Some years ago, I was engaged in a discussion with leadership peers on tackling a particularly challenging issue that seemingly had no answer to satisfy the trifecta of ambitions, resource constraints and ability to execute.

We’ve all been in this meeting. You circle until one of two things happens. Some person or faction gives in, by scaling back the stated ambitions or pouring money into the constraints. Or, time runs out and you adjourn with the promise to think it over, independently. Forgotten, the minute another fire crosses your threshold (or screen).

Occasionally, something else happens. On this day, instead of offering yet another answer, I posed a question to my peers with the intent to reframe our challenge, and shift the lens on our constraints. I don’t actually recall my question. But I vividly recall what happened next.

A peer complimented my question and asked me for the answer. Here’s the thing. I didn’t know the answer. I was merely looking to open a new line of thinking.

I replied that I didn’t know. That it was my job to ask questions, not always answer them. Well…

I broke two leadership norms. First, if you don’t know the answer, you can’t control the answer. So, asking is dangerous.

Second, and more significant, I implied that contributing questions, more specifically, stretch questions is as valuable as contributing answers.

Not my best moment. Or at least, not right then.

According to The Power of Asking Pivotal Questions article in Winter 2015, MIT Sloan Management Review, asking the right question is critical to strategic thinking, decision-making and opportunity spotting. And the true danger is not stretching our questions:

The questions leaders pose sometimes get in the way of solving the right problem or seeing more innovative solutions. They are often too narrow, overly protective of the current business, or assume that the old habits, business models and regulations will remain largely intact. At Google Inc., CEO Larry Page challenges leaders to anticipate the future better by not just asking what is or likely will be true, but what might be true, even if unexpected. The matter of “what is the right question” should be much more central when leaders tackle complex and important decisions, especially in an era of profound change.”

In the article, authors Paul J.H. Schoemaker and Steven Krupp offer six questions to encourage broader thinking and promote better questioning. The six questions are categorized as thinking outside in, exploring future scenarios, being a contrarian, looking for patterns, creating new options and learning from failure.

While the entire article is excellent, two points struck me as particularly relevant to digital era problem-solving.

In the discussion of thinking outside in, the authors don’t limit the “outside” to current constituencies and contexts. Rather, they encourage going wider — exploring adjacencies, identifying weak signals, understanding systemic impacts — in order to bring the future into focus, sooner:

Entrepreneurs like Elon Musk from Tesla Motors, Steve Jobs from Apple and Jeff Bezos from Amazon became known for spotting unmet market needs and figuring out how to serve them profitably. The best entrepreneurs excel at peeking around the corner and seeing the future sooner. We’ve found that leaders can learn to anticipate better by simply being more curious, looking for superior information, conducting smarter analyses and developing broader touch points with those in the know.
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Strategic leaders are focused on the future and are masters at asking discerning questions and exploring ideas and options that are outside the mainstream. They are wary of status quo views and prefer honest, transparent questions that focus on how much, or how little, is really known about the issue at hand. Many studies emphasize the importance of strategic thinking and anticipation, while also lamenting the shortage of leaders who do this well. Those who miss the early signals often come late to the party when customer tastes are changing or when nontraditional competitors are preparing to disrupt or blindside them.

To protect themselves, companies must keep an eye on innovations from both existing companies and startups. Some of the ideas could become game changers, and you may have to team up with the innovators, as a number of big pharmaceutical companies have done with biotech companies.”

Broadened mental models are a great start, but not enough. To avoid the lone (or no) questioner situation, leaders need to deliberately generate creative tension in problem-solving situations:

A persistent problem for many teams is promoting diverse thinking and creative friction. Leaders must always ask if the team has sought sufficient contrarian input and been exposed to all sides of an issue before reaching a decision. This can counter the tendency of many team members to go along to get along. Offering contrarian views is particularly essential when tackling major strategic decisions in an uncertain environment.

To promote diverse thought, Hala Moddelmog, former president of Atlanta, Georgia-based Arby’s Restaurant Group Inc., a fast-food chain with about 3,400 locations, surrounded herself with colleagues of different races, geographies, socioeconomic classes and personality styles. “You really don’t need another you,” she said. Staying open to different viewpoints helps ensure leaders are not unduly hindered by decision traps and can instead open their eyes to information or solutions that they may not have previously considered.

Research shows that creative tension promotes better idea generation and group problem solving. Constructive dissent and debate encourages people to reexamine current assumptions to make room for creative thinking…”

A helpful tip to grow everyone’s thinking and not negatively brand a top thinker as contrarian, is to rotate devil’s advocates:

Before meetings, ask someone to prepare the case against the prevailing view, and rotate this role. Train people to question the status quo and get them to appreciate the benefits of such questioning.”

As for my fellow questioners, rejoice our time is here:

Typically, we don’t judge leaders on the quality of their questions, nor do we design our educational systems or corporate training to develop this crucial skill. If anything, we do the opposite. Television game shows reward contestants who know answers to preset questions — and usually very trivial questions at that. Having encyclopedic knowledge may win you a million dollars on a TV game show or yield good grades in school, but it won’t necessarily make you successful in today’s complex business world. In changing environments, the big prizes go to those who ask better questions and learn faster. In organizations, this comes down to leaders teaching and coaching others to think more strategically and ask deeper questions. If you think like everyone else, you are likely to be average. The best strategic thinkers, leaders and entrepreneurs distinguish themselves by how they frame decisions, the kinds of questions they ask and their mode of inquiry.”

Fire up the TARDIS.