Thirty Useful Questions

Most of us have toolkits that contain whatever is needed for addressing problems that have inherently well-defined structure. For example, we can all calculate how long a project will take given the list of tasks, their dependencies, and the effort and time required for each task. It might be laborious, but it's doable. And if we give that same set of data to two different people, the results would be in close agreement.

But some problems don't have inherently clear structure. Some cannot be expressed mathematically. For example, to determine why Lisa and Louis can't get along, mathematics is of no use. Even when we can imagine calculating an answer to a problem, we must be certain that we've expressed the problem completely, without duplication. For example, to determine the capital needs of a startup company, we need to have a complete list of its equipment needs. In that case, it's easy to generate a list, but not so easy to determine that the list is complete.

For unstructured For unstructured problems, it's useful
to have a list of questions to ask that
might serve as guides for ensuring
that we understand the problemproblems, it's useful to have a list of questions to ask that might serve as guides for ensuring that we understand the problem. For that purpose, I offer the list below, in no particular order.

• What questions would I like to know the answers to?
• If I had the answer to question X, what do I think the answer would be?
• If I had the answer to question X, what questions would I ask next?
• I don't know the answer to question X, but what do I know about the answer to question X?
• I don't know the answer to question X, but what do I know about the answer to question X that I've forgotten I know?
• What's the significance of the answer to question X? What does it matter?
• If I had the answer to question X how could it change what I'm doing now? How would it change what I plan to do next?
• The answer to question X was Y last week. Is the answer still Y this week?
• What did I believe to be true in the past that turned out not to be true?
• Among those of my past beliefs that turned out to be mistaken, is there any discernable pattern?
• Which cognitive biases have affected my judgment in the past?
• Which cognitive biases might at this moment be affecting my judgment?
• Among the cognitive biases that affected my judgment in the past, is there any discernible pattern?
• What questions would have been useful to ask in the past if only I had asked them?
• How do we know that we've included all the risks (all the expenses, all the revenue, all the …) that we needed to include?
• What am I assuming that I'm unaware I'm assuming?
• Why am I asking question X?
• How do I know what I know about X?
• Why do I not know the answer to question X? What missing pieces would let me find that answer?
• What am I not asking questions about?
• I know that solution S is a solution to Problem P, but how do I know that there isn't a better solution?
• Have I confirmed that this problem is my problem to solve?
• How do I know that this problem is my problem to solve?
• How do I know that solving this problem is necessary?
• How much is the solution to this problem worth?
• How much will solving this problem cost?
• If X worked so well in situation S, why is X not working in situation S'?
• If X and Y both worked well in situation S, why is X working in S' while Y isn't working at all in S'?
• If X always produces Y in situation S, and Y always produces Z in situation S, why doesn't X produce Z in situation S?
• If Person A works well with Person B, and Person C works well with Person B, why can't Person A work well with Person C?

One final question: if you were to add four questions to this list, what would they be?  Top    Next Issue

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