"Healthy" Skepticism

I've been confronted with the concept of skepticism in the past few days, and I've pondered how skepticism and the idea of being a skeptic fits in with my faith. People say that it's always good to have a healthy dose of skepticism when approaching situations and people, but I've come to wonder whether it can honestly be healthy, or whether approaching people with that worldly attitude is wrong. And, it may be that it's not a clear cut issue - when you become skeptical, it is usually based on experiences and situations that you've confronted within the confines of our everyday lives.
That being said, I can't help but think that being skeptical is a form of judgment. Being skeptical causes one to have a pre-conceived notion about another person, whether there are valid circumstances to have that notion or not. Being skeptical is not a common description that I would hope others would think of when they think of me, but I confess, I fear that there are those who do perceive me as such. I can't help but think that the mere fact that they think I'm skeptical is a result of a way that I have treated them or interacted with them in the past. Which leads me to wonder the reasoning and feelings left behind by that previous contact that they had with me - whether my skepticism or quick judgement is the basis of their opinion.