How to Ask Better Questions

Sherlock holmes

“Literature is the question minus the answer.”

[Roland Barthes]

Our questions reveal our real intent more than we suspect. There is such a thing as a leading question —a statement camouflaged as question by the inflection, or a lazy question, for example “who is going to win?” 

“The future is the intersection of choice and interruptions,” say Christopher Locke and David Weinberger in The Cluetrain Manifesto. “The questions we ask aren't going to predict the future. They will create the future.” Things are what we make of them.

What happens next?

In a recent paper Jean Twenge, a professor of psychology at San Diego State University, published the results of four studies covering seven million people. Her main question was to understand why are young adults depressed?

There has been “a notable shift away from internal, or intrinsic goals, which one can control, toward extrinsic ones, which are set by the world, and which are increasingly unforgiving,” noted Twenge.

When we're constantly on the lookout for what everyone else is doing, often without the benefit of comprehending their circumstances, including environmental factors, we neglect to become more engaged in our own questions —and putting in the work to develop it fully.

What looks good from afar may be less so once we experience it. The grass is always greener on the other side, says the proverb.

Focusing illusion

We talk a lot about the power of focus in business and in our lives. Yet, unless we learn to pay attention to the right things, the act of focusing becomes an illusion and our decisions bear that disconnect. In other words, we are victims of the focusing illusion.

In Rapt: Attention and the Focused Life, Winifred Gallagher draws on the work on decision-making of Daniel Kahneman and Amos Twersky “made the art of refined query into a science.” She says:

According to the principles of “bonded rationality,” which Kahneman first applied to economic decisions and more recently to choices concerning quality of life, we are reasonable-enough beings but sometimes liable to focus on the wrong things. Our thinking gets befuddled not so much by our emotions, but by our “cognitive illusions,” or mistaken intuitions, and other flawed, fragmented mental constructs.

Facing a choice, for example, you might focus on the quickest, most accessible solution, rather than taking the time to think things through. When making a choice that affects your long-term future, you might mistakenly concentrate on very short-term concerns. “That's why following every detail of your financial situation is a problem, unless you get pleasure from it,” says Kahneman. “If you focus too much on each issue separately, considering each loss and gain in isolation, you make mistakes.”

Overcoming loss aversion

Our loss aversion overwhelms any thought of gain or benefit from a situation, for example. We also tend to create abstractions when we look to answer questions about our lives. But, says Gallagher:

The problem is that this type of abstract evaluation “isn't looking at how people actually experience their lives,” says Kahneman, “but how they think about their lives. That distinction has been my entry into well-being research.”


How you decide to spend your time and make other choices that affect your quality of life is closely bound up with attention, which “governs how people think about well-being,” Kahneman says, “and also governs the experience.”

There is a gap between how we think about our lives and decisions and what we actually do with them. In The Ever-Transcending Spirit psychologist and professor Toru Sato says how our attachment to physical strokes in early childhood develops into the desire and need for attention and respect as later in life. We want ego strokes.

Sato says learning and growth is a constant process of rebuilding our self-system. This translates in us becoming more comfortable with a broader range of situations and experiences. The self-system consists of a memory of all experiences and how to respond to them.

it can be applied to interpersonal experiences. If we apply it to interpersonal experiences, the self-system is our understanding of how we deal with a variety of people in a variety of situations so that our energy level is maintained.

There is a universal language in all human relationships, including that we have with ourselves.

What is our self-esteem?

When we apply the concept of exchange of energy with people to our internal experiences, we realize that self-esteem is a reflection of how large our comfort zone is, of how much our self-system can accommodate.

Experience helps us develop into more sophisticated systems. The more experience, the more developed our self-esteem. The more developed our self-esteem, the better we are at handling specific situations with confidence.

Examples of self-confidence are when we know what to pay attention to and what to ignore to respond to a situation.

Do we focus more on the question about asking questions, for example what makes some people stop questioning and others continue? Or do we pay more attention to who is asking the questions and what we infer based on the perception of how successful they are?

Why would we favor social norms over curiosity? We should play more as children say psychologists, enjoy more unstructured time to experience four ourselves independence, problem solving, and learn about social cues.

Play is more than just fun, says Stuart Brown in Play: How it Shapes the Brain, Opens the Imagination, and Invigorates the Soul.

Staying with the questions

Brown's research on play exposes the areas of our culture most in need of “play hygiene”:

Most adults have “forgotten” what it was like to engage in free play when they were kids. And truthfully, they may have not had much experience with free play when they were young. Beginning in preschool, the natural mayhem that 3-5 year olds engage in (normal rough and tumble play) is usually suppressed by a well meaning preschool teacher and parents who prefer quiet and order to the seeming chaos that is typical of free childhood play.

We all have capacity to play. It is an indispensable part of being human. We learn empathy, trust, irony, and problem solving through play. When we view life as play and possibility we expand our options.

With play we engage curiosity, which is key to unconscious creativity where new connections form that lead to better questions. In A More Beautiful Question Warren Berger says this is the key to giving form to our questions. “The how stage of questioning is where the rubber meets the road,” he says.

What business are we really in?

Is a beautiful question when we use it as as starting point to become more curious about what makes us different. But it is a better question yet when we ask it to figure out our ultimate purpose. Because that can help guide us at all times as we make trade-offs for innovation, to attract talent, and in daily operational choices.

Uncovering purpose is a grounding force as we face exponential change. The late Andy Grove, one of Intel's co-founders, proposed the company's shift from chips, which were becoming a commodity, to microprocessors. Grove pose the question, “if we were kicked out of the company, what do you think the new CEO would do?” to his co-founder.

That was a beautiful question, and with hard work, it got Intel to greater differentiation and results. But Grove later asked a better question, should Intel create a low-end processor at the risk of disrupting itself? As Ben Thompson says, “that certainly cannibalized Intel’s top-of-the-line processor to an extent but also dominated the low-end, quickly gaining 35% market share.”


The advantage comes from the person who is looking and observant —the lens we use to ask better questions is based on our degree of curiosity and the experience we develop through deliberate practice. That is the it depends.

As Doc Searls says in The Cluetrain Manifesto about an acquaintance at a company that was free-falling out of the Fortune 500, “The cluetrain stopped there four times a day for ten years and no one ever took delivery.”


[image Getty Images]