MacGregor Cup Awards

As co-CEO of Power To Be, Jason Cole is one of those modest leaders who helps other people be a better version of themselves, just by spending time in his company.

Intentional to the core, Jay evolved this ability to elicit the greatness within others over time and with practice—lots and lots of practice. Through decades of guiding people to safely enjoy the outdoors, Jay honed his ability to quickly ascertain a person’s skill level and then tailor the appropriate stretch goals for them. Born of the necessity to keep guests safe, Jay’s continual practicing of this skill—this right-sizing of goals—has served him well as his path carried him through a variety of leadership roles and into the seat of chief executive. Now, he meets every interaction from this place of looking for the growth that is possible, and asking himself how he can best serve. In this moment, with this person, what is required of me here and now?

If Roy Group had to define a dream client, Jay would be the embodiment of it. He frequently revisits the stickers and models in his Practice book, adding notes from what he learns through their application and thereby exemplifying what we teach: learning from his own experience, in a continuous feedback loop. Nearly a decade after he first took The Leader’s Discipline™, he still reviews the stickers and models before important conversations, as they help him select the correct array of practices to ensure the conversation delivers value for everyone involved.

Jay’s ability to choose the right tool for the right context showcases a leader who is deeply attuned to the needs of those he guides. This commitment to preparing for high-quality exchanges helps others travel further toward achieving their goals, untangling their knots, and learning from their own experience. Jay’s commitment to mastery positions others well for the next challenge in their journey. He embodies what we mean when we say continuous improvement.

Jason Cole, co-CEO Power To Be receives the 2023 MacGregor Cup award from Iain Duncan, Roy Group Practice Lead, Social Impact.

Patient and observant by nature, Jay listens before he speaks, gathering input from others so that when he does ask a question or share an opinion, it’s of maximum service to the group and the group’s goals. He notices what it is time for, and shift gears elegantly. “Jay doesn’t need to say much,” says Roy Group Practice Lead Iain Duncan. “He doesn’t feel the need to influence a conversation, choosing instead to allow the dialogue to unfold, speaking only when it becomes clear that something important might go unsaid.”

A student of pattern and complexity, Jay understands that things often are more nuanced than they first seem, so he’s found it’s worth listening and asking questions rather than starting with an opinion. “I’ve found a lot of issues or challenges that we face as leaders are very complex, even though they appear to be quite simple,” he says. “But there are many layers in there that need to be considered. And by sitting back and informing your ideas with the viewpoints being shared, it allows for better solutions.”

He holds a storyteller’s powers of observation, his radar ever attuned to the subtleties of human connection. “Jay is a scanner. He’s always noticing,” says Power To Be Director of Programs and Impact Carinna Kenigsberg. “He’s noticing when a waitress is speaking to somebody who’s living on the streets and is using their first name. He notices when somebody holds a door open for somebody else. When there’s a path filled with debris, he’s wondering who’s going to clear that path for the person walking behind them? That piece of integrity is something he can’t turn off.”

When it’s time to instruct, Jay uses stories to break complexity down into concepts that people can readily understand. “He’ll find the appropriate metaphor for the conversation to explain something complex in a way that everybody understands,” says Carinna. “It’s very practical, but it also creates a very deep understanding.”

Guided by his inner drive to be of service, Jay leads from a place of compassion and humility, and conceptualizes leadership as a learning journey rather than an end state a person can reach. “I hold myself up as a learner, not an expert,” he says. “Holding a learning stance gives you a state of open-mindedness as you tackle a situation that may look similar to another one, but really isn’t.”

Regardless of whether he’s spending time at work or paddling the Yukon River with his wife and daughters, Jay’s conduct is remarkably consistent. He simply looks for every opportunity to bring out the leader in others. He enters into every exchange from that place of noticing, meeting others where they’re at and then accompanying them along the path toward who they want to become. “Watching him interact with others when we’re not working is just as inspiring as when I’m listening to him lead our team, take us through a journey of training, or navigate a challenging conversation,” Carinna says.

2023 MacGregor Cup recipient Jason Cole, co-CEO Power To Be

He can’t help but deploy his finest conduct in service of furthering others toward becoming their finest self. “People on the team at Power To Be were excited when we promoted Jay to work as co-CEO,” says Tim Cormode, founder and former CEO of Power To Be. “I think that speaks volumes about Jay’s character.”

Through his perceptive and responsive use of the right leadership tool at the right time, Jay positions others for greatness and in so doing, inspires others to see themselves as leaders too. He sets an exquisite example for other heart-centered leaders, providing a powerful model of servant leadership. Jay’s refusal to be anything other than humble, paired with his ability to shift gears between coaching, advising and instructing, gives permission to other service-oriented people to lean into leadership that is similarly unobtrusive and perceptive. “Jay shows people that they don’t need to change who they truly are to take up leadership,” says Carinna. “They don’t need to become overtly present in a crowd, or loud. I’m excited for others to be motivated by his type of leadership. To see themselves as future leaders who embrace the same qualities.”

We’re very proud and excited to honour Jason Cole this year for the way he occupies the ground of genuine leadership.