — and the equally important realization that we are in it together.

What steps can the next generation of leaders take to put them on the right path to leadership?

Start by seeing yourself in relation to others. By this, I mean that our worldview must shift from one based on individuals, independence, and rights to one that integrates others, cultivates interdependence, and builds on human relations.

“Seek first to understand others, and then to be understood.” — St. Francis. This practice will help to promote dialogue that is responsive, informed, and open to new ways of thinking and being in the world with others. Possibilities not thought of emerge and pathways open up for a new and shared perception of one another going forward. This kind of conversation, in the words of Mary Rose O’Reilly, “listens people into existence and saves lives.”

Align who you are with what you do. These words describe Purposeful Work at Bates College which is about helping students discover the joy and power that arise from identifying and cultivating their strengths and aligning them with their aspirations. Potential leaders will find the right path to leadership if and when they find what it is they love to do. In other words, do what you love. This is leading with integrity.

Lastly, Show Up and Participate as Informed Citizens. Margaret Meade once advised that we should, “Never doubt that a small group of thoughtful, committed citizens can change the world. Indeed, it is the only thing that ever has.” Putting this into practice, the next generation of leaders will need to be present, get informed, and follow through on what they say they will do.

How important is networking for successful leaders? How can the next generation of leaders best network right now?

Networks and networking reflect the very real way the world works — always in relation to others. Adopting this relational worldview puts each of us in touch with the people, resources, information, and opportunities to realize our human potential. The best way for leaders to network is through face-to-face conversation and dialogue. Where social media and the internet have their own effective uses and applications, I still hold that the best way to connect with others is to meet in person whether it is after class, over a coffee, at the conference table, or on a walk through the woods. Make time for it.

As a leader, how do you ensure your vision becomes reality?

I stay at it over a long period of time. I remind myself that small steps count as long as you’re headed in the right direction and paying attention. Fifteen years after starting a small, independent high school in midcoast Maine, I look around at what we have accomplished and know that this maxim holds true. Though your quiet determination might be overlooked by the bombast of others, stay true and focused on your goal with time on your side.

What’s the best advice that has been given to you?

“Be bold, persevere, and thank all those who helped you along the way!” — Thank you, Bob Rheault!


Reach George Harvey at: sports@penbaypilot.com