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Often, when someone calls me to talk about organising their Will, the discussion starts with: “I just need something simple.” Lately, technology enabled digital DIY Wills have also become a focal point.

Let me be clear: making it easier and more affordable for people to attend to their testamentary wishes is something we genuinely welcome and actively encourage.

Everyone should have these affairs in order. The uncomfortable truth is that far too few of us do. Recent ABC research indicated nearly half of all Australians pass away without a Will.

Measured against a number like that, anything which nudges more people to finally sit down and take action deserves a tick. Having a Will is almost always better than having nothing at all.

So this isn’t an article about why you shouldn’t do your own Will. For plenty of people, a straightforward Will is exactly right.

This is an article about the questions a form doesn’t know to ask you. In my experience, that’s where the real value of advice lies, and it’s where I see the most heartache when it’s missing.

Does what you want to happen actually match what a Will can do?

This is the one I see on repeat – over and over and over again.

Almost everyone believes they need a Simple Will. But a Simple Will is one tool of many available, and the right tool depends entirely on the job at hand.

Challenges arise where there is a gap between what you would like to happen and what a simple Will can actually deliver.

A few examples of where that gap quietly opens up:

  • You want to leave “your share” of something you own together with others – a property, a holiday van, a parcel of land – but the split was agreed around a kitchen table years ago and never written down. Your Will can gift your share, but it can’t in isolation prove what your share actually was.
  • You want to “leave everything equally”, but one child has already been helped financially, another has a vulnerability. This is where equal and fair can turn out to be very different things, and result in family provision claims.
  • You want to protect an inheritance to a child from their relationship or business challenges down the track – something a basic gift under a simple will can’t do, but the right type of will can achieve that.

Sometimes the most important conversation happens well before we reach the Will at all, about who actually owns what, and whether that ownership is recorded anywhere.

That last point matters far more than people realise. When an asset is co-owned on nothing more than a long-ago, unwritten understanding, simply gifting “your share” leaves your family to prove what your share was after you’re gone. That is one of the most common, and most expensive, ways an estate ends up in dispute. Establishing and properly documenting ownership now is often the single most valuable thing we do.

None of these are exotic situations. They’re ordinary families. The trouble is that a questionnaire can faithfully record your answer, but it can’t notice the question you didn’t know to ask.

Your Will is one document within an Estate plan – it is not the whole plan

Here’s another one which catches people off guard. Some of the things you most want to control may not be controlled by your Will at all. A complete estate plan usually reaches well beyond the Will itself.

Depending on your circumstances, it might include:

  • Enduring powers of attorney – so someone you trust can make financial and personal decisions if you lose capacity during your lifetime. Your Will does nothing while you’re alive.
  • Binding death benefit nominations for your superannuation – because super often doesn’t automatically form part of your estate, which means your Will may not direct where it ends up.
  • A letter of wishes – to guide your executor and trustee on the things the law can’t neatly put in black and white. Your emotional Will that has reasoning behind decisions and wishes.
  • A review of any company, trust or business documents – because assets held in a family trust or company aren’t owned by you personally, so your Will can’t gift them.

    Critically, I often find that what people think their trust deed or company constitution provides for, and what it actually says, are two different things.

  • An advance health directive – recording your wishes for medical care if you can’t voice them yourself.

You can see why “fifteen minutes online” sometimes can’t reach these corners – not because the technology is poor, but because it was built to produce a document, and not to understand your holistic situation.

The part people often never think about – and the part I’d ask you to think about most

Now to the part that matters most, and the part closest to my own work.

Alongside our planning practice, we do a significant amount of estate litigation and estate dispute work – it’s an area our firm is recognised in Doyle’s Guide for.

Spending years watching how Wills are challenged changes the way you prepare them.

Because here is something most people are never told: a Will is also a piece of evidence, and all the detail surrounding how it was prepared can be really important evidence.

And when a Will’s validity is questioned, the court isn’t really asking what the document says. It’s asking:

  • Did the person have the mental capacity to make a Will at the time they signed it?
  • Did they make it independently, of their own free will?
  • Was there duress, coercion or undue influence at play?
  • Did they know and approve the Will – did they understand what impact the Will has – who it affects and how?

And then the question that decides everything: can that be proven?

This is where the value of a properly prepared estate plan becomes real, and it stays almost invisible right up until the day it isn’t.

When I prepare a Will, the document is only half of what I create. Alongside it, I build a file which contains:

  • Contemporaneous notes of conversations.
  • My own assessment of your capacity and capacity tests conducted.
  • A record that I met with you on your own (or not), and what instructions you provided.
  • Notes of recommendations and advice given.

Most of the time, those notes are never looked at again. But on the painful occasion where someone might want to challenge your Will, those file records can be the difference between your wishes standing and your wishes unravelling.

This, along with me being an independent person, is the gap no online tool can close – and I want to be fair about why because it isn’t a criticism of the platforms.

A digital or paper form completed quietly at the kitchen table can capture your answers, but by its nature, it can’t independently observe your state of mind, confirm you were free from pressure, or stand as a witness years later to the fact that the decisions were genuinely yours.

And this matters more with each passing year. With property values where they are, and trillions of dollars set to pass between generations over the coming decades, there is simply more for people to dispute – and the appetite for disputing it is already there.

Recent Fidelity International research found that around 60% of Australians anticipate some form of inheritance dispute within their own family. If someone contests your Will after you’re gone, the people left to defend your wishes are the people you love, at the worst possible time.

The question I’d gently leave you with is this: if it ever came to that, what evidence would speak for you?

The take home message!

Online Wills and DIY kits have made estate planning more accessible, and that is genuinely a good thing. For some people, a simple Will is the perfect answer.

But “simple” should be a conclusion you arrive at with the help of legal advice, and not an assumption you begin with.

The real work of estate planning isn’t filling in the document. It’s making sure that what you want to happen and what your documents actually do are one and the same – that your plan reaches your desired outcome and that your wishes can stand up if they are ever called into question.

That’s the part worth a conversation. If you’d like to talk yours through, I’d be glad to help.