As a leader, regardless of what you are leading, you should surround yourself with a strong group of individuals who share your vision of the goal that you are working towards. WoW is no exception to this. It is important that each and every member of the organization know that their leadership is on the same page in terms of the goals. Any cracks in the leadership will destroy the organization. In other words, your leadership is like a foundation of a home. Everything that is done is going to be done on that initial groundwork so you must be careful as to who you invite into leadership positions.
In the past I have given in to petitions for members of the guild to be given an opportunity at leadership positions. Sometimes these individuals have peformed their rolls admirably and efficiently. Other times they have been a dismal failure and a giant headache. However, there was one person that I had as an officer for a short period of time who constantly questioned every decision that was made. They did it in an open way to the best of my knowledge, but never failed to always question everyone in officer chat. I know some folks became so aggrevated over this individual that they begged for their removal from their position. I on the other hand appreciated this person's openess. They did nothing wrong, but always led with their heart when they asked a question. Often times they were satisfied with the answers but on some occassions would push the matter again after they had some time to reflect. As time wore on this person left our guild and honestly it was a good decision for them to leave. (And no I will not say whom this was or whether it was good or bad conditions that they left under.)
My point of bringing this person up was not for a QQ or Hatefest '09 on them, but rather to point out that we need those kind of individuals in our guild officers. I am blessed, all of our officers are highly oppinionated and loud (hee hee love you guys!), so getting an opinion never takes long. However, sometimes I miss that one person who just wants to take the extra five or ten minutes to debate me on the merrits of whatever the topic is. Did they aggrevate me? Absolutely, I hate to be questioned when I have made up my mind. However, I also realize that absolute power corrupts absolutely. So if you are running your own guild now or plan to start one in the forseeable future, then I would recommend to find yourself at least one nay sayer and bring them on board. So long as they share your goal and vision, then their viewpoints will always help you consider other angles you may not have thought of.