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  • Writer's pictureRyan Panzer

Critical thinking, part three: 9 coaching questions to develop critical thinkers

We become critical thinkers when we put emotions, assumptions, and biases (what Daniel Kahneman refers to in "Thinking Fast and Slow" as "System 1 thinking") into a constructive dialogue with data, evidence, and strategy (or "System 2 thinking"). Before we can think critically, we have to put ourselves in a mindset where our slow, deliberative reflection can overtake rapid, spontaneous reaction (or to paraphrase Jonathan Haidt, where the rider can guide the elephant). For more on the basics of critical thinking, check out part one and part two of this blog series!

As critical thinking becomes more of a sought-after skill, the workplace leader of today has a responsibility to bring out the critical thinkers within us, the rational minds that are often buried under heaps of unread emails, calendars packed with meetings, and to-do lists that never seem to clear. A leader can approach this in two ways: by taking their people away from their jobs to learn about critical thinking in a classroom - or, to be more efficient, by asking powerful, in-the-moment coaching questions. By asking the right questions, a workplace coach can inspire more constructive reflection than any book, seminar, or conference breakout.

Let's look at nine coaching questions directed at facilitating critical thinking. Each question can be asked as a one-off in a 1:1 meeting, and each should take no longer than a few minutes to discuss. I'll divide these questions into three categories: those that challenge assumptions, those that further contextualize our thought, and those that help us to step outside ourselves in order to increase objectivity.

To coach for critical thinking, we can challenge emotions, assumptions, and biases through the following questions (listed next to trendy descriptive names!):

  • The decelerator: If I could give you an entire week to think about nothing other than this situation, how might your thinking and decision-making evolve?

  • The rejuvenator: Imagine somebody was brand-new to our organization and faced a similar situation. How might a fresh vantage point lead to a perspective different than your own?

  • The time-traveler: Tell me about a recent experience that informs your thinking about this situation. If you didn't have that experience, how would your thinking change?

We can also better contextualize thoughts with the following:

  • The reminder: Think about your most significant, most pressing goal. If you only thought about the situation in the context of that goal, would it change your thinking or your decisions?

  • The evaluator: Think about the last colleague to provide constructive feedback on your performance. How would your thinking or decision-making align with that feedback?

  • The calculator: Can you provide three pieces of quantitative evidence in support of your perspectives? Can you provide three pieces of quantitative evidence that would challenge your perspective? What evidence seems stronger?

Finally, we can help our teams to step outside themselves to increase perspective with the following questions:

  • The externalizer: Name one stakeholder involved in this situation - perhaps a customer, maybe a shareholder or another employee, maybe our local community. How would they perceive this situation? How might your current line of thinking affect them?

  • The advisor: If you were giving advice to someone in the same situation as you, what advice would you give them?

  • The helper: If you had a full-time assistant that could approach this situation for you and accomplish everything you have in mind, where would you tell them to start? How would they feel about that task?

Ultimately, as much as I might want to, we don't have time in the efficiency-driven workplace to give every worker a college-level course on critical thought. But we do have the ability to ask questions. Coaching questions create the training ground on which we build the skills of critical thought. It is only by asking such questions that we can prepare our workplace for the disruptions of the future.

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