21 High-Value Questions To Ask An Entrepreneur (Every Chance You Get)

There’s nothing worse than having a spontaneous opportunity to pick a successful entrepreneur’s brain and then going blank on good questions to ask.

Seriously, that’s the worst… or at least, that’s what my friend-who’s-totally-not-me says.

When you’re an entrepreneur, these sorts of opportunities can be surprisingly common, but how much value you pull from them will be directly correlated with the quality of questions you ask.

That’s why today, I’ve put together a list of 21 insanely valuable questions to ask an entrepreneur every chance you get.

Some of these are geared toward business planning while others are geared towards life issues. All of them are valuable.

Let’s get started.

1. What made you take the leap into entrepreneurship?

This one seems a bit basic, but if you are asking as a wantrapreneur or even a new entrepreneur, the answer can be life-changing.

Some people are creating businesses from the time their 10 years old. Other people get started after losing a job they thought they’d retire from in 20 years. Others spend 40 years rocking a career and then decide to take the plunge.

The answer is always different, always interesting, and always carries the potential to inspire your own journey.

Sometimes it just helps to be reminded that anyone, from any background, with virtually any manner of motivation, can succeed as an entrepreneur

2. What were the biggest initial hurdles to building your business and how did you overcome them?

This question is one of my personal favorites. Early hurdles are not only responsible for derailing countless businesses, but they also prevent an even greater number of entrepreneurs from even getting started.

In my experience, the most successful serial entrepreneurs are experts at understanding, attacking, and adapting around early business hurdles.

Learning about the challenges an entrepreneur had to overcome in the first year or two of building a business will inform your own journey and help you think outside the box when dealing with the challenges facing your own business.

3. Did you ever deal with contention from your family concerning your entrepreneurial pursuits? How did you handle it? What would you do differently in hindsight?


Not every entrepreneur has to deal with this, but if you do, it can be a MASSIVE hurdle that affects literally every part of your life and work. To be honest, I can’t think of a more difficult scenario than being in contention with a spouse over your choice to start a business.

When you’re in the trenches, it can be very difficult to view the situation objectively and many, MANY entrepreneurs look back on how they handled relationship issues with deep regrets. At the same time, many other people look back and wish they would have taken the plunge, despite the contention.

Ultimately, nothing beats experience, and that’s why I love asking this question to entrepreneurs who have gone before me. Hearing them describe their unique situation, how they handled it, and what they would do differently is incredible insightful and immeasurably valuable.

4. What was your business’ original mission? How has that mission evolved in the time since?

One of the toughest questions you’ll face as an entrepreneur is whether or not to dig deep and invest more in a given direction as opposed to pivoting into a slightly different or even completely different direction.

The modern marketplace is very fluid, and you’ll find success stories from businesses on both ends of the spectrum.

My own business pursuits have evolved significantly since I first got started, and I’m always intrigued to learn how other businesses have pivoted to meet the market, solve emerging problems for their customers, or apply their technology in an entirely different context.

It’s also really helpful to hear stories of entrepreneurs who were headed in the right direction, had a rough start, and then persevered through the growing pains and into profitability.

5. Do you prefer to pursue funding or build organically, and why?

This is a MUST ASK if you are considering going the Venture Capital route.

There are some major upsides and some major downsides to going after a business model that requires outside capital. It’s very important that you prepare yourself for that journey as best as possible, and that starts with talking to people who have gone through the process of funding, launching, and even selling a startup.

If you can find someone who has been on both sides of the coin, that’s even better. They will be able to compare and contrast the two experiences and help you get a feel for what would be a better fit for you.

6. Did you have major competitors when you started, how did you plan to compete with them, and how did that plan play out?

Very few startups are first-to-market innovators. Most successful businesses are filling the gap left by another product in the space.

It’s never good to put too much focus on your competitors. Creating a great product and keeping your customers happy is always the most important part of launching a startup. That said, no business plan is complete without a defined strategy for handling the competition, and I love learning from entrepreneurs who have done this successfully.

Be sure to ask about both the initial plan and how that plan evolved once the battle began.

7. What do you look for in a business partner?

Partnering with other entrepreneurs can give you a HUGE boost right out of the gate.

It can also derail your startup before you even liftoff the runway.

How you choose the people you partner with is insanely important, and while you might think you know what to look for, the difference between your perspective and a seasoned entrepreneur is sort of like the difference between how a high-school couple and a 40-year married couple view love.

8. What do you look for in an employee?

What you look for an employee will be very different than what you look for in a partner, yet the impact your first handful of employees will have on the business can be equal and even greater than that of your business partner.

Hiring is not an intuitive process for most people. You will make mistakes along the way, but learning from other entrepreneurs is a fantastic way to mitigate those mistakes and find the right people for your business.

9. How do you facilitate a positive work environment that attracts and retains talent?

The first step is hiring the right people.

But then what?

Hiring a few world-changers won’t do you much good if they leave as soon as the next offer comes along. Plus, once you have a core team, the culture you create and faciliate within that team will dictate how well you are able to attract and retain talent as your company grows.

There are a lot of different approaches to creating a positive work environment, many of which can be successful in their own way. In other words, there’s no “right” answer to this question, which makes for a fascinating discussion every time you ask it.

10. How did you build a consumer culture around your product?

Why can Apple create overpriced junk and sell it by the truckload?

Well, it’s because they spent nearly a decade leading their industry with innovate designs and creating a die-hard consumer culture around their products.

Very few brands will reach the level of Apple in terms of customer loyalty, but many companies are actively creating some level of positive consumer culture around their products. Learning from the entrepreneurs behind these companies is one of the best things you can ever do with your time.

11. What would you say was the single most influential factor in your business’ success?

This is another favorite of mine. There are many factors that influence success, but it’s fascinating to hear people point to one and say, “This was the single biggest factor to our success.”

Admittedly, you’ll get a lot of lazy answers on this one, but every now and again, you’ll get an absolute gem.

Understanding why people succeed is even more important than knowing how they succeeded.

12. What is the biggest mistake you’ve made as an entrepreneur?

A few weeks ago, I asked 18 entrepreneurs to tell me about the biggest failure of their career.

The answers were incredible.

We often learn more from our failures than we do from our victories, and by extension, we can often learn more from other people’s failures than we can from their successes.

I highly encourage you to ask this question to ANYONE who has accomplished something noteworthy. The answers will be entertaining at worst and life-changing at best.

13. What has been your greatest moment of success?

Similar to the “most influential factor” question, you’ll get a lazy answer here more often than not. And once again, the occasional gem you’ll get will always be worth the duds.

It’s amazing to ask a multi-millionaire, “What has been your greatest moment of success?” and here them talk about the birth of their child, the success of a favorite employee, or even a business milestone you wouldn’t expect to be a big deal.

I’m perpetually fascinated by the way “successful” people view success.

14. What do you do to recharge when you’re feeling drained?

Being an entrepreneur is difficult. It takes a lot of work, a lot of time, and a lot of intense focus.

If you want to have a sustainable career, you need to learn how to recharge.

I tend to prefer Tim Ferris’ “mini vacations” as my own systematic way to step back from business and recharge, and I never would have tried out that strategy if I hadn’t read The 4-Hour Work Week. It’s not the first method for recharging that I’ve tried and it probably won’t be the last.

Asking fellow entrepreneurs this question, as well as other questions related to work/life balance, will help you get new ideas for managing your own lifestyle.

15. How do you approach marketing your business?

Marketing ≠ Entrepreneurship

To hear people on the interwebs tell it, you might not really these two things are different, but running a business and marketing a business are two entirely different things.

Some entrepreneurs have a knack for marketing and like to be heavily involved. Others are better equipped to fill other roles and either find partners with marketing talent, hire talented marketers, or simply outsource that part of the business to a marketing agency.

As a marketer myself, I love hearing how other entrepreneurs approach this part of a business and learning from the good, the bad, and the ugly of their experiences.

16. How do you believe evolving technology will impact the way we do business over the next 10 years?

This one is a bit more of a fun conversation piece, unless you’re talking to someone who is doing business at the cutting edge of technological advancement, in which case give Elon Musk my number and tell him to call me.

Technology flips the market on a regular basis and alters our framework for entrepreneurship. Most of the people reading this post would be doing something drastically different if they had been born just 30 years earlier.

I really enjoy discussing the impact of technology and business, and I often learn useful new things as well when asking about this topic. It’s definitely not a top #10 priority on this list, but if you have the time, and you’re talking to the right person, fire away.

17. What do you know today that you wish you would have known when you first got started as an entrepreneur?

This is cliche for a reason.

It’s one of the absolute best questions you can ask ANYONE and it consistently results in the most valuable comments you can possible hear.

Think about it.

If you could go back 20-30 years and talk to yourself, what would you say? What would you recommend? What would you tell your younger self to change or do different?

I’m not even that old, and I already have a laundry list of suggestions for my younger self, which I try to provide for new entrepreneurs in our Entrepreneur Alliance Facebook group.

They say hindsight is 20/20, and it would be foolish not to get some 20/20 commentary from every seasoned entrepreneur you know.

18. What is the most unpopular opinion you have on entrepreneurship?

This question tends to get some of the most passionate responses on this list. It’s also one of the best questions to ask to connect with someone and resonate with them on a level that leads to future relationship.

We all have that one thing that bugs us – that thing that EVERYONE agrees on, yet we think it’s absolute bull.

When you ask someone for their most unpopular opinion, you are inviting them to talk about something they’ve spent a lot of time thinking about and talking about in their head. You are inviting them to share a pet peeve, and giving yourself a chance to resonate with them on a level very few do.

You are also going to get some really incredible insights – the type of stuff you rarely hear discussed or written about in a blog post.

19. What 3 books would you recommend that every entrepreneur read?

I’m a major reader, so I pretty much always end any conversion with this question. Great books are a fantastic tool for personal development and can even double as a relaxation method.

I’m so passionate about books that I put together a list of the 28 best entrepreneur books you can read in 2017. Make sure to check those out, and if you are at least a moderate reader, don’t miss a chance to be introduced to some life-changing books.

If you happen to be a bit nervous about starting off your entrepreneurial conversation, this is also a great ice-breaker question. Briefly mention an insight you gained from a book you’ve been reading, and then ask about the books your fellow entrepreneur has been reading.

20. What are some strategies that you would recommend for making the best use of one’s time?

Productivity tips are one of the most over-discussed topics in all of entrepreneurship.

Shaving off minutes here or there isn’t nearly as important as focusing on the right things, and that’s why when I sit down with seasoned entrepreneurs, my question isn’t, “How can I be the most productive?”. Instead, my question is, “How should I distribute my time? What should I be focused on? What are some strategies for making the best use of my time?”

Time is our most limited resource. It’s really important how we spend it. I don’t mind losing a few minutes here or there. What I care about is devoting the lion’s share of my time to the wrong things.

While I don’t bring this question up every time, it’s one of those questions I always have up my sleeve.

21. Who is your hero and why?

I think we can all point to a handful of people we consider personal heroes. I know I certainly can, at least.

Sometimes our heroes are historical figures. Other times they are well-known contemporaries. And sometimes they are people who have played a positive role in our personal lives.

Regardless, who we look up to says a lot about who we are and what’s important to us. When I’m looking to make a personal connection with a fellow entrepreneur, this is one of my go-to questions. It’s also really exciting when a new acquaintance happens to share your feelings towards a given “hero”.

I tend to ask this question towards the end of a conversation or if some of the more technical questions aren’t being met with a warm response.


Well there you have it: 21 questions to ask an entrepreneur whenever you get the chance.

I’ve asked these questions a hundred times, and I still learn something new from them every time I get an opportunity to sit down with a fellow entrepreneur.

Before we call it a day, I’d love to hear what your go-to questions are. Let me know your top #3 in the comments!


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  • Jerry Li