Critical thinking, part four: What critical thinking really looks like

Our present-day, project-based work culture is predicated on hustle and hurry.

In this project-based workplace, our sense of value (as understood by oneself and one's employers) is increasingly determined by task completion. The most highly-regarded team members are those who get the most done: the reps that close the most deals, the agents that take the most tickets, the engineers who complete the most tasks (eg, cards) in a time period known as a "sprint."

The indicators of hustle and hurry are widespread, particularly in the words we use to describe our work. Much of the business blogosphere is dedicated to improving efficiency and helping employees to work faster. Much, if not all rhetoric from business leaders is focused on increasing velocity. We use terms like "accelerator" to describe organizations that help firms get their start, and adjectives like "rapid" are used to define everything from prototyping to feedback.

But there's a problem with the need for speed.

Speed and efficiency come at the expense of our ability to think critically. When we are moving fast, we are unable to systematically sort through evidence and data and to make well-reasoned decisions.

When we are moving fast, we are depending on System I mental processes related to intuition, assumption, and emotion. Meanwhile, we are suppressing the System 2 processes defined by logic and problem-solving. Daniel Kahneman, in his best-seller Thinking Fast and Slow, describes our aptitudes for reason and logic as strong, yet somewhat lazy. Most of the time, our mind is content to trust the rapidity of System 1, and to let System 2 lie dormant in a state of blissful slumber. And the consequences of this can be severe: we make mistakes in planning, we are overly-beholden to initially positive impressions, we make decisions to mitigate loss but not to actualize gains, we are beholden to unconscious bias.

In the automation-driven workplace, AI has eliminated mindlessly transactional jobs. If the demands of the workplace are indeed shifting from that which requires the rote and repetitive towards that which requires the complex and consultative, we don't need more speed. What we need is the space to think critically about the depth of change around us.

And that is the most visible indicator of a workplace that thinks critically.

If we truly coach our teams to be critical thinkers, we will know it not through improved speed and efficiency. Our decision-making will be slower. Our execution may become less efficient. Time to project completion will increase.

But there's a tradeoff. We'll make fewer errors in planning and forecasting. We'll act less frequently out of inference, and ensure our behavior is consistent with the data. We'll make fewer mistakes, we'll engage more contributors in the collaborative process, and we'll continuously evaluate the efficacy of our processes. Each of these takes time and energy - but each is worth pursuing in and of itself. Each is necessary as our careers require more complex problem solving, and less button-pushing.

If you want your workplace to be more adept at critical thinking, you might take three specific actions. These actions may not gain you friends, followers, or a seat on the hot-shot panel at an upcoming conference. But they will defend your team's capacity to think critically against the ever-encroaching bias towards velocity. These three actions are:

1. Gently challenging leaders who demand increased speed. When a leader states that something must become faster, ask them to describe the costs of greater velocity. What may we fail to consider? What assumptions might grip us? What biases may become more pervasive? By asking this question, you aren't advocating for lethargy: you are promoting critical thinking about the trade-offs between speed and quality.

2. Encouraging your highest performers to slow down. Often, the most productive performers on the team move the fastest. Give them permission to pause, reflect, and do some critical thinking of their own. Encourage them to consider what they might gain by being more deliberate, analytical, and intentional - and how they could share those gains with the greater team.

3. Setting an example by narrowing your priorities. Critical thinking is essentially an exercise in elimination. We can't think critically about an endless to-do list. In the AI-disrupted workplace, we must learn to ruthlessly prioritize those tasks that will have the most benefit for our stakeholders: our colleagues, our team members, our communities.

Critical-thinking is becoming ever-more important. But our preference for speed is inhibiting our ability to pivot from task execution towards creative problem-solving. If a leader is really successful in building a culture of critical thinking, they'll know it by one visible indicator: their organization will be slower.

And that will make all the difference.

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.