Earlier this year I wrote a blog post on our company blog about one of our core values "Challenge the World". This is not only one of our company values but something I have been subscribing to myself for quite a while. This has often been a successful way of approaching things for me. However in certain instances my questioning didn't lead anywhere and I've come to reflect over why this might be.
I think that in many of the situations the people I questioned saw what I see now. They saw that at that point in time I didn't have sufficient knowledge to be questioning the ideas I was questioning. Bjarte Bogsnes hits the nail on the head when he starts one of his presentations by saying:
"[Looking back] I've done a lot of stupid things [...]. But it [...] gives me a platform to be quite critical because I've done it. I've been on the inside."
Bjarte is referring to all the years he spent doing classical management and budgeting and asserts his position as a critic of these things since he has "[...] been on the inside".
In my opinion it's important that we aim to understand things first before we jump in and start questioning them. I think that premature questioning often arises when we are second order ignorant, that is when we don't know what we don't know. When second order ignorant we are usually driven to question things purely because we don't understand them but we think we have the full picture. It also makes the work of our counterpart very hard and we can often get comments such as "You just don't understand" or "It's more complicated than that". For me it has been useful to go through the moves of something new before I suggest improvements or alternatives at least this gives me the security of knowing I have a somewhat complete picture.
It is also useful to try suggesting alternative ways or ideas when questioning things. If you can't and the only comments you have are "this is wrong" or "this feels off" you may also be second order ignorant.
I think challenging is a good thing but it might be a wasted effort if done on the wrong basis.