"Never once did Jesus scan the room for the best example of holy living and send that person out to tell others about him. He always sent stumblers and sinners. I find that comforting." - Nadia Bolz-Weber, "Accidental Saints: Finding God in All the Wrong People"
I, like Nadia Bolz-Weber, find this very comforting about Jesus as well. In many depictions, the disciples were a bunch of stumblers and sinners, as was Mary Magdalene.
The upside to this theology as it relates to leadership is that there are stumblers and sinners a-plenty. The best examples of holy living are few and far-between, and even if you could find them, most of them will only fool you for so long. Even more, those who are perhaps seen as "less than" are more capable of taking their stories to the masses and tend to be more open to loving others, as they do not think too highly of themselves. As a leader, they may not expect you to stay on your pedestal and are happy to find that you, too, are stumbling and sinning. Nadia Bolz-Weber is a recovering alcoholic and, I believe, regularly attends AA meetings. There is no shortage of humility and willingness to listen in those meetings and leadership is shared easily.
The downside to this theology with regard to leadership is that there may be a lot of explaining and re-explaining concepts. Leading a group who does not grasp concepts easily is difficult and requires a significant amount of patience. There may also be a tendency of the congregation to rely very heavily on the pastor for emotional support, which could result in burn-out.