How to Talk to AI (From Someone Who's Been Doing It Since Day One)

After two decades in marketing, I've used every tool, platform, and shortcut that's come along. None of them changed how I work the way AI has.

I jumped on ChatGPT within the first two weeks of it launching. Used it every day. It learned my business, my tone, my preferences. I was its biggest fan.

Then the hallucinations started.

It would fabricate statistics, invent URLs that didn't exist, and present made-up information like it had just looked it up. I'd catch one mistake, correct it, and it would immediately make a different one. I went from evangelist to swearing at my screen daily.

So I moved on. Found a platform that was better at admitting when it didn't know something, better at being corrected, and better at actually listening. We've been working together daily for over a year. It's built tools, written client deliverables, caught my mistakes, and argued with me when I was wrong.

Here's what I've learned about doing it well.

Stop Prompting. Start Talking.

The "prompt engineering" industry wants you to believe you need magic words and secret formulas. You don't.

Talk to AI like you'd talk to a smart colleague. Instead of "generate a professional follow-up email template," try "Help me write a follow-up email to a prospect who opened my last two messages but hasn't replied — he's a serial entrepreneur, probably busy, not uninterested." Instead of "create a marketing strategy," try "I run a roofing company in Denver, we get most of our work from referrals but that's slowing down, what are my options?"

One is a conversation. The other is a vending machine request. There's no formula. There's barely a framework. If someone told you there was a secret technique for talking to your accountant, you'd laugh.

Tell It Who You Are

This was the single biggest upgrade in my experience. When AI knows my business, my clients, and my background, it stops giving generic advice and starts giving advice that fits.

You don't need anything fancy. Just say it. "I run a plumbing company in Portland with 12 employees. Been in business for 15 years. Most of my customers find me through Google or word of mouth." Three sentences. Watch how different the responses become.

Push Back On It

Most people accept the first answer. That's like accepting the first draft of anything.

When something feels off, say so. "That sounds too corporate — I'm emailing a guy I met at a trade show, not writing a press release." "I wouldn't say it that way." "You're being too cautious here — push back on me, am I wrong?" That back-and-forth is where the real value lives. The first answer is the starting point. The conversation after it is what makes it useful.

Bring the Half-Baked Idea

You don't need everything figured out before you start talking. Some of the best work I've done with AI started with "I have a rough idea" and then we shaped it together.

If you come with every detail locked down, all it can do is execute your plan. If you come with a loose concept and you're willing to engage with what comes back — question it, redirect it, build on it — you'll end up somewhere better than either of you would have reached alone.

That's not laziness. That's using a strategist the way you're supposed to.

It Has the Knowledge of the World. Use That.

This still amazes me. AI has access to more accumulated human knowledge than any person could absorb in a hundred lifetimes. And most people use it to write emails.

Ask it to analyze your pricing against market benchmarks. Ask it to explain a regulation you don't understand. Ask it to compare your service offering against what your competitors are promoting. I've asked it questions at 11pm that would have taken my accountant a week and a meeting to answer — and gotten something useful back in thirty seconds.

It knows more than any of us about almost any knowledge-based topic. Not pounding nails — but strategy, research, analysis, positioning? Use that.

Let It Be Wrong

AI makes mistakes. Confident ones. I've caught mine fabricating information about a client's business that sounded completely plausible but was invented from nothing.

That's not a reason to stop using it. It's a reason to stay engaged. The people who get burned are the ones who stop paying attention. The people who get the most from it treat it like a brilliant colleague with a habit of occasionally making things up. Verify what matters. Question what sounds too convenient.

The Best Assistant You'll Ever Have

AI is available any hour. It never complains about scope. It remembers what we discussed last week. It understands my typos and corrects them before they ever reach a client. Try getting that from a spell checker.

Is it weird talking to a machine every day? A little. I got over it around month three when it caught something in a client proposal that would have cost me credibility. At 11pm on a Sunday, nobody else is there. The AI is.

You get used to it. Then you depend on it. Then you wonder how you built anything without it.

And since we're keeping the tradition going — every observation above came from real experience. But I had some help putting it into words. That's the whole point.