A mí me desconcertó cuando él preguntó adónde iba.

Questions & Answers about A mí me desconcertó cuando él preguntó adónde iba.

Why is iba in the imperfect tense here?
This is past reported speech. The original direct question was likely in the present tense: ¿Adónde vas? (Where are you going?). When reporting a present-tense question in the past (triggered by preguntó), the present tense backshifts to the imperfect (iba).
Why does adónde have an accent mark if this isn't a direct question?
Question words like adónde, qué, and cómo keep their written accents in indirect questions just as they do in direct ones. Because he is asking "where to?", it remains a question word and keeps the accent.
Is it necessary to say A mí me desconcertó, or could I just say Me desconcertó?
You can absolutely just say me desconcertó. Adding a mí at the beginning simply adds emphasis, highlighting that you were the one who was bewildered, perhaps in contrast to someone else who found it totally normal.
Since iba can mean "I was going", "he was going", or "she was going", how do we know it means "I was going" here?
Without more context, it is technically ambiguous! However, because the first half of the sentence establishes that the speaker is the one being affected (A mí me desconcertó), it's naturally assumed the speaker is the subject of the question. If they meant someone else, they would likely add a pronoun like adónde iba ella.
How does the verb desconcertar work in this sentence?
It functions similarly to gustar. The thing causing the bewilderment is the grammatical subject, and the person experiencing it is the object (me). Here, the entire event of him asking the question acts as the subject that "does the bewildering" to the speaker.

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