Why your AI prompts aren’t working (and how to fix them)

Most people talk to AI like it’s a person and end up disappointed. Here’s a better way.

Most people don't get far with AI because they treat it like a guessing game. They keep rolling the dice and hoping for a different outcome.

I know this because I used to do it myself. Last week, I shared a simple, structured prompt that helps genealogists start researching with a deliberate plan, but what I didn't mention was how I discovered the difference between casual and structured prompting in the first place. It was through my own frustrating trial and error, spending an hour going back and forth with ChatGPT giving it enough context so it could do its best. I was treating AI like a guessing game, adding one detail at a time, hoping it would eventually figure out what I really wanted. The results were unpredictable, and I assumed that was just how AI worked.

Then I learned about structured prompts. The difference was like night and day.

My own casual prompting disaster

Here's what my early AI conversations actually looked like when I was trying to write about my great-grandmother's story:

Me: Can you help me write about my great-grandmother born in 1889? Here’s a timeline of her life.

ChatGPT: Sure! Here's a story about your great-grandmother…

(generic, vague, possibly fictionalized output)

Me: Where did you get that context for her life? It’s made-up drama. Remove that and use verified historical information.

ChatGPT: Got it! Here's a revised version.

(still vague, now padded with assumptions based on stereotypes)

Me: She lived with her parents until she was 30, according to census records. Can you include that?

ChatGPT: Absolutely! Here's an updated version…

(still lacks voice, historical depth, and purpose—just a pasted-together sketch)

Me: This doesn't sound right. Can you make it more personal?

ChatGPT: Sure! Here's a version written in the first person.

(new draft starts over again, still lacks any sense of style or direction)

Sound familiar?

I was essentially playing 20 Questions with myself. I wasn't actually doing anything productive. I was testing the boundaries of a machine I didn't understand, while assuming this back-and-forth was just "how AI works."

But that's not how AI works best.

Feeding it scraps of data and hoping it would give something useful is not just a waste of my time, it’s also cheating myself out of what AI could actually do for me.

Then I discovered structured prompts

Everything changed when I stopped trying to guess what AI needed and started telling it what I was trying to accomplish.

Instead of my usual vague opener, I tried this:

"You are an expert genealogy writing coach. I'm writing a 300-word story about my great-grandmother based on census records and family interviews. Ask me five questions that will help me get started."

What happened next was completely different from anything I'd experienced with AI before.

The AI asked meaningful, targeted questions. I answered them and in the process, clarified my own thinking about what story I actually wanted to tell. Then, and only then, it helped me draft something that reflected my data, my voice, and my purpose.

AI really did collaborate with me like a writing coach.

The inside knowledge I wish someone had told me

Here's what I learned: AI isn't here to decode my vague ideas one sentence at a time. Its real strength is being a thinking partner, but only if I invite it into the problem-solving process from the start.

The people dismissing structured prompts as "too rigid" or "too formal" are missing the point entirely. They're the same people still stuck in that frustrating loop, wondering why AI doesn't work for them.

But now you know better.

If this helped you avoid the months of trial and error I went through, share it with someone else trying to figure out how to use AI in their research.

And if you want more posts like this—real talk, practical examples, and the structured prompts that actually work—make sure you're subscribed.

We're just getting started.

—Denyse

P.S. I’m building an archive of structured prompts for paid subscribers this summer, starting with this post. Here’s a prompt you can copy and paste into a new chat and write a short biography on an ancestor which had a story arc to it. AI will interview you to get the details needed and you’ll receive an engaging short story in return.