The Canadian financial industry knows the Great Wealth Transfer is coming: 99% of advisors are aware, and most say they are prepared. Yet, only 28% of families expect a smooth transition. This gap between industry confidence and family reality was the catalyst for Empathy Unbound Toronto, where leaders gathered to ask the harder question: aware isn't the same as ready. So what does ready actually look like?
The thought leaders and panelists for the day included:
Jay McMahon: President & Chief Operating Officer, Specialty Life Insurance
Michael Aziz: CDO, Foresters Financial
Rick Williams: President, WFG Insurance Agency of Canada & WFG Securities of Canada
Amber Kanwar: Financial Journalist, Formerly at BNN Bloomberg
Linda Nazareth: Economist and Author
Nicholas Thompson: CEO, The Atlantic
The event also highlighted Empathy's latest research: The Hidden Barriers to the Great Wealth Transfer.
The day surfaced five key takeaways for the Canadian financial industry.
The relevance problem
The average Canadian advisor is 60 years old. The average heir inheriting wealth over the next decade is a millennial or Gen Z.
The panelists were candid about what this generational shift looks like on the ground. Younger clients, particularly millennials and Gen Z, have a fundamentally different definition of wealth compared to Gen X. For Gen X, wealth meant building assets, following Warren Buffett's principles, and accumulating for the future. In contrast, many younger Canadians see wealth as enabling lifestyle, impact, and flexibility—focusing on what they can experience and achieve now rather than what they can leave behind. Advisors who lead with portfolio allocation and compound interest often speak a language that resonates less with younger generations.
And the competition isn't other advisory firms. It's social media, actively shaping how young people think about money, success, and whether an advisor is even necessary. Reddit, TikTok, and Wall Street Bets are creating narratives about easy money and financial hacks that the industry is consistently losing ground to.
Our biggest competition is social media and how they influence everyone. We need to change that narrative, and that's where we work with our advisors to become ambassadors.
- Jay McMahon
Advisors who are making progress aren’t waiting for younger clients to come to them. They’re rethinking how the first conversation happens, who is involved, and what really matters in that discussion. The advisors who will succeed aren’t just experts in products. They’re the ones who can sit down with a 28-year-old and make the conversation meaningful.
Women at the center
The stat that should be on every institution's mind: approximately 80% of women who inherit after a husband or partner passes away change advisors. This isn’t just about targeting a demographic. In many Canadian households, women are already leading the most important financial decisions, and the industry is finally forced to pay attention and restructure accordingly.
The panel was honest about where the industry has historically fallen short: an advisory model built around one head of household, transactional selling, and a relationship style that doesn't translate. The fix isn't cosmetic but structural, and it shows up in how the best practices are already operating.
If you're not sitting down with both heads of the household to walk through the plan, you're not really doing a plan.
- Rick Williams
At its core, the ask is simple: meet women where they are, not where the industry has always been. That means rethinking how we connect. Less time on the golf course, more conversations that fit real lives. The wealth is moving. The real question is whether the relationship moves with it.
The annuity comeback
One of the bolder predictions to come out of Toronto: annuities are due for a revival, and many of the advisors who will need to use them have never actually recommended one.
With over $1 trillion expected to transfer in Canada over the next two decades, and heirs who often have very different financial habits and risk tolerances than the people who built the wealth, the case for structured income products is becoming harder to ignore. Term certain annuities and life annuities offer something the market can't: predictability for beneficiaries who might otherwise deplete an inheritance quickly.
I think with $1 trillion-plus transferring over the next 20 years in Canada, the annuity should play a big part in that. A lot of younger advisors have never used one.
- Jay McMahon
AI speeds things up, advisors make them matter
The industry question around AI isn't whether to use it. 97% of advisors already do. The real question is what you do with the time it gives back.
The operational gains are already visible in day-to-day practice. Post-policy letters that used to take an hour now take five to ten minutes. Advisors whose first language isn't English are running client communications through AI to ensure clarity and professionalism. Client plans are being stress-tested against AI before delivery, so the advisor walks into the meeting already knowing where the gaps are. The compliance process, long a source of friction, is getting faster and more consistent.
That time has to go somewhere, and the advisors who will win are the ones who are deliberate about where it goes: back into the relationship and into the conversations that only a human can have, into the moments AI cannot reach.
Because there are moments AI cannot reach. The panel was specific about what those look like: the feeling questions, the stories drawn from years of watching real families navigate inheritance, grief, and conflict. The experience of sitting across from a client who thinks they have it figured out and knowing, from having seen it before, exactly what they haven't thought of yet. No prompt surfaces that. No agent replicates it.
The advisors that are good at storytelling, knowing the right questions to ask, and creating the right emotional connection — AI is not going to solve that. It's only going to react to what you're prompting it.
- Michael Aziz
The prospecting challenge makes this even more urgent. The panel flagged a near-term reality: younger clients will increasingly arrive having already run their situation through AI. They'll feel informed. They may feel done. The advisor's job in that moment isn't to out-information the algorithm. It's to ask the question the algorithm didn't think to ask and to make the client feel, in a way a chatbot never can: that someone is genuinely in their corner.
Meeting Canadians where they actually are
The Great Wealth Transfer is a global story, but Toronto surfaced something specific to the Canadian lens: the $1 trillion changing hands over the next two decades arrives at a complicated moment, and the advisors and institutions that recognize that complexity will be better positioned to serve the families navigating it.
Linda Nazareth was candid about the backdrop. Canada faces a persistent productivity gap, expensive technology imports, conservative lending, and a small domestic market that makes capturing AI's promised gains harder than the headlines suggest. The economic tailwinds that would make wealth transfer straightforward aren't guaranteed.
AI, if used properly, can kick up productivity. This is an opportunity for Canada. But you have to get the right labor force in place.
- Linda Nazareth
That context matters for wealth transfer planning in a specific way. The $1 trillion transfer in Canada arrives at a moment when many heirs are already under housing and income pressure, and genuinely uncertain about what AI means for their careers. Inherited wealth, for many of them, will feel less like a legacy to build on and more like a cushion to land on.
The opportunity is real. But it requires meeting Canadians where they actually are—not where the wealth transfer headlines suggest they should be.
About the event
Empathy Unbound Toronto brought together industry leaders for an afternoon focused on one of the most consequential shifts in Canadian financial services.
The day opened with a deep dive into Empathy's latest research: The Hidden Barriers to the Great Wealth Transfer. A panel moderated by Amber Kanwar, featuring Jay McMahon, Michael Aziz, and Rick Williams, explored how advisors on the front lines are navigating the transfer today. A fireside chat between Nicholas Thompson and Linda Nazareth addressed AI, generational dynamics, and the future of work in Canada.