How to make a difficult decision with AI

By the end of this, you will have a clear, weighed-up view of a tough choice: the options laid out, the pros and cons on the table, and the trade-offs made plain. The final call is still yours, but you will make it with a clearer head.

What you will need

• Any AI chat tool: Claude, ChatGPT, or Gemini all work well.
• The decision you are facing, and the options you are weighing.
• A quiet 20 to 30 minutes to think it through properly.

A quick word before you start: AI is a good thinking partner, but it does not know your life, your values, or how you will feel about the outcome. Use it to see the choice more clearly, not to make the choice for you.

Step 1: Lay out the decision

Start by telling the AI what you are deciding and what your options are. Getting it out of your head and into words is often the first thing that brings some clarity.

I'm trying to make a decision and would like help thinking it through, not being
told what to do. Here's the situation:

[describe the decision]

The options I'm weighing are:

- [option one]
- [option two]
- [any others]

Please don't recommend anything yet. First, ask me any questions that would help
you understand what matters to me here.

What to expect: the AI will ask about your priorities, your worries, and what a good outcome looks like to you. Answering honestly is what makes the rest useful.

If it does not work: if it jumps to a recommendation, reply with “Please hold off. Ask me your questions first, and don’t tell me what to choose.”

Step 2: Weigh the options side by side

Now ask the AI to set your options against each other. Seeing them laid out in one place makes trade-offs far easier to spot than turning them over in your mind.

Lay my options out side by side. For each one, give the main pros and cons, and
note the biggest trade-off. Show it as a simple table so I can compare them at a
glance. Base this on what I've told you matters to me.

What to expect: a clear comparison that makes the differences and trade-offs visible. Read it and notice where you find yourself agreeing or resisting, that reaction is useful information.

If it does not work: if it feels one-sided, reply with “Be even-handed: give each option a fair set of pros and cons, and don’t nudge me towards one.”

Step 3: Pressure-test your leaning

Once you feel a pull towards one option, it helps to have it gently challenged. Ask the AI to play devil’s advocate so you are choosing with your eyes open.

I'm leaning towards [option]. Challenge me: what am I possibly overlooking, what
could go wrong, and what would I regret if I chose this? Then do the same for the
option I'm least keen on, in case I'm dismissing it too quickly.

What to expect: a set of honest challenges and blind spots for both sides. Some will not apply, but the ones that make you pause are worth sitting with.

If it does not work: if the challenges feel soft, reply with “Be tougher: give me the strongest possible case against my leaning.”

Step 4: Sum it up and sit with it

Finally, ask for a plain summary of where things stand. A clear recap gives you something to reflect on rather than deciding in the heat of the moment.

Sum up where this decision stands: the strongest case for each option and the key
trade-off I'm really choosing between. Don't tell me what to pick. I want to make
the final call myself.

What to expect: a fair, balanced summary that frames the real choice. Read it, then step away for a while before you decide.

Wrapping up

You now have a clear, weighed-up view of your choice, with the trade-offs out in the open. The decision itself is yours to make, and it should be, because you are the one who lives with it. If the AI mentions any facts or figures along the way, check them yourself, since AI can occasionally state something with confidence that is not quite right.

A tip for the final step: once you have decided, imagine yourself a year on, having chosen it. If that thought brings relief, that tells you something. If it brings a knot in your stomach, that tells you something too.