The first episode of Cover Your Assets opens with a premise that is at once simple and, for many advisors, quietly uncomfortable: the conversation that matters most is often the one that never happens1. AdvisorAnalyst’s Pierre Daillie and Ayal Cohen, President of Highpoint Life and Benefits Solutions, frame the problem with clarity. Compliance has grown heavier every year. Clients arrive better informed than ever. And each insurance specialty feels like a second career to master. So the conversation gets postponed. And postponed again. Until another advisor has it instead, and the assets follow.
Their inaugural guest, Michael Wills, Director of Business Development for Southwestern Ontario at PPI, knows what happens when the conversation arrives too late. Before entering the insurance industry, Wills spent years as a paramedic, showing up after the worst had already occurred. The parallel to financial planning is not metaphorical for him. It is structural. "I was just managing risk in a different way," he says. "I just didn't know it."
Wills carries that clarity into everything he does now. And the message he delivers to wealth advisors is one of the most practically useful things a working advisor will hear: you do not need to become the expert across all lines of insurance. You need to know where the expertise lives, and how to bring it to your client's table without losing the relationship, the revenue, or your weekend.
The Paramedic at the Table
Wills describes his paramedic years as an education in asking the right questions under pressure. Arriving at someone's worst moment demanded a rapid assessment of known and unknown risk, the development of an immediate plan, and the discipline to refer the patient to the specialist who could do what the paramedic could not. "I'd come in, I'd talk to the patient, I'd ask them a lot of questions, I'd dig deep, and then I'd figure out what I'm looking at just from the information I'm gathering."
The instinct transferred without translation. His personal experience of a critical illness in the family while going through a divorce, with two young daughters and a first responder's salary, gave him the conviction that the conversation about protection is not a product pitch. It is, as he frames it, the difference between showing up early and showing up too late.
At PPI, Wills describes his role as something between a people connector and a roadblock remover. "I remove roadblocks for advisors when they get stuck, and I really work on helping them identify planning opportunities within their practice. I bring in the expertise to help them when they need it, or we just have conversations that make them more comfortable about having those conversations themselves."
The Real Reason the Conversation Doesn't Happen
The compliance burden is real. Wills confirms that PPI has tripled its compliance team in the last two to three years, not to police advisors but to make sure they are equipped when an audit arrives. But compliance is not the deepest reason for the silence. The deeper reason is psychological.
"We have a lot of A-type personalities in this industry," Wills observes. "And we always want to know the answer. And it's okay not to." The advisor who cannot admit a knowledge gap on insurance is the same advisor who postpones the conversation rather than risk appearing incomplete. The result is a gaping hole that someone else eventually fills.
Wills is direct about what fills it. "A lot of people just assume that somebody else is having the conversation. The wealth advisor's assuming the CPA or the lawyer's having the conversation. The lawyer and the accountant are thinking that the wealth advisor's having a conversation. And there's this gaping hole in everybody's plan."
The advisor who can say "this isn't what I do, but I have a team behind me that does know what they're doing" is, in Wills' view, not diminished by that admission. The advisor is elevated by it. "What we want to know is the people that we can call if we don't have the right answers. And we have the answer for the client."
Bringing in the Experts: Protection Without Losing the Relationship
The fear that stops many advisors from bringing in a third-party insurance consultant is not ignorance of the opportunity. It is fear of losing the client. Wills addresses this directly and without softening it.
"Make sure that they're trusted, make sure they're either accredited or linked to some kind of insurance consultancy program, that there's legal agreements in place, make sure you sign things to protect yourself, protect your business."
MGAs including PPI formalize this through written agreements with insurance consultants. These agreements are explicit: the consultant does not disrupt the referring advisor's business, does not approach the client independently, and does not compete for the relationship. "We have legal agreements with these consultants to never disrupt your business, to never steal a client, which is one of the major concerns. We have agreements in place and we have a team of consultants that'll come in and help you write business."
Daillie draws the analogy that applies to every referral-based profession. In commercial real estate, every sign reads "brokers protected." The advisor who brings in an estate lawyer or accountant does not worry that the lawyer is going to walk away with the client. The same logic must apply when bringing in an insurance consultant. The written agreement is not bureaucracy. It is the scaffold that makes the partnership possible without anxiety.
Wills puts it plainly: "You do not need to know everything. You just need to recognize when there's an issue or an opportunity for planning. And that planning might involve insurance."
Two Portfolios, Not One
One of the session's most powerful conceptual contributions is Wills' framing of the insurance portfolio as a second folder sitting alongside the investment portfolio. Clients who understand there are two should have both reviewed, both updated, and both actively managed.
"They know there's another portfolio. There's not just a portfolio of investments and wealth. There's an insurance portfolio. That is part of their ultimate plan. There should be two folders."
The real estate case he walks through illustrates the stakes at the high end. A client who has accumulated multiple properties as a wealth-transfer strategy faces a forced liquidation problem at death if insurance is not in place to fund the estate's tax liability. The family that planned to inherit the portfolio may be forced to sell the best assets to pay CRA. A well-structured insurance solution converts an illiquid estate problem into a clean, private, tax-efficient transfer. "I know another product that does that. Tax free. Also grows."
For younger clients, the entry point is simpler. Term insurance is the starting point, the foundation, and, critically, the option. Cohen frames it with the precision of an options trader: term is a call option on future insurability. A client who is healthy today and buys term retains the right to convert to whole life or universal life later, regardless of what their health looks like then. No medical underwriting required. "If you become diabetic, if you've had a heart attack, whatever it is, you can. It's literally the option to buy other insurance later on."
The Monday Morning Move
When Daillie pushes Wills toward the actionable close, the answer is precise. "Tomorrow, how well do you really know your top twenty-five clients? How robust of a KYC do you have on those clients? Do you know everything about them?"
The audit begins with triggering events: clients approaching retirement, aging parents, inheritances incoming, business succession outstanding. From there, the advisor does not need to have the answers. The advisor needs to ask the questions and know who to call. "Don't be afraid to bring in the experts or bring in somebody that can help you have those conversations."
Wills closes with the line that captures the entire conversation in a single sentence: "Do what you do best and find a team that will work with you to support you in all ways so you can build the best practice possible."
5 Key Takeaways for Advisors and Investors
1 Expertise mapping is a core professional competency. Advisors do not need to master every insurance line. They need to know precisely where the expertise lives, have trusted relationships with the specialists who hold it, and bring those specialists to the client table efficiently. The advisor who can say "I know who to call" is more valuable than the advisor who pretends to know everything.
2 Formalize every consulting relationship in writing. Before bringing any insurance consultant into a client case, advisors should have a signed agreement that defines boundaries, protects the client relationship, and clarifies that no solicitation or independent approach to the client is permitted. MGAs like PPI provide these frameworks. The agreement is not a formality. It is the mechanism that makes collaboration safe.
3 The insurance conversation protects the advisor's book, not just the client. An advisor who has not had the insurance conversation has left the door open for someone else to have it. That is not just a missed revenue opportunity. It is a relationship vulnerability. Wills' case studies demonstrate that advisors who build insurance planning into their practice build a fence around their client base.
4 Think in two folders, not one. Every client should carry an investment portfolio and an insurance portfolio. The insurance portfolio is not a liability column. It is a risk-mitigation strategy, an estate-preservation tool, and, in many cases, a tax-efficient wealth-transfer vehicle. Advisors who frame it as such create a new planning dimension that clients have often never considered.
5 Start with term and preserve optionality. For advisors not yet comfortable with complex insurance products, term insurance is the entry point. It is straightforward to explain, provides foundational protection, and, through its convertibility feature, keeps all future planning options open regardless of the client's future health. The conversation that starts with term often ends with a comprehensive estate plan.
Footnote:
1 Podcast, Cover Your Assets. “The Gap in Every Client File: The Conversation Advisors Keep Skipping.” AdvisorAnalyst.com. N.p., 20 July 2026. Web. 20 Jul. 2026. <https://advisoranalyst.com/2026/07/20/the-gap-in-every-client-file-the-conversation-advisors-keep-skipping.html/>.
