Well, first of all we have to be pretty discriminating as to whom we show our weaknesses to. We have to learn how to trust them, and perhaps that may take some time. To realize whether they will actually expose our weaknesses to others is important to consider. We have to develop a bit of trust, to see to whom we want to expose our weaknesses. Because being very practical, we see that there are quite a lot of people in the world who will take advantage of others' weaknesses. I know I was disappointed some time ago in telling somebody something, which I thought this person wouldn't tell anyone else about it. But then I realized that they did, and so I lost a trust in that moment in that person, and I found out that I had to be more careful about who I told things to.
This has also made me very cautious about what I tell other people because many people will try to take advantage of this. Maybe not the person we tell, but if they have a tendency to tell others, some other people may want to take advantage of our weaknesses. So we have to judge for ourselves whether we want to trust another person. And that also means if we don't really want to ask questions which are personal, we need to be very skilful in the way we ask something. Perhaps so that they don't know that it is ourselves whom we are talking about. We may actually say, "You know, if a person has such and such, what would you say to that? How would you work with something like that?" Not saying that it is ourselves, until you actually realize that you can trust this person. And then it may be helpful for you to make it clear to that person, "I'd like some help, but what I tell you, I would like to remain just between you and me". Don't assume that this person will not tell anybody, make it clear to that person. As well, you have to try to develop more courage, realizing if you have a problem, and you have seen that you can maybe trust this person, that it may actually pull you back from understanding more if you don't actually be more honest with that person, and ask the questions when you have the opportunity.
One thing that has helped me ask questions from certain teachers when I didn't feel like I wanted to, is to remember what the Buddha said in the scriptures. "If a person has the opportunity to ask questions of a teacher, and they don't ask these questions, then they will be reborn stupid." Well, one thing I don't want to be reborn as is stupid! So this encourages me to ask questions. And even if you don't believe in rebirth from life to life, looking at it more moment to moment, yes, if we don't ask questions and we remain in our ignorance of the answer that someone may have the correct answer to, then in that next moment we are going to be reborn stupid again. By seeing it as an opportunity to increase our understanding, this quote is often in the back of my mind. Often when our assistants don't ask questions we remind them of this particular teaching of the Buddha! Next retreat, if you have the opportunity, try to remember that one. That if you don't ask questions, then you are reborn stupid.