The art of communicating with machines
Want better answers from ChatGPT and the like? An NTU academic explains why it starts with asking better questions – and why it’s not so different from talking to people
by Ian Tan
Visual: Ian Tan, using Google AI Studio
I often quip that in my NTU undergraduate courses, I teach people how to talk to people. And when I’m conducting generative artificial intelligence (Gen AI) workshops, I teach people how to talk to machines.
While many people think that you need to be highly technical to use Gen AI, I have never worried about my lack of coding ability. In 2022, when I first started using imaging platform Stable Diffusion, I quickly realised that using Gen AI was about figuring out what questions to ask.
And I have no problems asking questions because I worked for a decade as a journalist. I spent years mastering how to press the right buttons with carefully selected words. Then, as I began using Gen AI more often, and also coaching others in it, I saw how it responded well to good communication techniques.
Why? While this machine has no soul, it has absorbed massive amounts of human conversations. That is why it is likely to work better when you are a good conversationalist.
Here are a few ways you can engage with both man and machine alike.
Get them to show off
Whenever you meet a stranger, it’s good to get them talking about themselves. You know the standard icebreakers, like “So, what do you do for a living?” or “Do you have any pets?” People often love telling you about what they like, or what they can do well.
In the same way, I like to ask Gen AI apps if they can do a challenging task, so they can show off their prowess.
I’m always asking them weird questions, like “Can you count the number of calories in this photo of my lunch?”, “Can you tell what I’m thinking from this selfie?”, or “Can you create an app to solve my budgeting problem?”
That is how I’ve discovered Gen AI’s undocumented abilities – not because someone told me about them – but because I ask it something I’d love to ask another human.
Try asking AI this: “What is my greatest character flaw?”
It told me: “Ian, you have too much drive applied in too many directions.”
Hey, that’s quite true.
Remember that nobody can read your mind
Many relationships turn sour because both parties behave like the other is an expert mind reader.
When your significant other is unhappy with you, it is your responsibility to find out why, and not to make assumptions.
Or take a work email that says: “Can you take a look at this?” What exactly does that mean? Do they want feedback? Approval? A rewrite? A miracle?
So, when Gen AI gives me poor answers, I don’t get angry with it. Instead, I remind myself that I have not explained myself clearly enough. Good communicators are always explicit about their intentions.
Instead of “Take a look,” I would write: “Can you check if the argument in paragraph three is convincing?” Whether with a person or with Gen AI, if you ask vaguely, you will get vague answers. If you ask clearly, you will get clearer answers.
If you simply say: “Summarise this article,” Gen AI will do a decent job. But if you add more context with keywords like “Summarise this article, 100 words, casual style”, the machine begins to align with your vibes.
And instead of prompting “Write something about NTU,” try something like: “Write a 500-word piece on the history of NTU’s Yunnan Garden and how love has blossomed there.”
I also like to sketch out my ideas on paper and then feed it to Gen AI.
Go deeper, ask more
there. But good conversations rarely end after one sentence.
When journalists conduct in-depth interviews, they almost never stop at the first answer. If something is unclear, we ask a follow-up question. If something is interesting, we dig deeper to uncover another insight or saucy tale.
its full potential when you iterate your questions, or ask questions in different ways.
You might ask: “Explain this concept simply.” Then follow up with: “Give me an example.” Then ask again: “Make it concise.”
I can spend many minutes iterating on my prompts. People complain that it is tiring, and they want instant results. I reply that that is not how Gen AI works.
You can’t rush a good conversation, even with a machine.
When NOT to converse with AI It’s fun to chat with Gen AI, but there are moments when no machine will do. When emotions are running high When you need to be challenged When the small things count When you don't know what you're asking |
This story was published in the Mar-Apr 2026 issue of HEY!. To read it and other stories from this issue in print, click here.
