5 Reasons Rewriting Your Content With AI Fails & How to Fix It

Have you ever used AI to rewrite your work? If you have, we bet you just ended up rewriting it yourself—we’ve been there, too! But don’t lose hope just yet because these five reasons are what’s holding your AI tool back from producing amazing rewrites and make it your own free AI rewriter. For the purposes of this article, we’ll reference ChatGPT, but these prompts can be used with any AI writing tool including Claude and Gemini.

1. Overly Generic Rewriting Prompts 

You’ve probably heard that ChatGPT is easy to use —all you need to do is enter your prompt, and bam! You have AI-generated content right in your palms. 

But most of the time, you end up getting a not-so-stellar rewrite with ChatGPT just using synonyms. The root cause? Your prompt. 

Many beginner AI writers think that prompts like “Completely rewrite this paragraph” are okay to use. But the thing is, using generic rewriting prompts leads to mediocre results. 

Think of it like asking a waiter to bring you ‘something tasty.’ They might get you a dish that you’re allergic to. But if you had specified that you like a “medium rare steak,” you’re more than likely not going to need an EpiPen or go on an expensive trip to the ER. 

The same applies to ChatGPT––it needs detailed, specific prompts to deliver the results you’re looking for. 

So, what should you consider adding to your rewrite prompt? Here are some: 

Target Audience and Readability 

Specifying who the content is for can help ChatGPT tailor the tone and complexity of the rewritten text. 

If your audience is 6th graders, ChatGPT will use simpler word choices and phrases and break down complex ideas to make the readability easier. 

For example, instead of saying, “This theory persists in the interconnectedness of various variables,” 

ChatGPT might change it to say:  “This idea shows how different ideas work together.”  

In contrast, if your audience consists of college students, ChatGPT will adopt a wider range of vocabulary and complex sentence structure that’s more appropriate. 

So, ask yourself, who is this rewrite for? Then tell ChatGPT to write it for that audience.

Rewrite this article so that a second grader could understand it.

Length 

ChatGPT thrives on specificity, and this is especially true when requesting the length of your content. But what are the ideal lengths for different types of content? 

  • Landing pages can be anywhere from 200 – 1,000 words
  • Product descriptions range from 30 – 300 words, with more complex products typically requiring a longer description. 
  • Depending on their detail, blog posts will range from 700 to 2,000 words. 
  • Email newsletters can range from 200-500 words. 
  • Social media posts can be anywhere from 20-100 words, as each platform has its character limit.
Rewrite this article so that it is 250 words.

Tone and Style

Don’t leave anything up to chance with ChatGPT––be direct. In your rewrite prompt, describe the type of tone you want for the rewritten content. Is it formal or informal? Do you want the rewritten text to have a sarcastic or assertive tone? 

Tip: ChatGPT often matches the tone and style of your target audience. 

Rewrite this article so that it has a formal tone.

Format 

When asking ChatGPT to rewrite your work, you can specify the desired format so the final draft meets your expectations. 

If the writing requires academic or research-based content, you can ask for a specific citation style. For example, a prompt could include:

Rewrite this essay to follow MLA formatting. Include in-text citations and a works cited page.

You can also clarify the structure of the content and include how headings should be optimized. 

Tip: You can further clarify the structure by specifying the word count per section to maintain balance and flow. 

2. Lack of Context 

ChatGPT and other AI rewrite tools can misinterpret the context of the text you want to rewrite. This is why the tools tend to paraphrase what you already have written rather than give you an original concept. 

An example of an AI rewriting prompt that doesn’t have enough context is simply, “Rewrite this to make it better.” 

This prompt doesn’t give AI any insight on what they should change, who the rewrite is for, or how it should change. 

Your prompt should have more context like this:

Rewrite this paragraph to improve detail, clarity, and cohesiveness. Fill in any vague gaps or areas that lack context or are incomplete. Ensure the tone is professional yet friendly and cohesive throughout.

3. Overloading with Instructions 

While it’s excellent to have a detailed prompt from the get-go, overloading  ChatGPT with what you want can also lead to disappointing rewrites. 

Here’s an example of AI rewriting prompt overloaded with instructions:

“Rewrite this article to be more engaging, persuasive, and informative while keeping it concise. Make it sound professional but also casual and friendly. Ensure it’s SEO optimized. Use short sentences and include in-depth explanations where needed. Remove any fluff, avoid passive voice, and make it suitable for college students.” 

And here’s a concise rewriting prompt: 

Rewrite the following paragraph for [insert target audience]. Ensure a neutral but formal tone and active voice.

But what if you have multiple requirements? Consider using AI chain prompting.

AI chain prompting breaks down an enormous task into separate steps with multiple prompts. Each step will build on the previous result. 

To use chain prompting, break your request into steps. 

For example, start with:

Simplify this paragraph for clarity.

Then follow up with:

 Rewrite it with a friendly tone for a general audience.

4. Focusing Solely On Surface-Level Changes 

You don’t have to limit yourself to asking AI for only simple edits. You can ask ChatGPT for an insightful take on the topic, emphasizing more profound content revisions for meaningful rewrites. 

Here is an example of a vague AI rewriting prompt: “Rewrite this paragraph and improve it.” 

Here is an example of an AI rewriting prompt that asks ChatGPT for more insight: 

Rewrite this paragraph with a focus on [insert what you want to be improved]. Expound areas where detail is vague to make the content more valuable to the reader.

5. Expecting a Perfect Rewrite 

Although ChatGPT can generate rewrites in seconds, it rarely provides a perfect output on the first attempt. 

It will often overgeneralize, simplifying complex ideas or removing important details. Plus, it has context blindness, making it unable to retain information beyond what’s provided in the prompt. 

If the first draft isn’t what you’re looking for, you can: 

  • Refine your prompt.
  • Use chain prompting.
  • Add anecdotes, humor, or slight adjustments. 

You can use the strategies listed above to help you deliver a concise and clear prompt. Don’t forget to proofread and fact-check the content AI gives you because ChatGPT can make mistakes. 

Improve Your ChatGPT Rewrites 

Asking ChatGPT to rewrite something for the first time can be frustrating, but hopefully, our tips and tricks have convinced you to give ChatGPT another chance. Let us know in the comments what made your ChatGPT rewrites better.