That comes down to the skill of the reader in the end imo.
If the reading is "heavy" (as I describe it) - it's up to your skill to find some empowerment for the sitter.
I don't answer questions that would be for - a doctor/therapist, lawyer or financial advisor.
And I don't do 3rd party readings. Depends...very much on how and why they are asking.
I will look at "Circumstances around" these issues and what "likely options there may be"
- but not give flat ultimatums - of course. Lol. I'm not psychic and don't believe things are set in stone.
I may listen to their question and proffer a re-phrase for them, if I think their question is inappropriate - or as you describe "hurtful to them" in the end - because they're projecting and hoping for "the world on a platter" rather than how they might work things out for themselves.
But I may ask these questions for myself - if the reader entertains such questions - Lol.
And see what they come up with and whether I agree.
I do always think about what I'm asking - and generally I don't ask what I don't want an answer to. Lol.
I prefer empowering questions like "how can I best tackle X or in what ways can I improve my communication in Y".
I hardly read for myself. I'm way to invested in the outcome
I can read 'in a fun manner' - or sometimes it works if I skew the focus by "asking my guides" the question. But mostly I use the cards in other ways for myself.
Medidation and visualisation, working through my feelings about things, using them in magick and ritual (another form of personal psychotherapy - if you like), and exercises for learning meanings...
Tarot authors do cover how to ask questions most constructively for Tarot...
I'm sure Benebell Wen must have a weighty section in her book 'Holistic Tarot' (I've read it - I must read again - lol). Biddy does (Birgit Eiselmount)... can't remember any others right now...