When most people think about estate planning, they picture signing a will, a few pages that decide who gets what when they’re gone. But a will is only one small piece of a much larger plan. Comprehensive estate planning is more than documents, it’s how you leave the people you love, the values you want to protect, and the kind of care and dignity you want at the end of your life. It creates peace of mind for you and your family.
After years of helping clients through both routine planning and crisis situations, I’ve learned that the most meaningful estate plans start with questions, not forms. These questions guide not only the legal structure of your plan, but the emotional heart of it. Here are some of the most important questions to ask yourself.
Who do you trust to speak for you when you can’t?
Many people assume that their spouse or children can automatically make medical or financial decisions for them if something happens. Unfortunately, that’s rarely true. Without properly executed Powers of Attorney — ideally one for healthcare and one for finances — your loved ones could be left unable to access accounts, pay bills, or even talk to doctors on your behalf. That often leads to court involvement, delays, and stress during an already difficult time.
Ask yourself: Who truly understands my wishes and values? Who would make decisions the way I would, even under pressure?
That person should be designated as the agent in your Power of Attorney. The person you choose to be the agent for your Power of Attorney should be someone who lives nearby, handles stress well, and has your full trust. Just as importantly, you should think about who you don’t want in that role. A well-drafted Power of Attorney gives you control over both.
What kind of care would you want if you became seriously ill?
A will only applies after you die. But what about the months or years before, when you may need medical care, assistance, or decisions made about life support? An Advance Directive or Living Will allows you to decide, in advance, what kind of care aligns with your values. This is one of the most valuable documents you can have at the end of your life.
Ask yourself:
- What does “quality of life” mean to me?
- Would I want every possible medical intervention to keep me alive, or comfort care that eases my passing?
- Would I prefer hospice, hospital care, or dying at home surrounded by family?
These choices are deeply personal. But I’ve seen families torn apart when no one knows what their loved one would have wanted. Taking time now to clarify your wishes spares those you love from painful uncertainty later.
Who would care for your children if something happened to you?
If you have minor children, choosing a guardian is one of the hardest, and most important, decisions you’ll ever make. Who among your family or friends shares your values around education, discipline, and faith? Have you asked them if they’re willing to take on that responsibility? Who’s your backup if they can’t?
I include contingent trusts for minor children in my estate planning for clients to ensure their inheritance is managed wisely and for their benefit. A six-year-old can’t handle an estate, but you can plan so their care and finances are handled exactly the way you want.
Do you have loved ones who need special consideration?
Every family is unique. You may have an adult child with special needs, a loved one struggling with addiction, or a blended family where “fair” doesn’t always mean “equal.” Estate planning helps you protect vulnerable beneficiaries while preventing conflict. For example, we can plan so that a loved one can inherit without losing vital disability benefits. Or, if certain family relationships are strained, you can specify who should and shouldn’t be involved in your medical or financial affairs. These are sensitive issues — but ignoring them only creates greater challenges later.
How do you want to be remembered?
This is a question that often takes people by surprise. Beyond the legal documents and financial planning, what do you want your family to remember about you? I encourage clients to write an ethical will — a letter that passes on stories, values, and lessons. It doesn’t distribute assets. It shares meaning.
What personal items hold special meaning?
Often, it’s not the house or bank accounts that cause disputes. It’s the jewelry, the photographs, the heirlooms, the special items that carry memory and emotion. A comprehensive estate plan gives you space to decide who receives those items, and to document it clearly. That clarity helps preserve relationships and prevents hurt feelings later.
Are there potential sources of family conflict?
Disputes often arise not from greed, but from surprise. When children or family members don’t understand your choices, they may feel hurt or excluded. If you plan to leave different amounts to different people, or to disinherit someone entirely, include a brief explanation. A clear, compassionate statement goes a long way in preventing legal challenges and emotional fallout.
Have you shared your plan?
Even the best estate plan can fail if no one knows it exists. Once your documents are complete, talk to your family about what you’ve done, at least at a high level. Let them know where to find your documents, who the agents for your Powers of Attorney are, and how to contact your attorney. These conversations don’t have to be heavy. They’re simply about clarity and peace of mind.
The bottom line: ask the questions now, not later
The most problematic situations are the ones based on assumptions, that your family “knows what you want” or that your spouse “can take care of everything.” Your estate plan should do more than distribute property, it should tell your story and make sure your voice is heard when it matters most. If you haven’t started that conversation yet, now is the time.
If you would like a more thorough guide to the questions you should ask, and an understanding of what a comprehensive estate plan consists of, download our handout.
