Why Asking 'Why Will This Fail?' Can Save Your Business

There’s a single question that has saved me from more financial loss, wasted time, and squandered resources than any other piece of advice. It’s a question I learned the hard way, through a long list of failures and setbacks. Most people avoid asking it because it feels deeply uncomfortable, but ignoring it puts you in a dangerous position, like an ostrich with its head in the sand.

The reality is, you’ll get the answer eventually—either through a tough conversation now or a much more painful experience down the road.

My First Painful Lesson

Back in 2013, when I was 18, I learned this lesson firsthand. I was determined to build an online student platform called ‘Wallpark.’ After pouring three years of my life, my investors’ money, and all my energy into it, the project ended in complete failure.

Looking back, the reason seems painfully obvious: I was trying to compete with Facebook, a battle I never had a chance of winning. But I didn't need hindsight to see that. If I had just possessed the humility and foresight to ask myself one simple question, I believe I could have avoided the entire mess.

That question is:

It sounds simple, almost too obvious. Yet, when I surveyed over 1,000 founders about their , a staggering 87% were crystal clear on why their venture would succeed, while only 6% could clearly articulate why it might fail.

Most new ventures don’t make it. When they crash, the founders suddenly see the obvious flaws. Data from the U.S. Small Business Administration backs this up. Among failed founders, 52% admitted to underestimating the resources they’d need, 42% didn't realize the market didn’t want their product, and 19% confessed to underestimating the competition. I’m convinced that if they had started by asking "Why will this fail?", many of these outcomes could have been different. In business, prevention is always better than cure, and that starts with confronting the possibility of failure head-on.

The 5 Biases That Keep Us Blind

So why do we avoid this crucial conversation? There are five psychological biases that consistently prevent us from asking this essential question about our or next big idea.

As researcher Tali Sharot explained to me, about 80% of us have this bias. It makes us focus on the good and ignore the bad. It’s what stopped me from questioning Wallpark; I just innately believed things would work out. While this trait might have given our ancestors an evolutionary edge, in our professional lives, it makes us terrible at assessing risk.
We all tend to seek out information that confirms what we already believe. This bias caused me to latch onto any data that suggested Wallpark was a brilliant idea while ignoring all the feedback that hinted it wasn't. It boosts our self-esteem by making our worldview feel correct and consistent.
This bias leads us to attribute our successes to our own skill while blaming failures on external factors. It stopped me from considering Wallpark’s potential failure because I overestimated my own abilities and underestimated things like market conditions and competition.
This is what makes us stick with a bad decision simply because we’ve already invested time or money into it. It’s the reason Wallpark dragged on for three years instead of one. Subconsciously, I didn’t want to "lose" the investment, but by staying the course, I ended up losing even more.
This bias stops people in a group from disagreeing because they crave social cohesion. At Wallpark, none of the founding team ever seriously questioned if the idea would fail. We all conformed to the same blind hypothesis, creating a powerful pressure for any new team members to fall in line.

How the Question Saved a Future Business

Fast forward to 2021. My podcast, , was a huge success, and I had a bold new idea: launch an entire podcast network. The plan was to create a slate of new shows with famous hosts, using our team’s expertise to make them all hits. The concept seemed solid, a great path from a media empire.

I had the experience, the connections, the team, and the capital. I assembled a dedicated group of five people, and we spent a year meticulously planning the network. I invested hundreds of thousands of dollars and countless hours into the prep work. Six months in, I even offered the CEO job to the head of a major media company, who provisionally accepted.

After 12 months, the moment of truth arrived. I had to decide whether to give him the green light to resign from his high-paying job and join us. This was the point of no return for this .

In that critical moment, I gathered my team and asked the one question I’d learned to value above all others:

The discomfort in the room was immediate. It was a challenge they’d never considered. Within moments, the floodgates opened. One person pointed out our talent would be spread too thin, jeopardizing our existing success. Another highlighted how unreliable celebrity hosts could be. Others brought up the weakening economy and dwindling sponsorship opportunities.

Then, they turned the question on me. I realized my subconscious had been nagging me with one simple word: ‘focus.’ Our collective focus was our most valuable resource. Success tempts you to lose focus even more than failure does. Our existing podcast was still in a critical growth phase. We needed all our "shower thoughts" and late-night epiphanies to be aimed at making it better, not spread thin across a new, .

Minutes later, we unanimously voted to shut down the project—a project everyone had been excited to launch just an hour earlier. That single, uncomfortable question revealed the project's flaws in high definition. A year later, it’s clear we dodged a bullet. Our focus paid off; our existing podcast business grew its audience by 900% and revenue by over 300% in 2022.

The Pre-Mortem: Your Secret Weapon for Avoiding Failure

We often fail to act until disaster strikes. We don’t exercise until our health is at risk, and we don’t fix the roof until it’s leaking. This is where a formal process called the "pre-mortem" comes in. Developed by scientist Gary Klein, it’s a decision-making tool that flips the script. Instead of asking "What could go wrong?", you imagine the project has already failed spectacularly and then explain what go wrong.

Research has shown this simple thought experiment works. A 1989 study found that using the pre-mortem method increased participants' ability to correctly identify reasons for future outcomes by 30%. It's a game-changer for anyone or launching a .

Here’s the five-step process I use in my companies:

Gather your team and explain the goal is to identify risks, not to criticize anyone.
Ask everyone to imagine it’s a year from now and the project has completely failed. Encourage them to visualize it.
Have each person independently write down every reason they can think of for the failure. Doing this alone prevents groupthink.
Go around the room and have each person share their list. Foster an open, non-judgmental discussion.
Based on the risks identified, work together to create plans to mitigate or avoid those pitfalls.

This Isn’t Just Business Advice

The pre-mortem method isn’t just for a ; it’s a powerful framework for making better decisions in your personal life.

Imagine yourself ten years into a career path, completely miserable. Why? Maybe it’s a lack of growth, a poor work-life balance, or a loss of interest. Identifying these potential pitfalls now can help you make a better choice.
Imagine your relationship has ended. What were the contributing factors? Misaligned values, poor communication, different life goals? Addressing these potential red flags proactively can lead to a more informed decision.
Before buying a house or investing in the stock market, picture a scenario where you lose a significant amount of money. What caused it? A market downturn, not enough research, or overextending yourself financially? Understanding these risks helps you prepare.

We’re surrounded by messages telling us to "visualize success." While optimism is valuable, there is just as much power in contemplating failure. Balancing both gives you the foresight to build a more successful path forward. Your personal and professional growth is often trapped behind an uncomfortable conversation you’re not willing to have.