There’s something wild I learned about prompting, and it comes from an ancient story. It’s about how asking the right questions can increase the quality of your outcome.
About 3,000 years ago, David and his warriors were protecting local farms from raiders. Yeah, the same David from the Bible who killed the giant Goliath. (You can find this story in 1 Samuel 25.)
They had just spent weeks guarding thousands of shepherds, sheep, and goats for a wealthy guy named Nabal.
The interesting part?
They did it for free, just being good people!
So the time comes to shear the sheep (think of it as payday for the hard work). David asks Nabal:
Hey, we protected you for free all season. Could you spare some food for my men?
Nabal’s response?
David? I don’t know any David. Get lost.
Needless to say, David was ticked! He told his men:
Go get your swords. We’re killing every male in his household tonight!
So about four hundred of David’s warriors start marching towards an absolute massacre. The plan is set. Nabal’s fate is sealed.
But then…
Nabal’s wife Abigail intercepts David on the road.
She’s brought hundreds of loaves of bread, cakes of raisins, lots of wine, and more!
Now here’s the important part.
After giving David the gifts, she doesn’t beg for mercy. Instead, she asks him a few strategic questions:
When you become king, will you want this blood on your conscience? Do you really want to be remembered as someone who massacred a household over an insult? Isn’t God capable of dealing with fools like Nabal without you staining your hands?
Her questions hit David like cold water.
He realized what he hadn’t considered: That he was about to destroy his future reputation because of food. He wasn’t thinking strategically!
David’s response?
Praise God that you came to me! And blessed be your good sense! You kept me from murder and taking matters into my own hands, when God can handle everything.
The craziest part?
When Abigail went home and told her husband everything that happened… he had a heart attack and died!
(That’s karma for you.)
Now, as for a lesson, I think it’s fair to say that David was so filled with anger that his mind wasn’t thinking straight. All he could think about was revenge, not the bigger picture.
Sometimes when I’m working with AI, I face the same situation. It’s not that I’m angry. It’s just that I can’t think of all the other things I should consider when writing my prompt.
That’s where this prompting trick can help. It turns the AI into a strategic advisor who reveals important questions you should consider before proceeding.
Let me show you how it works.
How It Works: The Question First Trick
This prompting trick is super easy to use.
Start by writing your prompt. Then specifically tell the AI to dig deeper and ask questions about what you’re trying to achieve.
The AI will come back with questions you probably hadn’t thought of.
Now you can refine and expand your thinking based on those questions. You might answer them directly, or you might just update your prompt.
In the end, you’ll get output from the AI that considers all that expanded thinking. This output should be way better than what you’d get without using this trick.
One thing to keep in mind is that you’ve got different ways to tell the AI to dig deeper. Here are a few examples:
- Surface-Level:
"Before proceeding, ask me any clarifying questions you need to provide a better result." - Deep Dive:
"Before creating anything, identify and ask me about 5 critical factors I might not have considered that could make or break this result." - Guided Exploration:
"Before you begin, ask me questions about: technical constraints, concerns, success metrics, and any hidden dependencies I might have overlooked."
Let’s look at an example of this technique in practice.
Real-World Comparison: Answer First vs. Question First
Let’s imagine we need to create a YouTube ad script for PocketWatch, which is our imaginary subscription tracking tool. It finds subscriptions you didn’t know about but are paying for, and it cancels them for you.
We’re going to run two examples. The first is where we don’t use this question-first technique; we’ll just having the AI provide us the response. The second, we’ll use this question-first technique and see if there’s a quality improvement.
1. Answer First (Without Questions)
In this example, we’re just giving the AI the instructions and having it immediately give us the answer.
AI Prompt
I need a 30-second YouTube ad script for PocketWatch, my subscription tracking tool. Here’s what it does: PocketWatch automatically finds all your subscriptions by scanning your bank/credit card transactions, shows which ones you haven’t used in 30+ days, and can cancel them for you with one click. We handle the annoying cancellation calls and forms. Priced at $4.99/month.
AI Response
[Opening: upbeat but slightly dramatic tone]
Visual: a person scrolling through their phone, shocked at all the charges on their bank statement.
Narrator: “How many subscriptions are you secretly paying for? Netflix, gyms, apps… half you don’t even use anymore.”
[Middle: introduce solution with energy]
Visual: clean animation of PocketWatch scanning transactions.
Narrator: “Meet PocketWatch. It scans your bank and card activity, finds every subscription you’re paying for, and flags the ones you haven’t touched in over 30 days.”
Visual: one-click cancel button pressed, then confetti.
Narrator: “With one click, we’ll cancel them for you—no forms, no awkward phone calls. Just savings.”
[Closing: price + CTA]
Visual: bold text on screen: “$4.99/month” + happy person seeing extra money in their wallet.
Narrator: “PocketWatch costs just $4.99 a month—and it could save you hundreds. Download PocketWatch today, and stop wasting money on subscriptions you don’t use.”
What do you think?
It’s hard to tell if that’s good or bad, right? We don’t have anything else to compare it to.
But I think is that it’s pretty generic.
So let’s see what happens when we use the same prompt, but ask the AI to ask us some questions first.
2. Question First (Expose Blind Spots)
AI Prompt
I need a 30-second YouTube ad script for PocketWatch, my subscription tracking tool. Here’s what it does: PocketWatch automatically finds all your subscriptions by scanning your bank/credit card transactions, shows which ones you haven’t used in 30+ days, and can cancel them for you with one click. We handle the annoying cancellation calls and forms. Priced at $4.99/month.
Before writing anything, ask me strategic questions—especially about factors I might not have considered that could impact this campaign’s success.
See that last paragraph?
That’s the part that gets the AI to ask us some probing questions. You might not have thought about these questions before.
Let’s see how the AI responds:
AI Response
Got it — before drafting your 30-second YouTube ad script, let’s zoom out and ask some strategic questions that will shape the angle, tone, and effectiveness of the campaign:
Audience & Positioning
1. Target audience: Who are you trying to reach most? College students, busy professionals, families, tech-savvy users, or a broader consumer market?
2. Pain point priority: Is the bigger selling point saving money, saving time and avoiding hassle, or peace of mind from hidden charges?
3. Competitor landscape: Are you positioning PocketWatch against well-known services like Rocket Money or Truebill, or do you want to carve out a different niche?
Messaging & Tone
4. Tone preference: Do you want the ad to feel funny, urgent, trustworthy, or aspirational?
5. Trust & security: Since you’re asking users to connect their financial accounts, how do you want to address safety and data privacy (e.g., “bank-level security”)?
Call to Action & Funnel
6. Conversion goal: Do you want viewers to download an app immediately, visit your site, or sign up for a free trial?
7. Offer hooks: Are you open to using limited-time offers, free trials, or money-back guarantees to reduce signup friction?
Production Details
8. Visual style: Are you imagining live-action, animation, or a mix?
9. Budget/scale: Is this a scrappy, startup-style ad with clever visuals, or something polished and premium?
10. Regulatory/legal: Are there disclaimers you need about data use, cancellation success rates, or pricing?
Would you like me to help you map your unique positioning against competitors first, or go straight into shaping the script once you clarify the target audience and tone?
That’s a lot of questions! I hadn’t thought of many of them, to be honest.
Let’s answer them and see what happens next:
AI Prompt
1. I’m targeting new families, people in their 30’s
2. Saving money is the biggest pain point
3. Not sure. I’m trying to go after ease of use compared to these.
4. I want it to sound funny
5. I want something extreme, funny, way beyond bank-level security. It must be attention grabbing.
6. I want them to click the link in the description to download the app.
7. I have a limited time and limited quantity code for your first 6 months free, the code is in the video description.
8. Live action.
9. I want it to be scrappy with everyday stuff.
10. No.
When you answer the questions, you don’t need to be super detailed. Just share what you think is necessary.
Once we submit those answers, the AI responds with this:
AI Response
Perfect, thanks — that’s really clear. Let me reflect it back and sharpen the angle before I script:
– Audience: New families in their 30s → juggling expenses, stressed about budgets.
– Pain point: Saving money on unused subscriptions.
– Differentiator: Not “fancy finance app,” but super easy, one-click cancellation — PocketWatch does the dirty work.
– Tone: Funny, extreme, everyday situations → makes the message sticky and relatable.
– Trust angle: Instead of “bank-level security,” we’ll exaggerate to something absurd and memorable.
– CTA: “Click the link, use the code in the description, 6 months free.”
– Style: Scrappy live-action, looks like real life, not polished.
Before I draft:
👉 Do you want the humor to poke fun more at subscriptions themselves (e.g., “Why am I still paying for a gym I quit in 2019?”) or at the pain of canceling them (e.g., “Calling customer service feels like a hostage negotiation”)?
That will decide where the funniest “extreme” gag goes in the 30-second ad.
Another question…
To be honest, that question makes a lot of sense.
Do we want to poke more fun at the subscriptions themselves or the pain of canceling them? I think for our hypothetical product, we should poke fun at subscriptions someone didn’t even know they still had.
AI Prompt
I want you to poke fun at subscriptions you don’t even know you’re still subscribed too.
And here’s the result:
AI Response
🎥 PocketWatch YouTube Ad (30s)
[Opening shot: a dad opens his bank app, looks horrified.]
Dad: “Why am I paying $12.99 a month… for llama yoga?”
[Cut: living room. A llama in yoga pants stretches on a mat.]
Narrator (funny, upbeat): “You’ve probably got subscriptions you don’t even remember signing up for.”
[Mom checks her phone, confused.]
Mom: “Wait… I’m paying for a DVD rental club? Do those even exist?”
[Cut: delivery guy drops off a giant box of DVDs like it’s 2005.]
Narrator: “The PocketWatch app finds all your subscriptions, shows which ones you haven’t used in 30+ days, and cancels them with one click.”
[Quick montage: dad taps phone → llama walks out the door, delivery guy sadly wheels large box labeled DVDs away.]
Narrator (serious): “And your data? It’s protected with security stronger than a toddler guarding their snacks.”
[Shot: toddler clutches Goldfish crackers with iron grip.]
Narrator (fast, upbeat close): “Stop wasting money. Click the link, use the code below, and get your first 6 months free. PocketWatch. Cancel everything… except this ad.”
[Logo + CTA: “Download PocketWatch” + description link on screen.]
DANG!
To quote what my teenage daughter would say: that’s lit!
I know it’s a long scroll up, but compare this result to the original one the AI gave us when we didn’t ask it to respond with a question-first approach.
It’s a significant difference!
Now, I thought it’d be cool to turn this into an AI video. I didn’t spend a lot of time on it, and I just wanted to see what the AI could come up with based on our script.
I think it turned out pretty good!
The only things I’d need to change is getting an identical narrator voice for each scene. I also had a hard time getting the second llama to match up and also go “poof” into a cloud of smoke. But hey, not bad for a few minutes of work!
When to Use (and When to Skip) the Question-First Trick
Perfect For:
- Complex problems with multiple variables
- Situations where you feel you’re missing something but can’t identify what
- High-stakes situations
- Creating anything others will use or depend on
- When working outside your expertise area
- First attempts at unfamiliar tasks
Skip It When:
- You need quick, simple factual information
- Following established, proven processes
- Time-critical situations where speed matters more than optimization
- You genuinely know all parameters and just need execution
- Asking for definitions or explanations of concepts
The Hidden Power: Revealing Your Blind Spots
The real value of this trick isn’t filling in gaps you know exist. It’s discovering the ones you didn’t know existed.
When the AI asks about things you hadn’t considered, edge cases you overlooked, or things you forgot about, it’s exposing those unknown unknowns that can make or break the result.