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From Friday Deep-Dive · Friday, July 10, 2026 · 5 min read

The project: turn it into your newspaper's creative director

Here's this week's project, and it takes about twenty minutes. Instead of asking ChatGPT to "write an ad," you're going to hand it a real advertiser — their website, their old ads, their photos — and tell it to act as a thirty-year newspaper advertising creative director. Then you make it interview you, analyze the business, build three completely different campaigns, expand the winner into everything from a full-page ad to a radio spot, write instructions for your designer, and finally tear its own work apart and rewrite it to win an award. Every prompt is written out for you, ready to copy.

Trevor Slette headshot
Trevor SletteCo-founder, Quadd.ai

Try this and tell me what happened.

Did it work? Hit reply. Did it come back sounding like a stranger? Hit reply harder. That’s the interesting failure, and it’s almost always fixable.

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← Back to GPT-5.5 wrote your ads. GPT-5.6 thinks like a creative director.