Business Questions to Ask an Entrepreneur

by / ⠀Entrepreneur Interviews Entrepreneurship Startup Advice / June 7, 2022
why become an entrepreneur

The following answers are provided by the Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world’s most promising young entrepreneurs. What are some business questions to ask an entrepreneur?

Business Questions to Ask an Entrepreneur

1. What Is That One Thing?

As a founder, you’re likely doing dozens of things at once. A good way to get yourself to focus is to ask yourself, “What is that one thing we can do to move the needle?” Then be sure to prioritize that “thing” within the company.
– Jeff Epstein, Ambassador

2. Have My Employees Signed Invention Assignment Agreements?

Investors often primarily invest in the intellectual property of a company. They will insist that anyone who has done work for the company has signed an invention assignment agreement, making it clear that the work product belongs to the company. For most startups, it’s the top legal priority.
– Doug Bend, Bend Law Group, PC

3. What’s My Exit Strategy?

It may sound odd to ask about how you’ll exit the business you’re thinking about founding, but it’s absolutely critical. It determines how you need to grow your business. If you expect to be out in five years, you’ll need to do things quite differently than if you expect to be in that business for 20 years. Begin with the end in mind so you don’t end up with no good end in sight.
– Charlie Gilkey, Productive Flourishing

4. Are We Systematizing?

In startup mode, it’s easy to go with the flow. But if you’re going to achieve consistent results, you’ll need to systematize and document your processes. Otherwise you won’t know what worked and why.
– Kelly Azevedo, She’s Got Systems

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5. Am I Focussed?

The hardest thing about being an entrepreneur is maintaining focus. It is so easy to get caught up in more and more exciting ideas, from small features to entirely new products. However, if you can’t focus on achieving your mission better than anyone else, then you’ll never achieve your goals. Everything your startup does should follow a focussed mission and work towards those goals.
– James Simpson, GoldFire Studios

6. Where Do I Want to Be in 10 Years?

If you can start to visualize where you want to be ten years down the road, you can start to build backwards. You can build a straight line of tasks and projects that will guide you towards that goal. You’ll have more clarity because you’ll always be doing the tasks that lead to your long term goal. This provides great peace of mind and focus on what really matters to you.
– Dave Nevogt,

7. Would My Business Survive Without Me?

If you weren’t around tomorrow, would the business survive? It’s important to build a company that is sustainable beyond your involvement. This is freeing to both you and your employees, and you will not grow as large as possible until it happens.
– Joseph P. DeWoody, Clear Fork Royalty

8. What’s My One-Sentence Mission?

If you can’t answer this, you’re going to lose a lot of potential gains to a lack of focus.
– Sam Saxton, Salter Spiral Stair and Mylen Stairs

9. Do I Enjoy My Work?

If you are not enjoying what you’re doing, now is the time to start something else — while you are young!
– Ioannis Verdelis, Fleksy

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10. Do People Need My Product/Service?

There are a shockingly high number of businesses and products we can all live without. Ask yourself if what you are creating solves a real need in the marketplace, or if it’s just a flash in the pan that people might like in the short term. Starting a business is one thing, but staying in business is quite another.
– Michael Portman, Birds Barbershop

11. What Is My Definition of Success?

It can be easy to get lost in the day-to-day operational tasks. Make sure you have a bigger picture of where your company is headed so you don’t get bogged down solving problems that might not matter in the long run.
– Elton Rivas, One Spark

12. Are My Prices High Enough?

A lot of young founders don’t realize what their products or services are worth, and they’ll never know if they don’t push the envelope a little. I’ve seen some great startups under-price themselves for years before realizing it.
– Maren Hogan, Red Branch Media

Related Post: Create a Bulletproof Mission Plan

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.