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My company wants to promote me but needs me to work in Brazil. This is like your teacher telling you you’ve done well and allowing you to skip a grade.

In the above sentence, the gerund "telling" is the object of the preposition "like", and "your teacher" functions as the actor of the action "telling". Am I right?

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You might be understanding the underlying grammar, perhaps. But let me parse it for you anyway. :)

This is like [ your teacher telling you (that) you’ve done well and allowing you to skip a grade ].

The stuff that is in italics (the stuff within the brackets) is a subordinate non-finite clause:

  1. your teacher telling you (that) you’ve done well and allowing you to skip a grade

and it has the meaning of the following finite clause:

  1. your teacher is telling you (that) you’ve done well and is allowing you to skip a grade

From #2, it becomes transparent that "your teacher" is the subject of the clause; and so, it is the subject in both #1 and #2. The meaning of both #1 and #2 is:

  • Your teacher is telling you X and is allowing you to do Y.

So yes, for your original example, the noun phrase "your teacher" functions as the subject (or "actor") for the clause which has the form of a coordination of two verb phrases: a verb phrase headed by "telling" and a verb phrase headed by "allowing".

Which is basically what you've already said in your OP. :)

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I am not sure whether the way you are parsing the sentence is correct. I am sure that there is a different way to parse it.

This is like your teacher telling you [that] you’ve done well and allowing you to skip a grade.

There are two phrases beginning with -ing words. These -ing words could be gerunds, or they could be participles. If they are participles, then the participial phrases must modify something. In this sentence, they can modify "teacher".

The preposition "like" needs an object. If the -ing words are participles, then they can't be the preposition's object. However, the word "teacher" can be the object of "like".

As I parse the phrase, the preposition "like" takes the first available object, "teacher". The genitive pronoun "your" modifies "teacher". The two participial phrases also modify "teacher".

When the phrase is parsed in this way, we can still consider "teacher" to be the actor of the participles, but we do not consider it to be their subject. It's just the thing that the participial phrases modify.

 
Regardless of whether we consider the -ing words to be particples or gerunds, they each start a complete phrase. Within the first phrase, the pronoun "you" is the indirect object of "telling", and the nominative subordinate clause "[that] you've done well" is the direct object. Within the second, the pronoun "you" is the direct object and the infinitive phrase "to skip a grade" is the object complement.

It doesn't make much sense to separate "telling" from the rest of its phrase.

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I would say that like refers to the whole phrase your teacher telling you... and allowing you...

And yes, your teacher is the actor for both telling and allowing.

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