Are You a Critical Thinker?

Note: Critical thinkers are as scarce as hen's teeth. Enjoy. (Previous installments of all of my blogs can be found on my website at

A few years ago, I wrapped up a slightly offbeat assignment into the world of workplace culture. One of the best things that came out of this engagement was not necessarily the results, but, rather, my immersion into a culture of diversified thought.

I happened to meet a Senior Vice President for the Rocky Mountain Region of a big box retailer at a social function, and we started talking about workplace culture and its importance. I shared my experience in assisting businesses and organizations in creating the culture they wanted to create or change and my observations on the same. He was intrigued and suggested we talk further during the following week.

We met at his office, and he assured me that his company was the market leader in big box retail. “Customers will not leave us for our competitors,” he added. “It costs too much to switch to them.” Within weeks, the company's stock had plunged due to a bad earnings report. The SVP was shocked — but he shouldn’t have been. As we talked, I asked him how interested he really was in finding out the reason for this occurrence and shared that, in my experience, most of the ills that any business suffered from stemmed from leadership and rolled downhill from there. 

For more than 30 years, I’ve helped struggling organizations. Sometimes they reach out because they have been mismanaged. Sometimes they have not stayed in front of changing technologies. In a few cases, members of the senior team were simply negligent. But in my experience, these organizational problems shared a root cause: A lack of critical thinking.

Too many business leaders are simply not reasoning through pressing issues, taking the time to evaluate a topic from all sides. Leaders often jump to the first conclusion, whatever the evidence. Even worse, C-suite leaders will just choose the evidence that supports their prior beliefs. A lack of metacognition — or thinking about thinking — is also a significant driver, making people simply overconfident.

The good news is that critical thinking is a learned skill. Based on my personal experience, I’ve pulled together three simple things that you can do to improve your critical thinking skills:

  1. Question assumptions

  2. Reason through logic

  3. Diversify thought

Now, you might be thinking, “I do that already.” And you probably do, but just not as deliberately and thoroughly as you could. Cultivating these three key habits of mind go a long way in helping you become better at an increasingly desired skill in the job market.

1. When I work to turn around an organization, I’ll typically start by questioning the firm’s assumptions. I once visited dozens of stores of a retail chain, posing as a shopper. I soon discovered that the company had presumed that its customers had far more disposable income than they really had. This erroneous belief made the company overprice its clothing. They would have made millions more each year if they had sold lower-priced shirts and pants.

Of course, it’s hard to question everything. Imagine going through your day asking yourself: Is the sky really blue? What if the person next to me isn’t my colleague but her twin sister? How do I really know that the economy won’t implode tomorrow?

The first step in questioning assumptions, then, is figuring out when to challenge assumptions. It turns out; a questioning approach is particularly helpful when the stakes are high.

So if you are in a discussion about long-term company strategy upon which years of effort and expense will be based, be sure to ask fundamental questions about your beliefs: How do you know that business will increase? What does the research say about your expectations about the future of the market? Have you taken time to step into the figurative shoes of your customers as a “secret shopper”?

Another way to question your assumptions is to consider alternatives. You might ask: What if our clients changed? What if our suppliers went out of business? These sorts of questions help you gain new and vital perspectives that help hone your thinking.

2. Years ago, I took on the task of turning around the division of a sporting goods company. The growth of one of its primary product lines had been declining for years. No one could figure out why.

It turned out that the company had made the reasoning mistake of over-generalization, drawing a sweeping conclusion based on limited or insufficient evidence. Namely, the company believed that all of their customers had similar preferences in sporting goods. So it shipped the same products to every store across America.

When I started talking to staff and consumers, we realized that customers in different regions of the US reported very distinct preferences. Because of the extreme heat and humidity, people in the South tend to buy different sporting goods related to water sports than people in the Northeast. For example, they tended to buy the company's products for a completely different reason, like hiking and mountain biking. And those in California led the country in purchases of volleyball and skateboarding equipment.  

For this company, improving their reasoning helped the firm dramatically improve its bottom line. The good news is that the formal practice of logic dates back at least 2,000 years to Aristotle. Over those two millennia, logic has demonstrated its merit by reaching sound conclusions.

So at your organization, pay close attention to the “chain” of logic constructed by a particular argument. Ask yourself: Is the argument supported at every point by evidence? Do all the pieces of evidence build on each other to produce a sound conclusion?

Being aware of common fallacies can also allow you to think more logically. For instance, people often engage in what’s known as “post hoc” thinking. In this fallacy, people believe that “because event Y followed event X, event Y must have been caused by event X.”

So, for instance, a manager may believe that their sales agents rack up more sales in the spring because they’re fired up by the motivational speeches offered at the annual sales conference in February — but until that assumption is tested, there’s no way the manager can know if their belief is correct.

3. Seek out diversity of thought and collaboration

Many look, but few see. By virtue of my background and life experiences, I tend to see things differently from the people around me. This has often played to my advantage. But I’m not immune to groupthink, either. When I’m around people similar to me for whatever reason — age, politics, religion— I try to solicit different points of view. It makes me a better thinker.

It’s natural for people to group themselves together with people who think or act like them. This happens especially readily online, where it’s so easy to find a specific cultural niche. Social media algorithms can narrow our perspectives further, serving up only news that fits our individual beliefs.

This is a problem. If everyone in our social circles thinks as we do, we become more rigid in our thinking, and less likely to change our beliefs based on new information. In fact, the more people listen to people who share their views; research shows the more polarized their views become.

It’s crucial to get outside your personal bubble. You can start small. If you work in accounting, make friends with people in marketing. If you always go to lunch with senior staff, go to a hockey game with your junior colleagues. Training yourself this way will help you escape your usual thinking and gain richer insights.

In team settings, give people the chance to give their opinions independently without the influence of the group. When I ask for advice, for instance, I typically withhold my own preferences and invite team members to email me their opinions in separate notes. This tactic helps prevent people from engaging in groupthink.

While these simple tactics may sound easy or even obvious, they’re rare in practice, particularly in the business world, and too many organizations don’t take the time to engage in robust forms of reasoning. But the important work of critical thinking pays off. While luck plays a role — sometimes small, sometimes significant — in a company’s successes, the most critical business victories are achieved through thinking smart.