These are questions that deal with how to enter into and maintain a desirable positioning in life.
What position do you aspire to be in?
What do you want to be able to do?
What don't you want to have to deal with?
What state of being would you like to be in?
What do you need to be able to do to enter and maintain this position indefinitely? What would need to be the case in order for this position to be sustainable?
What obstacles may you come across? What resistance may you have to overcome? What is going to keep you from being able to enter this position and maintain it indefinitely?
What methods can you use to overcome or manage these challenges?
Winning Strategy Questions
These are questions related to assessing whether a given strategy is a good bet or not.
If successful, will the strategy be profitable?
Is the strategy protected?
Is the strategy easy to execute?
Can you execute the strategy quickly?
Is the strategy surprising?
Simplicity/Efficiency Questions
These are questions geared towards simplifying your life or making it more efficient.
How can I do less to achieve more? In other words, how can I use the least amount of expense to achieve the greatest amount of effect?
How can I use my strengths to exploit weak points (opportunities) in this situation?
Is there a way to do x [benefit] without doing y [cost]?
Knowing what I now know, is there anything that I am doing today that I wouldn't start again if I had to do it over?
Control Questions
These are questions around how do you increase control in a given situation - the aim of strategic living.
What desirable outcomes can I generate in this situation?
What undesirable outcomes can I stop or prevent in this situation?
How can I increase my ability to do both?
Will exercising control now allow me greater control in the future?
Tactical Hell Questions
These are questions geared towards assessing the daily battles or struggles you're facing in life.
In what areas of my life do I feel the same struggle or battle or conflict is recurring?
In what areas of my life am I frustrated, with the feeling of wanting someone or something else to change?
In what areas of my life do I not have an overall positive, optimistic feeling about? From where do I often try to escape?