Wisdom and Strategy

10 Questions To Ask An Entrepreneur

One of the best things that you can do for your personal growth is to develop an inquisitive mind. The more questions that you are willing to ask, the more answers that you’ll receive. It’s as simple as that.

Learning from the mistakes of others is by far the easiest way to prevent mistakes in your own life.

Sure, you could go through all of those mistakes yourself, learn the hard way, and set yourself and business back for years… or you could just use the wisdom and experience of others to prevent those mistakes from happening in the first place.

Just the same as if you’re a student who’s asking experts “please, do my homework” to learn from them.

Entrepreneurs are a different breed of people. They know what it takes to overcome challenges and build an empire against all odds. The fact that they’re standing in front of you at any given instance is proof enough that they have valuable information to teach you. 

And many of them are surprisingly interested in sharing this wisdom, whether that’s in the context of informal networking in person, on panels at conferences, or even online learning courses.

Many successful entrepreneurs take their life and business experiences and monetize them in the form of books, online courses, and more.

If you get the opportunity to pick their brain face-to-face, you should never pass it up. Here are the top 10 questions that you should ask an entrepreneur the next time that you get a chance.

1- Are You Happy And What Would You Change?

Happiness is important. There are some entrepreneurs who have sacrificed their health, sanity, and happiness in pursuit of money. The ones who are truly happy, however, are the ones who have found a way to balance all of the various facets of their life.

Happy entrepreneurs will be more than willing to tell you everything that they did to get to their current position, and unhappy entrepreneurs will be more than happy to give you advice on how not to end up like them.

Either way, this question presents an opportunity to really get to know the person and learn from their personal life.

2- What Are Some Of The Mistakes You Wished You Could’ve Avoided?

When you first start a business, you’re going to make mistakes. It’s unavoidable. The fewer mistakes that you make, though, the better.

If you’re really smart, you’ll pay attention to all of the mistakes that businesses before you have made, and avoid them like the plague.

The best way to find out about some of these easily avoidable mistakes is to ask an entrepreneur.

The sting of failure is hard to forget, and they will always have a few stories of how they got themselves into a pickle and what they did to get themselves back out.

3- How Did You Know When You Had The Right Idea?

One of the unfortunate things about having a business-oriented mindset is that we’re creative people. People often call us “the jack of all trades.” Every day, we come up with new business ideas and how we can go about implementing them as soon as possible.

With all of these fresh ideas, it can be hard to figure out which one to zero-in and focus on.

Every entrepreneur has gone through this at least once. Asking them how they decided where to direct their focus could enlighten you as to what you should focus on yourself.

4- How Did You Handle Adversity And Doubt?

Your friends are going to doubt you, your family is going to encourage you to make the safe move, and strangers you’ve never even met will sit around plotting on your downfall.

The business world isn’t a very friendly one, and any salty businessman who’s lived to tell the tale will have a few stories about how to handle adversity and overcome both self-doubt and doubt from others.

Often, they’ll give you the motivation that you need to keep your head up and keep moving forward.

Paul, founder of PJG Financial Limited, a firm dedicated to helping people in the UK find the cheapest loans available to them gave us the following advice: “Keep things simple, what’s the end goal and is what you’re doing now really going to get you closer? Simplify and focus on what’s important.”

5- How Do You Plan On Growing Your Business?

A business that never grows is slowly falling. Even if you want to maintain your current level of success, you will need to have a plan for sustainable future growth to keep up with the economy and demographic trends.

Asking other entrepreneurs about how they plan for the future can give you a good blueprint for how you should structure the future growth of your company in the coming years.

6- How Did You Build Your Team?

Accomplishing great things requires a class-A team. As much as every entrepreneur wants to be that self-made man who did everything by themselves, this is just a pipe dream that you’re better off forgetting. Even if you look at some of the most famous artists and musicians of our era, they would be nothing without their team of producers, promoters, and their fans.

7- How Can I Be A Good Leader?

Now that we’ve established that you need a team, you need to learn some good leadership skills to keep them motivated and hustling just as hard as you are. Leadership skills are among the best things that you can learn from a fellow entrepreneur, especially if they’re older and have more experience than you.

8- What’s Your Approach To Marketing?

This question will always yield interesting results. Depending on their niche and business they may reveal that they get more business from referrals or that they may get more from social media marketing. Try to glean some knowledge about the way that they developed their own marketing strategy, and use it when formulating your own.

9- Do You Plan On Retiring?

Some people are entrepreneurs because they’re workaholics and they always want something to work on. These people will likely never retire until their doctor forces them to one day. Other small business owners are in it to make their money, get out, and live comfortably for the rest of their lives. This is always an interesting question, and the answers you receive may help you to make sense of your own business and financial motives.

10- Did You Experience Failures? If So, What Did You Learn From Them?

Failures are different from mistakes. Every entrepreneur will make some mistakes during their lives, but these are usually easy to recover from and serve as valuable lessons for what not to do in the future. A businessman who can recover from a total failure and revive themselves is somebody who you definitely need to have a conversation with.

The knowledge you’ll glean out of this particular conversation could easily be worth more than any of the other questions listed above. The next time that you hit rock bottom, you’ll be armed and prepared to dig yourself out of the hole and keep on hustling towards greatness.

Final Thoughts

Entrepreneurs are busy people. If you happen to bump into some of the most successful ones, you’ll be lucky if they give you more than a couple minutes of their free time. You probably won’t have the chance to ask them all 10 of these questions in an interview format, but you should always have a couple of the important ones resting on the tip of your tongue.

After talking with them and getting their answer, you should make it a point to write it down in sketch book, notepad, or record it on your phone. This will help you to remember the conversation and will give you a valuable reference to look back on in the future.

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