Q & R: Asking better questions … and prayer

A reader writes …

My fellow church members are open minded, loving, gracious, and compassionate people. They embrace far more folks who are “different” from themselves than most in their own circles actually do. It’s quite a “home” for our family, in particular the smaller groups we discuss issues of faith.
I even have opportunities to teach and lead discussions about those issues of faith. Yet I am always being cautious and careful about what to say and what not to say. Certain doctrines seem to be non-negotiable, and questioning them openly would leave me too vulnerable. Which ones aren’t important to this email, but my question is this:
As somebody who feels like I’m “on the other side” (to use a title of your first book), how do I help others ask better questions without being demeaning, condescending, or perceived as blasphemous? I really want to help them ask better questions, so I’m curious what tips you have.
Also, a completely different topic, I think many of your blog readers would love to know how you personally pray for your small sphere of friends and family members. Not details, of course, but just a gist of what your prayer life is like.
(If you were to pick one of these to answer, please answer the prayer one!)

Thanks for these excellent questions. On your first question …

It seems like neither Jesus nor Paul “succeeded” in challenging people to a bigger and fuller way of thinking without being considered blasphemous … so I know it’s impossible to please, help, instruct, challenge, or serve everyone. Some people just aren’t willing or able to think new thoughts at any given moment. (That might sound condescending or demeaning … but I think that socially, psychologically, intellectually, and emotionally, many people are – at any given moment – in such a bind that asking them to change their thinking is unrealistic, if not uncompassionate. The good news is that an hour, month, or year from now it might be different.)
In my experience, we all have options. We can a) help highly resistant people become a millimeter less resistant, b) help open people take some steps forward, c) help highly open people take major leaps forward. Being “all things to all people” means that we adapt our communication strategies depending on whether we’re working on a, b, or c. I do think you can be all things to all people (relatively speaking) but not at the same time! So I respect some folks who specialize in a, even though I’ve decided to focus more on b and c.
On prayer, it’s encouraging to get your note, because really this is a thrust of my upcoming book … The book is about twelve simple words which represent postures we take in God’s presence. For now, this beautiful song by David Wilcox comes to mind … In my prayers, I seek to hold people up to the Light – to God’s mercy, compassion, grace, and care.