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.

Coaching for critical thinking, part two: What does it mean to coach critical thinkers?

With the continued growth of automation and artificial intelligence, we will lose the ability to earn a paycheck for rote, repetitive thinking (see part one for more). The only problems that we will have left to solve are the messy, complex, and cumbersome problems that require critical thinking. This presents an opportunity for today's workplace leader, to coach their employees not merely to be more productive and engaged (though certainly, these are important), but to be critical thinkers.

What does it mean to coach critical thinkers?

It starts with challenging easy assumptions and rapid reactions. NYU moral psychologist Jonathan Haidt (author of "The Righteous Mind: Why Good People are Divided by Politics and Religion") suggests that our minds operate with two competing systems: a rational rider, capable of critical thought and strategic thinking, and a reactive elephant, driven by emotions, assumptions, and subconscious thinking. The elephant is physically stronger than the rider and lumbers wherever its elephant mind would go.

For Haidt, the critical thinker is not one who never acts with emotion, assumption, and subconscious thinking, but one who can put emotion, assumption, and subconscious thought into conversation with logic, reason, and evidence. To coach a critical thinker is to facilitate this dialogue.

Emotions and assumptions are fundamental to who we are as people, but in and of themselves aren't particularly useful in a workplace where all of our problems require long-term, perspective-expanding consideration.

In today's complex work environment, emotions and assumptions need to be balanced with strategy, direction, and data. Accordingly, today's managers should think of themselves as quasi-elephant tamers, tasked with helping their teams to be more consciously aware of how emotions and assumptions are shaping their behavior.

This can begin with the simple act of thoughtfully challenging snap-judgments. Coaching for critical thinking involves pushing back on snap-reactions, personal criticisms, and negative opinions that seem divorced from facts and data. This push back should come with a fair bit of humility - as leaders, it's not your job to eliminate snap-reactions, personal criticisms, and negative opinions, but to bring them into alignment with the big picture, with an organization's mission and vision, and with the objective facts of the situation.

This thoughtful challenging of perspectives can be applied in a rather common workplace situation: griping about decisions made by our leaders. It seems that many of our reactions and assumptions are targeted at specific individuals who occupy higher positions in the company org chart. Strolling Madison's Capitol Square neighborhood each day over my lunch break, I overhear dozens of conversations where an individual is ruthlessly criticizing a manager, a director, or executive.

I've overheard these types of conversations from tech employees, state workers, baristas, personal trainers, and parking enforcement officers, to name just a few. It seems that "Wisconsin nice" doesn't apply when our bosses are out of earshot! Either all of our organizations are plagued by incompetent leaders, or we have a tendency to target our emotions and reactions to specific people!

Coaching critical thinkers involves cultivating empathy towards the targets of our assumptions. It does not mean we need to defend other managers, leaders, and executives.

Rather, as coaches, we should be placing our team members in a position where they can thoughtfully and carefully consider what they would do differently, were they in the leader's situation.

A good coach asks their team members how they, given an opportunity to confront the relevant facts, analyze the available resources, and consider possible alternatives, would decide differently.

After this careful consideration, if a team member would still decide differently, the coach must encourage them to articulate why they would do so - and ideally, to put this articulation into writing. This process isn't likely to reverse business decisions or convince an executive to change course, but it is likely to give the rider a less-obstructed view of the landscape.

To coach a critical thinker can involve many other practices: evaluating alternatives in the context of a guiding strategy, prioritizing work in the context of a shared goal or purpose, or charting a course based on the needs of multiple, divergent stakeholders. It's to some of these practices that we will turn in part three of this series, Coaching Questions for Critical Thinkers.

Coaching for Critical Thinking, Part One

Does your job seem excessively rote, tedious, and repetitive?

If so, automation threatens your job security.

According to Brookings, 25% of all American jobs are at risk of elimination from automation and artificial intelligence. While automation will first disrupt low-wage tasks such as food service, it will also change or eliminate jobs in high-tech fields like information technology and web design.

When we are reminded of this imminent automated future, it is natural to feel some anxiety and apprehension. Many stable jobs that exist at the start of 2020 will not exist at the start of 2030.

Yet many, myself included, believe that such disruption in the labor market will create more benefits than it eliminates. That's because these technologies create more jobs than they eliminate. The jobs they create will not be rote or tedious. Rather, they will require critical thinking, creativity, and innovation. They will allow us to be consultative, rather than transactional. These technologies will change the focus of our labor from task completion to problem-solving.

As an instructional designer for Zendesk's customer experience teams, I'm well aware of how automation and AI have changed the customer service space for the better. As automated bots and self-service content have reduced transactional customer contacts, customer support professionals have pivoted towards solving bigger, more audacious problems. The end result is that customer support agents spend less of their time repeatedly answering the same questions, and more of their effort experimenting, seeking to solve previously unanswered questions. The role of the customer support agent is becoming more dynamic, more fun, even more human.

As jobs evolve into more meaningful work, managers must evolve as well. Gone are the days of the task-master manager, focused on delegating to-do lists and enforcing completion. Today's workplace is the domain of the workplace coach who can empower their teams with critical thinking skills. The most effective leaders in this new economy are those who can coach their teams to pause and reflect and to consider many possible solutions. They are those who can coach their teams to be detectives, to find new solutions to questions that were previously unasked!

The manager in an age of automation must be a coach of critical thinkers.

What is a critical thinker? It is simply one who carefully aligns their thinking in service to a goal.

That might sound simplistic, even easy to do. In fact, it's incredibly difficult. Critical thinking requires the suppression of bias, implicit and explicit. It involves a commitment to slow and steady analysis in a world that expects velocity. It demands consideration of feedback and even pushback. In this age of 240-character thoughts and 24-hour news, it turns out that critical thinking is deeply counter-cultural.

In this blog series, we'll explore what it means to coach for critical thinking. In upcoming blogs, we'll look at:

• What it means to coach critical thinkers

• How to ask powerful coaching questions that lead to critical thinking

• How to determine whether your coaching is, in fact, creating critical thinkers

Together, let's hit the pause button on the rapidity around us. It's time to think, about thinking.