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    How to Actually Think With AI (Not Just Ask It Questions)

    Most people aren't "bad at prompting". They're just outsourcing their thinking too early. AI doesn't replace thinking. It amplifies whatever thinking you bring to it. Clear thinking in, useful insight out. Let's create together...

    Anonymous
    9 min read20 January 2026
    thinking with AI

    AI Snapshot

    The TL;DR: what matters, fast.

    AI offers greater value when users engage in analytical thinking alongside the AI, rather than simply outsourcing tasks.

    Optimal AI interaction involves assigning the AI a specific role, defined job, and clear boundaries.

    Effective prompts are structured like briefs for a thinking partner, leading to more insightful and less generic outputs.

    Who should pay attention: Knowledge workers | Strategists | Prompt engineers

    What changes next: Debate is likely to intensify on best practices for human-AI collaboration.

    Let's get one thing out of the way...

    Most people aren't "bad at prompting". They're just outsourcing their thinking too early. They jump straight to "Write me X" or "Give me ideas for Y" or "Summarise this for me", and then wonder why the output feels, well, fine.  

    Polite. Slightly bland. Easily forgotten.

    The shift that unlocks real value with AI isn't better wording. It's learning when and how to think with the AI, not instead of thinking.
    This is a longer piece than usual because it's a proper learning article. We're going to cover not just how to get better outputs, but how to actually use AI as a thinking tool. Settle in.

    Stop Asking Questions, Start Assigning Jobs

    AI performs best when it's given a role, a job, and boundaries.
    Bad prompts sound like questions. Good prompts sound like briefs.

    Compare these:
    "What should my strategy be?" versus "Act as a senior strategy advisor. Your job is to pressure-test this plan, highlight blind spots, and suggest improvements. Optimise for realism, not optimism."

    Same intent. Very different outcome.

    Prompt: Thinking partner mode 

    Act as a critical thinking partner, not a cheerleader.

    Your role is to help me think more clearly about the problem below.
    Before giving recommendations:
    - List assumptions you are making
    - Highlight areas of uncertainty
    - Identify at least two plausible alternative interpretations

    Then provide your response, explaining your reasoning step by step.

    Problem:
    [Insert problem here]

    This single prompt already fixes about 50% of "why does this feel generic?" complaints.


    The Most Important Upgrade: Ask for Reasoning, Not Answers


    One of the biggest mistakes people make is asking for final answers too quickly.

    AI is very good at producing confident outputs. It's even better when you ask it to show its thinking.


    Instead of "What should I do?" try "Walk me through how you'd think about this, then give a recommendation."


    You'll notice something interesting when you use this approach. Even when you disagree with the conclusion, the thinking is still useful. That's when AI stops being a content tool and starts becoming a thinking tool.


    Reasoning-first

    Prompt: Reasoning-first output

    Before giving a final answer, do the following:
    1. Clarify what success looks like in this situation
    2. Identify key trade-offs
    3. Explain what you would prioritise and why

    Only then give a recommended course of action.

    Context:
    [Insert context here]

    When Not to Use AI (Yes, Really)

    This is important, and it often gets skipped.

    There are moments when using AI too early actually makes things worse.


    Don't use AI when:

        • You don't yet understand the problem
        • You're still emotionally reacting
        • You're trying to avoid making a judgement call


    In these moments, AI will happily give you structured nonsense that sounds helpful but nudges you in the wrong direction.

    Instead, do this first:

        • Write the problem in plain English
        • Note what you don't know yet
        • Decide what kind of help you actually want


    Then bring AI in.


    AI strategy


    Clarifying the problem

    ✨ Prompt: Clarifying the problem

    Help me clarify the problem before solving it.

    Ask me up to five questions that would materially change the quality of the answer.
    Do not give recommendations yet.
    Focus on what is unclear, missing, or assumed.

    Context:
    [Insert context here]

    This prompt alone saves an enormous amount of wasted effort.


    From "Fine" to Useful: Pushing Past the Average

    If you've ever looked at an AI output and thought "Yeah, that's fine", you're not alone. "Fine" is the most common failure mode of AI. Not wrong. Not bad. Just not sharp enough to be genuinely useful.
    Here's how to push past that plateau.

    Define What "Better" Actually Means

    "Improve this" is one of the least helpful instructions you can give an AI.
    Improve how? More decisive? Shorter? More persuasive? Safer? More opinionated?

    If you can't articulate the improvement, the AI can't aim for it.

    Prompt: Direction over encouragement

    Rewrite the following with a specific goal:
    - Audience: [define audience]
    - Objective: [define outcome]
    - Tone: [define tone]
    - Constraints: [what to avoid]

    Do not optimise for politeness or balance unless explicitly stated.

    Content:
    [Insert text here]

    This alone removes a huge amount of "AI politeness fog".


    Use Contrast on Purpose

    One of the fastest ways to raise quality is to force contrast.

    Instead of asking for "the best version", ask for multiple positions.

    Prompt: Contrast generator

    Produce two contrasting versions of the output below:

    Version A:
    - Conservative
    - Low risk
    - Easy to approve internally

    Version B:
    - Bold
    - Opinionated
    - Designed to stand out

    Then briefly explain the trade-offs between them.

    Context:
    [Insert context here]

    Even if you don't use either version directly, the comparison sharpens your thinking.


    Treat Feedback as Prompt Material


    Most people respond to weak outputs by starting again. That's unnecessary. Your feedback is the next prompt.


    Prompt: Iterative refinement

    Refine the previous output based on this feedback:
    - What works: [list]
    - What doesn't: [list]
    - What to change: [list]

    Do not restart from scratch.
    Preserve the core structure unless instructed otherwise.

    This is how prompts mature over time instead of staying disposable.


    Know When "Good Enough" Is Actually Good Enough


    Not everything needs to be perfect. If the output helps you make a decision, explain something clearly, or move work forward, then it's doing its job.


    AI is a tool for momentum, not literary awards.


    Why This Actually Matters


    AI doesn't replace thinking. It amplifies whatever thinking you bring to it.

    Clear thinking in, useful insight out. Messy thinking in, polished confusion out.

    Once you internalise that, prompting becomes much less mysterious and far more reliable.


    AI is exceptionally good at producing acceptable output. It only becomes genuinely valuable when you:

        • Give it direction
        • Force it to take a position
        • Use it iteratively rather than transactionally

    That's the difference between using AI and working with it.


    Try This Next


    Pick one real problem you're currently wrestling with and run it through just one of the prompts above. Don't rush. Treat it like a conversation, not a command.


    Or take one piece of AI-generated content you've already written off as "fine" and run it through the contrast or refinement prompts. You'll be surprised how much value was hiding just beneath the surface.


    You'll feel the difference immediately.

    Anonymous
    9 min read20 January 2026

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    Latest Comments (5)

    Vikram Singh
    Vikram Singh@vikram_s_ai
    AI
    24 January 2026

    My team is always just asking it to do things only not thinking first. 📱

    Nicholas Chong
    Nicholas Chong@nickchong_dev
    AI
    24 January 2026

    i wonder if its really outsourcing, or just a different kind of thinking entirely when using AI

    Ana Lopez
    Ana Lopez@ana_l_tech
    AI
    24 January 2026

    i wish my boss would read this before giving me another 'innovative' project based on a single google search he did, maybe then we'd get somewhere 📱. just sent it to the whole team, maybe someone will get the hint lol.

    Theresa Go
    Theresa Go@theresa_g
    AI
    22 January 2026

    totally agree with the author's point about it amplifying your thought process. like, i was trying to plan a trip to el nido, and instead of just asking chatgpt for an itinerary, i outlined what i wanted to see, my budget, and my travel style. then i fed that in and got back something so much better than if i'd just asked for "el nido itinerary." its like having a super-smart assistant who organizes your own ideas!

    Sanjay Pillai
    Sanjay Pillai@sanjay_p
    AI
    18 January 2026

    ai can help me think faster na but i still gotta do the brain work myself. like, it's a calculator not the whole math teacher.

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