Ask Better Questions

The ability to analyse and effectively break down an issue in order to make a decision or find a solution — is going to be core to your success. To enable effective critical thinking, you need to ask deep, different, and effective questions.

You should have a curious approach and be rigorous using the 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 ask good questions on even the most difficult topics:

Keep your opinions back…
Don’t leap to an initial answer too quickly. Avoid formulating an early answer to a problem and then look for supporting evidence to back up that point of view. Hold your initial views loosely. If you are too embedded into 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 actively…
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 perspective seriously, which keeps them engaged in the conversation and more open to your perspective.

Start your questions with the right words…
When you start enquiring, avoid asking questions that deliver a yes-or-no answer. Instead, pose queries that force the respondent 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 encourage critical thinking in a group, offer an individual the opportunity to expand on their viewpoints, and leave people the space to actively problem-solve.

Provide an alternative point of view…
When problem-solving, we often quickly fall into group think. 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 alternative point of view, 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 alternative and needs someone unafraid to pose it, in case you need change course.

Sleep on 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.

Just as a good stew takes time to simmer, a thoughtful conclusion or question may need space. 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.

Follow up diligently…
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 organisation, or simply face a conundrum. Learn to formulate and ask questions, rather than simply answering them.

Need some help in asking the right questions in your business? Contact us at or call us on 01162325231.

The Tinderbox Team