In his book The Answer to How is Yes - Acting on What Matters, Peter Block says
Getting the question right may be the most important thing we can do. We define our dialogue and, in a sense, our future through the questions we choose to address: Asking the wrong question puts us in the philosopher's dilemma: We become the blind (person) looking in a dark room for a black cat that is not there.
Block adds that "The right questions are about values, purpose, aesthetics, human connection, and deeper philosophical inquiry. To experience the fullness of working and living, we need to be willing to address questions that we know have no answer."
Both Koestenbaum and Block challenge us to find the right questions.
Within a business or government organization the questions that are most often asked are about things that are near the surface of our existence. We ask how to make the greatest margin or profit on our product, how to attract and serve customers and gain market share, how to motivate people; in short, we ask how to be successful (however we measure success) in our chosen field.
Although Peter Block would perhaps disagree with me, I believe these are all important questions that need to be addressed. However, I agree with both Koestenbaum and Block in that these are not the first questions that should be asked by an individual or group.
When viewed through the Leadership Diamond, the most important questions become those that take you more deeply into the individual's or group's purpose for being.
In the opening section of Kevin Cashman's chapter on Personal Master (see Leadership From the Inside Out - Becoming a Leader for Life) there is a story that sums up, at least for me, the value of asking the right question:
I once heard this story about a priest, who was confronted by a soldier while he was walking down a road in pre-revolutionary Russia. The soldier, aiming his rifle at the priest, commanded "Who are you? Where are you going? Why are you going there?" Unfazed, the priest calmly replied, "How much do they pay you?" Somewhat surprised, the soldier responded, "Twenty-five kopecks a month." The priest paused, and in a deeply thoughtful manner said "I have a proposal for you. I'll pay you fifty kopecks each month if you stop me here every day and challenge me to respond to those same three questions."
Therein lies the beginning of a very deep and valuable discussion with yourself, your business, or your organization: "Who are you? Where are you going?", and "Why are you going there?"
The story of the Russian priest and soldier is from Kevin Cashman's Leadership From the Inside Out - Becoming a Leader for Life, and can be found online in a slightly different version at this link.
Other references include:
The Philosophic Consultant, by Dr. Peter Koestenbaum
The Answer to How is Yes, by Peter Block