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Friday Deep-Dive
Why ChatGPT keeps giving you the same answers
An attendee asked me this at a webinar I was presenting on Wednesday. but I've heard the identical frustration from many different people: “Why do I keep getting the same thing back from ChatGPT?” It's the number-one complaint about these tools, and the honest answer is that “the same thing back” is really two different problems with two different fixes. One takes two minutes, once. The other is a small change to how you ask, each time. Get both right — whatever kind of work you do — and the machine stops sounding like a bored stranger. Here's how, in plain steps, for ChatGPT and Claude.
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The same answers every time? It's two problems, not one.
When that attendee asked why ChatGPT keeps handing back the same tired ideas, everyone on the call nodded — and so would every realtor, shop owner, and nonprofit director I know. Here’s the part almost nobody explains: “the same thing back” is two complaints wearing one coat. Sometimes it’s generic — the safe answer anyone would get, whatever their business — and the fix is telling the AI who you are, once, so every answer is written for your world. Other times it’s repetitive — the same ideas every time you ask — and no setting on earth fixes that, because you’re handing it the same request. That one takes a different move: changing what you ask, using the easiest fresh material there is — what’s happening right now. Below, both fixes in plain steps for ChatGPT and Claude, plus an optional setup that runs itself.
Most people set up half of this — or none of it — and quietly decide the AI just “doesn’t get” their business. It isn’t the AI. Generic and repetitive are two different problems, and you’ve probably only ever been handed one fix, usually the wrong one for what’s actually bugging you. Do both, and it stops sounding like a stranger and stops circling the same three answers.
Read the full post →
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What is?
System Prompt
What it is: The standing set of instructions an AI reads before it ever sees the message you type. Part of it is hidden (the maker’s own rules), and part of it is yours to write — what ChatGPT calls “Custom instructions” and Claude calls “Instructions for Claude,” or a project brief — where you tell it who you are and how to answer. Your typed question is a one-off request; the system prompt is the standing order behind every one of them.
Why publishers care: It’s the difference between an AI that treats you like a stranger every time and one that already knows what you do and who you serve. Writing your own system prompt once is the highest-return two minutes most people never spend. Just remember what this issue is really about: a strong system prompt makes answers yours — it can’t make them new. That second job belongs to what you feed it each time.
Visit help.openai.com →
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— Trevor
Trevor Slette
Co-founder, Quadd.ai · 28-year community publisher
trevors@quadd.ai
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Book a 15-min call
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LinkedIn
P.S. P.S. Reply “kit” and I’ll send you the starter pack from this issue — the fill-in-the-blanks profile, an “Our Year” template, and the ready-to-paste project instructions — for whatever kind of work you do. Works in ChatGPT or Claude.
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From meeting audio to usable copy.
Upload a council meeting, an interview, a coach's post-game scrum. Get a clean transcript and an AI summary, then ask Quadd to compose a first-draft story or paste your own prompt — formatted output in your publication's exact style. No more scrubbing through forty minutes of audio at 9pm because the lede quote was somewhere in the middle. Trained on the way reporters actually use audio, not the way podcast editors do.
See how transcription works →
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