Type "write me a will" into a chatbot and you'll have a document in under a minute. It will use the right vocabulary, it will be neatly organized, and it may even mention Maryland. That polish is what makes it risky.
People question a document that looks sloppy. They sign one that looks professional, put it in a drawer and rely on it for years. An estate plan gets tested after you've died or become unable to speak for yourself. The person who finds the mistake is your spouse or your child, and you won't be there to explain what you meant.
We use technology in our own practice and have no quarrel with it. It is worth being clear, though, about what a document generator can do and what it can't.
It sounds right. That doesn't make it right.
AI tools can misapply state law, skip signing requirements, overlook a blended family, miss tax and creditor issues, or produce language that reads well but doesn't do what you intended. Some will cite rules that don't exist. Because the output sounds confident, nothing on the page tells you something is wrong.
It can't ask the follow-up question
A plan has to work in a real family, with real history and real friction. Much of my job is asking questions people haven't thought to ask themselves:
Why this child as your backup trustee, and will your other children understand?
Is anyone pushing you to make this change?
Would an outright inheritance help this beneficiary, or put the money at risk?
How do you take care of your spouse and still provide for children from a prior marriage?
A chatbot answers what you type. It can't notice that you paused before naming a guardian, or that the conversation changed when we got to one of your kids. Those moments are usually where the real planning starts.
The hardest decisions are personal
Leaving unequal shares. Disinheriting someone. Protecting a child who struggles with money, addiction or an unstable marriage. These are legal decisions and family decisions at the same time.
We talk through how a choice will land with the people affected, and what can head off a fight later: a family meeting, a letter explaining your reasoning, protections built into a trust, or language precise enough to leave nothing to argue about. A chatbot can't sense guilt, grief or hesitation, and it can't tell whether someone is pressuring you.
Maryland has its own rules
Whether a will or trust is valid depends on state law, and states differ on witnesses, notarization, spousal rights, how property is treated and how probate works. A general-purpose tool can blend rules from several states without telling you.
In Maryland, for example, a will must be in writing, signed by you, and attested by two credible witnesses who sign in your presence. Maryland also has its own estate tax, with a $5 million exemption that sits far below the federal exemption of $15 million per person in 2026, and an inheritance tax that can apply to gifts to nieces, nephews and friends. A generic template won't account for any of that, and it won't warn you that it hasn't.
A will signed the wrong way may not count
A missing witness, a witness who didn't actually watch you sign, or a signing nobody documented can put an otherwise good plan in question. Plenty of estate disputes start with how a document was signed.
A chatbot can produce the document. It can't run the signing, confirm the witnesses qualify, or make sure you understand what you're signing. We handle every signing ourselves.
Your will doesn't control everything you own
A will or trust works alongside how your assets are titled and who is named on your beneficiary forms. Any of these can undo a well-written plan:
A 401(k) or IRA beneficiary form that names the wrong person or was never updated
Life insurance payable to someone you no longer intend to benefit
A house titled in a way that doesn't match the trust
Transfer-on-death designations on bank accounts that point somewhere other than your will
Assets that were never moved into the trust
When the beneficiary form and the will disagree, the form usually wins. Part of planning is checking that all of these point in the same direction.
What you type into a chatbot isn't confidential
Estate planning conversations often involve the most private things in a family: who gets less, who can't be trusted with money, who isn't speaking to whom. Typed into a public AI tool, that information generally isn't protected by attorney-client privilege, and it may be stored or used to train the system. What you tell your lawyer is protected by professional duties of confidentiality and, in most cases, by privilege.
Where that leaves you
A will or trust records your decisions. Planning is how you arrive at good ones. Someone asks why you chose your second child as trustee and notices when you hesitate. Someone checks that your beneficiary forms and your trust point in the same direction, supervises the signing so the witnesses qualify, and makes sure the people you've named know what they're expected to do.
If you've already drafted something with an online tool or AI, the time wasn't wasted. You've worked through decisions that will make a planning meeting faster, so bring the draft with you. What matters is whether it will do what you want when your family needs it.
Does your current plan do what you want it to? If not, let's talk. A First Conversation takes 15 minutes.
This article is provided for general informational purposes only and does not constitute legal advice. Every family's circumstances are different, and the laws governing wills, trusts, probate and estate administration vary by state. If you have questions about your estate plan, consult a qualified estate planning attorney in your jurisdiction.
