Sponsored by I've been using AI tools almost every day for the past year.

And for a long time, I kept getting mediocre results — generic answers, vague outputs, responses that felt like they could've been written by anyone. I blamed the tool. Turns out, I was the problem.

After testing hundreds of prompts across ChatGPT, Claude, and other AI tools, I've figured out the patterns. And the three mistakes I'm about to share? I made all of them. Probably longer than I'd like to admit.

Let's get into it.

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Test Catch for free Mistake #1: You're being too vague — and calling it "simple"

Most people write prompts the way they'd send a quick text message.

"Write me an email." "Summarize this." "Give me some ideas." And then they're surprised when the output feels generic, flat, or completely off-target.

Here's what's actually happening: AI doesn't know your context unless you give it your context.



It doesn't know who you're writing to, what tone you want, or why this matters. When you leave those things out, the AI fills the gaps — with the most average, middle-of-the-road answer possible.

The fix: Add three things to every prompt — your role, your audience, and your goal.

Instead of "Write me an email," try: "Write a follow-up email from a freelance designer to a potential client who went silent after the proposal. The tone should be warm but confident, and the goal is to get a reply — not sound desperate." Same task. Completely different output.

Mistake #2: You give the AI no constraints — and wonder why it rambles

Here's a counterintuitive truth: the more freedom you give AI, the worse the output gets.

No word count. No format. No restrictions. Just "write something good." What you get back is a five-paragraph essay that technically answers your question but isn't actually useful to anyone. AI, like most people, fills available space when there's no reason not to.

Constraints aren't limitations — they're directions. They force the output into a specific shape. And specific shapes are useful. Shapeless things aren't.

The fix: Tell the AI exactly what the output should look like.

"Give me 5 subject line options. Max 8 words each. No emojis. Direct and curiosity-driven." That's a prompt with walls. The AI works inside those walls,



and what comes out is actually usable.

Mistake #3: You treat the first response as the final answer

This one is the biggest shift in how I use AI now.

The first response is a draft. A starting point. A rough sketch. Most people read it, feel underwhelmed, and either accept it anyway or give up on AI entirely. Both are mistakes.

The people getting the best results out of AI aren't better at writing the first prompt — they're better at the conversation after the first prompt.

They Push Back. They Redirect. They Say Things Like "This is too formal — make it sound like I'm talking to a friend." "Cut the last two paragraphs and add a specific example instead." "The hook is weak. Rewrite just the opening line." That back-and-forth is where the real output lives. The first response just gets you in the room.

The fix: Treat every AI session like a collaboration, not a vending machine. You don't put in a coin and walk away. You iterate.

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I wasted weeks getting bad AI output because I didn't understand this. I thought I just wasn't "good at prompting." But prompting isn't a talent — it's a skill. And like every skill, it gets better when you know what you're actually practicing.

Context. Constraints. Iteration.

That's the whole framework. Everything else is just a variation of those three things.

Try it on your next prompt and see what happens.

— Career OS

If this was useful, forward it to one person who's been complaining that "AI doesn't work for them." It probably just needs better instructions.

📌 Almost everyone makes these 3 mistakes when writing AI prompts (I did too) (Jun)
🏢 Career OS
📍 Jun