"How do you like to be when...?"

Question

I had an argument with my teacher; in an exercise which was ordering words to form a sentence, I perhaps created a strange one. The sentence I made is this:

How do you like to be when a business partner close(s) to speak (with) you.

As you can notice I have some marked questions about the grammar of the sentence, but the most important question is regarding if it makes sense or not. My teacher told me it really doesn't make sense but I don't think so. Here are my arguments:

1. "How do you like to be" I know the made pattern, how do you like + noun, that is an opinion request question, but I think we can change the meaning of, how do you like, if we add an infinitive verb instead of a gerund or a noun. e.g. The famous interview question "How do you like to be managed?"
2. The meaning of close, my teacher told me that I can't use close as a verb synonym of — get nearer; approach; or get close. I looked up in the online dictionary, Merriam-Webster, the definitions of close and found, as a verb, this one:

• To draw near—the ship was closing with the island.
  So, what do you think? Is it common or not? Does the phrase make sense with this verb?

3. I'm doubtful about the use of this conjugation close/s. I think it should be without the "s" because of the subjunctive mood.
4. Is the use of the preposition "with": spoiling the phrase; necessary; or it really doesn't matter adding or skipping it?

Answer 1

It's odd, and certainly I'd have no idea what kind of answer you are expecting.

"How do you like to be" - this is problematic. Sure it is possible to ask "How do you like your eggs" or "How do you like to be managed", but I would have no idea what you want kind of answer you expect here: Sorry but this is not the correct question to pose!

"when a business partner closes to speak with you" Again, this is odd. It sounds like the partner is some kind of homing missile, or you are in a race and the partner is catching you up. Sorry, but "closes" is the wrong verb.

The subjunctive is not triggered by "when", and so "...when [she] close" is grammatically incorrect. Anyway the subjunctive would be inappropriate in this semi-formal context.

However the use of "with" is correct, but "to" is also possible (with nuanced change in meaning). The preposition can't be skipped; "speak" is not a transitive verb.

And so the sentence is not "correct"; it is not the best way to express yourself.

Instead of "How do you like to be", you could ask "How do you present yourself...", maybe using the word "demeanour", or perhaps completely rephrase to something like "Do you maintain a friendly demeanour...". For the second part, "when a business partner comes to talk with you" is a better expression.

What demeanour do you present when a business partner comes to talk with you?