So it’s clear who a pronoun represents, a writer must make an introduction first.
“Dick ate a slice of chocolate cake, then he helped himself to a scoop of cinnamon ice cream.”
The “he” who helped “himself” to ice cream is clearly Dick, because no new “he” has come between the chocolate cake and the ice cream.
This is easy enough to follow, when you’ve got a sole “he” to manage, but what happens when you introduce more than one character into a piece of writing.
“Dick wished Jane a Happy Birthday. Harry went to the table to fetch the first gift she was to open.”
The identity of “she” is easy to guess. Jane is a girl’s name. Begging the pardon of any boys bearing it.
What about this sentence?
“Dick gave Jane a Mickey Mouse watch for her birthday. Harry gave her a stray black kitten he found in the alley behind his house.”
Since Harry is the person introduced at the beginning of that sentence, it’s assumed that the “he” and “his” identify him.
If we add a third sentence, “He said it had fleas,” the reader would naturally assume that it was Harry who pointed out the kitten’s defects. To make it clear that Dick mentioned the fleas, the writer would need to reintroduce him. “Dick said it had fleas.”
While we’re on the subject of clear identification, the “it” that has fleas might just as easily be the house as the kitten, though it is far more likely that kittens have fleas than that houses do. Nonetheless, it would be just as easy and far clearer to say, “Dick said the kitten had fleas.”
There are times, however, when reintroducing a “he” makes the sentence awkward—worse, unnatural. And any unnatural syntax is going to draw readers out of the story they are reading. You don’t want that.
Here’s an example from a short steampunk story I recently read. I have changed the names to conceal the story’s identity—and shield the writer, who, for the most part, wrote a good story.
“It was always Dick’s job to bring meals down from the kitchen, and every time he climbed the stairs he made a point to secure Harry by turning it off and leaving it lying on its back, on Dick’s cot.”
In this particular story, Dick is a boy and Harry is an automaton he made from scrap metal. Since the reader knows Harry is only a mechanical toy, it is easy enough to guess the cot belongs to Dick, not Harry.
“It was always Dick’s job to bring meals down from the kitchen, and every time he climbed the stairs he made a point to secure Harry by turning it off and leaving it lying on its back, on his cot.”
Grammar rules were invented for clarity. If the meaning is clear already, there is SOME wiggle room. However, if violating the pronoun-introduction rule is just too much for the writer to personally overcome, he or she (sorry, but I still think the blank-check “they” is lazy writing, even if it is more polite) ought to reword the sentence.
“Any time Dick left the cellar, he made a point to secure Harry by turning it off, leaving it lying on its back on his cot.”
Since Harry is an “it” there is no confusion with the “he.” Also, by shortening the sentence, I put Dick closer to his pronoun. I’m not sure why the writer felt it necessary to point out that it was Dick’s job to bring down meals from the kitchen. Dick surely left the cellar more frequently than those times when he had kitchen duty. Since he secured Harry each time he left the cellar, it wasn’t necessary to tack the kitchen duty onto the front end of that sentence. After the writer established Dick’s habits, she (or he) could open the subject of that one time when Dick went up for the dinner tray and came back to find Harry—
Well, I won’t ruin the story for you.
If you have an awkward pronoun placement, the best way of correcting it, in most cases, is simply to rephrase the sentence.
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