Vanilla

Jun 02, 2025

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How to Bring Up Conversations About Estate Planning With Clients

Estate planning is one of the most important—and frequently overlooked—aspects of a client’s financial life. Despite its importance, a significant number of adults don’t even have a basic will in place. This gap represents both a risk to clients’ families and a tremendous opportunity for advisors to deepen relationships by addressing a crucial area of need.

While estate planning conversations can feel awkward or emotional, avoiding them may result in confusion, unnecessary expenses, or the client’s final wishes not being carried out. When advisors take the lead in these discussions, they provide peace of mind, safeguard client legacies, and position themselves as holistic financial partners. This article offers practical strategies to help advisors introduce estate planning conversations with empathy, clarity, and confidence.

How to overcome resistance to estate planning conversations

Why clients resist estate planning

Clients often resist estate planning for deeply personal reasons. The topic may evoke discomfort because it forces them to confront mortality or acknowledge family dynamics. Others procrastinate due to the perceived complexity or expense of planning, or believe it’s only necessary for the wealthy. Some fear the legal process, while others simply don’t know where to start.

Advisors should approach these concerns with empathy. Recognizing the emotions behind the hesitation helps establish trust and opens the door to a productive conversation.

Strategies to overcome hesitation

To overcome this hesitation, advisors can:

• Lead with empathy: Reassure clients that estate planning is about care and protection, not just death.
  
• Reframe the conversation: Focus on outcomes like protecting family or preserving a legacy.
  
• Share real-life stories: Illustrate how thoughtful planning avoided hardship—or how lack of planning caused it.
  
• Educate simply: Explain that estate planning isn’t just for the wealthy or elderly and can be more accessible than clients assume.
  
• Offer support: Position yourself as a partner who will walk them through each step, coordinate with professionals, and simplify the process.
  

Common client concerns about estate planning

Addressing common objections directly can reduce anxiety and spark engagement:

• “I’m not wealthy enough for an estate plan.” Estate planning isn’t just for millionaires. It ensures that wishes are honored—whether related to personal belongings, guardianship, or healthcare directives.

• “It’s too early – I’m too young and healthy to worry about this.” Life is unpredictable. Planning ahead while healthy allows for thoughtful decisions and flexibility to update later.

• “Estate planning is expensive and complicated.” Basic plans, like a will and beneficiary designations, are often affordable and straightforward. Not having a plan can lead to higher legal fees and stress later.

• “I don’t want to think about death or incapacity.” Frame the conversation around love and protection—planning is a positive act that ensures loved ones are cared for.

When and where to initiate estate planning discussions

Knowing the right time to start the conversation

Opportunities to raise estate planning include:

• Major life events like marriage, the birth of a child, home purchases, or retirement.
  
• Regular financial reviews and planning sessions.
• Whenever a strong relationship is established and trust has been built.
  

Advisors shouldn’t wait indefinitely—timing the conversation thoughtfully increases client receptiveness.

Setting a comfortable environment

Choose a private, quiet space—whether in-office or via secure virtual meeting—where clients can focus without feeling rushed. Let them know in advance that estate planning will be on the agenda. Encourage clients to include spouses or family members when appropriate. This normalizes the topic and emphasizes the advisor’s commitment to holistic planning.

How to start estate planning discussions

Starting the conversation can be the hardest part. Here are some warm, non-threatening openers:

• “I want to make sure every aspect of your financial life is in order. Have you thought about how you’d want your assets managed if something happened to you?”
  
• “One area we haven’t covered yet is estate planning. What are your thoughts on how you’d like to provide for your family in the long term?”
  
• “Many clients find peace of mind through estate planning. Would you be comfortable talking about ways to protect your legacy?”
  
• “As we look toward your retirement and beyond, have you thought about who would take care of things if you weren’t able to?”
  

Start with curiosity and care. Asking about a client’s values or family goals naturally leads into the topic, and using relatable stories can help normalize the discussion.

Estate planning communication tips and best practices for advisors

Effective communication is the foundation of successful estate planning conversations. Here are six best practices:

Use clear, simple language

Avoid jargon. Instead of “probate,” say “the legal process after death.” Keep terms approachable to help clients feel at ease.

Example: “A healthcare directive is simply a document that lets others know what kind of medical care you want if you can’t speak for yourself.”

Demonstrate empathy and patience

Validate emotions. Let clients know it’s okay to feel unsure or emotional.

Example: “I know this isn’t easy to think about, which is why I’ll guide you through it one step at a time.”

Frame estate planning in positive terms

Shift the focus to protection and peace of mind.

Example: “This plan ensures your family is protected and your values are honored, no matter what happens.”

Invite and encourage client questions

Questions signal trust. Make space for them.

Examples: “What concerns you most about estate planning?” or “Is there anything you’re unsure about in this process?”

Position yourself as a guide, not a salesperson

Your role is to support—not to sell.

Example: “I’m here to help you navigate this, so the plan truly reflects your wishes and protects your family.”

Pace the conversation according to client readiness

Some clients need more time. Break it down and revisit the topic over multiple meetings if needed.

Check in often and ask: “Would it help if we took this one step at a time?”

Applying these principles builds stronger advisor-client relationships and eases clients through a process they might otherwise avoid.

Conclusion 

Bringing up estate planning is a crucial part of every advisor’s role. Though these conversations can be emotional or complex, initiating them demonstrates care, builds trust, and ultimately provides clients with peace of mind.

Don’t wait for clients to ask—be proactive. By leading the conversation, you ensure their wishes are honored, and you strengthen your role as a lifelong financial partner.

Want to make estate planning even easier for you and your clients? Vanilla’s estate planning software simplifies the process, enhances collaboration, and ensures plans are accurate and actionable.

Get a demo today and start delivering the estate planning support your clients truly need.

The information provided here does not constitute legal, financial, or tax advice. It is provided for general informational purposes only. This information may not be updated or reflect changes in law. Please consult with an estate attorney, financial advisor, or tax professional who can advise as to your particular situation.