Estate conversations that convert

Imagine this scenario: You’re at a social gathering with family and friends. Someone you’ve known for years walks over, exchanges a few pleasantries and then asks, “How do you help your clients reduce probate fees on their estates?”

Much like I did early in my own advisory career, most advisors would immediately dive into reciting technical strategies: reduce the estate by gifting assets to intended beneficiaries before death, putting assets into joint ownership, naming beneficiaries on registered and insurance products or establishing inter vivos trusts to bypass probate altogether.

All valid strategies. All correct. And, in almost every case, all offered far too soon.

Leading with solutions isn’t always the most effective way to strengthen relationships or convert casual inquiries into meaningful business opportunities. In fact, the advisors who consistently create opportunity from estate conversations aren’t the ones who provide the fastest answers — they’re the ones who ask the smartest questions.

Research consistently shows that asking great questions creates stronger interpersonal connection. A 2017 study in the Association for Psychological Science found that follow-up questions significantly improve likability. And as Robert Cialdini illustrates in Influence: The Psychology of Persuasion, likability is a powerful driver of influence.

Layer in the principles of active, constructive listening — an approach outlined by Groysberg & Abrahams in Harvard Business Review — where advisors bring cognitive, emotional and behavioural awareness to every conversation, and you move the relationship from surface-level likability toward actual trust.

That shift is where estate conversations become client-acquisition opportunities.

Start with one simple question

So, back to your party-going friend asking about lowering probate fees. Instead of immediately diving into estate-reduction tactics, consider a single, strategic response: What has you asking this question?

This open-ended question accomplishes three things at once:

1. It slows the conversation down. It gives you time to understand the real issue behind the question.
2. It invites them to share the personal context. It could be a family situation, a recent death or a concern about their own estate.
3. It reveals the role. Are they thinking about this from the perspective of testator, executor or future beneficiary?

Once you know the role, the conversation becomes both easier and more valuable. You can ask smarter, more empathetic and more relevant questions that deepen the exchange and position you as a thoughtful advisor — without ever appearing sales-driven.

Role-driven questions

Here are questions tailored to each role, along with the purpose behind each one. These aren’t scripts. They’re conversation activators that help uncover needs, clarify misunderstandings and build trust.

If they’re a testator:

• Do you have a will? A foundational discovery question — and surprisingly revealing. The number of Canadians without a valid, up to date will remains high. Their answer tells you immediately whether the discussion is about optimization or starting from scratch.
• Who do you have to support now . . . and in the future? This shifts the conversation away from legal documents and toward the people they care about: spouses, children, dependant parents, charitable causes. It’s a more emotional — and more impactful — way to begin estate planning.
• Have you named a family member, friend or professional as your executor? Perfect for surfacing common issues: unequipped adult children, friends who don’t want the job or blended-family tensions that could complicate administration. It also opens the door to discussing corporate executors, fairness and the workload involved.

If they’re an executor:

• Have you ever administered an estate before? If so, how did it go? Most executors are appointed without a clear understanding of the responsibility. This question reveals their baseline experience and emotional state — two critical factors when determining how overwhelmed they may be.
• Have you reviewed the will and supporting documents in detail yet? This question often triggers the realization that they may not know where the documents are, which version is current or whether the estate includes complex assets. It positions you as someone who brings clarity, not complexity.
• What do you think will be the biggest challenges in settling the estate? Every executor anticipates something — family conflict, tax questions, liquidity issues or simply not knowing where to begin. Their answer will signal where they need guidance and how you can help.

If they’re a future beneficiary:

• Have your parents involved you or your siblings in their estate planning? In many families, the answer is no, which opens the door to an important conversation about transparency, expectations and preparedness.
• Do you think that you might need to help your parents financially in the future? This explores the direction of wealth flow. It reframes estate planning as a multi-generational conversation.
• Are your parents planning to leave everything to you, or have they implemented any generation-skipping strategies to reduce future tax exposure? This question sparks curiosity because most beneficiaries have no idea of what you’re speaking of. You are now positioned as an educator — not a salesperson.

The purpose behind the questions

These follow-up questions do more than keep the conversation going. They uncover the true context behind the initial probate inquiry and build likability through genuine curiosity.

They move the relationship toward trust, which is the real currency of advisory work. They position you as the advisor who listens. And they signal expertise without needing to prove it upfront.

This article is based on a presentation delivered by Daniel Collison at the National Estates & Legacies Summit.