First you have to ask yourself if you are sufficiently experienced with the topic. How many times have you seen this or a highly similar situation before? Did you guess then validate in those situations? If you consider it sufficient or are looking to acquire the intuition you invest the time guessing. After guessing you try to guess what accuracy you expect your guess to have. THEN you do the validation or analysis to see how well you did.
More often than not I'm almost completely wrong and I imagine my intuition to be highly accurate. It's very humbling. I learn not to depend on it.
I've seen others do much better to the point it looks like magic.