Strategic Questions: Engaging People’s Best Thinking


Stop asking so many questions,” many children hear at home. “Don’t give me the question, give me the answer,” many students hear at school. “I’m not interested in hearing what you don’t know, I want to hear what you do know,” many employees hear at work. The injunction against discovering and asking questions is widespread in today’s family, educational, and corporate cultures. That’s unfortunate, because asking questions that matter is one of the primary ways that people have, starting in childhood, to engage their natural, self-organizing capacities for collaborative conversation, exploration, inquiry, and learning. In our own work with creating positive futures, we are discovering that the usefulness of our knowledge depends on the quality of the questions we ask. Clear, bold, and penetrating questions tend to open up the context for new learning and discovery, which is a key component of strategy innovation.

Strategic learning can occur, not only through formal planning activities, but also through webs of informal conversations and networks of relationships, both within an organization and among key stakeholders. Choosing to ask and explore “big questions” — questions that matter to the future of the organization — is a powerful force.

When people frame their strategic exploration as questions rather than as concerns or problems, a conversation begins where everyone can learn something new together, rather than having the normal stale debates. In effect, people begin looking at “the map of the territory” together. The questions encourage them to wonder “What is the map telling us?” rather than to push preconceived ideas of what they think it shows.

Why Don’t We Ask Better Questions?

If asking good questions is so critical, why don’t we spend more of our time and energy focused upon discovering and framing them? One reason may be that much of our Western culture is focused on knowing the “right answer” rather than discovering the “right question.” Our educational system focuses more on memorization and static answers rather than on the art of seeking new possibilities through dynamic questioning. We are rarely taught how to ask powerful questions. Nor are we often taught why we should ask compelling questions in the first place. Quizzes, examinations, and aptitude tests all reinforce the value of correct answers, usually with only one correct answer for each question asked. Is it any wonder that most of us are uncomfortable with not knowing?

Perhaps our aversion to asking creative questions stems from our emphasis on finding quick fixes and our attachment to black/white, either/or thinking. Often the rapid pace of our lives and work doesn’t provide us the opportunity to be in reflective conversations where creative questions and innovative solutions can be explored before reaching key decisions. This dilemma is further reinforced by organizational reward systems in which leaders feel they are paid for fixing problems rather than fostering breakthrough thinking. Between our deep attachment to the answer — any answer — and our anxiety about not knowing, we have inadvertently thwarted our collective capacity for deep creativity and fresh perspectives in the face of the unprecedented challenges we face, both in our own organizations and as a global human community.

The World’s Best Industrial Research Lab

One of the best corporate examples of how a “big question” — a truly strategic question — can galvanize collective conversation, engagement, and action occurred at Hewlett-Packard. The director of Hewlett-Packard Laboratories wondered why HP Labs was not considered the best industrial research lab in the world. As he thought about it, he realized that he did not know what being the “World’s Best Industrial Research Lab” (WBIRL) really meant.

One key staff member was charged with coordinating the effort

One key staff member was charged with coordinating the effort. Instead of looking for “answers” outside the company, she encouraged the director to share his “big question” with all lab employees around the world. Instead of organizing a senior executive retreat to create a vision and then roll it out, she encouraged organization-wide webs of inquiry and conversation, asking people what WBIRL meant to them, what it would mean personally for their own jobs, and what it might take to get there. She invited the entire organization to join in exploring the question through informal, ongoing conversations; and she took advantage of more formal internal survey and communication infrastructures. When the lab director acknowledged his “not knowing” — an uncommon stance for a senior executive — an open field was created for multiple constituencies and perspectives to be heard.

The conversation continued for several months. The WBIRL leader developed a creative “reader’s theater” piece which reflected 800 survey responses, detailing employee frustrations, dreams, insights, and hopes. Players spoke the key themes as “voices of the organization,” with senior management listening. That made a difference to everyone’s thinking by literally putting a variety of points of view on stage together. But it wasn’t the only venue in which the “big question” was explored. Senior management met in strategic sessions, using approaches such as interactive graphics and “storytelling about the future” to see new opportunities that crossed functional boundaries. In these strategic conversations, they considered core technologies that might be needed for multiple future scenarios at HP Labs to unfold.

People throughout the labs, meanwhile, were initiating projects at all levels, resulting in significant improvement in key areas of the lab’s work. Weekly Chalk Talks for engineers, “coffee talks,” an Administrative Assistant Forum, and a Community Forum created opportunities for ongoing dialogue, listening, and learning. A WBIRL Grants Program provided small stipends for innovative ideas, enabling people to act at the corporate grassroots level, taking personal responsibility for work they believed in. In all of these efforts, the leader of the WBIRL project spent most of her time “helping the parts see the whole” and linking people with complementary ideas.
And yet, while productivity was improving rapidly, something was missing. During an informal conversation while planning for a “Celebration of Creativity” to acknowledge what had already been accomplished, one of the lab engineers spoke up. She wondered what was really different about HP that distinguished it from any other company that wanted to be the best in the world. She said, “What would get me out of bed in the morning would be to become the best for the world.”
Suddenly a really “big question” had emerged. What would it mean for HP Labs to be the best both in and for the world? (See “What Makes a Powerful Question?”)

Stakeholders in any system already have within them the wisdom and creativity to confront even the most difficult challenges.

A senior engineer created an image of what “for the world” meant to him. It was a well-known picture of the founders of HP looking into the backyard garage where the company began. He added a beautiful photo of Earth placed inside. This picture became the symbol of “HP for the World.” A “town meeting” of 800 Palo Alto employees with live satellite hook-ups enabling a global conversation focused on the question, “What does ‘HP for the World’ mean to you?” The “HP For the World” image spread throughout the company — appearing in lobbies, featured in recruiting brochures, and offered as executive gifts. More than 50,000 posters were purchased by HP employees around the world, stimulating a growing network of conversations about the meaning of the big question for the future of the company.

In the course of this exploration, people rediscovered that the company founders, Bill Hewlett and Dave Packard, had always maintained a commitment, as Packard put it, that “the Hewlett-Packard company should be managed first and foremost to make a commitment to society.” Growing numbers of people throughout HP reconnected to that founding governing idea — stimulating investigations into breakthrough technologies for education, remote medical care for third-world nations, and global environmental issues.


We’ve asked hundreds of people on several continents, “What makes a powerful question?” The following themes have emerged:

A Powerful Question

  • Is simple and clear
  • Is thought-provoking
  • Generates energy
  • Focuses inquiry
  • Surfaces assumptions
  • Opens new possibilities

As part of this effort, the same senior engineer who had created the “for the world” poster image was persuaded to pursue a 25-year old dream: To create a mile-long educational diorama, placing human life in the context of evolutionary history. In 1997, this work — “A Walk Through Time: From Stardust to Us” — was featured at the annual State of the World Forum. There, the question of what it means to be for the world was posed to global leaders gathered from every continent. Public and private partnerships evolved from these conversations. Clearly, this is a powerful question that “travels well.”

Big Questions and Strategic Thinking

This approach to discovering and asking the “big questions” — strategic questions for which we truly do not have answers — is grounded in the assumption that stakeholders in any system already have within them the wisdom and creativity to confront even the most difficult challenges. Given the appropriate context and support, members of an organizational community can often sense where powerful strategic possibilities and opportunities for action may lie. Is it simply “luck” that enables us to stumble onto questions that really matter for strategic thinking? Or can we actually design processes that make it more likely for those questions to emerge? (See “How to Use Questions Effectively” on page 4.)

“Discovering strategic questions,” says one colleague, a senior executive at a major multinational corporation,


  • Well-crafted questions attract energy and focus our attention on what really counts. Open-ended questions — the kind that don’t have “yes” or “no” answers — are most effective.
  • Good questions need not imply immediate action steps or problem solving. Instead, they invite inquiry and discovery rather than advocacy and advantage
  • You’ll know you have a good question when it continues to surface new ideas and possibilities. Bounce possible questions off key people to see if they sustain interest and energy

“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.”

To evoke strategic thinking based on discovering powerful questions, several activities may be useful. They

may not apply to all situations and they may not always follow the same sequence, but they suggest ways that formal and informal processes can evolve together to support individuals as well as teams in discovering “gold” for themselves.

Assessing the Landscape. Get a feel for the larger context in which you are operating. Scan the horizon, as well as the contours of the current business and organizational landscape, related to the system or project you are working with. Like trackers in the mountains, look for obvious and subtle indicators that point to storms as well as to sunny skies. Allow your curiosity and imagination to take the lead as you begin to identify the many questions that the business landscape reveals. It will be tough, but important, to frame your findings as questions, rather than as concerns or problems. To help in framing those questions, ask yourself: “How does A relate to C and what questions does that suggest? If X were at play here, what would we be asking? What is the real question underneath all this data?”

Discovering Core Questions. Once you think you’ve posed most of the relevant questions (and there may be many of them), look for patterns. This is not a mechanical process, even though it can be disciplined and systematic.


Here are some questions you might ask yourself as you begin to explore the art and architecture of powerful questions. They are based on pioneering work with questions being done at the Public Conversations Project, an organization that helps create constructive dialogue on divisive public issues.

  • Is this question relevant to the real life and real work of the people who will be exploring it?
  • Is this a genuine question — a question to which I/we really don’t know the answer?
  • What “work” do I want this question to do? That is, what kind of conversation, meanings, and feelings do I imagine this question will evoke in those who will be exploring it?
  • Is this question likely to invite fresh thinking/feeling? Is it familiar enough to be recognizable and relevant—and different enough to call forward a new response?
  • What assumptions or beliefs are embedded in the way this question is constructed?
  • Is this question likely to generate hope, imagination, engagement, creative action, and new possibilities, or is it likely to increase a focus on past problems and obstacles?
  • Does this question leave room for new and different questions to be raised as the initial question is explored?

You are on a treasure hunt, seeking the core questions — usually three to five — which, if answered, would make the most difference to the future of your work. Cluster the questions and consider the relationships that appear among them. Notice what “pops up” in order to discover the “big questions” that the initial clusters reveal.

Creating Images of Possibility. Imagine what your situation would look like or be like if these “big questions” were answered. Creating vivid images of possibility is different from pie-in-the-sky visioning, especially if people with a variety of perspectives have participated in the earlier stages of the conversation. This part of the conversation can also provide clues for evolving creative strategies in response to the “big questions.” It often reveals new territory and opportunities for action while remaining grounded in real life.

Evolving Workable Strategies. Workable strategies begin to emerge in response to compelling questions and to the images of possibility that these questions evoke. Of course, the cycle is never complete. Relevant business data, ongoing conversations with internal and external stakeholders, informal conversations among employees, and feedback from the environment enable you to continually assess the business landscape revealing new questions.

Many organizations are stuck in a “problem-solving orientation” when it comes to strategy. They can’t seem to shake the focus on fixing short-term problems or seeking immediate (but ineffective) solutions. Simply by moving their attention to a deliberate focus on essential questions, they can develop an inquiry-oriented approach to evolving organizational strategy (see “How Can I Frame Better Questions?”). In a knowledge economy, this approach provides an opportunity for developing the capability of strategic thinking in everyone, and for fostering sustainable business and social value.

How Can Leaders Use Powerful Questions?

In today’s turbulent times, engaging people’s best thinking about complex issues without easy answers represents one key to creating the futures we want. Leaders need to develop greater capacities for fostering “inquiring systems” in order to learn, adapt, and create new knowledge to meet emerging needs (see “Is Your Organization an Inquiring System?”).

The leadership challenges of the next 20 years are likely to revolve around the art of catalyzing networks of people rather than solely managing hierarchies as in the past. The ability to bring diverse perspectives to bear on key issues both inside and outside the organization and to work with multiple partners and alliances will be a critical skill for effective leaders. We believe the following core capabilities, rarely taught in today’s MBA or corporate leadership programs, will help define leadership excellence:

Engaging Strategic Questions. In a volatile and uncertain environment, one of the most credible stances leaders can take is to assist their organizations in discovering the right questions at the right time. A key leadership responsibility is creating infrastructures for dialogue and engagement that encourage others at all levels to develop insightful questions and to search for innovative paths forward. Leaders also need to consider reward systems that provide incentives for members to work across organizational boundaries to discover those challenging questions that create common focus and shared forward movement.

Convening and Hosting Learning Conversations. A core aspect of the leader’s new work is creating opportunities for learning conversations around catalyzing questions. However, authentic conversation is less likely to occur in a climate of fear, mistrust, and hierarchical control. The human mind and heart must be fully engaged in authentic conversation for the deeper questions to be surfaced that support the emergence of new knowledge. Thus, the ability to facilitate working conversations that enhance trust and reduce fear is an important leadership capability.

Supporting Appreciative Inquiry. Opening spaces of possibility through discovering powerful questions may require a shift in leadership orientation from what is not working and how to fix it, to what is working and how to leverage it. Shifting the focus in this direction enables leaders to foster networks of conversation based on leveraging emerging possibilities rather than just on fixing past mistakes. Leaders who ask, “What’s possible here and who cares?” will have a much easier time gaining the collaboration and best thinking of their constituents than those who ask, “What’s wrong here, and who is to blame?” By asking appreciative questions, organizations have the opportunity to grow in new directions.

Fostering Shared Meaning. Leaders of organizations in the 21st century will discover that one of their unique contributions is to provide conceptual leadership — creating a context of meaning through stories, images, and metaphors within which groups can discover relevant questions as well as deepen or shift their thinking together. To tap into this pool of shared meaning, which is the ground from which both powerful questions and innovative solutions emerge, network leaders need to put time and attention into framing common language and developing shared images and metaphors.

Nurturing Communities of Practice. Many of the most provocative questions for an organization’s future are first discovered on the front lines, in the middle of the action of everyday life. Key strategic questions that are critical for creating sustainable value are often lost because few of today’s leaders have been trained to notice, honor, and utilize the social fabric of learning that occurs through the informal “Communities of Practice” that exist throughout an organization. A Community of Practice is made of up people who share a common interest and who work together to expand their individual and collective capacity to solve problems over time. Nurturing these informal learning networks and honoring the questions they care about, is another core aspect of the leaders new work.

Using Collaborative Technologies. Intranet and groupware technologies are now making it possible for widely dispersed work groups to participate in learning conversations and team projects across time and space. As these tools become even more widely available, leaders will need to support widespread online conversations where members throughout the organization can contribute their own questions and best thinking to critical strategic issues. The Hewlett Packard case shows how important enabling technology infrastructures are for strategic innovation. Collaborative tools will be a critical factor in how well strategic questions travel both within the organization and among customers and other stakeholders who are key to success.


Here are some questions for assessing your organization’s capabilities:

  • To what degree does the leadership in your organization foster an environment in which discovering the “big questions” is as much encouraged as coming up with workable solutions?
  • Does your organization have rewards or incentives for members to work across functional boundaries to find those challenging questions that create common focus and forward movement for knowledge creation?
  • Do your leadership development programs focus as much on the art and architecture of framing powerful questions as they do on techniques for problem-solving?
  • Do your organization’s strategic planning processes include structured ways to discover the “big questions” that, if answered, would have real strategic leverage?
  • Are there collaborative technology tools that enable people on the front lines to ask each other questions related to their daily work (for example, customer service, equipment maintenance) and receive help with these questions from colleagues in other locations?
  • Do senior leaders in your organization see the process of strategy evolution as one that engages multiple voices and perspectives in networks of conversation that contribute both to discovering the “big questions” as well as to finding innovative solutions within individual arenas of responsibility?

Co-Evolving the Future

we can make a difference to the whole

It is quite easy to learn the basics of crafting powerful questions. However, once you have begun down this path, it’s hard to turn back. As your questions broaden and deepen, so does your experience of life. There is no telling where a powerful question might lead you. Transformative conversations can result from posing a simple question such as: “What questions are we not asking ourselves about the situation in the Middle East?” Tantalizing possibilities emerge from the simple act of changing a preposition from “in” to “for” as in the HP example. Profound systemic change can emerge from creating a process for discovering and acting on the “big questions” within a business setting.

Where collaborative learning and breakthrough thinking are requirements for a sustainable business future, asking “questions that matter” and engaging diverse constituencies in learning conversations are a core process for survival. Because questions are inherently related to action, they are at the heart of an organization’s capacity to mobilize the resources required to create a positive future. Seeing the organization as a dynamic network of conversations through which the organization evolves its future encourages members at every level to search for questions related to their real work that can catalyze collective energy and momentum. It enables each one of us to realize that our thoughtful participation in discovering and exploring questions that matter — to our team, to our organization, and to the larger communities of which we are a part — we can make a difference to the whole. For it is only in this way that organizations will be able to cultivate both the knowledge required to thrive today and the wisdom needed to ensure a sustainable future.


  • Assess Your Organization’s Capabilities: Assess the degree to which your organization is an “inquiring system.” How is the organization developing people and infrastructures in ways that support discovering and asking catalytic questions to foster new knowledge and help shape the future?
  • Read, Read, Read: Begin with the resources listed at the end of this article. They will point you to more material about the power of “big questions” and the creation of knowledge through networks of conversations.
  • Surf the Net: You can find lots of interesting perspectives on questions and questioning by experimenting with different combinations on your search engine. Some we’ve found particularly useful are: asking powerful questions; strategic questioning; and questions and breakthrough thinking. Experiment! You might be surprised by what you learn.

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