Below is a list of features that are emblematic of effective strategic questions, but do not fully define every strategic question. This list includes explanations and examples that illustrate these features, including questions that invite multiple answers, keeping questions simple, avoiding “Why?” or “Yes/No” questions, and addressing taboo topics.
A strategic question is not a leading question.
Leading questions push questionees to respond in a specific manner and are often recommendations disguised as questions. They let the assumptions of the questioner dictate the conversation, which hinders the open-minded information gathering of first-level questions and the collaborative problem-solving of second-level questions.
As an example, suppose Sally is considering moving to a new home. She has heard of some good real estate bargains in Anchorage, but she feels a bit stuck on how to move forward and make decisions. One could say to her, “Why don’t you just move to Anchorage?” This question might be provocative, but it is not very helpful. It is actually a suggestion that is pretending to be a question and implies that she should move to Anchorage. This could even be a way of the questioner projecting his or her own desire to move to Anchorage into the question. Whatever the reason, this creates a situation that is leading Sally because the question is manipulative and it is possible that the more pressure Sally feels, the less likely she is to consider the Anchorage option.
Some alternative, powerful strategic questions to ask Sally include:
“What type of place would you like to move to?”
“What places come to mind when you think of living happily?”
“What is the meaning of this move in your life?”
Such questions encourage Sally to talk about the qualities she wants from her new home or to set new goals. Once Sally shares those goals and insights, you can then work with her to achieve them. By asking questions in an open way, you can avoid leading questions that prevent the questionee from making their values and perspective known.
A strategic question creates options.
One could also ask Sally, “Why don’t you move to Lagos?” This question is focused only in one direction (Lagos), and it limits the options she is challenged to consider.
A more powerful strategic question presents a multitude of options, such as:
“Where would you like to live?”
“What are the three or four places that you feel connected to?”
These are much more strategic questions to ask her at this time. Sally might have been so busy thinking about the career opportunities in Lagos that she lost a sense of all the other possibilities and her real goals. This type of question would redirect that tunnel vision into a more expansive frame of thought.
A strategic questioner would help Sally consider many options equally. Suppose Sally says she could move to New Delhi or Lima. It would be disrespectful to think, “Lagos is the best and Sally should be encouraged down that path.” A more ethical approach would be to help Sally sort out her own direction by questioning all the options even-handedly, with the same enthusiasm and interest. Not only that, but it might be more helpful to ask if there are any more options that occurred to her during the questioning time. Out of these questions, a new option may emerge.
It is particularly important for a strategic questioner to avoid focusing on only two options. We are so accustomed to binary thinking – by considering only Lagos or New Delhi, Lima cannot emerge as a viable alternative. Usually, when someone is only considering two options, they simply have not done creative thinking that considers all the possibilities. People are usually comfortable when they have two options and think they can make a choice at that level. This is part of the delusion of control. Since two alternatives are already more complex than one, people stop thinking. Two options create the feeling of a choice, however limited, being made but the world is far more varied and exciting than any two options would indicate.
It’s clear how this feature is relevant to second-level questions, which ask us explicitly to consider alternatives and possibilities. It’s also important to remember that we should be just as open with our first-level questions, taking care to avoid questions that only present two options (e.g., “Do you feel good or bad about this situation?”).
A strategic question often avoids “why”.
Sometimes a “why” question is very powerful when focused on values and meaning, but it may also undercut the momentum created in a conversation. The previously mentioned question, “Why don’t you move to Anchorage?” focused on why she doesn’t do something rather than creating a more active and forward motion on the issue. Most “why” questions are like that. They force you to defend an existing decision in terms of the past or rationalize the present. “Why” questions can also have the effect of creating resistance to change.
For example, consider, “Why don’t you work on poverty?” and “What keeps you from working on poverty?” The second question will likely be more effective for thinking about possible ways to move forward from the issue. Be judicious with your “why” questions, saving them for opportunities where they can move a conversation forward rather than push someone into a defensive position.
A strategic question typically avoids “yes” or “no” answers.
Again, these type of questions (“Have you considered…?”) don’t encourage people to dig deeper into an issue or possibilities for changing it. A question that is answered with “yes” or “no” almost always leaves the person being asked in an uncreative and passive state. A strategic questioner rephrases their queries to avoid the dead end of a “yes” or “no” reply. It can make a huge difference to the communication taking place by preserving the forward momentum of the conversation.
A strategic question is empowering.
A quintessentially empowering strategic question is, “What would it take for you to create change on this issue?” This question lets the other person identify the path for change. Imagine an environmental protester going to a lumber mill owner and asking, “What would it take for you to stop cutting down the old-growth trees?” This question is an invitation to the mill owner to co-create options for the future of her business with the community. The owner might tell the questioner the obstacles she faces in making changes to her business and they might then work together to satisfy some of their mutual needs so that the old-growth trees can be preserved. The planning that comes out of asking such a strategic question may not exactly resemble what either party wanted in the beginning, but a new reality is born out of the dialogue and could well work to achieve both the protester’s and the mill owner’s goals. The example here is a second-level question, and first-level questions can also be just as empowering since they can help the questionee articulate their situation in more nuanced ways. Knowledge (even the acknowledgment of what you don’t know about a situation) can be empowering.
Empowerment is the opposite of manipulation. When you use strategic questioning, rather than putting ideas into a person’s head, you are encouraging that person to take what’s already in their head and develop it further.
A strategic question might ask the unaskable questions.
For every individual, group, or society, there are questions that are considered taboo. Because those questions are taboo, there is tremendous power in them. A strategic question is often one of these “unaskable” questions and it is usually unaskable because it challenges the values and assumptions that the whole issue rests upon.
Questioning values is a strategic task of our times. This is because the values behind highly politicized issues are what have usually gotten us into trouble in the first place. Taboo strategic questions look at a tacitly accepted value, habit, or institutional pattern and ask:
“What is this value doing for us?”
“What work do we want our values to do for us?”
“How can we make our values work for the common good?”
If you can ask the unaskable in a non-partisan way, not to embarrass someone but to probe for more suitable answers for the future, it can be a tremendous service to anyone with feeling stuck in an issue.
A strategic question is a simple sentence.
A strategic question should not require overblown analysis. The attention required to decipher a convoluted question is better spent forming answers to more direct, simpler questions. The sentence should not be complex. For instance, the question, “What are the tasks that would need to be done in moving and getting a new job?” is focused on two separate things: moving and getting a job. It would be better to ask the questions separately by starting with, “What tasks would need to be done to move?” and waiting for an answer before asking, “What would need to be done to get a new job?”