Build awesome content: the AI interviewer

How to utilize AI's ability to probe you to draw out your best ideas.

Think about iconic interviews that have stuck with you.

Princess Diana, being painfully honest about what life inside the royal family actually cost her. OJ Simpson, looking into the camera and swearing he had nothing to do with it. LeBron James, sitting down to tell everyone which direction his career was about to go in. Dave Thomas of Wendy’s, solemnly explaining why the SuperBar salad bar had to go (okay, fine, I made that last one up).

Love the person or loathe them, an effective interview hands you something the public eye could never pick up on its own. The good ones get under the surface and pull out the thing that was actually sitting there the whole time.

So here’s a thought I can’t shake. What if you ran an interview exactly like that, except you were the one in the chair, and the thing asking the questions was your chatbot?

Not that kind of AI interview

We’re living in the era of rampant AI use. However you feel about it, the stuff is everywhere now (though thankfully not omnipresent, because boy, would that be a different and much scarier article).

And in all the hype and all the fear, there’s a genuinely useful way to get your actual voice and your actual intent into the work, and it almost never shows up in the headlines. It’s the AI interview.

Not the dystopian kind, to be clear. I don’t mean the bot that screened you for that analyst job and judged your blinking patterns. I mean an interview where you’re the subject, and the whole point is to collect context.

“Thank you for sitting down with me today”

Here’s the trick at its most basic. You ask your chatbot to interview you. That’s the gist of the whole thing that we’re about to get into.

Why would you want that? Maybe you want it to capture your voice so you’ve got a sharper writing partner instead of a generic one. Or maybe you’re trying to build something and you need the tool to actually understand what you’re going for. A perfect-burger-algorithm calculator, for instance (which I need I need to go patent, the moment I finish this sentence).

Here’s roughly how you’d kick one off. You send something like this:

I am looking for ideas for an app I want to code. Give me an in-depth interview to learn my likes, 
dislikes, and preferences when it comes to the apps I use every day. Use the context of this 
interview to create a tastemaking profile for me, then use that profile to give me up to 10 app 
ideas. The interview should be 100 questions, divided into 10 rounds.

You fire it off, the chatbot asks a couple of clarifying questions, and the interview begins. A hundred questions about how you actually use the things you use.

But is that all there is to it? Not quite.

“I want to circle back to something you said earlier”

“Context and memory play powerful roles in all the truly great meals in one’s life.” — Anthony Bourdain

Bourdain was talking about food, but the man might as well have been talking about the things we build.

Here’s the rule underneath all of this. The more context you give the tool, the better the thing it hands back. And a one round interview, however long, is rarely the whole meal.

Think about ordering a burger. Walk into a good diner and ask for the cheeseburger, and you’ll get something solid. But tell them you also want grilled onions, bacon, and sauteed mushrooms, and now you’ve got a delicious burger built specifically for you (though, AI output can’t be literally delicious, sadly, unless you own some machine I’m not aware of, in which case please DM me immediately). What does this all mean? The more you specify, the more the result actually fits.

So say those 10 app ideas come back, flatter than a smash burger patty. You’re not stuck with them. You send a follow-up that goes something like this:

Look back at all the responses I gave to your questions. With my answers in mind, ask me 
clarifying questions on anything that seemed vague or anything I sidestepped. Once you’ve 
gathered enough clarity, generate a new list of 10 app ideas.

What did that actually do? You told the tool to press you a little harder so it could understand you a little better. And once it has that extra clarity, the second list tends to land in a completely different place than the first.

That’s the difference between “an app that gives you recipes” and “an app that helps you build customized recipes around what’s already in your fridge.” Same person, same starting point, but a few more questions in between. You went from just “okay” to “wait, that’s actually good!”

But I thought this was supposed to make things easier

Right about here, I can hear an objection forming. “Isn’t AI supposed to do all of the work for me? I wanted to type one thing and get a finished thing back. What’s with all the rounds and the follow-ups and the homework? And where’s my burger?*”

Fair points. And yes, you can absolutely have AI crank stuff out on the fly. If that’s your prerogative, I’m not going to get on a soapbox and shout at you with a megaphone.

But the wing-it approach reliably produces wing-it results. That’s just the reality of the thing. You get the bland, forgettable output, and then you blame the tool or you blame yourself, when the real culprit was that nobody ever asked you what you actually wanted.

Here’s the reframe that changed it for me. The questions aren’t the busywork standing between you and the work. The questions are the work. The interview is how you figure out what you’re really after, and most of us almost never slow down long enough to do that on our own.

Think about how rarely anyone asks you a hundred good questions about a thing you care about. A friend might get to three before the conversation drifts (which is fair and does not mean they’re a bad friend, unless it’s weirdo Steve talking about his “sausage orchard” again). Whereas, the AI interview is a hundred, and somewhere around question sixty you start saying things you didn’t know you thought. The app idea, the essay, whatever you came for, the goal you’re chasing but can’t quite name. The thing you actually walk out with is a clear picture of what you wanted the whole time, finally said out loud.

Fred Rogers (yes, Mister Rogers) had a whole song about liking to take your time and do a thing right. I think about that more and more as an adult typing prompts into a robot. Turns out the cardigan master was onto something.

And I’m not pointing you toward any of this because it’s the disciplined, virtuous choice. I’m pointing you toward it because it can work effectively, and because the version of the thing you get on the other side actually serves what you were trying to do, instead of being something generic that makes you say, “it’s gonna be a no from me, dawg.”

“I appreciate your time”

Come back to those interviews for a second. The ones that stick with us aren’t the ones where someone recited their talking points. They’re the ones where a good question, asked at the right moment, drew out something real that we never would have heard otherwise.

That exact thing is sitting right there, available to you, every single time you open one of these tools. You just have to be willing to be the one in the chair (the chAIr, if you will).

Because it turns out that one of the most useful things the AI can do for you isn’t answering your questions. It’s asking you theirs.

^{*Would ya stop asking the AI for a burger? Trust me, I’ve tried.}

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