Wilson College’s inaugural practitioners-in-residence came from different disciplines and tackled very different projects, but there was one thing they had in common — a firm belief that community is key for leadership to be truly successful.
Dana Cramer and Monique Pitt spent the 2025-2026 academic year working with Wilson College students in a variety of ways: workshops, office hours, mentorship and opportunities to participate in external events.
Cramer’s work focuses on internet governance, especially related to empowering the next generation of digital policy changemakers. A PhD candidate in a joint program between Toronto Metropolitan University and York University, she is the president of the Young Digital Leaders of Canada (YDLC) and worked with Wilson College students on the responsible and ethical use of AI.
As a result of Cramer’s mentorship, Wilson student Dayle McKay attended YDLC’s Youth Internet Governance Forum in Ottawa in 2025.
Pitt is a registered social worker whose project with Wilson College focused on developing innovative, play-based wellness experiences that foster leadership, collaboration and civic engagement.
The founder of GYALLIVANT, a wellness brand that centres the well-being of Black women and women of colour, Pitt also supports diverse community through her clinical practice.
We spoke with them about their experiences and their thoughts on leadership.
Leadership is often presented as something serious and results-driven. Monique, how do you define play in the context of leadership, and why does it matter?
Monique Pitt: When I think about play, I think about curiosity, adventure and experiential learning. It’s about creating space for people to engage in an activity without focusing on performance or productivity.
In my work with Wilson College, alongside project support assistant Sara Paterson, play-based wellness was about helping students slow down enough to be present. One practical way to do that was through activities connected to the five senses. Students would complete familiar activities, but at a slower pace, paying attention to what they could see, hear, feel, smell, and taste, and experience alongside others.
Play is especially important for leaders because leadership is often defined by what you produce and how you produce it.
Many people assume leadership is something done individually. Play provides space for people to build things together in a communal environment that feels less pressured and more exploratory.
That often leads to greater creativity and more meaningful outcomes.
Did you find that students recognized that they needed this kind of play and wellness — or that it was valuable?
Not always. Many young people don’t realize how much they need it until they experience it.
A lot of us are focused on completing tasks quickly and moving on to the next thing. When students are invited to approach a task through play, their reaction is often “That was actually fun,” or “I really needed that.”
What excites me about this work is seeing people realize there isn’t just one way to accomplish something well. Play reminds them that there are many different processes to tap into when achieving a goal, and some of them can be enjoyable. For many students, that realization comes as a surprise.
Dana, we know that artificial intelligence is reshaping society in ways we can’t yet predict. What role do you see young people playing in the AI space?
Dana Cramer: AI is changing not only the way we work but also how we understand ourselves socially. Young people are using AI in many aspects of their lives, including legal advice, relationship-building, personal wellness, research and decision-making. That creates important questions around the ethics of AI, the responsible use of AI, and the policymaking that needs to happen at the domestic and international levels.
Young people should be viewed as lived-experience leaders in AI. Just as previous generations grew up alongside the internet, today’s youth are growing up in an AI-native environment. They understand this technology from a unique perspective — one which is fresh and not competing with the digital environment of yesterday.
Research I completed at Wilson College found that young Canadians have consistently been at the forefront of global digital leadership. They have contributed to conversations around internet governance, telecommunications and global digital policy. The challenge is sustaining that leadership over time.
One way of enhancing that leadership ability is to bring young people together.
We need strong community-building at the local level to sustain momentum — spaces where young people can learn together, discuss AI together and actively participate in shaping policy.
We also need public policy that recognizes young people as stakeholders in AI development and governance.
Then you have the capacity for young Canadians to have a sustained effect on global dialogues and for us to be a real leader in the world as a middle power.
Both of your projects emphasize bringing people together in person. Why is community so important?
MP: We spend a great deal of time in isolation. In leadership spaces, isolation is often glorified—the idea that you should keep your head down, work hard and accomplish things on your own.
I think we need to remember how critical and necessary community is as we do this work. Leadership is not only about what you create; it’s also about how you feel while creating it. The people around us influence our energy, motivation and well-being.
I’m of Jamaican descent, and a big part of how we do everything is in community. Community has always been central to the way many cultures thrive and stay well. If we want leaders who are sustainable and healthy, we have to create opportunities for people to build and lead together.
DC: Leadership is inherently connected to community. You have to bring people together for them to understand their leadership potential. There are many definitions of leadership, but almost all of them involve relationships with others. Whether a leader inspires, serves or uplifts, community is part of the equation.
We also live in a world where our digital and in-person lives are deeply interconnected. We have this second lens of our experience being in our digital worlds as well. But if people only engage online, they miss an essential part of civic life. Bringing people together allows them to build relationships, learn from one another and better understand their own leadership potential.
MP: Part of what’s been great about the Wilson College Practitioner-in-Residence program relates to what Dana just said — we’ve been able to create a space where students aren’t just learning about these concepts online or reading about them, but are actually learning alongside other students in real time.
What skills do you think young leaders need?
DC: The first skill is resilience. Rejection is part of leadership, and they need to learn not to let rejection stall their progress.
I often share three rules about opportunity that I developed for myself in my 20s:
- Opportunities don’t come to pause; they come to pass. When one appears, take it and figure out the details later.
- Opportunities build opportunities. Once you gain one experience, others often follow.
- If opportunities aren’t appearing, create your own.
Young leaders also need innovation. No one is handed a pre-packaged life. You have to build your own path.
Just as important is learning to maintain what you create. Leadership isn’t only about starting things. It’s about sustaining them.
Finally, develop soft skills. Learn how to build relationships, communicate effectively, and engage with people from different backgrounds and levels of authority. Those skills often determine whether ideas gain traction.
MP: For me, when I think about skills, I think a lot about the power of self-reflection.
We spend a lot of time thinking about what other people want or what other people are doing. Leaders need to understand their own values and motivations. What do you care about? What do you want to contribute to society? What resonates with your values and who you are?
Another important skill is being willing to try something new.
I often say, “Try a ting,” which is a lesson from my Jamaican background. Don’t be afraid to step into unfamiliar opportunities. If something isn’t working, you can pivot. Leadership is not about getting every decision right. It’s about learning and adjusting.
I also believe leaders must celebrate their wins. People often move from one accomplishment directly to the next without taking time to acknowledge their progress. If you never pause to appreciate your growth, burnout can happen very quickly.
Most importantly, be yourself. The world doesn’t need more copies of existing leaders. It needs authentic leaders who understand who they are and lead from that place.
What are some different ways of being a leader?
MP: There are so many spaces and places that people can lead. Leadership can happen in government, business, technology, wellness, education or community spaces. It can start at home, in a classroom or through supporting someone who needs help.
Growing up, many of us were taught to think of leaders as being on TV, or in Parliament. While those roles matter, leadership also happens in everyday moments, meeting people where they are. People want leaders they can relate to and connect with — leaders who look like them.
When you recognize the leader within yourself and show up with authenticity, people often respond naturally — not because you claimed authority, but because you lead with care.
DC: Before leading others, you have to learn how to lead yourself.
Part of that process is understanding who you are, what motivates you and what kind of life you want to build. Self-discovery helps people find work and causes that genuinely matter to them. When you find that sense of purpose, leadership becomes much more sustainable.
Through self-discovery and the new knowledge you accumulate from it, you can be a leader of others once you become a leader of yourself.
Any last thoughts?
MP: I think that everything we come to in this life is a gift — and the support of Wilson College for the practitioners in residence has been amazing. The number of doors that have opened for me since completing this work, including receiving awards, meeting amazing students and developing newfound confidence in myself as a leader, has been inspiring.
DC: I also want to say thank you to Wilson College, and say that I didn’t realize how much the students would change me when I started this work. They taught me to meet them where they were, and it was phenomenal to get to know them. I’ve actually started writing a book inspired in part by what I’ve worked on this year.