How To Talk To AI — Iteration Beats Perfection

We’ve talked about roles, goals, structure, clarity, using more words, asking questions, and slowing it down. These are all important to help you get what you want. 

But also, it’s a conversation. So have the conversation.  

Whichever LLM you’re using, it understands the conversation. It knows the history. It remembers what you told it. Work through the problem iteratively, much like you would with a real person.

Try stuff in layers. Try different stuff. Go this way. Now go a different way. 

If you want a great result, don’t expect to get it on the first try. Instead, build in feedback cycles. Test tone, style, structure. Ask for rewrites. Push it further.

Boss directive:

“We need to figure out the right message for our audience.”

Prompt Sequence:

Round 1 – Exploration:
“You are a senior B2B marketing strategist and copywriter. Start with thinking aloud: ask me 3 clarifying questions about our audience’s biggest pain point, our unique differentiator, and what we believe success looks like (metric, emotion, action). Then generate 5 headline + sub‑headline pairs based on your responses. Each pair should vary in tone (confident, curious, direct, metaphorical, risk‑avoidant).”

Round 2 – Iteration:
“I’d like to combine versions 1 and 3. Now give me 3 more that combine those concepts.”

Round 3 – Refinement:
“Let’s go with numbers 2 and 3. For each, rewrite the headline + sub‑headline to emphasize measurable benefit in the first 3 seconds of reading. Then draft 2 versions of the short body copy (~100 words) for each pair.”

Round 4 – Iteration:
“No, I don’t like any of those. I do like the direction of the first headline, but it needs to feel more urgent. Scrap what you have and give me 3 more headlines + subs that are along the line of the first one.”

Round 5 – Iteration:
“Ok, I like 2. Now let’s go back to the draft versions of the short body copy. Give me 2 ~100 word versions of copy for this.”

Round 6 – Polish & Finalize:
“I like the first one. Now you’re the final editor. Provide the final headline + sub‑headline + final body copy. Then propose 2 alternate body copy tweaks (tone or style change). And provide a short rationale (~50 words) explaining why this version will convert best, based on audience insight and our goal.”

Round 7 – Iteration:
“I like the 2nd one, but can you pull in the style from the first?”

And so on. 

It takes patience and work from your side. Your still the boss. Be the boss. 

Next up: Use my voice.