For nearly three decades, Jack Armstrong has had a front-row seat to greatness. As TSN’s Basketball Insider and the voice of the 2019 NBA Championship-winning Toronto Raptors, he’s witnessed the electric moments that define champions — the buzzer-beaters, the comebacks, the triumphs. Before broadcasting, Jack was the youngest Division I basketball coach in NCAA history. This unique dual perspective has given him unparalleled insight into what separates championship cultures from the rest.
Jack recently joined us as part of our client-exclusive event series, At The Spotlight, where he delivered an inspiring masterclass in leadership that transcended basketball. Through captivating stories infused with humour, wisdom from a life well lived, and lot’s of NBA insider tidbits, he unpacked the essential elements that create winning cultures both on and off the court.
Excellence is a Habit: The Foundation of High Performance
Successful teams — whether in basketball or business — share a consistent pattern. “High achievement takes place in the area of high expectation and high standards,” Jack said. Excellence is a habit, he added.
Take Steph Curry for example. Jack has known him since he was a child as his father, Dell Curry, spent the last three years of his career playing for the Toronto Raptors. “His habits are precise. Practice does not make perfect. It’s perfect practice that makes perfect,” Jack said.
This same principle applies across all high-performing organizations — habits separate winners from everyone else. We need to set the bar high, Jack said, and demand that of ourselves and others.
The Tools of Championship Leaders
Before building championship teams, leaders must develop themselves first. This starts with two essential practices:
1. Self Reflection: Seek Outside Perspectives
Too often, we get caught in the inertia of our jobs without recharging our batteries or investing in our own growth, Jack said. Early on in his coaching days, Jack had a boss who challenged him every off-season with a simple assignment: come back to me in the fall and tell me three people you met outside of coaching that helped you develop your leadership skills.
Great leaders seek outside perspectives — what Jack calls “quality control.” Jack has his own “kitchen cabinet” as he calls it. Six or seven trusted advisors from different walks of life who “tell me what I need to hear, not what I want to hear.”
2. Fight for Your Reputation
Self-improvement is only part of the equation. Leaders must also be intentional about how they’re perceived.
We’re in the business of wanting more business. How do we get that? The three R’s: Recruitment, Retention, and Referral.
“The biggest decisions that happen in your career happen when you aren’t in the room,” Jack said. “What are they saying about you? You personally, your company, how you do business, how you treat people — that’s really important.”
People can spot the actors — those who have style versus substance. Fight for your reputation. “The companies and the people who really value that stuff, that stuff matters. That makes a difference. That’s what winners do.”
Rules without relationships equal rebellion. Rules with relationships equal respect and results.
Building Championship Teams
Once leaders commit to their own growth, they can turn their focus outward to building championship teams. This requires understanding a fundamental truth about human behaviour.
Jack calls it the seven R’s: Rules without relationships equal rebellion. Rules with relationships equal respect and results.
The commonality? Communication. Relationships. Connecting on a human level. So how do you build those relationships? It starts with how you show up as a leader.
Lead Personally, Not Electronically
One of the biggest mistakes leaders make today is leading from behind a screen, Jack said. They’re sitting in their office all day firing out emails instead of working the room and getting to know their people. The risk? “If you decide to lead electronically, you’re going to be replaced by AI.”
Building relationships requires showing up. Face to face interactions builds connection and creates clarity and understanding in ways emails never can. Make yourself valuable through your ability to lead, inspire, motivate, connect, mentor, and help people grow. That’s what will matter even in an age of electronic dominance, Jack said.
Create Dialogue, Not Monologue
Great leaders create environments where everyone’s voice matters. Something Jack learned as a young assistant coach was that you want to make sure everyone’s heard. “You never know when a really good idea is in the room,” Jack said. “You want people to express their opinion, not suppress their opinion.”
This requires genuine listening. When people feel heard, they engage. When they’re ignored, they check out. Dialogue builds the relationships that earn respect and deliver results.
Why Teams Fail
Teams fail when individual agendas take over, Jack said. People not checking their egos at the door, not making the sacrifices needed, and not buying into to the team vision.
This is where Jack’s five Ps come in: Proper planning prevents poor performance. As legendary coach John Wooden warned: “Let us not mistake activity for achievement.” Everyone’s busy. What matters is results — the tangible outcome of your work.
“We live in such a distracted society that we lose our way, we lose our focus, we lose our vision,” Jack said. Without a clear plan with a focus on results, individual agendas fill the void.
The Championship Blueprint: Success vs. Significance
Early in his coaching career, Jack attended a clinic where legendary Notre Dame coach Lou Holtz spoke. Holtz kept repeating one phrase: “It’s all about the dash.” When you go to a cemetery and see a gravestone, there’s a birth year and a death year. But between them is a dash. “The dash represents your life. The dash represents the impact you’ve made on others. Have you left this place a better place?”
That’s when it dawned on Jack: “There’s a big difference between being successful and significant.”
Success is about what you achieve. Significance is about who you impact. You can make all the money in the world, win every award, climb every ladder — but if people don’t care who you are as a person, what does it matter?
Championships aren’t built on talent alone. They’re built when leaders commit to high standards, continuous growth, genuine relationships, and the courage to prioritize impact over accolades. Championship cultures aren’t built by successful people — they’re built by significant ones.
Ready to Transform Your Team into Champions?
We laughed, we cried, but most importantly, we all walked away a little wiser from Jack’s incredible story-driven keynote. He brings his energy, coaching philosophy, and three decades of championship insights to every stage. Having interviewed countless NBA stars and coaches throughout his career, Jack delivers compelling stories from basketball’s biggest stages alongside proven frameworks that help teams connect, collaborate, and commit to something bigger than themselves.
Contact us today to book Jack Armstrong for your next event.
