What separates a strategist from a master strategist? A strategist’s plan can succeed or fail; a master strategist’s plan takes into account as many variables as possible which increases the likelihood of success. A master recognizes that opportunity exists in the unknown. After a strategy has been laid out, how well those plans can incorporate the inevitable unknowns that arise, determines the odds of success. Strategies have to operate in a dynamic environment where people, processes, and events can come into play in an unpredictable fashion. Adaptability is a powerful tool for working with uncertainty. Inflexible assumptions can be the death of a strategy.

A simple way to think of it is that for every assumption, you make, ask yourself, “what if I’m wrong?” If you were planning a presentation at a hotel, your assumption would be, OK I will need to bring my presentation equipment, I’ll use the hotel’s sound system, and have them set up the room for my attendees. Now try to think of everything that could go wrong. The sound system doesn’t work with your equipment. More people show up to your event than expected. Your computer with your PowerPoint presentation decides to be difficult right before the presentation starts.

The more crucial the assumption is to your plan, the more critical it is to ask the “what if” question and plan accordingly. In some ways strategy resembles a decision tree – if x happens, then do this, if x doesn’t happen, then do this other thing. For the master strategist, doing the “other thing” will also involve looking at what caused the deviation from the original assumption and finding opportunities in the deviation.

A master strategist recognizes that people, processes, and events hold both positive and negative aspects, and is able to look at something that is negative on its face, and find a positive aspect that will aid their plan. In the execution of a plan, a master strategist will put aside a personal opinion in the face of non-effectiveness. It may have worked a hundred times before, but if it isn’t working now, they are willing to try something different. A master strategist never stops learning and trying new things.