Why Financial Advisors Must Rethink Leadership—and What Comes Next

Fresh Insights I’ll Be Sharing at Advocis South Saskatchewan’s Fall PD Day

After years of speaking across the financial services industry—from Advocis to MDRT to NAIFA—I’ve learned that the one thing more dangerous than outdated information… is an outdated mindset.

So when the Advocis South Saskatchewan Board invited me to speak for 90 minutes at their Fall Professional Development Day on October 16, 2025, I knew it was time for a refresh. Not just of slides or stories—but of perspective.

Truth be told, dealing with change and transition on a daily basis inspires me to create. I wanted to challenge myself to design something that truly reflects the evolving world we live in—a world where financial advisors are no longer just managing portfolios. They’re managing people. Teams. Businesses. Legacies.

That led to a fresh presentation I’ve titled:

The Leadership Transition: Evolving from Salesperson to Consultant, to CEO, to Successor

How Financial Advisors Grow Into Leaders, Build Sustainable Businesses, and Create Their Legacy

This new keynote is drawn from the real transition work I’ve been doing with my clients—helping individual advisors evolve from transactional salespeople to trusted consultants, business leaders, and ultimately succession architects.

What We’ll Explore Together

In this 90-minute session, I’ll guide the audience through four predictable stages of professional maturity:

• Salesperson → Consultant
  Letting go of transactional selling and building trust-driven, advice-based relationships.
• Consultant → Business Leader
  Navigating the awkward middle: hiring, delegation, systems—and the identity shift from “doing” to “leading.”
• Business Leader → Succession Architect
  Redefining what succession really means and how to create continuity, culture, and capacity in your firm.
• Leader → Regenerative CEO
  Exploring the mindsets, habits, and systems that support long-term flow, purpose, and fulfillment.

We’ll also dive into psychological and emotional frameworks—like William Bridges’ work on change and transition—and explore how to break through the barriers that hold many advisors back from stepping into their next chapter.

This isn’t just about business transformation. It’s a personal one too.

For Every Stage of the Journey

Whether you’re still deep in production or you’re eyeing succession, this session will meet you where you are. It’s designed for boutique financial advisors who want to move from managing chaos to leading with clarity.

If you’ve ever felt stuck in your current role, unsure how to build a team, or wondering what legacy really means in your business—this talk is for you.

I’m grateful to Advocis South Saskatchewan for the invitation and the opportunity to contribute. And I can’t wait to share this with an engaged and evolving community of professionals.

Are you a financial advisor or agency owner with a growing team—or an Association Board Member looking for a fresh, relevant speaker for your next conference?

Whether you’re navigating leadership, growth, or succession—or curating meaningful experiences for your members—I bring practical insights grounded in over two decades of coaching and speaking in the financial services industry. Let’s explore how I can support your goals as a Fractional Chief Operating Officer and keynote speaker.

👉  https://leadingadvisor.as.me/callwithsimonreilly