It isn't so much about how well you plan for things, but rather how you #lead when you don't.
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As successful leaders and learners, we know that planning is extremely important. We want to make sure that we've accounted for everything, both for our own learning, and the learning of those we work with.
If we lead and learn successfully, we've seen how necessary solid planning is.
But, the true test for a leader is not how well they lead when they've planned for thingsl. But rather, the test of a leader's capabilities and resolve is how they lead when they haven't planned; when they're totally surprised by a situation, or at worst, when horrible things happen.
Leaders who are truly great are able to react effectively and quickly to these unplanned scenarios. Often this is due to an ability to showcase leadership characteristics, regardless of a situation. But, on a number of occasions, this is simply due to resolve, "stickwithitness," and a desire to never leave anyone behind.
These leaders also know the strengths and weaknesses of those they work with, and can effectively dispatch others to address key areas of an unplanned crisis. The best leaders are able to do this because even though they haven't planned for the scenario they are faced with, they have met regularly with those they work and live with to explore "what ifs." The imprinting of being prepared is sometimes more important than the actual planning itself.
Another key aspect of approaching situations you haven't planned for is to debrief and reflect on them after they have occurred. Often, people don't want to think about bad situations that have taken place. Yet, the importance of deep reflection and considering how a response could have been made better actually helps seed future planning, thereby reducing the chance of "surprises" in the future.
So, plan, and plan well. But realize that it is how you respond when faced with situations that you haven't planned for that truly showcases your current capacity as a leader.