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I'm not going to go much in depth since I was very young when these happened but from I've learned about leadership in and out of politics is that you can not know everything and you better start learning to take advice from multiple experts in the particular field you are working with.
Iraq for example, from what I remember, I did not see much debate on what would happen when we did invade Iraq. We did not challenge the assumption that Iraqis would accept Western democracy with open arms and that turned out to be our biggest mistake. That is something that could have been easily prevented and should have been looked at more and hence my leading argument against Bush for this conflict.
This "action based on unbacked assumptions" is one of the biggest flaws I see in this administration when not going into depth and talking about foreign policy and it is something that should be valued as a leader by questioning every assumption to make sure that the generalization can hold. My other big flaw I saw is the "you are with us or against us attitude". We had most of the world at our knees, even Iran, after 9/11 but we blew it by pushing other countries to do what they did not want to do and ostracizing others.
I can't really say on the rest because I feel I was too young to remember what was actually happening but that is my two cents.
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