The Estate Planning Conversation Clients Don’t Want to Have (But Need To)

Written by Estate Planning Attorney Regan Caruthers 

Understanding why people avoid estate planning and how to navigate these difficult estate planning conversations can help clients move from procrastination to action. 

As professionals, we spend a lot of time helping clients prepare for the future. Yet some of the most important estate planning conversations are often the hardest to start. Whether you are an estate planning attorney, financial advisor, CPA, or elder law professional, you have likely encountered clients who avoid discussing death, incapacity, or what happens when the unexpected occurs.  

At Gravis Law’s Knoxville office and locations across the country, we regularly see how meaningful guidance can help families address sensitive topics before a crisis forces the conversation. 

Why People Avoid Estate Planning 

Many clients understand they need an estate plan. The challenge is not a lack of information. The challenge is often emotional. 

Some common reasons clients avoid estate planning include: 

• Fear of discussing death or disability 

• Anxiety about family conflict 

• Uncertainty about making the “right” decisions 

• Concern about aging and loss of independence 

• Belief that they have “plenty of time” 

For many people, talking about estate planning feels like acknowledging something they would rather not think about. As trusted advisors, recognizing that hesitation is often rooted in emotion rather than logic can help shape a more productive conversation. 

Helping Clients Reframe the Conversation 

Instead of focusing on death, focus on control and protection. 

Clients are often more receptive when the discussion centers on protecting loved ones, preserving family harmony, maintaining financial stability, and ensuring your wishes are honored. 

This simple shift can help overcome estate planning procrastination and make the conversation feel more empowering. 

How to Have Difficult Estate Planning Conversations With Your Clients 

One of the most effective ways to approach difficult estate planning conversations is to ask direct, specific questions rather than open-ended ones. When clients are overwhelmed by the idea of death and dying, broad questions can leave them stuck in their own heads. 

Instead of asking “How do you envision your assets passing at your death?”, try something more direct: “When you both pass away, how do you want your estate split between your children?” Specific questions give clients something concrete to respond to rather than an emotional spiral to navigate. 

It also helps to bring some levity to the conversation. Estate planning is a heavy topic, and humor can be a surprisingly effective tool. Framing a catastrophe beneficiary question as “Okay, if a meteor hit the family reunion, what do we want to happen to everything?” sounds lighthearted, but it gets clients thinking through real scenarios without the emotional weight of imagining actual loss. 

Finally, help clients see that this process is a gift to their family, not just a task for themselves. A simple reframe like “Your children will be grateful you went through all this trouble” shifts the entire tone of the conversation. Reminding clients that good planning can save their family real money and stress down the road moves the focus from something they are dreading to something they are doing for the people they love most. 

With the proper framing, good questions can lead to fruitful discussions about estate planning by focusing on practical scenarios that clients can easily understand and relate to. 

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Small Conversations Create Big Progress 

Not every meeting needs to resolve every issue. Sometimes success looks like: 

• Identifying a decision-maker 

• Starting beneficiary discussions 

• Clarifying healthcare preferences 

• Scheduling a follow-up meeting 

Progress often happens one conversation at a time. 

What Happens If All of My Beneficiaries Have Passed Away? The Beneficiary Question Clients Avoid 

One question my clients commonly struggle with involves contingent or catastrophe beneficiaries. 

In simple terms, what happens if everyone they intended to leave assets to has already passed away? 

This question often creates discomfort because it forces clients to imagine multiple losses occurring within a family. 

Yet, failing to answer this question can create significant challenges during Probate. 

When discussing catastrophe beneficiaries, encourage clients to think about: 

• Extended family members 

• Charitable organizations 

• Religious institutions 

• Educational foundations 

• Other causes important to them 

The goal is not to dwell on worst-case scenarios. The goal is to ensure their wishes remain clear no matter what happens. 

“What Happens If One of My Children Dies Before I Do?” 

This is another incredibly difficult topic my clients frequently avoid but should definitely consider. Many parents find this possibility emotionally overwhelming and unimaginable. As a result, they often leave important decisions unaddressed or they decide, “Well, it will never happen, so I do not need to plan for it.” 

This discussion affects: 

• Beneficiary designations 

• Trust planning 

• Distribution structures 

• Future generations 

Questions worth exploring include: 

• Should a deceased child’s share of the inheritance pass to their children? 

• Should assets be divided among surviving siblings or other beneficiaries? 

• Should a trust be created for grandchildren? 

These conversations often connect naturally to discussions about Wills & Trusts. 

While uncomfortable, addressing these issues today can prevent confusion and conflict for future generations. 

Helping Clients Move From Avoidance to Action 

Estate planning is not simply about documents. It is about helping people make thoughtful decisions during moments that can feel emotionally challenging. 

Whether you are helping clients with estate planning as an attorney, advisor, CPA, or other trusted professional, your ability to guide these conversations may be one of the most valuable services you provide.  

By approaching sensitive topics with empathy, patience, and practical guidance, you can help clients create plans that protect the people and values that matter most. 

Questions? I’m Here to Help. 

At Gravis Law’s Knoxville office and offices nationwide, we help individuals and families navigate estate planning conversations with confidence. If your clients need guidance creating or updating an estate plan, our team is here to help.  

Contact us today to learn more about our estate planning services and how we can support the families you serve. 

About the Author 

Regan Caruthers is an attorney with Gravis Law in Knoxville, Tennessee, where she focuses her practice on estate planning and probate administration. She helps individuals and families prepare for the future through wills, trusts, powers of attorney, and other planning tools, while also guiding loved ones through the probate process after a loss. Regan is passionate about helping families navigate difficult transitions with confidence, clarity, and peace of mind. 

A Knoxville native, Regan earned both her bachelor’s degree and Juris Doctor from the University of Tennessee before being admitted to practice through the Tennessee State Bar. Known for her attention to detail and compassionate approach, she strives to make complex legal matters feel approachable and manageable for her clients. When she is not practicing law, Regan enjoys reading, knitting, and spending time with her dog.