AI Generated Wills – would you entrust your legacy to an algorithm?

10 April 2025

SHAY COLLINS – ASSOCIATE

Succession Planning,
Wills and Estates

In true lawyer fashion, I’ll start with a disclaimer: I’m NOT anti-AI.

I’m the first to admit it has its place—I use it for many things from getting a quick dinner recipe based on the minimal ingredients in my fridge, to creating home workouts based on the equipment in my shed. I even used it to craft a polite way of asking guests not to bring their kids to my wedding! I get it—AI can be super useful.

There is however one place AI absolutely doesn’t belong: helping you write your Will.

I recently put this to the test, trying out various marketed AI Will writing platforms, including ChatGPT, to draft a Will. As both an estate planning lawyer and a deceased estates lawyer, I have the perspective of not just drafting Wills but also witnessing how they’re applied in real life once someone passes. I see firsthand how a poorly drafted Will or one that misses critical elements can wreak havoc on families, both emotionally and financially. After conducting the online experiment, I was left with a very uneasy feeling about this AI movement in the legal world.

You Don’t Know What You Don’t Know

To the average person, the finished result of these AI-generated wills may seem acceptable. These platforms capture the very basic elements of a standard will and use familiar legal language. However, what concerned me most was the input process, and the complete lack of follow-up prompts once basic questions were answered.

Even in the most straightforward legal consultations, each answer typically leads to further questions and pathways. Clients’ body language, tone, pauses, and facial expressions provide valuable cues, guiding me towards the right follow-up questions.

As I navigated the AI questionnaire, I found myself thinking, “Surely, it will now ask me about X, Y, or Z.” But no, it didn’t.

Unfortunately, without the depth of understanding that a lawyer brings, you wouldn’t even know the critical questions that should be asked or the personalised options available to address your unique situation.

A crucial factor in determining the validity of a Will is whether the person at the time of making it had testamentary capacity. This is a legal assessment that a computer cannot make.

Capacity, Coercion and Claims Against Your Estate

Arguably, the most crucial factor in determining the validity of a will is whether the person at the time of making it had what’s known as testamentary capacity. This is a legal assessment that a computer cannot make. This legal test carried out by your lawyer during the appointment, is documented in detail afterward, and supported by an affidavit by said lawyer in the event the will’s validity is challenged after you die.

It saddens me to admit how often I’ve had to ask family members to leave the room while taking will instructions from elderly or vulnerable clients. In those moments, we become your advocate—standing as your voice when you feel pressured. We take on the difficult role of setting boundaries, protecting your true wishes, and ensuring we get to the heart of the matter: Is this what YOU want? AI can’t offer this. If someone’s behind you, influencing your choices, the computer won’t intervene—it can’t read the room and step in like we can.

In an era where entitlement is on the rise, the increase in contested estates is deeply concerning. AI simply cannot identify red flags or risks of a potential future Part IV claim against your estate. It cannot offer guidance on how to mitigate these risks or help you establish safeguards during your lifetime to prevent them.

The Client Lifecycle

In matters as profound as death and dying, there’s a unique bond that forms between a lawyer and their client. When guiding someone through the loss of a loved one or helping them plan for their own mortality, the relationship extends beyond mere professionalism. You’re not just their lawyer; you become a trusted figure in a family’s life, learning the intricate dynamics, sometimes working with their children, siblings, or even parents, depending on the situation.

As I’ve spent more time in this role, I’m seeing a shift. More often, clients are reaching out: “I want to see Shay. She helped me through my mother’s passing, and I want her to handle our affairs now.”

It’s a privilege to assist families at such a critical time, and I find myself more frequently managing estates of clients whose wills I drafted personally. Having been in the room with them and involved from the start, I already have a clear understanding of their wishes and family structure before meeting with the executors.

When it comes to something as significant as your Will, there is no substitute for qualified legal advice. While AI has its place, it simply cannot offer the depth of understanding, legal insight, or duty of care that this process demands. Your legacy deserves nothing less than the expertise of someone who understands both the law—and you.

Don’t entrust your legacy to an algorithm.