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Would you please explain the differences among these sentences?

Ian hadn't been working at the factory long when he was made a manager.

Ian wasn't working at the factory long when he was made a manager.

Ian didn't work at the factory long when he was made a manager.

Ian wasn't worked at the factory long when he was made a manager.

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Your when fixes the "narrative (reference) time" as being the time at which he was made a manager.

Since your initial clause refers to a time before that (he was working there before he was made a manager), you need to refer to it using Past Perfect Continuous (the first version - Ian hadn't been working at the factory long when he was made a manager).

The second and third versions would be valid if we change when to before, but the last one is simply ungrammatical - we don't inflect multiple elements (wasn't and worked here) for tense when they're both part of the same "compound verb".

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  • The reason that there's a difference between when and before is that before is enough to fix the first clause before the second, so we have more choice of tenses- past simple or past continuous. On the other hand, when does not fix clause 1 before clause 2, so we need to use past perfect in clause 1, to fix it before clause 2.
    – JavaLatte
    Commented Sep 5, 2016 at 19:08
  • @JavaLatte: I think you're right there, but I'm not sure how that plays out when we consider non-negated contexts. In constructions like He had been working there long before they promoted him it seems long before is a single compound element modifying the first clause, whereas in OP's versions they're two completely separate elements (only long refers back to the first clause, before refers forward).
    – FumbleFingers
    Commented Sep 5, 2016 at 21:13

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