Troubleshoot Like a CEO: The Questions Entrepreneurs Ask Themselves When in Trouble

“Not everything that is faced can be changed. But nothing can be changed until it is faced.” -James Baldwin

“The significant problems we face cannot be solved at the same level of thinking we were at when we created them.”- Albert Einstein

We hear a lot of this every day, don’t we? Has it ever worked practically? Have you spotted the Hotspot? That’s the difference between a layman and an entrepreneur who strive to get out of the hurdles.

They consider the problem as opportunity and questions as stepping stones. To some, it might seem as figurative and theoretical but it, indeed, is pragmatic.

Do you not believe it? You certainly would, when we will go through the detailed logical reasons why entrepreneurs stand out from the crowd.

Sometimes, reframing the words can make you optimistic and let you pass through the obstacles. Example: “can’t” is a negative word, and saying it makes you feel stuck.

But, reframing it to “I can” will boost your spirit to step further and the conscience speaks, “don’t back out”. Here is the list of questions that will assist you to push through any robust problem. In fact, it will lead to a creative opportunity (as mentioned above) and, ultimately achieve new innovation and breakthroughs. I call them, creative openers.

Related Article: The Top 10 Qualities That Define An Entrepreneur

Imagine If?

We all have our own world of imagination and possibilities where we are passion pursuer, the protagonist of a movie, CEO of a company, minister of a province, chief of a reputed organization, legal adviser of a brand. By its very nature, “Imagine if” is a powerful world and put your dreams right there in front of you. It helps you open up ideas and cultivate really juicy options to what once felt like an impossible challenge. Entrepreneurs do that, seriously; we are not talking about day dreaming.

The 2-word phrase is knock-down for silly difficulties you come across. The only difference is entrepreneurs say it within and we don’t, sadly. That’s it, it won’t take a day to be motivated like you get while reading an inspiring book; it won’t take 2 hours to get enlivened like you get while watching a popped up movie.

How About?

Try it. How about? deliberately permits you to play a little and immediately lays the foundation for strong collaboration and teamwork. The destination in asking “how about” questions is to allow people to involve and confront them. This not only decreases the scary feelings inside us but also yields an elaborative discussion.

What if?

Asking “what if” amplifies on the challenge and once it has been assessed and articulated. It provides the space to think big, full of wonder, free and without barriers. The question might seem accessible and provocative. The main advantage of this question is that it raises the child-like curiosity and encourages you to think in open space and that puts you in the creative space you need in order to reframe your situation. In order to get unstuck and cultivate some creative solutions to the problem, you’re looking to solve.

What if it doesn’t work? What if I fail? What if no one likes me? Smart Entrepreneurs use it as a tool to help identify when people feel stuck.

Related Article: 6 Traits of Highly Successful Serial Entrepreneurs

Why Not?

One of my favorite questions I ask to myself and sincerely you ought to yourself. Try adding this couple of words at the end if you’re looking to spark some great dialogue around a particular issue start with a “Why not?” question. This phrase has a magical and magnificent impact on the listener as if there is a stiff mindset behind it. “Why not” shows confidence you have in yourself and while raising it among the community you stand in, you make yourself seen. Entrepreneur’s trick. Isn’t it interesting? Some examples are:

Why not take this deal even though there are some risk factors? Why not grab this opportunity as it’s our only speculative chance to do it? “Why not?” questions are productive and will avail you twist your brain tissues.

What if I Don’t?

This is a key question that clarifies what’s at stake if you are not going to figure out the problem. “Asking ‘What if I don’t?’ is a powerful tool to sort out how you feel about an issue. Sometimes, all you need a big enough reason to do something in order to kick your creative energy into high gear and accelerate with full throttle.

Related Article: 6 Characteristics of a Dynamic Entrepreneur


Asking “why” gets to the heart of the matter. “Why” is a fascinating question to ask before solving any problem. If you ask “why” five times in response to any situation, you will find yourself drilling down into the center gist of the challenge you are trying to resolve. It allows you to discover the truth of any given problem.

When we’re in troubles, we unwittingly box ourselves into a prob instead of tapping our muscle to unlock it. If we can listen, and empathize asking wise questions (just like entrepreneurs do), then we can rule out the problems from roots. “You Are a Powerful Creative Person Full of Solutions to Any Problem.”

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