Make ChatGPT Think Harder and Smarter

The smartest tip you’re not using is also the simplest — prompt your AI like a strategist, not a search engine.

Ever feel like your ChatGPT replies sound a bit, well, basic? You’re not alone.

Many users across Asia are still prompting OpenAI’s bot as if it were Google circa 2005: dropping in keywords and hoping for a miracle. But to unlock ChatGPT’s true potential, especially if you're shelling out for ChatGPT Plus or Pro, you need to stop asking and start collaborating. For more on maximizing your AI tools, check out our guide on Top AI Tools: What They're Really For.

ChatGPT performs best when you provide rich context, not just keywords,Asking the AI to "think harder" leads to deeper, more strategic responses,Getting ChatGPT to compare, rank and evaluate can improve your decision-making

The Keyword Trap: Why Old Habits Are Hard to Break

Google taught us well. For decades, we’ve trained ourselves to think in short, sharp search strings. "Best ramen Bangkok" or "affordable coworking Jakarta." But ChatGPT is not Google. It’s not built to crawl links and spit back the top ten answers. It works by interpreting intent, goals and tone. Which means prompts that lack nuance will get you vague or underwhelming replies.

So instead of typing "career growth plan marketing manager," try this: "I’m a 34-year-old marketing manager in Singapore looking to transition into product management over the next 3 years. What are three potential career roadmaps I could follow? Rank them by likely impact and feasibility." For more practical tips, see 20 menial tasks ChatGPT handles in seconds.

Ask It To Think, Not Just Tell

This might sound obvious, but most people don’t do it. A simple shift in language — from "give me a plan" to "evaluate and compare these plans" — pushes the AI into more sophisticated territory.

Let’s say you’re planning a move to Ho Chi Minh City and trying to weigh lifestyle, cost and career options.

Instead of asking "Is Ho Chi Minh good to live in?", go for: "Rank Ho Chi Minh City, Bangkok and Kuala Lumpur for a single expat working remotely in tech. Consider lifestyle, affordability, coworking culture and visa ease."

Instead of asking "Is Ho Chi Minh good to live in?", go for: "Rank Ho Chi Minh City, Bangkok and Kuala Lumpur for a single expat working remotely in tech. Consider lifestyle, affordability, coworking culture and visa ease."

That small change turns the AI into a strategic advisor. It stops guessing what you want and starts analysing what matters.

Decision-Making, Deconstructed

We all get stuck when facing choices with no clear right answer, whether it’s choosing between MBA programmes or weighing up two business ideas. Here’s where ChatGPT becomes genuinely valuable.

Try this three-step approach:

Even if the answers aren’t perfect, the process can clarify your thinking. You’ll spot gaps, refine your goals and develop a sharper strategy — all without hiring a consultant. For a deeper dive into AI's impact on business, consider the insights from a Deloitte report on AI's role in strategic decision-making here.

When ChatGPT Becomes a Thinking Partner

This technique isn’t just for big life choices. You can use it for writing prompts, roleplaying scenarios or even planning your next holiday. Imagine saying,

"Give me three weekend trip ideas from Jakarta. Evaluate them for travel ease, vibe and budget."

"Give me three weekend trip ideas from Jakarta. Evaluate them for travel ease, vibe and budget."

You’re not just outsourcing answers; you’re co-creating better ones. And that, really, is the quiet magic of generative AI when used properly.

Push Back. Iterate. Then Push Again.

Here’s the kicker: never settle for the first response. Ask ChatGPT to reconsider, to reframe, to challenge its own answers. Try prompts like:

"What would a contrarian say about this?","Give me a higher-risk, higher-reward version.","Now re-rank these assuming I’m risk-averse."

The more you push, the better it gets. It’s like having a curious intern, a strategist and a devil’s advocate rolled into one. And if you’re paying for the service, why not stretch it to its limits? You might also find value in exploring how Claude brings memory to teams at work for enhanced collaboration.

So next time you open ChatGPT, don’t just ask it something. Challenge it. Make it earn its keep. Because the best AI isn’t a passive assistant — it’s an active thought partner.