In the life of a great leader, they are most typically considered GREAT because they achieved something that was above them. For example, if someone who is already high up accomplishes something that is on that "high" level, it is considered their job. The achievement isn't something special per say, it is simply what is expected of them.
A great leader however, probably started as someone who was a nobody. Look at Napoleon Bonaparte, or George Washington. They both climbed the ladder of success, stumbling at times, completely falling at other. Through learning and becoming respected these leaders achieve something, let it be dignity, respect, truth or even freedom.
In the real world however, these great leaders have many setbacks, but these setbacks are almost more important than their achievements, because these setbacks taught them what they needed to learn, and molded them into the leaders we know them as today.
I personally do not think less of leaders who show weakness or encounter failure. Some people might call the ability to feel sympathy and cry a weakness in leaders. I on the other hand think it is a sign of humanity. A cruel leader who can show no sympathy for his enemies will also be unable to show sympathy and understanding for his own people. As for failures, I don't have a problem with people who fail, failure isn't something that defines a person. How they stand back up is what defines them, how they use their mistakes to their advantage.
A few years back I learned about the upbringing of Napoleon Bonaparte. His story amazed me. From his childhood as an outsider to his legacy of standing up for himself at all costs. Bonaparte inspires me because even through all the triumphs leading up to his banishment and death, alone on an island guarded by enemy soldiers he was still living a triumph, never giving up what he could control, his love and appreciation for himself. His last words where his greatest loves. "France, armée, tête d'armée, Joséphine."("France, army, head of the army, Joséphine.")