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Let's say I'm asking people about characteristics of their ideal workplace.

"Ideally, how old would the company you work for be?"

"Ideally, how many people would also work at the company you work for?"

Personally, this sounds rather awkward. I'd attribute it to the item in question being "the company you work for" as it ends with "for". Any clean-sounding, easily understandable alternatives here?

I was thinking about "How old would your ideal company be?" or "How long would your ideal company have been in business?" but these don't really convey the fact that the person would actually be employed there.

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    There's a seemingly unkillable pseudo-rule about not ending a sentence with a preposition that 18th-century grammarians unfortunately succeeded in injecting into the teaching of English. (I say 'unfortunately', because ending sentences with prepositions is actually a very natural outcome of English word order.) Is it this prescription which leads you to feel that the sentence ending in 'for' sounds awkward? – Erik Kowal Jul 19 '14 at 3:50
  • Well it's probably that but if this is a question, then others are bound to feel that way if it's an "unkillable pseudo-rule" right? Or am I being on edge :) – rch Jul 19 '14 at 4:08
  • The second statement probably sounds awkward because of its asymmetry: the other people work at the company whereas you work for it. How many people would also work at the company you work at? or How many people would also work for the company you work for? sounds better to my ear. – Anonym Jul 19 '14 at 4:09
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I've never liked ending sentences with prepositions, whether it's an unfortunate idea or not. I'd rework the first one to be:

Ideally, how old would the company for which you work be?

^ this syntax being how I generally avoid ending with a preposition.

As for the second one,

Ideally, how many other people would work at the company for which you work?

  • I like "for which". I don't know why it didn't occur to me before. – rch Jul 19 '14 at 4:08
  • Sorry, "for which you work" sounds unnatural. As Winston Churchill mockingly said, "this is the kind of arrant pedantry up with which I will not put!" – Merk Jul 19 '14 at 4:43
  • It's been taught as the "correct" way to me and many others. And thus it sounds natural to us. – user85526 Jul 19 '14 at 5:09
  • That Churchill quote sounds like it's mocking German/other Germanic languages' influence, whose separable prefix verbs resemble "to put up." They would put the prefix in that location. But in English, I believe "this is the kind of arrant pedantry with which I will not put up" sounds correct. – user85526 Jul 19 '14 at 5:15
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    The "for which" order always sounds formal. But I think the first example here is terrible, because of the tiny predicate be stranded behind the longish relative clause. – Colin Fine Jul 19 '14 at 9:23

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