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I thought maybe this would be a better fit for interpersonal.stackexchange.com but noticed a lot of answers given there are strange.

I recently started working for a small company. In the interview I noticed the manager was very long winded. I took it as a bad sign but the rest of the good things outweighed it.

The job is very independent and I shouldn't actually need to speak to the manager a lot. However I noticed her communication style is very long and confusing. She doesn't use proper grammar, for example she mixes periods, ellipses and new lines.

There was just a misunderstanding about a schedule. Instead of simply asking "are you free at time x" she said "hi, sorry for delayed message...my assistant is coming back tomorrow...i think we still have an opening on thursday but the location cancelled and another is open. can I tell my assistant you would be able to do it in and the one on friday which you had said you're free for." I replied "ok" but I shouldn't have because I got confused by what she was asking.

I explained I misunderstood her message. Is there any way I can be more direct considering she is the manager? I would like to tell her to just ask the question and keep it to one or two sentences.

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This kind of free-thought ambiguity isn't uncommon.

What you can do to combat this is read the content twice over and try to gain some kind of sense from it, and then repeat back your interpretation.

Many thanks for the response, I'll assume that you're free on Friday, I'll set up a meeting accordingly.

Basically, summarize as clearly and concisely as possible and give your respondent the opportunity to correct your assumption (if you couldn't make any sense of the mangled verbiage).

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    On a positive note, I've found people like this usually don't mind repetition so usually they won't mind if you repeat the same message back, rephrased even a couple of times.
    – user10399
    Jun 27, 2019 at 10:57
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    For setting up meetings and similar communications I like to repeat back my understanding even if the original message was crystal clear.
    – Patricia Shanahan
    Jun 27, 2019 at 13:09
  • It's good to put your clear understanding back to someone that is vague/unclear "So you want to meet on Thursday at 10am instead? Yep, no problem". I quite often have to figure out what a problem is given 5 vague issues, so I summarise and repeat back what I think the situation is. "Just to clarify, the problem is X, X and X ?"
    – Smock
    Jun 27, 2019 at 16:02

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