It makes sense to put it all in one sentence, but you are right that it's a little bit awkward and hard to follow. You can improve it by adding a comma and the word "to" in exactly the right place:
The SI encouraged mom to work with pictures and ask Jonathan questions such as "What is the girl doing?" or "What is the boy doing?", or to describe the picture, saying "the boy is eating a banana."
One problem in the original sentence was that it wasn't clear whether "or describe…" was something that mom could do instead of asking Jonathan a question, or something that mom could ask Jonathan to do. The comma and the word "to" help the reader understand that "describe" is an alternative to "ask". In English, you wouldn't say "…ask Jonathan describe the picture", but it sounds like you might have intended "describe" as a third possibility for what mom could ask Jonathan. A reader isn't sure if you said what you meant to say or if you made a mistake.
The revised sentence above means that mom will describe the picture. If mom is supposed to ask Jonathan to describe the picture, then you could say this:
The SI encouraged mom to work with pictures and ask Jonathan questions such as "What is the girl doing?" or "What is the boy doing?" or ask him to describe the picture.
The revised sentences are still awkward, though. A second problem with the original sentence still hasn't been fixed: "the girl", "the boy", and "the picture" occur before a specific girl, boy, and picture have been clearly introduced.
Here is one way you could split the original into two sentences to make it easier to understand. Part of the reason the original sentence is tricky is because it uses "and" to explain what "work with pictures" means. Often that's fine, but to be clearer, you can say explicitly that you are explaining the meaning:
The SI encouraged mom to work with pictures. This would mean showing Jonathan a picture, say, of a boy eating a banana, and either asking him questions about it, like "What is the boy doing?", or describing it.
The SI encouraged mom to work with pictures. This would mean showing Jonathan a picture, say, of a boy eating a banana, and either asking him questions about it, like "What is the boy doing?", or asking Jonathan to describe it.
The word "either" helps make these sentences easier to understand, because it announces in advance that there are two things the mother could do. Also, the indefinite article introduces "a picture" and then "a boy" before the sentence refers back to them.
P.S. Notice that I changed "the boy eats banana" to "the boy is eating a banana." When describing action shown in a picture, we nearly always use the present continuous tense, not the simple present. (You might want to ask a separate question about that.)
12The sentence is fine. It can be split to make the meaning clearer but to me the meaning is clear even without splitting. – CowperKettle – 2017-05-21T17:48:22.963
It looks fine to me, too. – BillJ – 2017-05-21T18:03:37.480
3What is an SI?? – James K – 2017-05-21T18:21:29.360
Is "mom" intended to be a proper noun or a descriptor? It should be "Mom" in the former case, "the mother" or "the mom" in the second case. – Greg Martin – 2017-05-22T05:52:26.877
2@CowperKettle The sentence triggers an alarm in my head: that maybe the writer isn't saying what he or she intended to say. It doesn't flow in the ordinary way, introducing things before referring to them (like "the picture"). So, I wonder if the writer is struggling, and meant, in the second alternative, something like asking Jonathan to describe the pictures—which would make more sense if the idea is to get Jonathan to actively perceive the pictures or put things in his own words. Long before I've sorted that out, though (which is quite hard!), the alarm has sounded. – Ben Kovitz – 2017-05-22T09:28:04.107
Does this belong on ell? It's a question about English for sure, but I have often struggled to deal with such sentences when reviewing documents from native English speaking colleagues. – Martin Bonner supports Monica – 2017-05-22T11:00:32.220
@MartinBonner Indeed native speakers often fail to notice the ambiguity and even a professional copyeditor can struggle trying to reword it. I think the question belongs on ELL because one can reasonably seek the kind of answer that ELL is for: a teaching answer, which doesn't presume English fluency, doesn't go into esoteric linguistics, and offers help with fundamentals like articles, common cultural references, or other obstacles that non-natives must overcome. Asking about it on, say, linguistics.stackexchange.com, one would be seeking a very different kind of answer. – Ben Kovitz – 2017-05-22T11:35:37.257
1
@JamesK Looking at https://en.wikipedia.org/wiki/Si, I think SI must mean "Swarm Intelligence", given the context. Though The SI is a former name for Vencore, a US defense contractor - more likely that than Scouting Ireland, which is also a possibility.
– SusanW – 2017-05-22T12:36:51.8931I would guess that a "SI" is a sensory integration therapist. Although it is not a common enough abbreviation to not explain. – skymningen – 2017-05-22T14:58:22.170