Putting together a solid estate plan is more than just signing legal documents and filling out forms. Great estate planning starts with great conversations. And great conversations start with asking the right questions and truly listening to your clients to understand their values and wishes.
Why asking the right estate planning questions matters
When you take the time to understand what your clients value most, you can help ensure their wishes are truly reflected in their plan. Many families put off the harder conversations about death and legacy. By asking the right questions, you can help them face these topics and move forward with confidence.
According to Empathy research, while 87% of families say they’ve had some conversation about future plans, more than two-thirds admit those conversations have not led to clear decisions or outcomes. Our data also revealed that, even among the families with estate documents, only 47% say those documents are complete and easy to access.
As a financial advisor, you’re in a unique position to help clients spot gaps in their estate plan and start the conversations they may have been putting off. Together, you can work through what matters most and build a plan that fits their needs.
Questions about estate planning goals and financial values
Start by asking your client about their goals and financial values. This helps you understand what’s most important to them and sets the stage for a plan that fits their life.
What are your main goals for estate planning?
When you know what’s driving your client’s estate planning, every decision becomes clearer. Someone who wants to fund their child’s education will need a different approach than someone focused on supporting charities. The right questions help you tailor the plan to their real priorities.
What does financial security look like for your family if you’re no longer here?
This helps clients move from broad goals to specific outcomes. It brings out who they’re most concerned about, what financial security means to them, and whether their current plan actually meets those needs.
Are there values, conditions, or restrictions you’d like attached to any inheritance?
Many clients want their legacy to reflect their values, such as supporting education, encouraging entrepreneurship, or ensuring funds are used responsibly. This question can open up options like incentive trusts or conditional gifts.
How concerned are you about your estate being diminished by taxes or legal fees?
There's no right answer here, but knowing where your client stands can affect how you structure their plan. If they want to preserve as much wealth as possible for the next generation, you may want to have a conversation about tools like irrevocable trusts or gifting strategies.
What questions do you have for me about estate planning?
Open-ended questions like this invite your client to share what they need or expect from the process. It helps keep the conversation meaningful and focused on their real concerns.
Questions about assets and ownership
Questions about assets and ownership help you and your client get a clear picture of their financial situation.
What are your major assets and debts?
Talk through assets like real estate, bank accounts, investments, business interests, personal property, and any outstanding debts. This helps ensure nothing important is missed.
Do you hold any assets jointly with someone else, and do you understand how those transfer at death?
Jointly held assets usually pass straight to the surviving owner, no matter what the will says. Many people don’t realize this, which can lead to surprises or outcomes they didn’t intend.
Do you have assets that you would like to avoid probate?
This question is a good way to talk about estate planning tools like trusts, which can help clients avoid the time and cost of probate.
Have you made significant gifts in recent years, and do you understand how those affect your estate tax exposure?
Unreported or untracked gifting can create tax complications. This question surfaces a common planning blind spot, particularly among higher-net-worth clients.
How would you like to handle the distribution of your digital assets?
Digital assets such as social media accounts, online bank accounts, and cryptocurrency require specific planning because loved ones may not automatically gain access to them after the owner passes away.
Do you own any businesses that require succession planning?
Talk with your clients about who they want to take over their business and how they see that transition happening. This helps make sure their wishes are clear and actionable.
Questions about wealth transfer, key people, and roles
These questions help clients reflect on family dynamics and decide how they want their wealth to be passed on.
Who are the most important people in your life that you’d like to provide for financially if something were to happen to you?
An effective estate plan ensures that the right funds reach the right beneficiaries, prompting clients to think intentionally about their estate’s future impact.
Is there someone you would trust to make financial and healthcare decisions on your behalf if you’re unable to do so?
This question can help clients identify who they would want to legally authorize to make financial and healthcare decisions if they’re unable to do so themselves.
Who do you want to serve as executor or trustee?
An executor is responsible for settling a will, while a trustee is responsible for managing and distributing assets in a trust. Asking this question can prompt clients to determine who they can trust to handle those responsibilities.
If you have minor children, who would you want to serve as their guardian if something happened to both parents?
Guardian designation is one of the most emotionally significant and most commonly overlooked decisions in estate planning. Many clients with young children have never thought this through. Raise it explicitly.
Have you discussed your wishes with your beneficiaries or family members?
Data shows that more than half of people face emotional or relationship barriers when talking about wealth transfer and legacy. This question can help clients start those important conversations with their loved ones.
Questions About Life Insurance and Protection Planning
Life insurance is a key part of estate planning, but many families either don’t have coverage or aren’t sure what they have. These questions can help clients spot any gaps and see life insurance as a foundation for protecting their loved ones.
Do you have life insurance, and do you know whether your beneficiary designations still reflect your wishes?
Life insurance beneficiary designations supersede wills. An ex-spouse, a deceased parent, or a missing designee can completely derail the estate plan. This is one of the most common and most consequential oversights advisors encounter.
If you don’t have life insurance, what financial needs would you want it to fill for your family?
This opens the life insurance conversation around outcomes — income replacement, mortgage coverage, funding education — rather than products. It puts the client in the driver’s seat and helps you right-size the recommendation.
Have you thought about how a long illness or long-term care need could affect the assets you intend to pass on?
Long-term care costs can rapidly deplete even well-structured estates. This is a question most clients haven’t engaged with seriously, and it’s one of the most significant financial risks families face. Only 18% of families have long-term care or disability coverage.
Questions about existing documents
Be sure to ask about your client’s current estate planning documents. This helps you spot anything that’s outdated, incomplete, or missing.
Do you have an existing estate plan to review or update?
This question helps identify outdated information or planning gaps that may not reflect your client's current wishes or finances.
Have there been any major life changes since your estate documents were created?
Major life events like marriage, divorce, starting a business, or having a child can all change what’s needed in an estate plan.
Where are your estate planning documents stored, and does your family know how to access them?
Make sure your client knows that estate planning documents should be stored in a safe, secure location that is accessible to their loved ones.
How to approach the conversation
It’s normal for clients to feel uneasy about estate planning. These conversations often bring up tough topics like mortality and family relationships.
So when you bring up the conversation, lead with compassion. Reassure them that estate planning is about protecting their loved ones and not just preparing for death. For many clients, the conversation becomes much easier when it’s focused on outcomes, such as leaving a meaningful legacy and financially supporting their family. Another way to approach the conversation is by sharing real-life examples of how thorough estate planning helped past clients avoid unnecessary stress and financial trouble.
Most importantly, reassure clients that they do not need to have all the answers. Let them know you will guide them through the process, help them make important decisions, and connect them with the right professionals as needed.
Advisor FAQ
How often should I bring up estate planning with clients?
There’s no universal rule, but it’s a good idea to review your client’s estate plan every year or after major life changes like marriage, divorce, or the birth of a child.
Should financial advisors draft estate planning documents?
No. Advisors can help start the conversation, but it’s important to involve attorneys or use legally compliant software like Empathy LifeVault™.
What estate planning topics do clients most commonly overlook?
Beneficiary designations on retirement accounts and insurance policies are often overlooked, even though they override wills and are frequently out of date. Digital assets, healthcare directives, and long-term care planning are also consistently underaddressed. As a financial advisor, you can add significant value by helping clients spot these gaps.
About the Author
Andres Mazabel is Head of Estate Planning Solutions at Empathy. Across more than a decade in financial services and advisor support, Andres has focused on simplifying complex planning topics and empowering advisors with practical tools and data-driven insights.
Data referenced in this article is drawn from Empathy's original research report, The Hidden Barriers to the Great Wealth Transfer.