Estate planning is one of those things we tend to notice when someone else has not done it.
Maybe your parents keep saying they will eventually update their trust. Your brother just had his first child and has done no planning at all. A close friend is going through a divorce or recently bought a home. Perhaps someone you care about has told you outright that they do not have a will, trust, power of attorney, or healthcare directive.
You know enough to recognize that they should take care of it. What you may not know is how to bring it up without sounding intrusive, morbid, or as though you have suddenly developed an unusual interest in what happens when they die.
It can be an uncomfortable conversation, but it does not have to be. When it comes from genuine concern rather than fear or judgment, talking about estate planning can be a very practical way of looking out for someone you love.
Why Is Estate Planning So Hard to Talk About?
Most people who have not completed their estate planning are not ignoring it because they do not care about their families. More often, they know they should do something and keep moving it further down the list.
Caring.com’s most recent Wills and Estate Planning Study found that only 24% of surveyed Americans had a will in 2025. Among respondents without a will, 43% said they simply had not gotten around to it. More than half of those without a will or trust said either that estate planning was low on their list of priorities or that they did not believe they had enough assets to need one.
That sounds much more like procrastination than resistance.
Estate planning also asks people to think about subjects most of us would rather postpone. Who should make medical decisions if I cannot? What happens to my children if I die? Who should inherit my property? What if my family disagrees? What happens if I develop dementia or suffer a serious illness?
There is also money involved, and family relationships, and sometimes complicated histories people would prefer not to revisit. Put all of those subjects together and it is easy to understand why someone can spend ten years saying, “I really need to get my estate plan done.”
Knowing that helps when you are the person bringing it up. You are not trying to convince someone that death exists. You are simply helping them move something important from “I know I should” to “I finally did.”
Start With Your Own Experience Instead of Telling Them What They Should Do
One of the easiest ways to make an estate planning conversation uncomfortable is to begin by telling another adult what they need to do.
If you have completed your own planning, talking about your experience usually feels much more natural. You might tell a friend that you finally updated your trust and were surprised by how much had changed since you last looked at it. You could mention that the process made you realize your beneficiary designations were outdated or that you had never really thought through who would make decisions for you if you became incapacitated.
That gives the other person room to join the conversation without feeling like the subject of an intervention.
You can also be candid about having procrastinated yourself. Saying, “I put mine off much longer than I should have, and I was really relieved once I finally took care of it,” will usually land much better than, “You really need an estate plan.”
The point is not to deliver a speech. You are opening a door and letting the other person decide whether they want to walk through it.
Life Changes Give You a Natural Opening
Some moments make an estate planning conversation especially appropriate because the person’s life has just changed in a meaningful way.
Marriage is one of them. So are divorce, the birth or adoption of a child, purchasing a home, starting a business, receiving an inheritance, losing a parent or spouse, and moving to another state.
Rather than treating one of those events as an excuse to lecture someone about planning, connect the conversation to what has actually changed. A friend who just had a baby may be far more receptive to, “Have you guys talked about who you would want to care for her if something happened to both of you?” than to a generic question about whether they have a will.
Someone who recently remarried may need to think about how an existing estate plan works with the new marriage, particularly if either spouse has children from a prior relationship. A business owner may need to think about who has authority to operate the company during an incapacity and what happens to the ownership interest at death.
Those questions are relevant to what is happening in the person’s life right now, which makes the conversation feel less abstract.
Ask Practical Questions Instead of Talking Only About Death
Estate planning gets much easier to discuss when you stop treating it as synonymous with dying.
A significant part of estate planning deals with what happens while you are still alive. In California, a financial power of attorney can authorize someone to handle specified financial and legal matters, while an Advance Health Care Directive allows you to identify the person you want making healthcare decisions if you cannot make or communicate those decisions yourself.
That gives you other ways to start the conversation. You might ask an unmarried friend, “If you were in the hospital and could not make decisions for yourself, who would legally be able to step in?” Or you might ask your parents whether you would know where to find their important financial information if one of them suddenly became ill.
These questions tend to make estate planning feel more immediate because they involve situations people can imagine happening at any age.
They also get to the real purpose of planning. The goal is not simply to decide who gets your property someday. It is to give the people you trust clear authority and guidance when you cannot handle something yourself.
If You Are Talking to Your Parents, Make It About Their Wishes
Talking with parents about estate planning can be particularly delicate because adult children do not want to appear interested in their parents’ money.
The easiest way around that is to make the conversation about your parents rather than their assets.
You do not need to know their account balances or what everyone is inheriting. You do need to know whether they have put a plan in place, whom they want making decisions if one of them becomes incapacitated, and whether the people they have named know where the documents and important information can be found.
You could say, “I don’t need to know the details of what you’re leaving anyone, but if something happened to one of you, would I know who to call and where the documents are?”
That is a very different conversation from asking what is in the trust.
If your parents tell you everything is handled, you do not need to interrogate them. You can encourage them to make sure the plan has been reviewed recently and that the people who will eventually have responsibilities under it know where to find the appropriate information.
If You Are Talking to a Friend, Respect the Boundary
Friends can have extraordinarily close relationships, and for many people, close friends really are chosen family. That does not mean you need to become your friend’s estate planning advisor.
You do not need to determine whether they need a trust, tell them whom to name as trustee, analyze their beneficiary designations, or convince them that their current documents are wrong. Those decisions depend on facts you probably do not know and legal considerations you should not be expected to evaluate.
What you can do is raise the issue and offer a resource.
If you recently completed your own planning and had a good experience, tell them. If there is an article that explains an issue they have been wondering about, send it. If you know an attorney you trust, offer the name.
Then leave the decision with them.
People are much more likely to take action when they feel supported than when they feel pressured. Your role as a friend is not to make them complete an estate plan. It is simply to make it a little easier for them to take the next step if they are ready.
What Can Happen When Someone Never Makes a Plan?
There is a reason these conversations matter beyond checking an item off a to-do list.
When someone dies without a will or trust in California, state law determines who inherits assets that are subject to intestate succession. Depending on how the person’s property is owned and the value and type of the assets involved, a court probate may also be necessary. California Courts explains that when formal probate is required, the court appoints a personal representative to collect estate property, pay bills and obligations, and ultimately distribute the remaining assets to the people legally entitled to receive them.
That does not necessarily mean the state takes everything or that every estate becomes a disaster. Those are common exaggerations about dying without an estate plan.
The problem is that California law is now supplying the plan instead of the person who died.
The result may be exactly what the person would have wanted, or it may be very different. An unmarried partner or close friend may not have the rights someone assumed they would have. Family members may disagree about who should handle the estate. A parent of minor children may never have documented whom they would want the court to consider as guardian.
Incapacity creates a different set of concerns. Without appropriate advance planning, family members may discover that loving someone and being the obvious person to help does not automatically give them legal authority over that person’s finances or healthcare. California law provides court procedures such as conservatorships when someone needs assistance and less restrictive alternatives are not adequate, but planning in advance can give a person much more control over whom they want involved and what authority that person should have.
This does not mean every conversation needs to be filled with worst-case scenarios. It simply explains why encouraging someone to plan can be an act of care rather than an uncomfortable discussion about death.
Sometimes the Most Helpful Thing You Can Do Is Make the Introduction
I receive referrals from clients and professional colleagues regularly, and I think there is an important difference between referring someone and trying to sell them on estate planning yourself.
An introduction removes one of the barriers that keeps people from moving forward: figuring out whom to call.
Estate planning is personal. People are talking about their children, money, relationships, fears, family dynamics, health decisions, and what they want to happen after they are gone. It makes sense that they would rather begin that conversation with someone who has been recommended by a person they trust than choose a lawyer at random from an internet search.
If someone you care about tells you they have been meaning to get their planning done, you can simply say that you know an attorney you trust and would be happy to make an introduction. From there, let the attorney explain the process and let your friend or family member decide whether it is right for them.
That is enough.
Estate Planning Conversations Do Not Have to Be Heavy
You do not need to gather everyone around the dining room table for a formal family meeting every time estate planning comes up. Some of the best conversations happen casually, over dinner, on a walk, during a phone call, or after someone mentions a change happening in their life.
You also do not need the perfect words. If the conversation comes from a place of genuine concern, people usually understand that.
You might talk about something you learned while doing your own planning, ask a practical question about what would happen in an emergency, or simply tell someone you care about that you would feel better knowing they had their affairs in order. If they are receptive, keep talking. If they are not, respect that and leave the door open.
August is National Make-A-Will Month, so it happens to provide an easy reason to bring the subject up. The conversation, however, matters throughout the year because estate planning is not really about a particular month or even about making a will.
It is about making life easier for the people you love and making sure your own wishes are clear when you are no longer able to explain them.
At Cheever Law, our Life & Legacy Planning® process is designed to help individuals and families think through those decisions in the context of their actual lives, including what would happen during incapacity, how assets will be handled, who should make important decisions, and how the plan will work for the people they love.
If this article brought someone to mind, feel free to share it with them. If you are the person who has been putting your own planning off, contact us or schedule a 15-minute introductory call to learn more about getting your plan in place.