I think a lot of my questioning stems from my own haphazard education. I would beg my mom to buy me those super cool workbooks at the drugstore every time we were there, but I loathed being in the classroom so much that I would fake illnesses to get to hang out in the nurse's office. I loved books and would beg the librarians to let me take out just one more book because it was just too hard to choose which had to stay, yet I managed to miss 94 days in my 8th grade year and somehow had B's in all my classes - except P.E. where of course the only requirement was to be there and participate. By the time I was in high school I was missing more days than I was there and three weeks into 11th grade, just days after turning 16, I was DONE! I signed myself out and my mother consented, worn down by the years of fighting to get me to school. I took the GED just weeks later and passed it with perfect math and science scores. I then proceeded to tutor high school students until my class graduated and I was finally eligible for financial aid to start college classes. I loved learning so much I even started out on my college path to be a math teacher, I hadn't understood that it was SCHOOL that I HATED! Luckily I had KM during that first year and decided, upon returning, to change my major to behavioral sciences. I then took a child psychology class in which I did a paper on various educational methods and was astonished at the wide variety of options that were out there. That paper is what began my understanding of learning styles and led our family down the twisty path which brought us to home education.
Five years into this home education thing, I still question myself and our choices all the time. I create a list of literature titles that I think are important and that KM will enjoy, only to find that she hates most of them - why did I spend all that time scouring lists and hunting down copies of the books? KM will get stuck on a math problem that I can tell her the answer to and how to complete the formula or where she went wrong, but not why that is the answer - only to be left wondering, why do I even know that? While working on chemistry she has to create a graph that shows the electronegativity of a period of elements - will she ever need to figure that out in her life? Since it is nearly impossible to ever know what a child will retain, be inspired by or be utterly bored with, I think it is truly important to be flexible, explore a wide berth of topics, and be open to anything! I am always astonishing at the rabbit holes that can be found when you simply let the learner take any and all twists and turns that might pop up along the way.
So basically I think questioning is good! Question everything, don't take anyone's word for it and allow your learners to question things as well - even if that something they are questioning is you!