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A particularly curios student was so impressed with his classmates that he formulated a unique routine to learn from them. He would carry a notebook to class and write down the most insightful questions other students asked. He’d then go home and reflect on how and why the students had formulated them. Ever curious, he had laid the foundation for his own future insights by first studying the process by which people formulated their best queries. This student at HBS, Clayton M Christensen, went on to become one of the most influential management thinkers in the last decade. His most defining questions continue to provoke our thinking today. He’s asked us this – How will you measure your life? He’s also challenged us with, What is disruptive innovation?

[…] finding the right answer is impossible unless we have asked the right question.

~Clayton M Christensen [1]

Christensen went on to add, “Asking the right question is a rare and valuable skill. That done, getting the right answer is typically quite straightforward.” We’ve all been guilty of plunging into finding and executing the answer before ascertaining the right questions. Some appear to be naturally gifted in asking piercing questions. For the rest of us, the question is – How does one learn this skill?

The power of framing

When Shishir Mehrotra, currently founder & CEO of Coda, joined YouTube in 2008, the company faced one key dilemma [3] that deeply divided the company. Youtube received a lot of search traffic for content it didn’t have, such as popular TV shows like modern family. Says Shishir, “So the question was: if a user searches for something, and we knew that we didn’t have the best result, should we “link out” to a third-party website?”

The product and engineering group championing for the user, aligned for linking out, versus the business group aligned against it – wanting not to send traffic away from the site.

To resolve this, Shishir found a way to elevate the question, after taking time to deliberately re-frame the problem. He says, “ At an offsite to resolve the debate once and for all, I presented an alternate framing to break the standstill. Instead of thinking of this question as “link out” vs don’t, what if we thought about this as the choice between consistency and comprehensiveness? After much discussion, we settled it: consistency was more important than comprehensiveness [in their market]. And this led to a decision: /We would not link outside of YouTube for search results./ And the story doesn’t end there. Not linking outside of YouTube became one of our core principles and quickly framed a set of other difficult decisions. For example, we removed the ability for creators to opt content out of different devices and removed all third-party embed players. “

Framing a problem, as its name suggests, involves drawing a unique boundary around an ambiguous problem and then making that frame very clear. When done well, it elevates focus towards a small set of “clarifying questions”. Answering these helps in resolving several downstream trade-offs.

To frame a problem well, we need both creativity and rigour. A good starting point to frame, is to create a list of questions and group them into three segments:

  1. Givens – context and agreed principles
  2. Answer now – clarifying questions to define the frame
  3. Answer later – downstream questions linked to a clear frame

Merely asking questions doesn’t define a frame, answering it does. This needs rigour on two fronts; one – generating compelling alternatives and two – evaluating the trade-offs to decide. This is also a great opportunity to engage teams and drive alignment.

Driving alignment however is not just about framing. It needs another critical behaviour.

Listening to understand

It’s common for doctors to interrupt their patients within 11 seconds, even though patients may need only 29 seconds to describe their symptoms [4]. On the contrary, writer E.M. Forster’s biographer, Wendy Moffat, said of him,

“ To speak with Forster was to be seduced by an inverse charisma, a sense of being listened to with such intensity that you had to be your most honest, sharpest, and best self. “ [4]

Often, we’re only listening to respond, not to understand. Active listening, involves a a genuine sense of curiosity along with simple signals to let the other person know you are engaged. It also leads to a particularly effective form of inquiry – through “follow-on” questions. The best form of follow-on questions are the “What” and the “How” questions. “Why” questions on the other hand are best avoided -for they can lead to more philosophical responses that can become hard to reconcile. I’ve also found that writing these questions down as they come to mind keeps interruptions at a minimum and reduces the stress on the working memory. It also provides the extra few moments to phrase them better to gleam more insight.

I consider myself a good listener on most occasions. Yet, I’ve struggled with getting beneath the obvious. I’ve found one simple tool, although difficult to master, that’s helped me overcome this.

Open ended questions

“Where would you place this company on a spectrum of white to gray?” The legendary John Buchanan would ask to assess whether he should accept directorship of a company.

At first pass, this sounds like a classic piece of managementese – clever but meaningless. However, John’s distinguished career made this worthy of reflection. “Yet it is sufficiently open-ended to draw out replies on a wide range of subjects and sufficiently pointed to produce a meaningful response.” I cannot overstate the power of open ended questions over bounded, yes-no questions in uncovering the unexpected.

However, some situational awareness is necessary to use it well. Ask yourself this – “where in the spectrum of co-operative- combative does this conversation fall”. The answer to this is a good indicator of which approach might work better. At the co-operative end of the spectrum, starting with simple, open ended questions are best. For instance, investor Gokul R, says “Tell me your founding story” is a good first question when he meets startup founders. [6]. On the other end of the spectrum are tense win-lose negotiations or a “closure” conversation to take a decision. Open ended questions at this point could lead to a loss of control over the narrative. Depending on the level of trust, it is best to start with a strong opinion or with the most divergent point. It gets easier from there on, with both parties will to make concessions in the less difficult.

Strong opinions, loosely held

“Why the f@*& would we want to do that?” Steve Jobs snapped. “That is the dumbest idea I’ve ever heard.” In 2004, a small group of engineers, designers, and marketers pitched Jobs on turning their hit product, the iPod, into a phone. Jobs was worried about cannibalizing Apple’s thriving iPod business. He also hated cell-phone companies and didn’t want to design products within the constraints that carriers imposed. In private meetings and on public stages, he swore over and over that he would never make a phone.
Yet some of Apple’s engineers worked together to persuade Jobs that he didn’t know what he didn’t know and urged him to doubt his convictions. In about six months, Jobs became curious enough to give the effort his blessing, and two different teams were off to the races. Four years after it launched, the iPhone accounted for half of Apple’s revenue.
In start contrast was another a brilliant college drop-out turned billionaire Mike Lazaridis. As of the summer of 2009, the company he built, BlackBerry, not only had a cult following from the likes of Bill Gates to Christina Aguilera to Oprah Winfrey, it was also the fastest growing company on the planet. Yet, By 2014, its market share had plummeted to less than 1 percent. BlackBerry simply failed to adapt. As the cofounder, president, and co-CEO, Mike was in charge of all the technical and product decisions on the BlackBerry. Although his thinking may have been the spark that ignited the smartphone revolution, his struggles with rethinking ended up sucking the oxygen out of his company and virtually extinguishing his invention.

Adam Grant, in his book “Think Again” [4], gives us several tools to overcome this inability to rethink and reinvent, especially after stellar success. One of the simple techniques is to deliberately build a “challenge network” that you respect and feel safe inside. I’d recommend everyone who considers themselves “successful” to read the whole book.

Allow time for osmosis

Clayton Christensen’s ritual wasn’t quick on his feet. It was regular reflection at the end of the day. Allowing time for “osmosis”, the process of gradual or unconscious assimilation of ideas or knowledge, is key. I’ve found sleep to be a great refresher that helps reset mental thought patterns, allowing fresh perspectives to emerge.
Yet, time alone won’t suffice, a reflection ritual is a key catalyst to ensure osmosis. I’ve found end of the day routines and rituals difficult to maintain, given our fluid boundaries with work and life these days. Maintaining written documents to iterate basis discussions & learnings is a great alternatives – both for work and in personal journals.

Resist unnecessary urgency. Map a process that will allow you to solve a problem over several days or longer. Dig into it initially then reflect on what you learned and what you should have asked. The questions you formulate in quiet reflection may be more powerful than those posed in the moment.

Joe Coleman, in HBR article [4]

Create your questions toolkit

So how does one put this together and get better at asking questions. Part of the answer is to apply these principles in advance and prepare a range of “questions toolkits”, which form a great starting point. Focus your tool-kit on the types of issues that you are currently spending a lot of time on. Hiring questions tool-kit, for instance, or brainstorming meeting tool-kit.

The most important element underlying all this is to genuinely channel your curiosity. Haven’t we all come across people for whom questioning comes easily? It is a combination of natural inquisitiveness, emotional intelligence, and the ability to read people that puts the ideal question on the tip of their tongue. That might appear like it is talent, but as Christensen showed us, it can be learnt through rigorous curiosity.

Thought starter – curated questions toolkit
Types of questions
5 Strategy Questions Every Leader Should Make Time For
5 Questions to Ask When Starting a New Job
7 Rules for Job Interview Questions That Result in Great Hires

Sources

[1] https://www.suu.edu/graduation/pdf/11-christensen.pdf
[2] Critical Thinking Is About Asking Better Questions
[3] Eigenquestions: The Art of Framing Problems
[4] Think Again, the latest book from Adam Grant
[5] How to Ask Better Questions
[6] https://twitter.com/gokulr/status/1522590926282977281
[7] How to Ask Great Questions
[8] Book summary Leading with Questions
[9] Photo by Tim Mossholder on Unsplash

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