Imagine a friend asked you:
"I really want to make sure I look nice tonight. What do you think of this outfit I'm wearing?"
Do you just blurt out your opinion? Probably not. You want to be truthful and helpful. But you don't want to inadvertently step on a fashion landmine, either. That's why it's a tricky question, and the best way to gauge just how direct you can be in your answer is to subtly reverse the question and find out how she feels about the choice.
Do the same thing before you critique a student's college essay.
Whenever a student hands us an essay that we haven't seen or discussed with the student before, we always start by asking:
"How do you feel about what you've written?"
If the student tells us that she worked really hard on it and she's happy with how it turned out, we approach it differently than if the student admits that she's struggling and can't seem to make the essay work.
I'm not suggesting you should be dishonest about essays (or fashion). We've got an obligation to give good advice when a student asks. But kids are under a lot of college admissions pressure. And it's important that we don't tear down something they're proud of, especially when they're presenting us with a story about their lives.