How Advisors Can Pace the Estate Planning Conversation

We get it. Estate planning is not the most romantic conversation to have.

It brings up family, health, the unknown, responsibility, and questions most people would rather put off. Even advisors who know how important it is can hesitate, worrying about making clients uncomfortable or not even knowing where to start. 

But here is the reality: when the estate planning conversation is avoided, the relationship does not grow stronger. It simply misses an opportunity to deepen trust.

According to Trust & Will’s 2025 Estate Planning Report, 83% of Americans say estate planning is important, yet only 31% have a will. That gap exists not because people do not care, but because they are unsure how to begin. 

With Valentine’s Day approaching and long-term commitment top of mind, this is an opportunity for advisors to step in and thoughtfully bring the estate planning conversation into their client relationships.

I spoke with the Trust & Will Advisor Contributor Panel about how advisors can avoid moving too fast when introducing estate planning. Here are four ways to start the conversation with clients thoughtfully, without rushing it or avoiding it altogether

1. Incorporate Estate Planning Into Your Discovery Process

Nearly every advisor agreed on one thing: estate planning shouldn’t feel like a surprise topic or a standalone agenda item. Instead, it works best when it’s woven naturally into discovery.

Chitra Patel, Founder and CEO, WealthWorth, shared that at Wealthworth she “starts the conversation softly so it does not feel overwhelming. Estate planning is part of our discovery questionnaire and part of understanding a client’s priorities.”

Al Faber, CFP®, Founder of DIWY Financial Planning echoed that approach:

“As you go through accounts, beneficiaries, and whether they have kids, estate planning just comes up as part of the conversation.”

This matters because clients increasingly expect it. Trust & Will’s 2025 Financial Advisor Report found that 70% of clients believe advisors should offer estate planning services, and 40% would consider switching advisors to access them. Introducing it early is not pushing, it’s meeting expectations. 

2. Let Family and Values Lead the Conversation

Estate planning often feels uncomfortable when it starts with documents, legal jargon, and all the financials. It feels far more natural when it starts with people. This is where advisors should lean in. 

“I always start by learning about a client’s family,” shares Ryan L. Goldschmitt, WMCP, Founder of Geminus Wealth Partners, “I want to understand who is important to them and who they are responsible for.”

Matthew Ricks, CFP, founder of Haystack Financial Planning often leads with decisions that feel the most relevant to clients right now, like power of attorney and healthcare directives because “people care about what happens to them while they’re alive.”

When you begin by understanding who matters most to your clients and what they want to protect, estate planning feels relevant, personal, and easier to engage with.

3. Read the Room, Then Engage

Many clients signal interest well before they are ready to act. They mention they have thought about estate planning or acknowledge they know they should do it, but hesitate to take the next step. Like many meaningful commitments, the pause is rarely about a lack of care. There is uncertainty about how to begin.

“When I ask clients about estate planning, most say they’ve thought about it but haven’t gotten around to it,” shares Vinee Mehta, CFP®, AIF®, Founder of Truly Unbiased, “To avoid moving too fast, I have them focus on a few key questions at a time.”

Bob Chitrathorn, CFP®, CPFA®, Co-Founder & CFO of Simplified Wealth Management,  sees that hesitation not as resistance, but as an opening to lead with empathy.

“Life gets busy and emotions get heavy, but that delay doesn’t mean disinterest,” he explains. “It means they need help getting unstuck. What works best is reconnecting them to why they wanted to start in the first place. Not the documents. The people.”

When clients reconnect with who they are protecting and why it matters, momentum builds naturally.

“Then it’s about making the next step feel doable,” Bob adds. “Trust & Will removes the intimidation and meets clients where they are. When I can say, ‘Let’s log in together and walk through it,’ confidence builds quickly.”

Like any meaningful relationship, estate planning moves forward not through pressure, but when the timing feels right and the conversation is guided with care.

4. Progress Matters More Than Perfection

One of the biggest reasons estate planning gets delayed is the belief that everything has to be decided at once. Advisors on the panel were clear that this mindset often creates more friction than clarity.

Ryan L. Goldschmitt, reframes the goal for clients, “This is not about making perfect decisions right away. It is about avoiding default outcomes you would not want.”

It’s also important to help clients feel prepared before they ever sit down to complete their documents. “When clients think through the major decisions ahead of time, they don’t freeze,” says Charles Thomas III, CFP®, Founder of Intrepid Eagle Finance , “It helps them move forward instead of putting it off.”

When advisors emphasize progress over perfection, clients feel permission to take the first step and trust that the plan can grow with them over time. Like any lasting relationship, estate planning works best when it is allowed to develop gradually, with guidance, flexibility, and room to adjust as life changes.

Interested in partnering with Trust & Will to enhance your own clients’ estate planning needs? Learn more about how you can join over 20,000 financial advisors and firms who are delivering peace of mind to their clients by offering a comprehensive estate planning solution. Schedule a free demo today.

Trust & Will is an online service providing legal forms and information. We are not a law firm and we do not provide legal advice.