First, this is relatable. I volunteer with a few organizations that connect IT professionals with disadvantaged young people. I believe it’s super important in principle but in reality I find that many of the mentees are unfortunately facing HUGE obstacles that are difficult to help via a mentoring relationship. Example: needs an IT job and is taking classes but has no car, is on brink of losing their apartment, etc. etc. So I feel really ineffective giving interview and resume advice that only scratches the surface of what they need! It feels like I’m a doctor and someone is coming to me with a heart attack and a sore throat and I say, here’s some pills for your throat, good luck with the heart attack.
This person probably lacks a filter although I also know that some mentees are hoping for a fairy godmother and I don’t even blame them. But you want to be wary of anyone angling to take advantage of you.
All of this is to say, I would have done the same here and stuck to the professional question. For someone I am mentoring longer term and have a rapport with, Id give them more advice on what not to say in a professional situation. But it really has to be done with sensitivity and humanity that isn’t really possible in a one off random email.
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