Critical thinking is about asking better questions


Critical thinking is the ability to effectively analyze and break down a problem in order to make a decision or find a solution. At the heart of critical thinking is the ability to formulate deep, different and effective questions. For effective questioning, start by holding your assumptions loosely. Be prepared to fundamentally reconsider your initial conclusions – and do so without becoming defensive. Second, listen more than you speak with active listening. Third, keep your questions open-ended and avoid yes-or-no questions. Fourth, consider the counterintuitive to avoid falling into groupthink. Fifth, take the time to simmer a problem, rather than making unnecessarily quick decisions. Finally, ask for thoughtful, even difficult, follow-ups.

Are you tackling a new and difficult problem at work? Just got promoted and trying to both understand your new role and bring a fresh perspective? Or are you new to the job market and looking for ways to contribute meaningfully alongside your more experienced colleagues? If so, critical thinking – the ability to effectively analyze and break down a problem in order to make a decision or find a solution – will be essential to your success. And at the heart of critical thinking is the ability to formulate deep, different, and effective questions.

Consider this: Clayton M. Christensen was perhaps the greatest management thinker of the past 30 years. His “How will you measure your life” is a harvard business review best-selling and one of the top five personal development articles I’ve read, and his theories of innovation and disruption have changed business. But my most memorable encounter with Christensen was a talk at Harvard Business School where he discussed his own approach to his time as an MBA student decades prior.

He said HBS was where he learned to ask good questions. Impressed by his classmates, he brought a notebook to class and jotted down the most insightful questions asked by other students. He would then go home and reflect on how and why the students had formulated them. Always curious, Christensen laid the groundwork for his future prospects by first studying the process by which people formulate their best requests.

You can approach curiosity with equal rigor and use this process to gain insight into a new situation or solve some of your toughest problems. Here are some ways to improve your ability to interview even the most difficult topics:

Hold your assumptions loose.

As a former analyst at McKinsey & Company, one of the first things I learned was “thinking based on assumptions”. Based on the scientific method, this process is what enables McKinsey teams to solve problems quickly and efficiently. It involves formulating an early response to a problem, then digging deeper into the data to seek improvement and refinement. The heart of this approach, however, is to hold your hypothesis loosely. If you’re too attached to your initial response, you can refuse to let go of it, no matter where the data leads. But if you treat your own answer like a straw man, loosely sticking to your assumptions, you’ll be willing to drop it altogether if the situation calls for it.

In critical thinking exercises, we often quickly fall into an intuitive, shared “answer” or hypothesis – especially in groups – and ask questions that seek to prove rather than disprove our thoughts. Critical questions, however, may require us to fundamentally reconsider our initial conclusions, and we must be willing to do so freely without becoming defensive.

Listen more than you talk.

It sounds simple, but the key to big questions is active listening. Active listening is the process of understanding what another person is saying – both explicitly and implicitly – while showing that you are engaged and interested. Successful active listening allows you to fully grasp an argument, making it easier to question its logic.

Active listening also helps replace your brain’s “prediction engine” ask better questions. Our brains are wired to generate efficient and intuitive responses, but that can limit your perspective. Deep listening is a way to bypass this function and open ourselves up to a wider range of responses. It also allows you to demonstrate to your counterpart that you care about what they say and that you take their point of view seriously, which keeps them engaged in the conversation and more open to your point of view.

Leave your questions open.

When you begin your investigation, avoid asking yes or no questions. Instead, ask questions that force the respondent to open up and pontificate at length. Rather than asking, “Is this company stable?” ask, “If this business were unstable, how or why would that be?” Rather than asking someone, “Are you happy in your job?” ask, “What do you like about your job and what could be better?” or “Tell me about a time when you found joy in your work and a time when you felt unmotivated.” Then follow the dialogue that emerges with more questions. Open questions encourage critical thinking in a group, offer an individual to develop their points of view and give people the space to actively solve problems.

Consider the counterintuitive.

When solving problems, we often quickly fall into groupthink: the group converges too quickly on a path, and rather than periodically ensuring that it is heading in the right direction, it continues more and more away – even if it’s the wrong way. Be the person who asks the counter-intuitive question, the one who challenges conventional group thinking and reconsiders first principles. It is possible that your question is off topic and that the group is on the right path. And, yes, there is a chance that your colleagues who want to move quickly are bored. But every group has an obligation to consider the counterintuitive and needs someone who isn’t afraid to ask it, in case you need to change course.

Stew in a problem.

In today’s fast-paced world, we try to make decisions too quickly. But the best questions are often asked after thought and after a good night’s rest. Sleep can actually help your brain process a problem and see it more clearly.. And a deliberate process often leads to better conclusions. Research also shows that when we rush the decision, we often regret them even if they end up being correct.

What I love about Christensen’s approach to learning from his classmates’ questions is that instead of diagnosing them in the moment, he would take them home and carefully turn them over in his mind. I had a boss who called it “stew” in a problem. Just as a good stew takes time to simmer, a thoughtful conclusion or question can require space. Resist unnecessary emergencies. Map out a process that will allow you to solve a problem over several days or more. Dig into it first, then think about what you learned and what you should have asked. Questions you ask in calm reflection can be more powerful than those asked in the moment.

Ask the tough follow-up questions.

It can be easy to put our brains on cruise control, accept easy answers, or give in to social pressures that cause us to avoid questioning others. But the kinds of deep questions that enable critical thinking are often asked in deeper and deeper chains of follow-up inquiries. Every parent knows how children (nature’s most curious people) will ask “why” dozens of times when given an answer. And we parents often get stuck or reconsider our own answers at the end of this series of questions.

While we don’t need to ask a litany of “whys” to get to the heart of critical thinking, we should ask thoughtful, even challenging, follow-up questions. It takes energy to listen carefully and formulate these follow-ups, and it is often the only way to deepen your critical understanding of a subject.

Critical thinking is central to solving complex problems in new and exciting ways. Building this key skill will help you navigate new roles, establish yourself in your organization, or simply face a conundrum. Learn to formulate and ask questions, rather than just answer them.


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