The #1 Prompting Mistake I Used to Make (And How My Tool Helps You Avoid It)

I thought I was pretty smart when I first started using ChatGPT. Been writing for years, understand language, how hard could it be? Just tell the AI what you want, right?

Wrong. So incredibly wrong.

For months, I was making this one massive mistake that was sabotaging every single prompt I wrote. And the worst part? I had no clue I was even doing it.

The Mistake That Killed My Productivity

Here’s what I used to do (and maybe you’re doing it right now): I’d sit down at my computer, open ChatGPT, and start typing whatever popped into my head.

“Write me a blog post about social media marketing.” “Create an email for my newsletter.”
“Help me with some product descriptions.”

Seems reasonable, doesn’t it? Direct, simple, gets to the point.

But those prompts are absolutely terrible. Like, embarrassingly bad. And I spent six months wondering why my AI outputs always felt generic, boring, and completely useless.

The Day Everything Changed

Last April, I was working on this project for a client who runs a small fitness studio. She needed social media content that would actually connect with her audience – busy moms who felt guilty about not exercising enough.

My usual approach: “Write social media posts about fitness for busy moms.”

The result? Generic motivational garbage that could’ve been written by any fitness influencer on the planet. “You’ve got this, mama!” “Find time for yourself!” Blah blah blah.

My client took one look and said, “This doesn’t sound like me at all. My members don’t respond to that cheerleader stuff.”

That comment hit me like a brick wall. The AI wasn’t giving me bad content because it was broken. It was giving me exactly what I asked for – which was basically nothing.

The Missing Piece I Never Considered

After that embarrassing client meeting, I started paying attention to how I talked to actual humans versus how I talked to AI.

When I asked my friend Sarah for restaurant recommendations, I didn’t just say “suggest restaurants.” I said something like, “Hey, I need a place that’s good for a first date, not too expensive, somewhere we can actually have a conversation without shouting over music, and my date’s vegetarian so they need decent non-meat options.”

Context. Background. Specific requirements. Actual useful information.

But with AI? I was treating it like some kind of mind reader who should magically understand exactly what I wanted from three words.

That’s when I realized my fundamental mistake: I was asking AI to be creative with zero creative direction.

The Revelation That Fixed Everything

The breakthrough came when I accidentally wrote a really detailed prompt because I was frustrated and rambling.

Instead of: “Write an email about our sale”

I wrote: “You’re the owner of a small bookstore that’s been in the neighborhood for 15 years. Your customers are mostly local families and college students who come in regularly and know you by name. You’re having a clearance sale because you need to make room for new inventory, but you want to frame it as an opportunity for your book-loving community to discover hidden gems at great prices. Write a warm, personal email that feels like you’re talking to friends, not like you’re trying to sell them something. Keep it under 200 words and include a specific example of a book that’s on sale that you genuinely recommend.”

The result was incredible. Warm, personal, authentic. It sounded exactly like how a real bookstore owner would talk to their customers.

That’s when it clicked. The mistake I’d been making for months was assuming AI could fill in context I never provided.

Why This Mistake Is So Common (And So Destructive)

We’re used to talking to humans who share our context. When I tell my business partner “we need to update the website,” he knows our industry, our audience, our brand voice, our goals. He doesn’t need me to explain everything from scratch.

But AI knows none of that. It’s starting from zero every single time.

When you write “create a blog post about fitness,” AI has to guess:

  • Who’s your audience?
  • What’s your expertise level?
  • What’s your brand voice?
  • What problem are you solving?
  • What action do you want readers to take?
  • How long should it be?
  • What tone works for your brand?

It’s like asking someone to cook dinner when they don’t know if you’re vegetarian, have allergies, prefer spicy or mild food, want something quick or elaborate, or even what kitchen equipment you have available.

The Framework That Changed My Game

Once I understood this context problem, I developed what I call the “Context-First” approach. Every prompt I write now includes:

Who am I? (Role/expertise/perspective) Who’s my audience? (Demographics, needs, pain points)
What’s the goal? (Specific outcome I want) What’s the context? (Background information AI needs) How should it feel? (Tone, style, personality)

Here’s how that terrible fitness studio prompt became something actually useful:

“You’re an experienced fitness instructor who owns a small studio in a suburban area. Your typical clients are working moms in their 30s and 40s who feel overwhelmed and guilty about not having time for themselves. They’re intimidated by big gyms and prefer supportive, non-judgmental environments. Create 5 Instagram posts that acknowledge their real struggles with finding time for fitness while offering practical solutions that work with busy family schedules. Use an encouraging but realistic tone – like a supportive friend who actually gets it. Each post should be under 150 words and include a specific, actionable tip they can implement this week.”

Night and day difference, right?

Real Examples of This Mistake in Action

Let me show you some prompts I actually used (embarrassing as they are) and how I’d fix them now:

Old prompt: “Write product descriptions for candles.”

The problem: AI has no clue what kind of candles, who buys them, where they’re sold, what makes them special, or how they should be positioned.

New prompt: “You’re writing product descriptions for a small artisan candle company that sells handmade soy candles at local farmers markets and craft fairs. Your customers are primarily women aged 25-50 who value natural products and supporting local businesses. They buy candles as affordable self-care treats or thoughtful gifts. Write descriptions that emphasize the handcrafted quality, natural ingredients, and cozy atmosphere these candles create. Each description should be 50-75 words, highlight one unique scent note, and end with how the candle makes a space feel more welcoming.”

See how the second version gives AI everything it needs to write something actually useful?

How My Tool Solves This Problem

After months of manually building context-rich prompts (and still sometimes forgetting crucial details), I realized I needed to systematize this process. That’s what led me to create my prompt generator tool.

The tool asks you strategic questions that force you to think through context before generating your prompt:

  • What’s your role or expertise?
  • Who exactly is your audience?
  • What specific outcome do you want?
  • What background does AI need to know?
  • How should the output feel and sound?
  • What constraints or requirements matter?

Then it builds a comprehensive, context-rich prompt automatically. No more guessing, no more missing crucial details, no more generic outputs that don’t actually help anyone.

The Results Speak for Themselves

Since I started using the Context-First approach (and later, my tool to make it easier), my AI outputs have completely transformed.

My clients stopped asking for revisions because the content actually matched their needs. My writing projects took half the time because I wasn’t constantly re-prompting to get something usable. And honestly? Using AI became fun again instead of frustrating.

Last month, I helped a local restaurant create their entire social media content calendar using context-rich prompts. Every post felt authentic to their brand, spoke directly to their customers, and actually generated engagement. The owner said it was the first time social media content felt “like us” instead of “like everyone else.”

Why This Matters More Than You Think

Most people are going to keep making this context mistake for months or years. They’ll get frustrated with AI, decide it’s overhyped, and miss out on the massive productivity boost it can provide.

But the people who figure out proper context and prompting? They’re going to have an enormous advantage. Not because they’re smarter, but because they know how to communicate effectively with these tools.

Context isn’t just nice to have – it’s everything. It’s the difference between AI being a helpful partner versus an expensive random word generator.

Ready to Stop Making This Mistake?

If you recognize yourself in this story – if you’ve been writing vague prompts and getting frustrated with generic results – you’re not alone. This mistake is incredibly common because it feels natural to communicate with AI the same way we communicate with humans.

But once you start providing proper context, everything changes. Your prompts work better, your outputs are more useful, and AI finally becomes the powerful tool it’s supposed to be.

The Context-First approach takes practice, but it’s worth developing. Or you can use tools like mine that guide you through building context-rich prompts automatically.

Either way, stop leaving AI to guess what you want. Start giving it the information it needs to actually help you.


What’s the most frustrating prompt response you’ve ever gotten? Share it below – I bet the problem was missing context, and I’d love to help you fix it.

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