Thinking With It

Here are a few ways to steer clear of the missteps most people make early on.

Clarify fuzzy thoughts

Turn scattered ideas into structured arguments or plans. ChatGPT can help surface structure when you're not sure how to express what you're thinking, or even what you're thinking at all. It acts as a sounding board, organizing your fragments into something coherent. The process often reveals your actual stance or intent, even if your original phrasing didn't.

I once dumped a paragraph of half-baked notes about a product direction into ChatGPT. It returned a clear outline with key themes extracted. That outline later became the intro slide in a pitch deck.

Another time, while planning an article, I listed 10 ideas in a single sentence. ChatGPT broke it into three themes, which became the headers of my draft.

Pressure-test decisions

Ask it to argue both for and against your current direction. This is crucial, especially as ChatGPT as it’s been shown to evolve how it responds to prompts. This isn't about looking for affirmation. It's about inviting friction. You can test a product decision, a business model, a hiring plan. You can test anything by prompting it to take opposing sides. It's one of the fastest ways to spot weakness in your reasoning.

I’ve asked it to debate whether to launch a feature now or wait for more user feedback. Its "wait" argument made me realize I hadn't validated key assumptions.

For a startup I was advising, I asked ChatGPT to simulate an investor's critique. The result forced the founder to rewrite their deck to address key doubts.

Surface blind spots

Use it as a counterbalance. Ask, "What am I missing?" The model is particularly good at generating angles or risks you may have overlooked. It's not perfect, but it's wide-ranging and fast, and sometimes that's enough to trigger a useful pivot in your thinking.

In preparing for a partnership deal, I had ChatGPT generate a list of questions a skeptical lawyer might ask. It raised a point about liability we hadn't covered.

I even helped a colleague describe a hiring plan, and it flagged team dynamics and onboarding complexity that we hadn't considered.

Extract the real question

Often your first prompt isn't the question you meant to ask. The act of writing it down, then asking ChatGPT to refine can reveal what's actually on your mind. This is especially useful when you're stuck or spinning. You think you need an answer, but you might just need a better question.

I’ve often thought I needed a "how-to", such as launching this newsletter. ChatGPT responded with a list, but also asked why I wanted to start one. That led to a deeper conversation about audience strategy.

You can even ask how to handle "burnout at work," and it’s more than capable of reframing the issue as a question of identity and values, which might be exactly what you need to confront.

Use it to find the right language

Ask ChatGPT to describe something as a prompt. This helps surface the language you didn't know you needed and gives you a structure you can reuse and modify. It's particularly effective when you're trying to direct the model itself whether in writing, image generation, or code. Let it show you how it would phrase something, then tweak it to match your tone or needs.

I wanted to create an AI image of a my own home with new landscaping. I asked ChatGPT to describe the scene as a prompt, copied the result into DALL·E, and got exactly the directions I was heading for.

Do you need a recruiting post for a senior backend role? Ask ChatGPT to write one, then modify the language to sound more like your team. You might save 30 minutes or more and spark ideas you wouldn't have thought of on your own.

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