📰 How to get an honest answer out of ChatGPT

For a long time, I used ChatGPT like a vending machine. I would type a quick question, take whatever came back, and never once stop to ask whether it was actually right. I was not really using it. I was just poking it. Only about a quarter of adults over fifty have used ChatGPT at all, so if it still feels unfamiliar to you, you are in good company.

By the end of this short read, you will:

Here is something worth knowing before you ever ask ChatGPT what it thinks of your plan. These tools are trained to give answers people like, which makes them lean agreeable. Ask "is this a good idea?" and you will usually get a warm yes.

MIT Technology Review has written about this tendency – the term is sycophancy, a fancy word for the tool trying to keep you happy. It got pronounced enough that last year the company behind ChatGPT rolled back an update for being too flattering. The way I have come to picture it is an eager intern: quick, capable, genuinely useful, and also keen to please – willing to tell you what you want to hear. That is lovely, right up until you are trying to test whether a direction actually fits you.

Last week we talked about noticing whether a direction feels like you or feels forced. AI can help you pressure-test that, but only if you stop it from cheerleading. Ask it to bless your plan and it will. Ask it to challenge your plan and it will do that too and that is the version worth having.

Here is the whole thing, and it takes about two minutes. Open ChatGPT (the free version is fine) and paste something like this, with your own direction filled in:

Then read what comes back slowly. Some of it will miss. Some of it will land in a way a yes never could. You are not looking for the AI to decide for you – you are using it to surface the questions you have been avoiding.

Two small rules keep this safe and useful. Give it a little context, because a sentence about your situation makes the answer far better. And check anything it states as fact, since these tools can be confidently wrong – treat the reply as a thoughtful draft, not a verdict. AARP has a plain-English guide to prompting a chatbot if you want the basics.

If you would like a few more ready-made prompts to try, my free Simple Prompts for ChatGPT guide has a batch you can copy and paste. There is nothing to buy — it is yours to download and keep.

If you do this, one of two good things happens. Either the direction holds up under honest questioning and you walk away more sure, or a few real doubts surface early, while they are still small and cheap to deal with. Both are wins.

If you skip it and only ever ask AI to agree with you, you get a comfortable answer and no new information. That is the quiet cost of the vending-machine habit – you leave with exactly what you walked in believing.

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So here is the small ask, and there is no wrong answer. If you try the prompt this week, reply with one word: did ChatGPT tell you something you did not want to hear? Just "yes" or "no" is plenty. You do not have to share what it said. I read every reply, and I am always curious what the honest version turns up.

Talk soon,
Bob

A short story from my desk about the boring little tool that quietly runs this whole operation. No sales in it, just a look behind the curtain.