Critical thinking is the ability to analyze and effectively break down an issue 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 hypotheses loosely. Be willing to fundamentally reconsider your initial conclusions — and do so without defensiveness. Second, listen more than you talk through active listening. Third, leave your queries open-ended, and avoid yes-or-no questions. Fourth, consider the counterintuitive to avoid falling into groupthink. Fifth, take the time to stew in a problem, rather than making decisions unnecessarily quickly. Last, ask thoughtful, even difficult, follow-ups.
Are you tackling a new and difficult problem at work? Recently promoted and trying to both understand your new role and bring a fresh perspective? Or are you new to the workforce and seeking ways to meaningfully contribute alongside your more experienced colleagues? If so, critical thinking — the ability to analyze and effectively break down an issue in order to make a decision or find a solution — will be core 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 last 30 years. His “How Will You Measure Your Life” is a Harvard Business Review bestseller and one of the five best articles on personal development I’ve read, and his theories on innovation and disruption 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 before.
He said HBS was where he learned to ask great questions. Impressed with his classmates, 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, Christensen laid the foundation for his future insights by first studying the process by which people formulated their best queries.
You can approach curiosity just as rigorously — and use that process to get a better view of a new situation or solve some of your toughest problems. Here are a few ways to enhance your ability to interrogate even the most difficult topics:
Hold your hypotheses loosely.
As a former analyst at McKinsey & Company, one of the first things I learned was “hypothesis-driven thinking.” Based on the scientific method, this process is what allows McKinsey teams to work through problems quickly and efficiently. It involves formulating an early answer to a problem and then digging into the data to seek to improve and refine it. Core to this approach, however, is holding your hypothesis loosely. If you are too attached to your initial answer, you may refuse to let it go, no matter where the data leads. But if you treat your own answer as a strawman, holding your assumptions loosely, you’ll be willing to totally abandon it if the situation calls for it.
In critical thinking exercises we often fall rapidly into an intuitive and jointly held “answer” or hypothesis — particularly in groups — and we ask questions that seek to prove rather than disprove our thoughts. Critical questions, however, may force us to fundamentally reconsider our initial conclusions, and we have to be willing to do so freely without defensiveness.
Listen more than you talk.
This sounds simple, but the key to great questions is active listening. Active listening is the process of understanding what another person is saying — both explicitly and implicitly — while showing then 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 to override your brain’s “prediction engine” to ask better questions. Our brains are wired to generate efficient, intuitive answers, but that can limit your point of view. Deep listening is a way of overruling that function and opening ourselves to a wider array of answers. It also allows you to demonstrate to your counterpart that you care about what they are saying and take their seriously perspective, which keeps them engaged in the conversation and more open to your perspective.
Leave your queries open-ended.
When you begin your inquiry, avoid asking yes-or-no questions. Instead, pose queries that force the response to open up and pontificate at length. Rather than asking, “Is this business 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 love about your job and what could be better?” or “Talk to me about a time you found joy in your work and a time you felt unmotivated.” Then follow the dialogue that emerges with more questions. Open-ended questions critical thinking in a group, offer an individual to expand on their viewpoints, and leave people the space to encourage actively problem-solve.
Consider the counterintuitive.
When problem-solving, we often quickly fall into groupthink: The group converges on a path too rapidly, and rather than periodically assuring they are headed in the right direction, they continue further and further — even if it’s the wrong way. Be the person who poses the counterintuitive question, the one that challenges the group’s conventional thinking and reconsiders first principles. There’s a chance your question may be off-base and that the group is on the right track. And, yes, there’s a chance your colleagues who are interested in moving quickly will be annoyed. But every group has an obligation to consider the counterintuitive and needs someone unfraid to pose it, in case you need change course.
Stew in a problem.
In today’s rapid-fire world we try to make decisions too quickly. But the best questions are often formulated after consideration and a good night’s rest. Sleep can actually help your brain assimilate a problem and see it more clearly. And a deliberate process often leads to better conclusions. Research also shows that when we rush a 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 rather than diagnosing them at the moment, he’d take them home and carefully turn them over in his mind. I had a boss who referred to this as “stewing” in a problem. Just as a good stew takes time to simmer, a thoughtful conclusion or question may need space. Resist unnecessary emergency. 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.
Ask the hard follow-up questions.
It can be easy to put our brains on cruise control, to accept easy answers, or to yield to social pressures that push us to avoid interrogating others. But the kinds of deep questions that enable critical thinking are often delivered in chains of deeper and deeper follow-up inquiry. Every parent is familiar with the way children (nature’s most curious people) will ask “why” dozens of times when given an answer. And we parents often find ourselves stuck or reconsidering our own answers at the end of this train of questioning.
While we don’t need to ask a litany of “whys” to get to the heart of critical thinking, we should ask thoughtful, even hard, follow-ups questions. It requires energy to listen hard and formulate those follow-ups, and that’s often the only way to deepen your critical understanding of a topic.
Critical thinking is at the heart of solving complex problems in new and exciting ways. Building this key skill will help you as you navigate new roles, establish yourself in your organization, or simply face a conundrum. Learn to formulate and ask questions, rather than simply answering them.