AI Tools

Why AI Rewrites Sometimes Sound Worse Than the Original, and What to Do

What I wrote

The tiler showed up on a Tuesday, looked at the subfloor for about ten seconds, and left.

What came back

Upon arrival, the tiling contractor conducted a preliminary assessment of the subfloor and subsequently determined that conditions were unsuitable for installation to proceed.

17 words becomes 25 words     Lost: the Tuesday, the ten seconds, the annoyance 

Same event, twice the syllables, none of the point. This is the pattern the rest of the piece is about.

I kept that rewrite for about four minutes before pasting my own sentence back in. Then I got curious and started paying proper attention.

Over the following months I ran a few hundred paragraphs through various assistants. Some were genuinely broken and needed help. Others were already fine, and I fed them in purely to see what would happen to a sentence with nothing wrong with it. The results were not random. The same things went missing, in roughly the same order, almost every time.

What follows is that pattern: what these tools reliably strip out, the mechanical reasons behind each removal, and the specific changes to how you ask that stop it. Part of this is about the model. A larger part, I found, is about the instruction.

The swap you have probably already seen

Before the causes, the symptom. If you have used any of these tools on your own prose, at least three of these rows will look familiar.

Five swaps that turn up again and again

You wroteIt returnedWhat left the room
Sales fell 18% in Q3.Performance experienced a notable decline during the third quarter.The number, which was the news
It broke on Friday and nobody told us.An issue was identified and communication regarding the matter was delayed.The day, and the blame
Most of this advice is useless.Some of this guidance may be less applicable in certain contexts.The position you were taking
Don't. Seriously.It is generally advisable to avoid this approach where possible.The rhythm and the emphasis
She hated the redesign.She expressed reservations regarding the updated design direction.A real human reaction

Read the middle column on its own and nothing is wrong with it. Grammar is clean, the register is consistent, no editor would circle anything in red. That is exactly the problem. It passes inspection and says less.

Six reasons it happens

These are not personality quirks. Each one traces back to something specific about how the systems are built and how they are asked.

Cause 01 / Sampling

It picks likely words, not good ones

A language model generates text by repeatedly estimating which token plausibly follows the ones before it. Settings such as temperature and top-p decide how far it strays from the front runner. Near their defaults, it strays very little.

"Showed up" is a common phrase. "Upon arrival" is commoner still inside the formal register the model associates with words like polish and improve. Every single choice tugs toward the middle of the distribution. Do that four hundred times in a row and the middle is where you land, which reads as competent and anonymous at once.

Cause 02 / The brief

Your instruction was vaguer than it felt

"Make this better" is not a brief. It carries no information about audience, register, length target, or what you personally count as better. The model has to guess, and its guess is the average of everything ever labelled polished, improved or professional.

Those documents skew corporate. The word professional is a particularly reliable way to summon passive voice, nominalisations and hedging. Swapping it for a concrete constraint changed my output more than switching models did.

Cause 03 / Compression

Detail is costly, abstraction is cheap

Specifics are statistically rare. "4.2 seconds", "the tiler", "on a Tuesday" are low frequency and have no obvious tie to the words around them. Generic stand-ins such as performance, the contractor and at the outset are high frequency and fit nearly anywhere.

So when the model rephrases, the safe move is to climb one rung up the ladder of abstraction, because a vague claim is harder to get factually wrong. Sensible for a system penalised for errors. Ruinous for a sentence whose only value was the figure inside it.

Cause 04 / Preference tuning

Hedging and balance were rewarded

After pretraining, these models are tuned against human preference data. Raters, on average, approve of answers that sound balanced, thorough and careful not to overclaim. That preference gets baked in and then shows up in your paragraph as qualifiers you never asked for.

"This does not work" comes back as "this may not be the most effective approach in every context." Nothing factual was added. Certainty was removed, and your certainty was doing real work.

Cause 05 / Missing context

It cannot hear the rest of your document

Paste one paragraph and the model has no idea what surrounds it. It cannot tell whether you are three thousand words into a dry personal essay or opening a compliance memo.

With no register to match, it defaults to a neutral mid-formal voice that sits badly inside anything with a strong tone. This is why rewrites so often read fine in isolation and wrong in place. It is also the cheapest problem here to fix and the one most people skip.

Cause 06 / Iteration

Each pass compounds the last

Rewriting a rewrite is where it gets properly bad. Pass one sands the edges. Pass two treats the sanded version as the source of truth and sands that. By pass three, vocabulary has narrowed, sentence lengths have converged, and any surviving oddity has been read as an error and corrected.

Researchers looking at what happens when models are trained on their own output describe a similar narrowing at the training level, where rare cases vanish first. You can watch a small version of it inside one afternoon of editing.

What gets deleted, ranked by how often

Voice is not one thing. It is a stack of small habits, and the rewrite removes them in a fairly predictable order.

Voice markers, in the order they tend to disappear

MarkerExampleWhy it goesCost
Sentence fragments"Don't. Seriously."Reads as a grammar fault, gets repairedHigh
Concrete numbers and names"18%", "the tiler"Rare tokens, safer to generaliseHigh
Flat assertions"This is wrong."Preference tuning favours hedged claimsHigh
Contractions"don't", "it's"Formal register drops them by defaultMedium
Odd word choices"sanded", "binned"Lower probability than the neutral synonymMedium
Very short sentences"It broke."Output lengths converge toward the meanMedium
Direct address"you have probably seen"Neutral register prefers the impersonalLow

Notice that the top three are the ones carrying meaning, not decoration. A fragment sets pace. A number is the actual claim. A flat assertion is a position you have taken and can be held to. Losing those is not a style problem, it is an information problem wearing a style problem's coat.

The three minute check

Before you accept a rewrite, run it against these. If two or more fail, keep your version and try a narrower instruction instead.

Accept or reject, in six questions

Tick what survived

□ Every number, name and date is still there. Not paraphrased, not rounded, not turned into "significant".

□ The word count did not grow. A rewrite that adds 30% has almost certainly added padding, not clarity.

□ Your position is still the same strength. Search for may, could, often, generally, in some cases. Count them before and after.

□ Sentence lengths still vary. If every sentence now runs 18 to 24 words, the rhythm has been flattened.

□ You would say this out loud. Read it to the wall. Anything you would not say to a colleague comes out.

□ It still fits the paragraph before and after it. Paste it back in place and read all three together.

The one that catches most people

Word count. It is the fastest proxy for the whole problem, because nearly every failure mode on this page shows up as extra words. If the rewrite is longer and you did not ask for longer, that is your signal to look harder.

Tells that show up in the data

This is not only a matter of taste. Researchers at Tubingen and Northwestern analysed the vocabulary of roughly 14 million PubMed abstracts and found that a set of stylistic words jumped abruptly in frequency after 2023, well outside the gradual drift you would expect from normal changes in academic fashion. The flagged words were not technical terms. They were things like delves, showcasing, underscores, intricate and pivotal, the connective tissue of a paragraph rather than its subject matter.

Two things follow from that. First, the vocabulary shift is measurable at scale, which means it is a real property of the output rather than a hunch. Second, and more useful to you, the giveaways sit in the joins between ideas rather than in the ideas themselves. That is precisely the layer a rewrite touches most and the layer you are least likely to proofread carefully.

Connective phrasing worth searching for after any rewrite

Search forUsually replacedTry instead
it is important to noteNothing. It is filler.Delete the phrase, keep the sentence
plays a crucial role inA specific verbName what it actually does
a wide range ofA number or two examples"Four", or name two of them
can help toA direct claim"Does", if it does
in order to"To""To"
underscores the need forAn argumentState the argument

Instructions that fix it

The change that does the most work is telling the model what to leave alone. Most people describe the destination and say nothing about what must survive the journey.

Six instruction swaps, tested on the same paragraphs

Instead ofAsk forWhy it works
Make this betterCut 15% of the words. Change nothing else.Converts a taste judgement into a measurable constraint the model can actually satisfy
Rewrite this paragraphEdit this paragraph. Keep my sentence structure.Rewrite grants permission to regenerate from scratch. Edit implies a diff
Make it more professionalFix grammar and typos only. Keep contractions and fragments.Professional pulls in a whole corporate register you did not ask for
Improve the flowShow me three sentences that read awkwardly. Do not rewrite them.Diagnosis is what these tools are genuinely good at. You keep the pen
[paragraph alone]Here are the paragraphs before and after. Match that voice.Gives the model a register to match instead of defaulting to neutral
Make it punchierPreserve every number, name and date exactly as written.An explicit protection list stops the abstraction climb described above

Two more that are worth the extra typing. Paste three or four paragraphs of your older writing and label them as your voice sample, because a concrete example beats any adjective you can supply. And ask for the changes as a list rather than as replacement prose, along the lines of "list what you would change and why, but do not produce a new version." You then apply the ones you agree with by hand. Slower, and the result stays yours.

Worth knowing

These tools tend to go along with the framing you hand them. Ask "can you make this stronger?" and you will get something longer, which is a different thing. Ask "is this already clear enough?" and you will often be told yes. Phrase the question so that leaving your draft alone is a permitted answer.

When to bin the rewrite entirely

Sometimes the fix is not a better prompt. Some passages should never go through the machine at all.

A rough decision guide

Passage typeVerdictReasoning
Anecdote or personal storyDo not sendThe specifics are the whole asset and they are the first thing to go
Opening and closing paragraphsDo not sendThese carry the most voice per word, so flattening costs most here
Anything with a strong opinionDo not sendHedging will creep in and you will not notice on the first read
Technical explanation you find muddledSend itStructural clarity is a genuine strength and voice matters less here
Text in your second languageSend itGrammar correction is high value and the trade on voice is worth taking
Long draft that needs cuttingSend itAsk which paragraphs repeat each other, then cut them yourself

The workflow I settled on

This took a while to arrive at and it is deliberately ordered. The early steps protect the later ones.

01   Finish the ugly draft first

Never draft into the tool. If the first version came from the model, there is no original voice left to protect and everything downstream is a negotiation with an average.

02   Mark your own untouchables

Before pasting anything, note the sentences you would fight for. Usually five or six in a two thousand word piece. Those never go in, no matter how the prompt is phrased.

03   Ask for diagnosis, not surgery

First pass is always "point at what is unclear and explain why, without rewriting." This is where these tools earn their keep, and the output costs you nothing in voice.

04   Fix the top three yourself

Take the diagnosis and do the work by hand. It takes longer than accepting a rewrite and it is the entire reason the piece still sounds like you at the end.

05   Send only what is still broken

If two or three passages resist, send them individually with the surrounding paragraphs attached for register, plus an explicit list of what must not change.

06   Read the whole thing aloud, once

Every seam shows up in the voice. A sentence that came from the machine will make you stumble, because it is not phrased the way you speak. Stumbles mark the edits to undo.

Final verdict

Useful editor, unreliable writer

After a few hundred paragraphs and a lot of undoing, the split in my head is clean. As a reader, these tools are excellent. They will tell you which paragraph does not earn its place, spot the sentence where you lost the thread, find the point where you assumed knowledge the reader does not have, and do it in seconds without getting bored on page nine. I use them for that most days and would miss it.

As a writer, they are a downgrade on anything that had a voice to begin with. Not because the output is bad. Because it is average, which is worse in a way that takes longer to notice. The first rewrite I accepted felt like an improvement. The tenth one I accepted was the point where a piece stopped sounding like me, and I only caught it reading a printout in a coffee shop, wondering who had written it.

The practical answer is not to use less AI, it is to change what you hand over. Give it the diagnosis job and keep the prose job. Tell it what must not change before you tell it what should. Protect your openings, your closings and your stories, because those carry the most voice per word and lose the most in the exchange. And if you take one thing from all of this: check the word count. If the rewrite is longer than what you wrote and you did not ask for longer, you almost certainly just traded meaning for polish.

My kitchen paragraph still says the tiler showed up on a Tuesday. It is the better sentence, and it took me four minutes of owning a worse one to work that out.

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