How to Get Better ChatGPT Output with Directive Rewriting
For people who want to use AI like a pro
At Hoffbeck + Co, we don’t expect AI to give us the perfect answer the first time. We treat it like a collaborator we have to guide, especially if we want to get better output from ChatGPT.
Most people ask ChatGPT a question, skim the first draft, and assume that’s all it can do. But the real value shows up in the second, third—or thirtieth—round.
We call this directive rewriting.
What is Directive Rewriting?
Directive rewriting is the process of responding to AI like a creative director, not a consumer. You’re not just reacting to what it gave you—you’re actively shaping it.
Here’s the difference:
A consumer mindset reads a response and decides whether it’s good or bad.
A creative director mindset looks at the response and says, “Here’s how to make it better.”
You’re not expecting it to be right the first time. You’re giving feedback, adjusting the tone, tightening the structure, and layering in your strategy—step by step.
Sometimes that takes 3 replies. Sometimes it takes 30. We’ve gone over 100 rounds before—not because it was broken, but because we were building something highly specific and strategic.
With directive rewriting, you know where you want to go with an AI tool, like ChatGPT, yet you’re open to finding the strongest argument and information along the way. (What we mean by an “argument” is a case, a well-built point that’s backed by reason; not a quarrel or a fight.)
Directive rewriting holds the balance between knowing what you're aiming for and seeking value from what AI can offer. It’s the magic behind how you get better ChatGPT outputs.
The expert side of the equation is that you know what makes your idea sound and your argument tight. If you’re writing a blog post on a topic you know well, you’re going to want to make sure key concepts are captured—your insight, your voice, your spin.
But the other side—the part that makes AI useful—is openness. The willingness to let ChatGPT show you another way to say it. Maybe it’s clearer. Maybe it flows better. Maybe it helps your point land with less effort and more impact. Maybe it brings a perspective you hadn’t thought of yet.
When those two forces meet—your deep knowing and AI’s pattern-recognition, clarity, and scale—that’s where breakthrough output lives.
Prompt ChatGPT like you’re in a conversation—not like you’re giving a command. Forget Google-style searches. Just say what you’re thinking, like you would to a co-worker or like talking to a friend.
When you use directive rewriting, you give ChatGPT clear, directional feedback, while also adding context about the conversation as a whole. For example:
“The tone is too generic—can you make it sound more like me?”
“I like this, but can you make this section a little tighter?”
“Delete this section and reframe it with our target market in mind.”
“Can you remember that I like ____, and then weave that throughout this post?”
Cool Tip: You can highlight specific parts of the output AI gives and respond directly to that one section. This works especially well in Canvas Mode—a workspace in ChatGPT where you can write, read, and collaborate directly on content line by line. It’s one of the best ways to stay focused and go deep on structure, tone, or wording without losing the thread of the whole piece.
Each reply gives AI a better shot at hitting the mark.
Why It Works
AI tools like ChatGPT are powerful, but they aren’t context-aware. That means they don’t automatically understand:
Your voice or brand tone
Your specific audience
Your goals for the piece
Real-world conditions you’re working within
ChatGPT can follow instructions — but only if you know what to ask, and you’re willing to keep refining.
Directive rewriting helps you:
Replace vague drafts with clear, usable work
Align tone and structure with your actual voice
Avoid wasting time trying to fix generic content
Build momentum on complex projects, without burning out
The key is seeing AI as a drafting assistant — not a tool to create your finished product — and seeing yourself as a creative lead, not as an end user.
It gets even better when you learn how ChatGPT’s memory works. Long chats build context that shape the final output of the chat session. So, instead of ordering it around, try speaking in ways that add clarity and context.
Instead of: “Fix this to say X.”
Try: “I’m thinking it could say something more like this, because…”
That simple shift can dramatically improve the result.
Core Memories Shape the Output
If you're using a paid plan with memory enabled, ChatGPT will start to remember details across all chats. Not just within a single conversation, but across your entire profile. This is another game-changer.
So, if you often give the same kind of tone feedback or repeat the same brand details, you can tell ChatGPT once, and it will carry those preferences forward.
Examples of core memories might include:
Your brand voice ("plainspoken, warm, and strategic")
Preferences like “speak clearly and to the point”
Your company name, company location, services and products you sell
Audience notes ("this is for small business owners")
What kind of music you like...yes this helps guide your brand voice
Your values and mantras you live by
When used well, memory creates a working relationship over time. You don’t have to keep repeating yourself. And that saves you from starting from zero every time.
We recommend reviewing your memory settings every so often to make sure they reflect how you actually work and what you truly want ChatGPT to remember.
Cool Tip: Just start a new chat and say, "Can you remember some things about me?" Then start sharing whatever makes you... you. Give it context—what you like, what you value, how you work, who you serve. The more you share, the more it will respond in a way that actually feels tuned to you.
A Note on ChatGPT’s Paid vs Free Plans
If you're serious about getting high-quality output from AI, the free version of ChatGPT isn't going to cut it.
The paid plans (especially those with access to GPT-4) are a major upgrade in terms of tone, nuance, structure, and ability to follow direction over time. If you're judging the tool based on the free version alone, you're missing what it's actually capable of. The free plan doesn't feel like you are talking to a human, but the premium version does.
Think of it like hiring a contractor. You’ll get different results from someone with professional tools versus someone using whatever they found in the garage.
If you want outputs you can actually use in your business or with your clients, the premium plan is a smart move. The difference in quality is not subtle.
Debunking the "It Just Tells You What You Want to Hear" Myth
One of the biggest misconceptions about ChatGPT is that it just parrots back whatever you want to hear — or that it makes things up and can’t be trusted.
Let’s clear that up:
Yes, ChatGPT will reflect your tone and framing. That’s what makes it powerful in a creative workflow. But it doesn’t mean it can’t disagree, question assumptions, or surface alternative angles — if you prompt it to.
And yes, ChatGPT can get facts wrong. But so can Google. So can people. That’s why you always check facts before publishing, no matter the tool.
What matters is how you use it:
Want it to challenge your logic? Ask it to.
Want it to spot gaps in your argument? Invite that.
Want it to give you evidence-based suggestions? Ask it to cite sources.
The idea that ChatGPT isn’t trustworthy comes from misunderstanding how to use it. It's not designed to replace professional decision-making or offer final answers in areas like key life decisions or specialized and professional spaces like business strategy, medicine, or law. But it can absolutely help you think through those topics. It can help you brainstorm options, clarify questions, compare approaches, and identify what to ask a professional. That’s still incredibly valuable. The key is knowing when to use it as a thinking partner and when to take the next step beyond it.
But if you’re using it as a strategic, creative, collaborative tool? It’s incredibly effective — especially when combined with your judgment.
The more sophisticated you are on a topic, the more powerfully you can use ChatGPT. When you bring your own expertise into the conversation, you’re not just checking for accuracy — you’re actively guiding it. You can say things like, “I agree with you on that, but what about this_____, wouldn’t that help here?” or “That’s close, but it misses this nuance_____.
The back-and-forth isn’t a sign that the tool is weak. It’s a signal that you’re refining in real time, layering your lived experience and strategic insight into the process. That’s when AI becomes a real partner.
One of our favorite things to do when we’re deep in a chat and trying to figure something out is to highlight a specific part of the output and reply with: “How do you know this?” ChatGPT will often respond with the reasoning or evidence behind that line, and it’s pretty damn compelling.
If the response doesn’t feel airtight? Keep refining. Try prompting it with something like: “Could we do a deep dive research on this so I can feel more confident?” That kind of direction signals that you’re not just accepting answers, you’re building understanding. And ChatGPT can rise to meet that tone.
You can even do your own outside research: find an article, a case study, or something you trust that adds more understanding. Drop it into ChatGPT and ask, "Does this change your analysis at all?" That one move can spark a whole new thread of insight. It creates a feedback loop where you’re not just accepting its ideas, you’re shaping them based on what you know and what you’re learning.
Trust the process. Trust your knowledge. Test your knowledge. Test ChatGPT. Don’t expect it to be perfect. Just give it the right job, and it will impress you.
How We Use It
Here’s what this looks like in practice:
My Initial Prompt
“Can you write a blog post introducing directive rewriting to small business owners from the Hoffbeck + Co voice?”My analysis of output 1: It’s too cliché.
My Response:
“Try again, but can you make it less cliché and more clear?”My analysis of output 2: Better tone, but still not there. It doesn’t include everything we want to cover.
My Response:
“Add something about how sometimes we reply to a chat 30–100 times for directive rewriting.”Outputs 3 to 33+:
We keep refining. Voice. Structure. Emphasis. Flow. Not because we’re spinning our wheels but because we’re shaping it into something clear, sharp, and aligned. We have a vision, and we’re making sure the output supports it.
The more precise the goal, the more iteration it takes.
Trust-Level Tags: Spotting Hallucinations and Strengthening Accuracy
Another powerful move — especially for business, research, or anything that involves facts — is to have ChatGPT include trust-level confidence tags in its responses. These help you instantly spot what’s solid, what needs verification, and what might be made up.
Here’s the prompt we recommend, which you can copy and paste into ChatGPT:
“I want you to include trust-level confidence tags in every response so I can tell what’s solid, what needs a second look, and what might be made up. Use these three tags every time:
• [CONFIDENT + VERIFIED] = based on established data, strong logic, or best practices
• [LIKELY, BUT DOUBLE-CHECK] = probably solid, but worth confirming
• [CREATIVE GUESS / HALLUCINATION RISK] = speculative or possibly fabricated
Tag your responses clearly, and continue doing this by default unless I tell you otherwise.”
These tags don’t just help you assess the accuracy, they build awareness around where your own judgment is most needed. You can also ask it to explain why it gave a particular confidence tag.
It’s another layer of directive rewriting: you’re not just shaping tone—you’re shaping trust.
Example: What Directive Rewriting Looks Like in Real Life
Let’s prove the point. Below is a short side-by-side comparison showing what changed from the first draft of this blog to the final version you just read.
First ChatGPT Draft Opening:
At Hoffbeck + Co, we don’t chase perfection. But we do believe in precision. So if you’ve ever typed a beautifully clear prompt into ChatGPT, hit enter, and thought: “Not what I meant,” you’re not alone. That’s where directive rewriting comes in. It’s the secret sauce we use in-house, and the way we coach our clients to actually use AI in a way that respects their tone, their context, and their strategic brain.
Final ChatGPT Version Opening:
At Hoffbeck + Co, we don’t expect AI to give us the perfect answer the first time. We treat it like a collaborator we have to guide, especially if we want to get better output from ChatGPT. Most people ask ChatGPT a question, skim the first draft, and assume that’s all it can do. But the real value shows up in the second, third—or thirtieth—round.
We call this directive rewriting.
What Changed:
We cut metaphors and vague phrasing in favor of clear, grounded setup.
We moved from clever to useful. From “marketing voice” to “real person voice.”
We layered in lived experience—what we actually do.
We adjusted to our own taste.
We did SEO keyword research and incorporated the keyword into the first 100 words.
And that’s just the first few paragraphs. Over the course of 30+ iterations, we reshaped tone, structure, nuance, and insight until it felt clean, direct, and true.
That’s the power of directive rewriting.
Final Thought
If you’ve ever thought, “ChatGPT just doesn’t get it” — you’re not wrong to notice when the first output falls flat, but you're likely judging the surface, not the depth. The power isn’t in the first output or even the second. It’s in the long-form chat, the back-and-forth, the memory, and the refinement. It’s in the willingness to guide, reshape, and revisit. Directive rewriting is where things transform—where your clarity meets its capability. Stay in the conversation long enough, and it won’t just get it, it’ll help you make it better than you imagined.
Don’t discard the first draft. Lead it.
Give it direction. Keep going until it feels right.
If you want better ChatGPT output, you have to go deeper—refining, redirecting, and layering in what you know. Great output doesn’t come from clever prompts. It comes from leaning in and shaping each version—whether that takes 5 replies or 105.
Lane & Mahla
P.S. Need help building this kind of process into your team or creative workflow? We can help you get there, without burning out or lowering the bar.
More soon,
Lane + Mahla
CONSULTANTS + PARTNERS
P.S. Want to learn more about our AI-enhanced website copywriting service?
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