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A Quick Guide for the 4 Toughest Entrepreneurial Questions

Here are four toughest questions that you will be forced to answer during your entrepreneurial journey.

A Quick Guide for the 4 Toughest Entrepreneurial Questions

As an entrepreneur, you’re going to face some of the toughest challenges that you’ve faced in your life. You will see massive ups and downs, and you’ll find yourself in the middle of some heated arguments. Whether that’s because of employee tension or problems with suppliers, you will have to manage a lot of questions and breeze through them like a sailor in rough waters.

But sometimes the tough questions are internal. And often they are more so challenging and impossible to answer with 100% accuracy. These are the kinds of questions that nobody wants to face and waits till the last moment to answer with any sense of responsibility.

There isn’t a straight path to success, and the journey is almost exclusively full of regret and missed opportunities. You’ll be faced with many decisions that test your emotional makeup and making the wrong choices may seem out of the question. Your company depends on you and you depend on the performance of the company from the ground-up

Here are four toughest questions that you will be forced to answer during your entrepreneurial journey.

#1 Who should be my cofounder?

The question often arises, related to who should be on the founding team of your company? It’s a common question and it often takes you back to a time when you had met that person the first time and what your gut told you about it. What happens often is that there are short deadlines and long-hours of work.

This is where many people fall short and start having arguments and debates about who’s fault is where. This is a bad sign of a founding member team and it can lead to team breakups and long-term failures in the company.

Good arguments are a productive thing. In fact, Bill Gates would often scream and yell in the early years when he didn’t think that the work that was being done was at-par with his expectations. Steve Jobs did that for many years until he retired.

The founding team is important to the foundational structure of the organizational structure as the honeymoon period should be quickly thought-through.

You shouldn’t be married to each other, as that creates an imbalance in expectations and disjointed work-life relationship.  You shouldn’t pick a best friend as a business partner or vice versa. You need to ensure that your founder member has complementary skills to yours and you both inspire each other to do greater things in life.

#2 Should I step down?

This is quite common in tech companies that have shareholders who make a majority of the decisions that happen over time. When founders step down as CEOs and allow others to take over, it can create a vacuum in the hearts and minds of the team. This can also lead to a sense of emptiness in the heart of the founder, who worked hard and long to build his vision from the ground up. Often times, they step down reluctantly, but a lot of times they just don’t have the skills to lead an organization.

Maybe they’re better suited as CTO as they love coding and building new software. The challenges of business operation and leading the company to quarterly success isn’t exciting enough. Sometimes the leadership skills necessary to take a company to newer grounds just isn’t there.

A lot of the times what happens is that a natural leader emerges from the grounds of the organization, who goes up the ranks to one day lead the company. If you spot such a talent early on, then you should definitely consider this question with a lot of thought behind it. You can become an executive chairman and let somebody else take over the reins.

#3 Should I pivot?

When confirmation bias meets survivor bias, it’s a dangerous thing. Pivoting is a good idea when you’re not seeing revenue and you’re only burning investor dollars. Even when your customer base is increasing, but your time per usage is down – you should think about pivoting.

Sometimes you’re in the B2B service space and you don’t know where you are going in your career. This is the perfect time to pivot as well, because you don’t know what the future holds for you.

There is also a tendency to pivot right away and expect the chips to fall as they do. This is the wrong approach as you don’t want to be another failed startup. You should pivot with micro-experiments, to figure out where the revenue lies and where you can provide value in the marketplace.

#4 When should I quit?

Quitting is never an option, unless it's time to quit. When you think about where you are and whether your company is a long-term success or not, you should think about quitting. Quitting is a great move if you also aren’t seeing any growth in business and your employees are getting restless. Sometimes, it’s the right thing for everybody’s future.

Companies shut down and start up every day, and it’s not a new phenomenon by any stretch of the imagination. You have to shut down what you start up, otherwise you’re going to burn a hole in your pocket. There are so many cases of founders taking out huge loans and financing only to be $1M in debt and with no prospects.

You need to be strategic about your decision to quit and not rely on gut-feeling or market conditions to drive your decision. It’s a tough question that you need to take weeks to ponder over. You should think about where you want to be in life and ask yourself whether your current situation is helping or hurting that.


You will quickly find that the most challenging parts of business involve other people. How to deal with human emotions, dealing with friends and family, and coworkers that don’t have a clue as to what to make of an organizational challenge.

The key lies in handling “uncertainty”. Those that sink are the ones that don’t have the foresight to predict and challenge the uncertainty ahead of them. Others that do, have the fortitude to take on any challenge.

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