Johann Friedrich von Schiller (not one of my ancestors) said, "He who considers too much will perform little." While it is certainly true that facts are our friends (see http://blog.fastcompany.com/experts/dkarlin/2008/01/leadership_combined_forces_of.html?partner=rss), too much reliance on fact analysis becomes equivalent to lack of decisiveness. A true leader needs the ability to quickly ascertain the pertinent facts and then move on.
You may find yourself questioning decisions because you feel the facts were ignored. This may even be true of decisions that you made. Keep in mind that decisions are made in the gut and not the head. We make decisions first and then think of reasons afterward. This is being smart. If we sifted through all facts and reasonings first, we would never get anything done.
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I catch myself and my colleagues quite often in situation when we consider our options while no one ask if there will be any significant impact of our decision.
Sometimes it doesn't really matter if you start negotiations with 40% or 30% when the other side expects something close to 5%. Sometimes month and two months are equally good as the time isn't very important factor in the project. Sometimes it doesn't really matter how your interface will exactly work as system you integrate with isn't ready. Etc.
In those situations I try just to take a good guess and move on. When you don't have enough information to make a right choice, time spent on discussing the issue won't help much.
And for me it is rather about being reasonable than being smart.
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