ask your questions while you can

AI should help us ask better questions, not just find faster answers

I'll say it upfront: I use AI in my work.

Every day. By choice.

It helps me prepare.

It helps me think more clearly.

It makes me better at my work.

Before I founded Sorted Planning, I spent part of my career evaluating AI technologies for recruitment. I worked with vendors to understand not just what their tools could do, but how they worked, where they could fail, and whether we could use them responsibly.

So this isn't a piece about resisting technology.

It's about something I keep noticing at the intersection of AI and healthcare — a distinction I think we're at risk of missing while everything moves so quickly.

AI is becoming extraordinarily good at answering questions.

I'm more interested in whether it helps us ask better ones.

The difference, and why it matters

Last week I wrote about my dad — seven weeks in intensive care, and a family facing decisions we'd never imagined making, because we had never truly asked him what mattered most.

Here's the thing: the information we needed didn't exist in any database.

No search could have found it.

No model could have generated it.

It could only ever have come from him—spoken out loud, to the people who would one day need to make decisions on his behalf.

That's when I realised something I've been thinking about ever since.

Preparedness isn't having all the answers.

It's making sure the questions are asked while the people who can answer them are still here.

This is the drive underneath everything I do now:

Ask your questions while you can.

Not only the healthcare ones.

The family ones.

The ordinary ones.

The ones you assume there'll always be time to ask.

Because there is a particular kind of grief in realising — too late — that the one person who has the answers is the person you can no longer ask.

That experience shapes how I see every new tool that promises to make healthcare easier to navigate.

Because there are two very different problems hiding inside "people are unprepared for healthcare decisions."

One is an information problem. People don't know what a ventilator does, what a substitute decision-maker is, what questions to ask at an appointment.

AI is genuinely brilliant at this. It explains without judgment, at 2 a.m., in plain language, for free. That matters — and I'd never minimise it.

The other is a conversation problem. The people who may one day speak for you have never actually heard you.

And that problem cannot be solved by information, however good, however fast.

What a form never hears

In my facilitation practice, something happens in almost every session.

Someone starts a sentence — "if I couldn't recognise the people I love, I wouldn't want..." — and stops.

They sit with it. They try different words. Sometimes they cry. Then they finish the sentence. And from that moment, the words are theirs.

A form never hears any of that.

A person completing a digital questionnaire can finish an entire plan without once saying their wishes out loud to another human being.

The document gets completed. The conversation never happens.

And when the crisis comes, what a family needs isn't the document.

It's the memory of having heard it.

Last night, I heard this same idea from an unexpected source.

During a webinar on digital legacy, researcher Dylan Thomas Doyle was asked how we make sure the plans people create actually get read.

His answer was simple: you can't. You can create a plan, but you can't make someone read it. The closest thing to a solution is communication—a document should be handed over with a conversation, so the person receiving it understands it isn't just another file.

It struck me because we had arrived at the same conclusion from different directions.

A document only works when someone has been talked through it.

When people understand the work, the love, and the weight of what they're holding.

Saying it out loud is the preparation

Here's what I've come to believe is the heart of it:

When someone speaks their wishes aloud to me in a session, they are rehearsing.

They're finding the words while the stakes are low — so that when they sit down with their partner, their sister, their chosen person, they've already said the hardest sentences once.

The second time is easier because of the first.

Technology that removes the social weight of these conversations — no judgment, no witness, no one to see you hesitate — genuinely lowers the barrier to starting. For some people, that's exactly what they need to begin.

The social weight was never just an obstacle.

For the conversations that prepare a family, it's the mechanism.

A form can help someone think.

It can't help them practise the conversation they'll eventually need to have.

A litmus test

So here's the question I now ask of every tool in this space — and I'd offer it to anyone building, buying, or recommending one:

Does this help someone say it out loud to the people who matter — or does it help them avoid ever having to?

Tools that pass the test look like preparation: they help people reflect before an appointment, organise their thoughts before a difficult conversation, understand their options well enough to discuss them confidently.

Tools that fail it look like substitution: the technology absorbs the conversation so the humans never have to have it.

The output can look identical. A completed document. A tidy plan.

The difference only shows up later — at a bedside, when someone turns to the family and asks, "what would they have wanted?"

Either the family has heard the answer in their person's own voice.

Or they're meeting it for the first time, in writing, at the worst possible moment.

More humanity, not less

I wrote last week that preparedness isn't built by technology — it's built by conversations, and technology should simply help more of those conversations happen.

I believe AI can do exactly that.

It can make the reflection easier, the information clearer, the starting point less daunting.

AI can create the conditions for better conversations.

It cannot have them for us.

The conversation itself — the hesitation, the finding of words, the being heard — still has to happen between people.

Healthcare has become exceptional at responding to illness and injury.

The next frontier is preparing people for it.

Only people can prepare each other.

AI can help make that possible.

And the most important preparation still sounds like a human voice, saying a hard thing out loud, to someone who loves them.

So use every tool that helps you get there.

And then ask your questions—while the person who has the answers can still give them to you.