Honestly, honesty. Brutal is preferred. It's been my experience that most people, when asking/saying some obscure question/comment that casts them in a negative light (i.e., "Am I too much of a push over?", "Could I have done that differently?", "I'm no good at this," etcetera and so forth), they are not seeking truth. They're asking for someone to denounce the things they've said about themselves and all the insecurities on which those statements were based, regardless of the accuracy of the initial statement. Essentially, they're wanting you to lie to them so they can feel better about themselves. Honestly, this whole dance is manipulative and counter-productive. Therefore, I prefer to remain honest on all counts. This serves two purposes:

One: These "affirmations of self-worth", otherwise known as lies, only temporarily relieve the insecure person of their anxieties. Eventually, those insecurities will resurface once the ego-stroking has subsided, and they'll go back to asking moronic questions. What people fail to remember is that anxiety serves a purpose. It compels change and growth. When one manipulates others into "reaffirming one's self worth", they are suppressing those anxieties momentarily and, therefore, avoiding change. It's sort of like taking drugs to relieve pent up emotions, albeit less extreme. Instead of coping with those emotions in a positive and productive way, they seek whatever comfort (drugs, lies, booze, cheap thrill, sex) in an attempt to bury those emotions so they don't have to face them. But when I tell them the truth, those anxieties are amplified and they're forced to face them, which, hopefully, encourages growth. And they may continue to seek a good ego-stroking by means of manipulation in an attempt to rid themselves of the horrors they felt when they made the mistake of bothering me, but it'd be a futile effort because they know what I said was true. This will inevitably lead them and most others to believe I'm an a**hole. And that wouldn't be far from the truth...

Two: They stop asking me stupid questions.