Why Entrepreneurs Struggle With Critical Thinking (And What To Do About It)

You won’t realize you’re making flat-out assumptions until you test them.

Why Entrepreneurs Struggle With Critical Thinking (And What To Do About It)
[Photo: Flickr user Christopher Thompson]

Critical thinking is useful in just about every sphere of life you can think of, but it’s especially important for entrepreneurs. It prevents you from chasing every rainbow or going down dead ends. But startup founders and other business leaders aren’t always as good at thinking critically as they should be. There are so many other factors that lead us to see things too optimistically, discount important evidence, or play up other signs more than we should. Here’s why, and how to maintain a clear-headed, rational perspective.

Photo: Flickr user Véronique Debord-Lazaro

How Assumptions Let Others Down

When you make an assumption, you take everything you know from firsthand experience and use it to assess a new situation. That’s natural enough. But it can prevent you from verifying or updating the facts first. Entrepreneurs who are too quick to assume convince themselves they already know what others (whether customers or their own teams) need, and don’t always see the point of asking for outside perspectives, believing everyone else shares their own view. In other words, assumptions cloak themselves in the appearance of empirical fact. The result is poor decision-making and a much wider margin of error.

But while critical thinking and assuming are fundamentally opposed, the one is a surefire antidote to the other. While I may have had some preconceived ideas about what I thought was needed, it was only after asking open-ended questions, opening up discussions I might not have wanted to have, and listening, that I realized I actually had no solid basis for my previous notion. In that sense, critical thinking is a self-reinforcing habit: The more you practice it, the less likely you’ll be to make assumptions in the first place. By thinking critically, you can then go back and confirm what you think you understood and monitor the reactions of others to ensure you’re actually satisfying the needs of those who matter most to your business.

More Method Than Madness

Much of business is a fluid process, rather than a straight-shot pursuit of a fixed goal. I’ve gradually become more open to the idea that projects are learning opportunities that unfold over time. Entrepreneurs are prone to acting fast; speed can sometimes be decisive. But that can quickly backfire. Rather than rushing through something, I’ve learned to first make a hypothesis, test it, and then continually adjust my course according to whatever approach is showing the best results.

It’s easy to start a project and already visualize where you want it to lead–that foresight is one of entrepreneurs’ main skills. But that sense of vision can prevent you from discovering something entirely new and potentially better. In my own experience, once I got over my impulse to see a project as something with a set start and end date, I was able to give the creative process more flexibility. My critical thinking took over, and I could see how letting things naturally happen more often led to the real changes I sought.

Photo: Flickr user
Sarah Zucca

Critical Thought And Creativity

As an entrepreneur, I’d like to think I’m pretty creative. I see it in other entrepreneurs as well: Anyone who can dream up the next big thing or take an idea and transform it into a viable business is putting their imagination into action. But they’re harnessing their critical thinking abilities, too–even if that’s less apparent. Creativity may help you think up ideas and find unorthodox solutions to the barriers you face, but the capacity for critical thought helps test whether those ideas are viable.

As entrepreneurs, our creativity is constantly challenged to address any issues that pop up over the course of launching or managing a startup. Yet it’s critical thinking that lets us ask the hard, tactical questions while expanding the lens to see the wider picture. Without thinking critically, it’s hard to assess whether your most creative ideas really have life out in the world.

It’s A Team Sport

Critical thinking is not always a one-person job. As I developed a team for my own businesses and brought more people into the decision-making process, I had to ensure that they were also thinking critically. Entrepreneurs aren’t always amenable to disparate points of view, but I’ve learned to cultivate and embrace them. It’s extraordinary how much a team of critical thinkers can achieve when it comes to the hard work of formulating new ideas and putting them into practice.

Photo: wanying008 via Pixabay

Foods For (Critical) Thought

Sure, critical thinking is something you can practice, but what you eat can actually lay the groundwork for doing it. To keep my mind sharp, I stock up on brain-boosting foods: Nuts can prevent cognitive decline, while pumpkin seeds are known to carry a healthy dose of zinc, which can enhance memory and thinking skills. Will these snacks make you a better critical thinker? Of course not–but they’ll help give the actual “food for thought” that you need to do it.


We’re taught as children to think critically at school, and coached by our parents to make rational decisions. But many of the traits that make entrepreneurs successful depart from that advice at least as much as they draw on it. Once I made the conscious effort to think more critically about my basic assumptions, it opened up a whole new set of skills and ideas for me to explore. Is there anything entrepreneurs like better than that?

Murray Newlands is an entrepreneur, investor, business adviser and a columnist at Forbes and Entrepreneur. He is the cofounder of Due as well as the author of How to Get PR for Your Startup: Traction. He is a member of the Young Entrepreneur Council (YEC), an invite-only organization comprised of the world’s most promising young entrepreneurs.