Jocelyn Ayson: A Day at Government House

November’s Leadership Winnipeg session was nothing short of extraordinary. Our group had the privilege of gathering at Government House—a building I’ve passed countless times and even worked across from for years, yet never stepped inside. To finally visit was exciting enough, but to be welcomed by the Lieutenant Governor of Manitoba, The Honourable Anita Neville, made the experience truly special.

The day began with a keynote from Connie Walker, President and CEO of United Way Winnipeg. What stood out most was her honesty. Rather than a speech of grandeur, Connie shared stories of challenges and lessons learned. Her advice resonated deeply: lead with empathy, trust your team, and have the courage to ask why.

The session continued with conversations that were both inspiring and practical. Four incredible leaders joined us to share their journeys:

Kevin Selch, economist turned entrepreneur and founder of Little Brown Jug Brewing Company, encouraged us to pursue our passions and keep moving forward—even when challenges arise.

Sandy Chahal, COO at Lawton Partners Wealth Management, emphasized building a team you can trust. Her leadership philosophy mirrored my own, reminding me that I’m growing in the right direction.

Carly Edmundson, President and CEO of CentrePort Canada, spoke about perseverance and maintaining belief in your vision during tough times. Her advice: “Be kind, not just nice, and let others learn.”

Jessica Dumas, Leadership Winnipeg alumna, speaker, and coach, shared wisdom on confidence and impact: “If you’re not uncomfortable, you’re not making an impact.” Her feedback to me—“Share what you know with conviction”—was a powerful takeaway.

One moment that truly shifted my perspective came during a conversation with Kevin. I mentioned joining Leadership Winnipeg to gain tools for leadership, and he replied candidly: “Leadership Winnipeg won’t teach you how to be a leader—it gives you the chance to meet leaders and learn from their stories.” That honesty helped me realize what I was really seeking: insight into challenges, approaches, and confirmation that I’m on the right path.

This session was more than a visit to an iconic building—it was a day of learning, reflection, and connection. I left feeling inspired and reassured that leadership isn’t about having all the answers; it’s about listening, growing, and helping others succeed.