IDP Resource

Strategic Questioning


Strategic questioning is a communication tool that allows us to move back and forth between creating shared understanding of an issue and collaboratively exploring solutions. It starts with questions that focus on how reality is now and builds to include questions that focus on what reality could be. In this way, strategic questioning draws us forward to well-informed potential realities of the future. It synthesizes new information from what is already known and often brings to light the values, assumptions, and emotions underlying an issue.

Strategic questioning recognizes that questions can help identify details of a current reality and also help uncover new possibilities for the future. These two “types” of questions can be thought of as “first-level” and “second-level” questions. First-level questions ask someone to describe a situation at the present moment, reflecting how things currently are. They are “first” because we need at least some understanding about the situation at hand before thinking about possible solutions. Second-level questions ask someone to reimagine the situation differently. They encourage the other person to look ahead and/or imagine possibilities for the future to consider what “could be” rather than what “is”.

Because strategic questioning emphasizes openness and humility, it is useful when you are trying to work towards a common goal with someone who may have a different background or perspective. Strategic questioning is a process that may change the questioner as well as the questionee. When we open ourselves to another point of view, our own ideas often have to shift to take into account new information, new possibilities, and new strategies for resolving problems. This emphasis on openness and humility also makes strategic questioning a potent tool for social change. It helps identify underlying assumptions about how social change happens (which may prevent us from seeing alternative ways forward) and pinpoint concrete yet creative local strategies for alleviating inequity.

Ultimately, strategic questioning is a twofold skill. It involves deciding when a first-level or second-level question would be most helpful and asking those questions in ways that respect the knowledge and agency of everyone involved in the process. A strategic questioner typically starts with a first-level question to gain a more complete understanding of the situation before moving on to second-level questions. While it is easy to think of second-level questions as the more significant questions, this is not the case. Any effort to come up with possible solutions is stymied by a lack of clarity about the situation itself. For this reason, we should aim to spend roughly equal amounts of time and attention on both types of questions.

Moreover, intentionally switching back and forth between first-level and second-level questions is encouraged. At times, an answer to a second-level question illustrates a need for more information which a return to first-level questions can satisfy. Revisit first-level questions whenever you feel like it would be helpful to have more information about the situation as it currently is.

Types of Strategic Questions

Strategic questioning involves knowing when first-level questions are appropriate and when second-level questions are appropriate. Both question types serve very different aims in a conversation. It is important to familiarize oneself with what first- and second-level questions do, and which question families belong to each category.

You can think of choosing between the two levels of questions as exercising your own judgment in how to build a collaborative atmosphere. Asking a first-level question is akin to holding up a mirror to the questionee; it asks them to describe how things are at the moment and provides you with information that you may need to understand the intricacies of the situation. Asking a second-level question is akin to offering a window to look through. By asking second-level questions, you ask them to look beyond the present moment and to look for new possibilities. Once those possibilities are presented to you, you can take part in further conversation regarding steps to create change.

Finally, as stated earlier, we usually start with first-level questions. We can then switch between first-level questions (if more clarity around the present situation would be useful) and second-level questions (if we want to envision possibilities to change the situation).

First-Level Questions

First-level questions help us identify key features of an issue or a situation; they focus on what is. Consider first-level questions as an opportunity to seek clarification on points of confusion or assumptions held about the situation. Similarly, these questions present an opportunity for the questionee to organize their thoughts and focus squarely on the situation. Below are examples of question families that are first-level questions.


These questions identify the situation and the key facts necessary to understand the situation.

  • “What are you most concerned about?”
  • “What aspects of this situation are you most passionate about?”
  • “When you describe this issue to others, what aspects come to your attention first?”
  • “What have others suggested to you regarding this situation?”
  • “What is the order of events that led to the current moment?
  • “What about this situation do you care so much about?”
  • “What is the meaning of this situation in your own life?”
  • Keywords: describe, situation, concern, attention


These questions are concerned with what one sees and the information one has heard regarding the situation. Notice that these questions do not refer to the situation as a “problem,” for that would establish a barrier to creative thinking.

  • “What do you see?”
  • “What do you hear?”
  • “What have you heard and read about this situation?”
  • “Which sources do you trust and why?”
  • “What effects of this situation have you noticed in people, in the earth?”
  • “What do you know for sure and what are you not certain about?”
  • Keywords: see, hear, know, find


These questions are concerned with body sensations, emotions, and health. They help us empathize with the other person.

  • “What sensations do you have in your body when you think or talk about this situation?”
  • “How do you feel about the situation?”
  • “How has the situation affected your own physical or emotional health?”
  • Keywords: feel, suffer, tired, angry, sad, frustrated, needs


These questions help us imagine what it’s like to be the other person in the situation and gain a better understanding of their personal context.

  • “What motivates your initial response to this situation?”
  • “What contextual information do you think is important?”
  • “How do you see your relationships with others involved in the situation?”
  • “How does this situation impact how you think about your own personal narrative?”
  • “Who else is impacted by this situation?”
  • “What other perspectives are important when thinking about this situation?”
  • Keywords: motivation, context, relationship, position, viewpoint


These questions explore how this situation fits into a broader picture. They illuminate the situation’s underlying causes and its relationship to other events.

  • “What are the reasons for…?”
  • “How does this situation relate to other things you’ve observed?”
  • “How is the situation similar or different to what you’ve experienced before?”
  • Keywords: reason, trend, disruption, similarity, difference


These questions identify who has power in the situation (both interpersonally and structurally).

  • “Where do you have agency in this situation? Where do others have agency?”
  • “How does this situation relate to broader social systems related to identity?”
  • “How do privilege and oppression show up in this situation?”
  • Keywords: privilege, oppression, power, agency, identity, position

Second-Level Questions

Second-level questions help us to envision change and move us into possible futures. They focus on what could be and ask us to consider multiple possibilities about how to address an issue. Second-level questions bring forth ideas, goals, and options that lay the groundwork for creative steps toward progress that both the questioner and the questionee can discuss.  Below are examples of question families that are second-level questions.


These questions are concerned with identifying one’s ideals, dreams, and values for change.

  • “How could the situation be changed to be just as you would like it?”
  • “How would you like it to be?”
  • “What values do you wish to uphold when addressing the situation?”
  • Keywords: hope, wish, like, love, better, justice


These questions are concerned with how to get from the present situation towards a more ideal situation.

  • “What will it take to bring the current situation towards the ideal?”
  • “What exactly needs to change here?”
  • “Who can make a difference?”
  • “What are changes that you have seen or read about?”
  • “How did those changes come about?”
  • Keywords: what will it take, how could

Consider the Alternatives

These questions imagine more than two alternatives (contrary to our cultural training, the world of resistance is not dualistic). Be alert for other alternatives to pop up in other areas of questioning. Do not rule out any alternative.

  • “What other ways could you imagine meeting your goal of change?”
  • “Maybe that does sound like a far-fetched idea, but what is the wisdom in that alternative?”
  • “What are the consequences of each alternative you see?”
  • “How might those changes come about? Name as many ways as possible.”
  • Keywords: alternative ways, imagine, all the ways imaginable

Consider the Consequences

These questions help us think about what the effect of our actions may be. They help us consider the impact of our decisions in addition to their intent.

  • “How would your first alternative affect the others in your group?”
  • “What would be the effect of X on Y?”
  • “How would you feel doing (name each alternative)?”
  • “What would be the political effect if you did…?”
  • “What would be the result of letting the status quo continue?”
  • Keywords: effect, impact, result, unintended

Consider the Obstacles

These questions investigate challenges to changing the situation. They identify possible points of resistance in ourselves and in others.

  • ​​“What would need to change for alternative “a” to be done?”
  • “What keeps you from doing…?”
  • “What prevents you from getting involved?”
  • “What prevents others from getting involved?”
  • Keywords: resistance, prevent, challenge, barrier

Personal Inventory & Support

These questions are concerned with identifying one’s interests, potential contribution, and the support necessary to act.

  • “What would it take for you to participate in the change?”
  • “What do you like to do that might be useful in bringing about these changes?”
  • “Tell me what is special about you.”
  • “Tell me what strengths you bring to a solution to a problem like this one.”
  • “What support would you need to work for this change?”
  • Keywords: what will it take, part of the change, your part, everyone has a role

Personal Action

These questions get down to the specifics of what to do and how and when to do it. The actual plan begins to emerge in the answers.

  • “Who do you need to talk to?”
  • “How will you get an introduction to them that will establish your credibility?”
  • ​​“How can you join a group that is working on this?”
  • “How can you get others together at a meeting to work on this?”
  • Keywords: talk, who, establish, meeting

Strategic Questioning Mindset

When asking strategic questions, we must disengage from cynicism or arrogance. The questioner should approach the conversation with confidence that the questionee already holds crucial answers and the power to impact the situation. It is also important to relinquish the impulse to push for a specific outcome when asking strategic questions. A strategic question is not a leading question that pushes an agenda or an opinion held by the questioner. Instead, a strategic question invites answers that contain honest perspectives and ideas.

Strategic questioning respects the person who is being questioned. Without respect for the other person, the ability to ask strategic questions is undermined by a lack of confidence that anything useful can come from them. Strategic questioning assumes that there is something that everybody can do to uncover creative solutions for change. It assumes that knowledge resides and is alive in all people. People see and know intimately the problems they face, and they may well be in the best position to collectively design alternatives for themselves.

Strategic questioning creates an environment where people can see the solutions that are within themselves and explore their options. A strategic questioner listens for the opportunity to ask questions about the latent solutions hidden within every problem. The questioner is not merely passively listening but is focusing their attention on both the reality of now, as well as the clues of what could be. Similarly, it is important to exercise humility when using strategic questioning. By approaching strategic questions with humility, the questioner acknowledges that they do not have all the answers and may not be an expert on the topic at hand. Instead, the questioner helps articulate the facts and opportunities available to the questionee.

Here are some features of someone using strategic questioning:

  • Looking for the obstacles to caring and the impediments to action
  • Seeking to understand what is influencing the person and why they feel compelled to do, or not do, something about the issue
  • Exploring the person’s ideas of how they want things to be or how they see that things could or should change
  • Identifying how the person thinks about change and how change happens in their lives
  • Looking for paths to change that the person sees, however dimly and timidly they see it, and exploring those paths together by asking questions that allow fresh, creative thinking
  • Identifying ways to remove the resistance that is found on the path to change
  • Understanding what the person feels as they anticipate each possible choice or option in front of them
  • Finding what support the person would need to move on any path of change

Strategic questioning not only trusts the person being questioned, but also refuses to treat information as static. Strategic questioning instead views information like a river. In the river of information, ideas and relationships are constantly changing. Dipping into the river one day brings up different perspectives than the next day because the river has moved on with one more day of experience and thinking. Asking the same question today elicits a different answer than yesterday. What we did not know yesterday, we may know today. Whether we have learned new information or have simply created a solution from our own synthesis and analysis, both the question and answer have changed.

Is anything ever fully known? We find one piece of information and from that piece of information new questions arise and we dip into the river again. That cycle continues – discovery, new questions, new discovery, new questions, and on and on.

Strategic questioning trusts that solutions are within reach, but it doesn’t create pressure to have all the answers immediately. There is power in approaching a problem with the feeling of “I don’t know.” There is also power in allowing doubt into what we think we already know. Strategic questioning doesn’t have to be a threat to one’s status or professionalism. Through strategic questioning, we can allow questions to emerge and open doors to new possibilities. We can invite others with fresh resources and perspectives to create new solutions.

Effective Features of a Strategic Question

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?”

Adapted from Peavey, F. (1997). Strategic Questioning: An Approach to Creating Personal and Social Change. Vivian Hutchinson, ed., The Jobs Letter.

Additional Bibliography

  • McCormick, D. (1999). Listening with Empathy: Taking the Other Person’s Perspective. NTL Institute for Applied Behavioral Science (8th ed.), Reading Book for Human Relations Training. Alexandria, VA: NTL Institute for Applied Behavioral Science. 57-60.
  • Stroh, D. (2015). Systems Thinking for Social Change. White River Junction, VT: Chelsea Green Publishing.

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