When you teach you learn. I recently taught a workshop on Strategic Questioning at the Harvard John F. Kennedy School of Government, as part of a Leadership Survival Skills workshop series for New England alumni. For background, Strategic Questioning is a technique of asking open questions that inspire movement and new insights/ideas. Strategic questions are engaging, invite further learning, and are framed in a way that is truly open, meaning not a yes/no question or a question that contains or suggests a solution.

We discussed how to frame strategic questions and I shared stories of how they can be used in a range of situations, e.g., helping a team get clear on their focus, designing meeting agendas, or building buy-in from people on a new project. Hearing many questions over the course of a few hours helps develop a finer sense of what makes a question strategic. At the workshop, we did a Search for Insight, a large group exercise where people practice framing strategic questions in the context of one person’s current challenge. This was followed by time for people to practice in small groups on each other’s individual challenges.

Strategic questions are based in the premise that we can trust the person or group who is asked the question to have the wisdom to discover the answer. We ask the questions in service to their clarity and discovery; we do not need to have the answers to the questions we ask. As the asker, we need to learn to be patient with uncertainty and to be comfortable acknowledging that we do not know the answer. A different quality of creative possibility and ownership of the answer is created when we offer up a question without a predetermined opinion on the answer. I recognized what a shift this is for people, when most of us pride ourselves on having the answers and work to push our solutions out into the world.

Here are some additional insights from the workshop:

• People have a conditioned tendency to want to fix someone else’s problem and suggest a specific solution. For example, when a challenge is presented and someone asks: “Have you considered trying [   ]?” This is a yes/no question and is not open; it is actually an embedded suggestion disguised as a question. Examples of a more open strategic question are: “What are key things that have to be addressed for this to work?” or “Who else has dealt with this challenge successfully that you could learn from?”
• “Emergence” is a theme often talked about in our work with networks and large scale change: that by bringing diverse people or parts of a system together, something new can emerge that could not be predicted. It is important to recognize that no ONE person has the answer, it has to emerge from bringing multiple perspectives together. Strategic questions create the space for this new insight/intelligence to emerge.
• Slight nuances in how we frame a question can make a big difference. For example, notice the difference between: “Is there anything I can do to help you?” and “What are one or two specific things I could do to help you get this done?” The first question is easy for them to brush off and say no. The second invites more consideration and conversation.
• A perceived sense of urgency to make decisions can get in the way of valuable creative thinking. Strategic questions open up more possibilities, spur research or further learning, and often do not have an immediate answer. If we can sit with an open question, often a synchronicity will happen where new information, a person, or event arises that gives us clarity or an answer we did not foresee. This quote from Rainer Maria Rilke in Letters to Young Poet speaks to this:

“I want to ask you, as clearly as I can, to bear with patience all that is unresolved in your heart, and try to love the questions themselves, as if they were rooms yet to enter or books written in a foreign language. Don’t dig for answers that can’t be given you yet: you live them now. For everything must be lived. Live the questions now, perhaps then, someday, you will gradually, without noticing, live into the answer.”

For more information, this web site has a manual on Strategic Questioning, written by Fran Peavey, a social activist who developed the technique.