Questions are the central preoccupation of my work. I ask them of clients, we ask them together, we ask questions about questions to be sure that we are asking good questions and when we aren’t we ask questions about what would be the better questions. In uncertain situations, the quality of our inquiry often matters far more than the quality of our answers.

So much of my work deals with supporting groups and organizations as they explore uncertainty, ambiguity, and unknowable futures, that answers are usually less helpful than good questions. The question often then becomes, what makes a question good?

For years in the Art of Hosting I have avoided teaching about good or powerful questions. My reticence to do so was based in the idea that knowing what a good question is is so context dependant that I couldn’t possibly tell you unless we had a context to work with. I think the role of hosts is not arrive bringing the powerful question but to arrive bringing the attention needed to notice the questions that are alive in a field of work.

There are however a few useful pieces of scaffolding that might hep a person get started in thinking about questions. At a recent Art of Hosting, my colleagues taught a short introduction to powerful questions using a kind of hierarchy of questions that is contained in Vogt, Brown and Isaacs’ “The Art of Powerful Questions.” It looks like this:

from Vogt, Brown and Isaacs’ “The Art of Powerful Questions.”

This hierarchy started me thinking about this post. In re-reading the Art of Powerful Questions, I could see that there were two distinct practices discussed there. One was the practice of designing questions. The other is the practice of discovering questions. As one source in the publication says:

“Discovering strategic questions is like panning for gold. You have to care about finding it, you have to be curious, and you have to create an anticipation of discovering gold, even though none of us may know ahead of time where we’ll find it. You head toward the general territory where you think the gold may be located, with your best tools, your experience, and your instincts. And then you begin a disciplined search for the gold.”

THAT is what interests me.

A question does not have power on its own

Let’s stick with the first practice for a moment: designing questions. Every facilitator at some point has kept a journal of good questions. When you do you start to notice that it is impossible to speak with certainty about what makes a question powerful. What this hierarchy does is to put various English interrogatives into a kind of sequence, not of powerfulness actually, but ostensibly of openness. Yes/no questions are clearly more limiting than Why or What questions. But I don’t know if they are more powerful. One of the most powerful questions I ever asked was “Do you want to get married?” It was by far the most consequential question of my life and it really came down to yes or no. Likewise, one of the most debilitating questions I was ever asked was from a teacher who was frustrated by what I later learned was a classic presentation of ADHD who asked twelve year old me “Why do you disappoint me?” If a yes/no question has two answers, that Why question had zero. And perhaps it was powerful, but it wasn’t generative. It was, unknowingly to the frustrated teacher, cruel.

The other thing to note about how questions are skewed by context is that the questions above were put in a relational context. “What do you think you’re doing?” is not really a question, and it carries the overtones of disapproval from a person in power. Questions like that are carried in a medium of relationship that render the hierarchy of powerfulness almost useless.

There are lots of different kinds of questions. There are closed questions and open questions. There are questions that we have answers to, questions that lead us in a certain direction, and questions that invite us to keep uncertainty and openness and exploration alive. There are questions about the past, the present and the future. Lineal, circular, strategic and reflexive questions. Directed and undirected questions, and so on. I spend a lot of time helping people to NOT ask yes/no questions like “Did you receive good support for this problem? If no, please explain.” It’s better to ask “What kind of support did you receive?” and have people share a story and tell you themselves if it was good service or not. This is the basis of work with Participatory Narrative Inquiry

The Art of Powerful Questions as a document really came out of a conversation between a number of people involved in the World Cafe community as they were thinking about questions, and I recommend it as a good starting point. The World Cafe community continues to explore this question about questions.

After working with questions for many years and especially increasingly working in complex and emergent contexts, I think my practice has led me away from designing good questions to trying to discover them. As a leader in places where I have led sometimes framing the right question is the right thing to do, but it is about adopting the stance of inquiry that is ultimately more important that having a perfect, powerful question.

Questions are proposals embedded in contexts

Questions are embedded in contexts. The combination of the question and the context creates a kind of proposal for action. What has intrinsic power in a complex system is the questioner. As a facilitator, if I ask a question of a group, it collapses the field of possibilities in the room because I have made an implicit proposal about what is important right now. Even if I have spent time to craft that question with a bunch of people from the organization or group I am working with, the act of me asking that question is where the power lies. So, while it is important to pay attention to assumptions embedded in questions, it is also important to be aware of the proposals embedded in questions.

A question like “What is it you plan to do with your one wild and precious life?” is a beautiful question. But if I ask it in a group I am making as assumption that the people I am asking it about have similar thoughts about their lives as Mary Oliver does. I am also making a proposal, as Mary Oliver does, that I’m possibly not doing enough in my life to bring more attention or purpose or meaning. Or I may be assuming that folks, as she says

know how to pay attention, how to fall down
into the grass, how to kneel in the grass,
how to be idle and blessed, how to stroll through the fields,
which is what I have been doing all day.
Tell me, what else should I have done?

Not everybody has that kind of idleness at hand to be able to reflect on whether contemplating a grasshopper was a good use of time. Asking folks that question devoid of the context of their lives, the urgency of a situation, or the consent to be in that conversation is a hell of a proposal. Imagine asking a seasonal farm worker that question. Or the Dalai Lama.

Beautiful questions are not necessarily inviting questions

Mary Oliver’s question is beautiful. It stands on its own because it is a poetic statement. I’m not sure it actually wants an answer. It seems to invite a turning, a metanoia, a repentance. If it were offered in a therapeutic context, it might directly imply that I’m not doing the RIGHT thing with my one will and precious life. The question therefore intimidates me and subjugates me to the author’s intention. When that intention is hidden, I feel manipulated.

I do see this often in questions that come my way like “What would be possible if we trusted each other more?” That is a question that immediately drives me to thinking about its opposite. In my world, even as a person who tends to trust more than I should, there are definitely people I should be trusting less. The idea that MORE trust leads to more possibility contains an embedded assumption, an implicit proposal and a predetermined pathway of inquiry. It avoids the first principle of good complexity work and lets the framework determine the data and not the other way around. There is no new meaning to be made from a question like that, really. The conversation is likely to be abstract and opinionated at best. And might be a naive casting about in an unknown future at worst.

That’s not to say that we can’t learn from questions like that.

If we really wanted to examine trust I might start with having people tell stories about trust to each other. How trust operates in different contexts matters, and so if the exploration is not be useful, the stories have to be relevant to the context either because they are directly related to the context or they become connected to the context through reflection and collective sense-making. Nevertheless, it’s no good that assuming that MORE trust leads to MORE possibility if there is a chance that trusting some people less in order to opens up the possibilities for a field.

Good questions can be answered by everyone, and get the facilitator out of the centre.

Not all conversations are the same, but a lot of my work deals with looking at what’s happening and exploring change. This implies a trajectory to the questions, from the present state towards a direction of travel that we might discover together. My favourite questions for this, and still the ones I use as a basic template for work are Terry Borton’s reflective questions: “What? So what? Now what?” These are so simple, and yet they hold us, as facilitators, at a distance from the group’s work, which is a good thing. They ask of us to become hosts that works with the constraints of the system that shape actions, rather than the attractors that collapse what’s possible into a single, deep, valley of channeled conversation.

As basic source code these questions are helpful. Almost every change or planning process I work with starts with “What?” There is nothing better at getting directly to the urgency of a situation than by asking what the hell is going on and then shaping the constraints of the situation such that everyone can contribute to that conversation. There is not one answer. There is a survey of the field and the perspectives in the room that gives us enough information with which to act, because in complex situations that is what we need.

The “So What?” question invites the group to look at what they have said is the “What” and make sense of it. What does this mean for us? This is the area of exploration, negotiation, discussion, perspective sharing, learning. From this sense-making comes the turn to trying things out. “Now What?” is about the actions we might to take to address a problem, explore and option or move this into a new cycle of inquiry, Glenda Eoyang calls her version of this loop “Adaptive Action.”

There is a similar construction in the Technology of Participation body of work known as ORID, which helps people in inquiry look at Objective questions, Reflective questions, Interpretive questions and Decisional questions.

Again, these methods imply a directionality to an intervention, but as long as that intention is clear and transparent and lands a proposal for action, I think the direction is ethical. If the group refuses the proposal, then the question becomes “What do we do now?” I’ve had a few cases of these in my life and they are good lessons in humility and excellent examples of watching a group activate its collective capability to frame its own questions and inquiries.

The most consequential questions are often the ones the group recognize as their own

So this brings me around to the point. A question shapes the field of attention. In complexity terms it becomes a constraint and makes some things easier to notice and others easier to ignore. It channels attention and participation. If it is understood as a probe to that system, to see what else might emerge, it can be useful. If it is held tightly as The Thing We Are Here To Talk About then it becomes non-consensual and it suppresses the emergence that is needed for a group to discover and rely on its own capability and distributed knowledge. For complex and uncertain work, including planning, change, and culture, the questions are already in the field. They are the ones that everyone is asking in their minds. Not “What would be possible in five years if we became a more welcoming community?” but rather “What are we going to do about these damn tourists?” (That might be from a real situation. 😉 )

But what about my one wild and precious question?

So the most powerful question is not the one that the facilitator brings. In fact my advice would almost always be to start with “What’s happening?” and go from there. Bring attention, not intention. When a group develops enough shared attention sometimes the powerful question emerges there and it seems obvious. We need to not go looking for beautiful constructions, poetic and inspiring language, or even hierarchies of importance. We need to pay attention to the conversations that are already happening, the questions that people are asking themselves, the relational fields in which those questions are being asked and the larger context of need and purpose that forms the proposal for the intervention.

Practitioners intervene. That’s what we do. Letting go of the need to bring the powerful question helps us to do it better because it turns a predetermined intervention into a collectively help proposal for action, one that can be explored, contested, rejected, accepted, or changed. Start simple and be transparent. Start with a question that everyone can answer, one like “Can you share an experience of… What happened?” Take the answers to those questions and give them to people and ask them what they make of them. Then let the next question emerge from what the group has made visible together.