This year, I put a name to a long-standing part of myself: the child who doesn't know how to ask the question. You can never explain why a realization hits you and when, but I've been spending some time comparing the conversion candidate to the child who doesn't know how to ask. Baalei teshuva can also fit the bill, but I think there are (generally) more personalized resources for the BT than the conversion candidate.
We all lack some middot, and almost all of us fall prey to pride. We often fall victim to the "Hah! What a dumb question!" or "Wow, doesn't he know anything?" or the slightly less terrible, "Oh man, I remember when I didn't know anything either."
These are the attitudes we take with the child who doesn't know how to ask when that child has the strength and courage to speak up. Yes, sometimes people make ridiculous statements based on half-knowledge or being fed misinformation. But that's often the most effective way of asking a question you didn't even know you had. The strongest (and most humbling) lessons I've learned happened when I made a giant idiot of myself. Heck, I created a blog to help you avoid those moments I had (and continue to have in all areas of my life).
Conversion candidates are not being properly educated. Worse, they've not even being given the tools to get an education to decide whether a conversion is proper for them or not. The kiruv resources are dedicated to educating potential BTs, no matter how lukewarm they may feel, but the most dedicated conversion candidates can be alienated, shuffled around, and embarrassed by every "teacher" they encounter in our communities with little opportunity for recourse (or verification). Each one of us has the potential to teach someone (even inadvertently), and we should embrace that role. If you want to be selfish about it, I assure you that every teacher learns at least as much as his pupil, if not more.
Conversion candidates, yes, you will say dumb stuff about Jewish law or practice. So does everyone else. Those slip-ups are (generally) not your failure. They're the community's failure for not helping you find the right words to ask your question or for not even showing you there is a question. On the other hand, no one likes admitting ignorance, and people especially don't like discovering they were ignorant without knowing it. I personally hurt most from thoughts like, "WOW. I actually said that? What an idiot." As much as I'd love to stop dwelling on those moments, we need to find ways to stop dwelling on them. Admit when you're wrong, learn why, and learn from the experience.
Both sides of the conversation need to take a big bite of humble pie.
I googled around for discussions of the child who doesn't know how to ask. There aren't as many as I had hoped, but I found a very good discussion from the perspective of an educator: Helping the Child Who Cannot Ask:
"[W]e can also view the presence of that child at our seder as a gift. We know how to deal with the wise, wicked and simple child. But the presence of a child who doesn't know how to ask can transform the seder for everyone, even for the wise children. Who knows what unanticipated issues may arise. Our success in helping this child discover the buried questions can make the seder the genuine learning experience it was designed to be."
The conversion candidate (and convert) transforms the born Jews' perspective on Jewish life. Converts bring fresh blood literally (yay genetics), spiritually, and philosophically. These fresh perspectives and fresh enthusiasm make Judaism "the genuine learning experience it was designed to be." But that learning experience must be a partnership.
Only when the Jewish community properly educates prospective conversion candidates (especially about the idea that there are divergent views even within orthodox Judaism, rather than the "normal" kiruv approach that there is one hashkafah) will we have conversion candidates who know how to ask questions. Only once he or she has the right question can there be a right answer.