New Entrepreneurs and Seasoned Pros Won't Succeed Unless They Hone This One Skill

Staying in your bubble will only make you more rigid. Improve your reasoning instead.

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By Aytekin Tank • Jan 1, 2023 Originally published Jan 1, 2023

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"We have interest from new investors," a new acquaintance, Tom, told me a few years back after a conference. He assured me that this new injection of funds would help his startup reach new heights. Needless to say: He was overly confident, overzealous and wanted to grow as fast as possible.

It's a tale as old as time: Inexperienced entrepreneurs believe the only way to succeed is by focusing solely on immediate profits.

Unfortunately, Tom failed to take into account different variables such as a solid business plan and building a quality product with high market demand. His business became just another statistic in the 90% of startups that fail.

I've been CEO of my company, Jotform, for more than 16 years now, and I've seen the above scenario play out more times than I'd like to count. And what I've discovered is the same as what Harvard Business Review contributor Helen Lee Bouygues points out when she writes that the root cause of these organizational failures comes down to 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." However, she does offer some good news: Critical thinking is a skill we can all learn.

Related: Truly Independent Thinkers Have These 5 Traits

Why entrepreneurs need to hone their critical thinking

When I first launched my company in 2006, I did something that sounds unheard of today: I didn't quit my job. I had people insist I take the "all or nothing" approach. They told me my business wouldn't succeed unless I took things seriously and dedicated myself completely to my startup.

I'm glad I didn't listen.

We've eventually grown to have more than 15 million users, and we've done so with $0 funding.

And I can attribute a large part of this to prioritizing critical thinking.

You see, I went against the norm and didn't quit my day job cold turkey. I didn't feel the need to take on a co-founder or bring in investors. My company has always been a bootstrapped business. And I've preferred to grow slowly and steadily for the past decade-and-a-half rather than reach the top of TechCrunch.

So, let me tell you what did happen: By the time I left my job, the product I had worked on replaced my salary and gave me a runway to spend my time building Jotform.

For this reason, I'd like to help you develop your critical thinking skills — based on my own experience and expert advice — to ensure your organization's success.

Related: An Entrepreneur's Guide to Better Thinking

1. Don't be guided by assumptions

As I mentioned above, many people told me I was making a big mistake by holding onto my job. "You're taking on too much," some colleagues warned. "You're not fully committed," others would add.

I had to bypass their voices to hear my own.

As important as it is to question other people's assumptions, it's equally important to question our own. As Bouygues writes, "a questioning approach is particularly helpful when the stakes are high."

She notes that if we're thinking about long-term company goals that will take years of effort and expense, we need to ask the following ourselves the following questions:

  • Can we determine how business will increase?
  • Have we done our research about our expectations for the future market?
  • Have we questioned what possible alternatives there are?

All of this analysis is necessary for thinking critically and taking the best course of action.

Related: The Real Reason Why Most Businesses Fail (And What to Do About It)

2. Improve your reasoning

It's tempting to want to dive right into a new project without fully weighing all the pros and cons. And this doesn't just happen to newly minted entrepreneurs — it applies to even the most seasoned among us.

Yes, we can indeed gain more critical thinking skills with time and experience. But rather than learn through costly missteps, we can also improve our reasoning through logic. One way to do this is by examining different arguments and considering if they are supported by evidence.

"Do all the pieces of evidence build on each other to produce a sound conclusion?" Bouygues asks. "Being aware of common fallacies can also allow you to think more logically."

For example, before taking on a new project at Jotform, we make sure to do our homework by sending out customer surveys, analyzing feedback and taking the market and competition into account. Rather than let our excitement take the lead, we rely on a thorough process of solid reasoning.

Related: Escape Your Head: How Overthinking Can Injure Entrepreneurs in 2023

3. Step outside your bubble

Here's a trap many of us fall into — surrounding ourselves with only those in our industry.

"This is a problem," writes Bouygues. "If everyone in our social circles thinks as we do, we become more rigid in our thinking, and less likely to change our beliefs on the basis of new information."

To hone our critical thinking, it's imperative then that we leave our bubble. And we can do so by taking small steps.

One way I apply this is by taking up a practice of talking to people outside of tech or by having lunch with individuals who have different backgrounds than my own. Aside from these active measures, I also make it a point to switch up my daily reading — preferring books that are also outside my industry.

Experts agree. "Training yourself this way will help you escape your usual thinking and gain richer insights," Bouygues advises.

My suggestion? Don't just read or listen to podcasts about business or tech (if that's what you're normally into). Read novels and listen to talks given by thought leaders outside of your normal environment. And remember:

"While luck plays a role — sometimes small, sometimes large — in a company's successes," Bouygues adds, "the most important business victories are achieved through thinking smart."

In other words: Go against the herd mentality. Use logic, question your assumptions and above all, don't allow yourself to remain stagnant.

Related: Critical Thinking Is the Skill Many Leaders Lack

Aytekin Tank

Entrepreneur Leadership Network VIP

Entrepreneur; Founder and CEO, Jotform

Aytekin Tank is the founder and CEO of Jotform, the easiest online form builder. Jotform was ranked in the 2016 Entrepreneur 360™ List, an annual ranking of the most entrepreneurial private companies in the U.S. 

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