Considering the amount of uncertainty increases the longer into the future we try to see, planning once and then executing following our plan does not look like a winning strategy, no matter how much effort we put into planning. We may even be hurting the quality of our planning by doing too much of it at the onset.
What is a planner to do, then? We can spend just enough effort at the beginning planning our endeavor. Then start executing, and refine our understanding with periodic review of our progress and again spending just enough effort to (re)plan our work ahead. “Just enough” is a problematic expression.
How will we know how much is just enough initial planning? I don’t have a satisfying answer yet, but practice has led me to some heuristics I keep refining: If you are still uncovering risks and opportunities that you did not see before, that have the potential to alter your chances of success and which outcomes can be influenced by mitigation or preparedness of any kind, you ought to keep planning. When the risks or opportunities you uncovered had been trivial enough, then it is time to stop. If you have started running in circles, chasing “unknowables”, or pretending you know things you cannot know, it is also time to stop planning. Start with a not so large effort and then progress your initial planning in short loops, when the improvement done over previous cycle does not feel significant, and we still feel we put enough effort and made wise choices, it is time to stop.
Another difficult decision is how often should we review and re-plan. Again some rules of thumb may help us decide. The farther ahead we can see the longer we can keep our heads down busy with execution without planning again, and more effort we can put in each round of planning. In risky circumstances, unknown terrain or in the presence of unpredictable events we will be wise to plan often, looking ahead to a shorter time horizon, and spending less time doing so for each loop. Each loop should be firmly grounded in reality, considering all feedback we can get from our execution and the events unfolding around us.
No standard planning approach is universally adequate. The answers to when, for how long and how often to plan are highly contextual, and you ought to make a conscious choice. We are all called to lead our organizations making a explicit decision that is grounded in our context and then constantly refining our approach to this timing questions as get more and more feedback from reality.
This post is part of a series on planning. In the same series, you can also read:
The Adaptive Executive 
3 thoughts on “The Timing of Planning”