In what many at the time considered to be the omphalos – literally the center of the world – stood the most important shrine in all of Greece: the oracle at Delphi. People from all over the Greek empire and beyond would make the trek up Mount Parnassus near the Gulf of Corinth to get an answer to their questions about the future from the Oracle. The questions ranged in breadth and significance from personal matters to whether one empire should wage war on another.

On one such day, the Oracle’s friend Chaerephon asked the Oracle a question that would alter the course of human philosophy and logic for centuries to come. His question was: Is there anyone wiser than Socrates?

The answer – that Socrates was the “most free, upright, and prudent of all people” – did not surprise Chaerephon, but it left Socrates himself quite perplexed. How could someone who felt he knew nothing be considered wiser than others, Socrates wondered, calling it the great paradox. And so, he set out to test the Oracle’s answer. He found the politicians, poets, and skilled craftsmen of Athens revered for their wisdom and he began to interrogate them. By engaging in elenchus – what we would today call cross-examination – he soon realized that those known for their wisdom thought they knew much more than they actually did.

True wisdom – he concluded, finally affirming the Oracle’s assertion for himself – is accurately recognizing the limits of one’s own knowledge. Inspired by this exploration, Socrates embraced a calling to show people the limitations of their own knowledge, so they could possess true wisdom. And so, the Socratic method, which has since influenced much of Western philosophy and the teaching method at most modern law schools, was born.

The Power of Questions for Critical Thinking

What Socrates discovered some 2,500 years ago was the power of questions to make others think. In his book Blink, Malcolm Gladwell shows that much of our thought life takes place behind the closed door of our subconscious. As a result, we often don’t know why we do, feel, or think the way we do. Careful questioning exposes these gaps of darkness in our minds and helps us construct sound opinions and beliefs.

While we may not gather in Athens’ Agora to debate the ideas of the day, the construction of sound opinions, beliefs, and recommendations holds immense value in today’s economy – rated by many surveys as the most in-demand soft skill. This type of thinking – critical thinking – can be taught. We must reject the notion that critical thinking is either an innate gift that can’t be developed or a skill learned only through experience.

Through our research of three research-based critical thinking models, we created the Critical Thinking Roadmap and a corresponding toolkit to help people learn the science of building this skill.

In the toolkit, we included development exercises for each milestone of the roadmap’s four phases. While those development exercises offer a great starting point, they realize their full value when accompanied by intelligent questioning.

How to Use These Critical Thinking Questions

We’ve included five questions for each milestone below. There are five, rather than just one, for two reasons:

• Often one question alone won’t be sufficient to help someone fully unpack their thoughts.
• You will likely find yourself in a position to ask these questions many times a week, if not daily. It’s helpful to vary the question to cause people to approach their thoughts from different angles.

We would not recommend that you commit this list to memory, though you may find it helpful to print it out or post it somewhere you’ll see often. Here is our recommendation for how to get started:

1. Start by plotting your team members on the Critical Thinking Roadmap.
2. Once you do, you’ll know which questions you’ll want to use most frequently.
3. Pick one question from the milestones that relate to your team member and practice using it as much as you can
4. Once you feel comfortable using that question, add a second

When you do ask these questions, consider it the beginning of the conversation, not the end. In other words, expect to ask several follow-up questions.

Since we released the Critical Thinking Roadmap Toolkit, we’ve been asked a number of times if people can do the development exercises themselves to build their own critical thinking skills. The answer is, unequivocally, yes. And the same is true for these questions. Ask these same questions of yourself to push your own critical thinking.

100 Critical Thinking Questions

Execute

• BEGINNER
  • What work has been assigned to you?
  • Why is this work important?
  • How would you explain what you’re going to do to a child?
  • What are your key questions about this assignment?
  • What feels the least clear?
• PROGRESSING
  • What steps will you need to take to achieve the objective or complete the assignment?
  • What order should you take those steps in?
  • What will you do first?
  • How will you do step X?
  • What will you need to know or do before step X?
• INTERMEDIATE
  • Who is the best at doing the work that has just been assigned to you?
  • What are the best practices for doing this work?
  • What have you learned from doing this work previously?
  • What’s the hardest part of this assignment?
  • What are the common mistakes people make on these types of assignments?
• ADVANCED
  • How long will this take you to do?
  • Is the deadline reasonable?
  • How long will sub-task/step X take?
  • What intermediate deadlines have you created?
  • If you were to miss the deadline, what would be the most likely reason why?
• THRESHOLD
  • What should we/you do next?
  • How has the work you just finished change what we were thinking we would do next?
  • What could we do better next time?
  • How could you have done it more efficiently next time?
  • What do you wish you would have known in the beginning?

Synthesize

• BEGINNER
  • What are your takeaways from that meeting?
  • What did you learn from…?
  • What have been your key thoughts about the work over the last week?
  • What would you like to update me on?
  • What has happened this week?
• PROGRESSING
  • What are the most important takeaways from…?
  • What are the key insights on…?
  • Of the takeaways you mentioned, which are the least important?
  • If you had to cut some insights or points, which would you cut?
  • How would you prioritize these takeaways?
• INTERMEDIATE
  • What would you share if you could only share one insight?
  • What would you share if you only had 5 minutes to present?
  • What would you do if we only had $XXX to complete the project?
  • What would you do if we only had X months to complete the project?
  • What’s the 2-minute version of your update?
• ADVANCED
  • What is the most important thing I need to know about your work?
  • What questions do you have for me that you must get answers to?
  • You have X minutes. What have you learned?
  • You have X minutes. What do I need to know?
  • What’s the answer?
• THRESHOLD
  • Can you wrap this up?
  • What are our key takeaways?
  • What action steps do we have from this meeting?
  • What do we need to make sure we don’t forget from this meeting?
  • We’ve covered a lot of ground. Can you give us a brief recap?

Recommend

• BEGINNER
  • What have you already done or considered to answer your question?
  • What do you think?
  • How would you answer your own question?
  • What would you do if I wasn’t available to be asked?
  • What would you say if someone you were managing asked you this same question?
• PROGRESSING
  • How confident are you in your recommendation and why?
  • If you had to, how would you convince me your recommendation is a bad idea?
  • What parts of your recommendation are you least confident in?
  • If your recommendation were to fail, what would be the most likely way it would fail?
  • Who is least likely to support your recommendation and why?
• INTERMEDIATE
  • What other ideas have you considered?
  • Why is your recommendation better than other ideas out there?
  • Could you combine this idea with any others to make it stronger?
  • How have others approached this same challenge differently?
  • What have you learned from other approaches or ideas for this same work?
• ADVANCED
  • What is the logic behind your recommendation?
  • Could you walk me through how you came to this recommendation?
  • How would you convince a skeptic your recommendation is our best option?
  • Could you draw a mind map of your rationale for this recommendation?
  • Imagine your recommendation is a math equation, like A + B leads to C. How would you describe the rationale behind your recommendation like a math equation?
• THRESHOLD
  • What should team member X do next?
  • What would you do if you were team member X?
  • How would you answer team member X’s question?
  • How can team member X/the team apply lessons from your work to theirs?
  • What is most important thing for the team to do next?

Generate

• BEGINNER
  • What ideas do you have for our work, team, X?
  • How would you make this work, team, project, department, X better?
  • If you were in charge, what would you do?
  • What blind spots do we have?
  • What are none of us thinking about that we should be thinking about?
• PROGRESSING
  • How would you solve this challenge?
  • Nothing we have tried in the past has worked. What else can we try?
  • What are other analogous approaches we could learn from to help solve this challenge?
  • What would be a novel approach to this challenge?
  • What solutions could we borrow from elsewhere to help solve this challenge?
• INTERMEDIATE
  • What would it look like to make that vision a reality?
  • Is it feasible to achieve this vision? Why or why not?
  • How would we go about achieving that vision?
  • How would you structure our approach and resources to achieve that vision?
  • When could we reasonably accomplish that vision?
• ADVANCED
  • How do you think our work should be different in 1, 3, 5, X years?
  • How will things change over the next X years?
  • What must we do now to prepare for the future?
  • What early signals should we be paying attention to that will impact our future?
  • What are we doing now that we must continue to do for the next X years?
• THRESHOLD
  • How could fellow leader X expand her/his thinking further?
  • What is fellow leader X missing in her/his vision of the future?
  • How feasible is fellow leader X’s vision?
  • What should fellow leader X do to begin bringing about her/his vision?
  • What are the greatest risks associated with fellow leader X’s vision?

If you haven’t yet, download your copy of the Critical Thinking Roadmap Toolkit to accompany these questions.