Overcoming the Planning Paradox

Abstract

This article will explore productive approaches to dealing with the Planning Paradox.

"No plan of operations extends with any certainty beyond the first encounter with the main enemy forces.
Only the layman believes that in the course of a campaign he sees the consistent implementation of an
original thought that has been considered in advance in every detail and retained to the end."
~Field Marshal Moltke the Elder

The point of departure for this analysis will be a civilian reading of military theory, grounded in the appreciation that war is an endeavor with dynamic and unforgiving external constraints where leadership complacency is punished severely. The following is based on the premise that civilian organizations can learn from experienced military leaders accustomed to navigating volatile situations. The abstraction level for the analysis in a peaceful context is to seek inspiration in more wicked problems, on how to embrace uncertainty and adapt to surprises in a structured way that touches on all four course dimensions. On multiple scales, a popular strategy appears to be reducing organizational complexity by means of flattening leadership structures where swift action is required. This principle is also deployed where every member of a team has the competencies to dynamically transfer leadership based on who has the most situational awareness. The intent of this is to shorten the collective decision cycle or OODA loop in a dynamic situation, to avoid bottle-necking decision making in a single individual who might be denied sufficient situational awareness to make a productive decision. Here a short summary of factors for cohesion will be provided as well. In a project scale perspective, the wide array of Agile Frameworks have a common aim: Shorten development cycles to face reality in the form of stakeholder feedback on MVP’s. The intent of this strategy is to reality check assumptions and self-correct away from sunk-cost behavior with minimum investment. Here, dysfunctional implementations of Scrum will be explored as a warning against unreflected framework deployment.

Finally, on the Portfolio level this article will also explore the risks of Path Dependence with respect to situational agility. The case studies for this exploration will focus on hesitancies to exploit technological salients that big organizations otherwise appeared to be poised to dominate. This analysis will respect the good intentions of the leadership, attempting to contextualize their hesitations with the organizational complexity they had to work with as well as the corporate cultures they had to navigate. These examples will be picked up with a conclusion on the relative merits and limitations of the tools explored, followed by a recommendations to continually adapt leadership strategies and framework deployment to the situation at hand and keep organizational structure ready for changes as the situation permits.

Decision Making Lessons from a Fighter Pilot

John "Forty Second" Boyd was a United States Airforce (USAF) fighter pilot who, after his combat deployment in Korea, got his nickname from a standing bet he made as an instructor in the USAF Fighter Weapons School(FWS). The bet was that he, within forty seconds, could defeat an opponent from a position of disadvantage in Air Combat Maneuvering (ACM). After instructing he went on to contribute to the development of the F-15 Eagle, as well as laying the strategic foundations for the USAF Lightweight Fighter programme with his Energy-Maneuverability theory of aerial combat. However, his true legacy is one of tactical and strategical thinking. He was very critical of rigid structure of command and other symptoms of inflexibility. An example of this is found in his "Patterns of Conflict" presentation that compares Napoleon Bonaparte's early and late tactics, scolding the Emperor for his top-down approach to tactics. His critique was that Napoleons rigid flow of orders was a tactical waste of sound strategy, and that the lack of afforded initiative to the lower parts of the organization was a key factor in his defeat.

A key concept underpinning Boyd's strategic and tactical teachings is his decision cycle, better known as the OODA loop developed for aerial combat decision making. It is an abbreviation for Observation, Orientation, Decision and Action: