How questions are great, and they have their time and place. But when you are in the strategic phase, when you are trying to establish a perspective on the desired future state, and to develop insights to support going there, how questions get in the way.  Think about it.  If you ask “how will we convert all of our legacy data onto a new platform without disrupting business as usual”, you will get all of the reasons why moving is not practical. If you ask “why should we convert all of our legacy data onto a new platform, and risk disrupting business as usual”, you will start thinking strategically about the problem.

At that point, you will do one of three things that are critical for setting a strategic goal: you will identify and articulate a burning platform, you will identify and articulate a burning desire, or you will identify and articulate a clear reason to do nothing.

Any of those three outcomes is perfect for what you need to set strategy.  Too often, strategy work gets mired in the ‘how’ questions, and there is not clear articulation of either a burning platform or a burning desire….. or clarity that no action is needed or wanted. If you want to be effective with your strategy work, focus on the why, not the how, and discipline yourself and your team to stay on the ‘why’ until you have one of those three outcomes.  And once you have a compelling ‘why’, the ‘how’ questions are that much easier to get sorted.