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Asking Big Questions: A Leadership Skill for Discovering the Future

Futurists and foresight practitioners are no strangers to asking expansive questions. A standard tool in their repertoire is the "What if" questioning technique. Warren Berger, however, makes the case for questioning as a key leadership skill for dealing with constant change and uncertainty.

Photo Credit: Maria Teneva/ Unsplash

According to Berger, asking open, exploratory questions can help business leaders figure out what’s coming and where new opportunities lie, so that they can lead their company in new directions. In his book, A More Beautiful Question, Berger spoke with various business leaders who attest to an evolution in business questions. Keith Yamashita of SYPartners, for example, notes that “the era of small-minded questions is ending.” He continues:

“Company leaders are realizing that if they’re only asking the small questions, it’s not going to advance their agenda, their position, or their brands. In order to innovate now, they have to ask more expansive questions.”

Although closed questions (How many? How much? How fast?) still matter on a practical level, business leaders must increasingly ask sophisticated, open questions to thrive in an environment that demands a vision for the future and an appetite for change.

Ron Shaich, former CEO of Panera Bread, adds:

“When you are leading a team, a start-up, or a public company, your primary occupation must be to discover the future. A compelling or even a subversive question is an effective tool for navigating uncharted terrain.”

Indeed, a research study of thousands of top business executives conducted by Christensen et al. in 2009 found that the most innovative business leaders were also expert questioners. “They’re known to question the conventional wisdom of their industry, the fundamental practices of their company, even the validity of their own assumptions,” says Berger.

This sentiment is echoed in more recent work by Adam Grant. In “Think Again” Grant claims that rethinking, which requires intellectual humility and mental flexibility, can help us view old problems in a fresh light and generate more creative solutions in response. “If you can master the art of rethinking," says Grant, “you’ll be better positioned for success at work and happiness in life.”

What's more and increasingly apt today, is Berger’s observation that questioning is a uniquely human capacity:

“Until [artificial intelligence] acquires the equivalent of human curiosity, creativity, divergent thinking skills, imagination, and judgement, it will not be able to formulate the kind of original, counterintuitive, and unpredictable questions an innovative thinker – or even just an average four-year-old – can come up with.”

Berger suggests a three-step approach to asking good questions that spark innovative ideas:

The first stage involves asking “Why?” and aims to make sense of the context and frame the challenge. When situations are less than ideal, it’s worth asking why they occur in the first place rather than simply reacting to them. As Dan Heath notes in his book "Upstream":

“So often in life, we get stuck in a cycle of response. We put out fires. We deal with emergencies. We handle one problem after another, but we never get around to fixing the system that caused the problem.”

Heath refers to this focus on underlying causes as “upstream thinking.” He uses the stream metaphor deliberately to expand our thinking about solutions. When you ask Why you challenge the status-quo, the way things have always been done, and ignite a spark that can lead to dramatic change.

Sometimes, innovative leaders go out looking for their Why – searching for a question they can work on and answer. This pursuit is described as problem-finding. According to Min Basadur, whom Berger interviewed for his book, problem-finding is one of the most significant things a business should do:

“If you are able to find a problem before others do, and then successfully answer the questions surrounding that problem, you can create a new venture, a new career, a new industry.”

The Why question can be a flashlight that “shines a light on where you need to go,” says Dan Rothstein of the Right Question Institute. But once you decide on a compelling question to answer, you need to move from asking to doing. This is when you move to the What if stage. Berger writes, “If the Why has a penetrative power, enabling the questioner to get past assumptions and dig deep into problems, the words What if have a more expansive effect – allowing us to think without limits or constraints, firing the imagination.”

The worst thing we can do at this stage is trying to answer the question too quickly. When the mind is coming up with What if possibilities, these new ideas can take time to percolate and to form. To generate original ideas and insights – the kind of lightbulb moments that can inspire imaginative What if questions - involves combining existing ideas and influences in unexpected ways. This combinatory mental process is at the core of creativity and innovation.

Once we have broadened our scope of possibility, divergent, anything-goes thinking must begin to converge around what’s doable. For this to happen, What If questions must give way to How questions. The How stage of questioning is where you start acting on an idea and experiment with possible solutions. Prototyping, for example, is a basic form of giving form to an idea. As IDEO designer Diego Rodriguez put beautifully, “A prototype is a question embodied.”

As businesses find that “answers” are transitory and increasingly short-lived in today's dynamic business environment, they must respond to change by way of constant, cyclical questioning, moving from Why and What if to How.


Check out "A More Beautiful Question" for how asking the right questions can help identify new opportunities and spark innovative ideas.



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