Want better answers? Ask better questions.

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.

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.

Link: Why Nordstrom’s Digital Strategy Works (and Yours Probably Doesn’t) – HBR

From the esteemed Jeanne W. Ross on studying customer obsessed, digitally ambitious Nordstrom:


Only a small percentage of companies will gain competitive advantage from [social, mobile, analytics, cloud, and internet of things] SMACIT technologies. Those that do will focus less on the individual technologies and more on how they rally all those technologies, in unison, to fulfill a distinctive purpose. We don’t mean a generic, high-concept purpose like “generating shareholder value.” Instead, we mean something much more down-to-earth – a strategic focus that directs their technology spending.


It’s time to get serious about defining the purpose of your digital business model. Don’t worry about developing a strategy for social, mobile, cloud, or any other technology. Develop a strategy for succeeding in the digital economy—a purpose that leverages your unique capabilities and responds to market opportunities. Then grab every technology that takes you there.

via Why Nordstrom’s Digital Strategy Works (and Yours Probably Doesn’t) – HBR.

Connective thinking is rare, crucial – 1959 Essay by Isaac Asimov on Creativity

Connective thinking ability cited as key trait in newly published Isaac Asimov essay on Creativity:

But what if the same earth-shaking idea occurred to two men, simultaneously and independently? Perhaps, the common factors involved would be illuminating. Consider the theory of evolution by natural selection, independently created by Charles Darwin and Alfred Wallace.

There is a great deal in common there. Both traveled to far places, observing strange species of plants and animals and the manner in which they varied from place to place. Both were keenly interested in finding an explanation for this, and both failed until each happened to read Malthus’s “Essay on Population.”

Both then saw how the notion of overpopulation and weeding out which Malthus had applied to human beings would fit into the doctrine of evolution by natural selection if applied to species generally.

Obviously, then, what is needed is not only people with a good background in a particular field, but also people capable of making a connection between item 1 and item 2 which might not ordinarily seem connected.

Undoubtedly in the first half of the 19th century, a great many naturalists had studied the manner in which species were differentiated among themselves. A great many people had read Malthus. Perhaps some both studied species and read Malthus. But what you needed was someone who studied species, read Malthus, and had the ability to make a cross-connection.

That is the crucial point that is the rare characteristic that must be found. Once the cross-connection is made, it becomes obvious. Thomas H. Huxley is supposed to have exclaimed after reading On the Origin of Species, “How stupid of me not to have thought of this.”

But why didn’t he think of it? The history of human thought would make it seem that there is difficulty in thinking of an idea even when all the facts are on the table. Making the cross-connection requires a certain daring. It must, for any cross-connection that does not require daring is performed at once by many and develops not as a “new idea,” but as a mere “corollary of an old idea.”

Asimov also ponders the need and purpose of collaboration, along with providing a (still relevant) tip on sparking and extracting wisdom:

In the same way, a session-arbiter will have to sit there, stirring up the animals, asking the shrewd question, making the necessary comment, bringing them gently back to the point. Since the arbiter will not know which question is shrewd, which comment necessary, and what the point is, his will not be an easy job.

via Published for the First Time: a 1959 Essay by Isaac Asimov on Creativity | MIT Technology Review.

Links: Making the case for polymaths

Not everyone can be a specialist, and that’s a good thing. Four good sources on why we still need polymaths (generalists, versatility) in an age of increasing specialization, and complexity.

For natural polymaths, check out the bonus link on Maya Angelou, and then proceed as wired.


“The question is whether their loss has affected the course of human thought. Polymaths possess something that monomaths do not. Time and again, innovations come from a fresh eye or from another discipline. Most scientists devote their careers to solving the everyday problems in their specialism. Everyone knows what they are and it takes ingenuity and perseverance to crack them. But breakthroughs—the sort of idea that opens up whole sets of new problems—often come from other fields.”

Isaiah Berlin once divided thinkers into two types. Foxes, he wrote, know many things; whereas hedgehogs know one big thing. The foxes used to roam free across the hills. Today the hedgehogs rule.”

New Problems, New Approaches: The Rise of the Generalist | Reuven Gorsht

“The new Generalist is in fact a master of their trade.   They bring expertise and experience in several areas, fueled by insatiable curiosity and the ability to “hyper-learn” new concepts and ideas.”

“They complement specialists, by challenging them to think differently, but never compete with them or take credit for their ideas.   They approach challenges with an open mind, using a “how might we” mindset rather than come with pre-conceived ideas.”

Key attributes:

“Attitude first, not only experience. A “Can-do” attitude and a high degree of motivation are a must. The Generalist must note constraints, but has to creatively encourage ways to work around them.

Intellectually curious (to an extreme level). Can learn and (un)learn any topic (enough to be dangerous) in a matter of hours. Learns on their own as well as from others by asking questions.

Connects the Dots. Can bring in new perspectives and ideas from other disciplines, industries, etc.

Practices empathy. Can imagine the world from different perspective. Those of colleagues, customers, users, etc. Takes time to listen and understand before presenting their own ideas.

Leads by influence and collaboration. Can earn the respect of the specialists, influence new ways of thinking and an open mindset towards new ideas.

Constantly challenges the status quo and encourages new ways of doing things.”

Anyone can learn to be a polymath – Robert Twigger – Aeon

“Monopathy, or over-specialisation, eventually retreats into defending what one has learnt rather than making new connections. The initial spurt of learning gives out, and the expert is left, like an animal, merely defending his territory. One sees this in the academic arena, where ancient professors vie with each other to expel intruders from their hard-won patches. Just look at the bitter arguments over how far the sciences should be allowed to encroach on the humanities. But the polymath, whatever his or her ‘level’ or societal status, is not constrained to defend their own turf. The polymath’s identity and value comes from multiple mastery.”

“There is, I think, a case to be made for a new area of study to counter the monopathic drift of the modern world. Call it polymathics. Any such field would have to include physical, artistic and scientific elements to be truly rounded. It isn’t just that mastering physical skills aids general learning. The fact is, if we exclude the physicality of existence and reduce everything worth knowing down to book-learning, we miss out on a huge chunk of what makes us human. Remember, Feynman had to be physically competent enough to spin a plate to get his new idea.

Polymathics might focus on rapid methods of learning that allow you to master multiple fields. It might also work to develop transferable learning methods. A large part of it would naturally be concerned with creativity — crossing unrelated things to invent something new. But polymathics would not just be another name for innovation. It would, I believe, help build better judgment in all areas.”

All power to the polymath: Ella Saltmarshe at TEDxLSE 2013

POLYMATH BONUS: Growing Up Maya Angelou | Arts & Culture | Smithsonian

“I have a theory that nobody understands talent any more than we understand electricity. So I think we’ve done a real disservice to young people by telling them, “Oh, you be careful. You’ll be a jack-of-all-trades and a master of none.” It’s the stupidest thing I’ve ever heard. I think you can be a jack-of-all-trades and a mistress-of-all-trades. If you study it, and you put reasonable intelligence and reasonable energy, reasonable electricity to it, you can do that. You may not become Max Roach on the drums. But you can learn the drums. I’ve long felt that way about things. If I’m asked, “Can you do this?” I think, if I don’t do it, it’ll be ten years before another black woman is asked to do it. And I say, yes, yes, when do you want it?

My mom, you know, was a seaman. At one point, I was in Los Angeles. I called her in San Francisco and said, I want to see you, I’m going to New York and I don’t know when I’ll be back, so let’s meet mid-state. She said, “Oh, baby, I wanted to see you, too, because I’m going to sea.” I said, going to see what? She said, “I’m going to become a seaman.” I said, Mother, really, come on. She said, “No, they told me they wouldn’t let women in their union. I told them, ‘You wanna bet?’ I put my foot in that door up to my hip so women of every color will get in that union, get aboard a ship and go to sea.” She retired in 1980, and Asian, white and black women gave a party for her. They called her the mother of the sea.

So, yes, we cripple our children, we cripple each other with those designations that if you’re a brick mason you shouldn’t love the ballet. Who made that rule? You ever see a person lay bricks? [She moves her hands in a precise bricklaying manner.] Because of the eye and the hands, of course he or she would like to see ballet. It is that precise, that established, that organized, that sort of development from the bottom to the top.”