10 Questions to Ask Entrepreneurs

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There's no absolute formula for success, but you can greatly increase your chances if you know what's been proven to work. One of the best things a new business owner can do is rack the brain of fellow entrepreneurs who have been through it before. These 10 questions for entrepreneurs will give you insight that can help shape your own business model for the better.

1. What Is Your Biggest Mistake?

All businesses make mistakes, whether they’re in the early stages or they're massive, multibillion-dollar companies. Amazon founder Jeff Bezos once admitted, “I’ve made billions of dollars of failures at Amazon.com,” according to Wired’s account. Snapchat somehow managed to push forward after its Spectacles lost the company an estimated $40 million in unsold units in 2014. We learn from our successes but not as much as we learn from our failures, and failures are just part of the business.

One of the most important questions for entrepreneurs is asking a successful business owner or co-founder, “What is your biggest mistake?” The answer will reveal a lot about the hurdles a business has to go through to find success and can spell out any potential problems you may be able to avoid as your company grows. Learn from other people’s problems so you don’t have to fail in the same way.

2. What Do You Think Made You Successful?

Silicon Valley constantly has million-dollar ideas launching, but there’s something that sets apart the TikToks from the Vines and the Facebooks from the MySpaces. This is the spark that every business owner hopes he can capture, but trying to figure out which idea is the right idea out of the seemingly endless possibilities is completely daunting. It's especially difficult considering that most startups fail because there is no market need.

For this reason, it’s important to zero in on the process of how successful entrepreneurs chose the idea that made them so successful. For most entrepreneurs, there’s usually one “aha” moment that snowballed their startup into an industry leader. Knowing this can help sharpen your focus so you can spend most of your limited resources where it really matters.

3. What Do You Wish Someone Told You Before You Started?

It’s true that there’s a real learning curve to running a new business. Every industry has different kinks that you won’t be able to fully understand until you’re elbow deep, which is why having a successful entrepreneur as a mentor can make or break your startup. Just look at NBC’s "Shark Tank," where small business owners rarely choose a shark because they’re making the biggest investment. As much as money is important, a more-experienced person with less resources may be about to beat out larger companies because she already knows what will succeed.

It’s important to ask successful entrepreneurs, “What do you wish someone told you before you started?” This reveals any of the shocking, industry-insider information you’re going to have to learn one way or another. It’s best to not learn it the painful way (through trial and error) and just take it first from someone who has already been there.

4. What Businesses Do You Admire?

Do you want to learn the true secrets of success? Ask about the competition. When an entrepreneur explains why he admires a certain business, especially when that business is the competition, it can reveal his own weak points. What do we typically admire in other people? The things we can’t do as well ourselves.

Asking an entrepreneur, “What businesses do you admire?” can give you a wealth of information about business models, business plans, product launches, marketing strategies and growth trajectories, which is especially important because no two companies become successful the same way. You can use this to shape your own company as it continues to grow.

5. How Has Your Business Model Developed?

Let’s be real: Choosing a business model is daunting, and business models can change as a company expands. At one point, Apple was focused on selling iPods but then later completely sacrificed its iconic product line to create the iPhone, which helped skyrocket them to the top of the smartphone market. Sometimes, a business needs to cut something down before it can slingshot itself to even greater success, but this takes some careful planning.

One of the questions for entrepreneurs that can give you the most insight about the process of growing from a tiny startup to a successful company awaiting an IPO is, “How has your business model developed?” It will clue you in on the aspects of the business on which a company might have wasted efforts during the early stages and what risks it had to take to grow. A risk isn’t as much of a risk if you know that it has worked before.

6. How Did You Build Your Team?

According to a study by CBInsights, a whopping 23% of failed startup owners believe their business failed because they hired the wrong team. The right team can make or break a startup. Ideally, you want a carefully curated group of reliable people who are experts in their subject and have enough unique skills that they can each pick up the slack where the others are lacking. This is not easy to find.

Asking an entrepreneur how she built her team will give you insight on where the best kind of talent hangs out (LinkedIn? Networking events?) and what you need to do to retain that talent. Sometimes, a good salary isn’t enough on its own.

7. How Do You Market Your Brand?

In 2020, online marketing is easier than ever. Facebook and Instagram have ads that are targeted and boosted in three clicks. Services like Mailchimp offer free email lists with crucial analytical tools, and social networks are a dime a dozen. There are so many marketing tools available online that it’s often hard to narrow your focus, and most small businesses do not have a massive marketing budget. They need to conserve their resources.

Asking an entrepreneur, “How do you market your brand?” can help you narrow down your own marketing strategy to what’s most effective.

8. How Did You Get and Maintain Funding?

29% of startups failed because they ran out of money. Getting funding is a huge hurdle that many new co-founders never overcome, but the world of Silicon Valley isn’t what it used to be, and crowdsourcing has completely changed the game. It’s important to ask successful entrepreneurs how they got and managed to maintain the level of funding they needed to operate. You may just find some creative answers to standard cash-flow problems.

9. How Did You Handle Doubt and Adversity?

Creating a good product is one thing, but creating a good product that people believe in is an entirely different beast. Would Facebook have ever gained any real credibility if it didn’t open up its platform beyond the confines of college? How could a bunch of men renting out air mattresses — the least-credible type of sleeping arrangement besides a sleeping bag on the floor — become trusted enough to grow Airbnb to a $35 billion valuation?

There’s no one way to build credibility and handle doubt, but asking an entrepreneur how he overcame negative public perception and secured consumer trust can help you position your business as a serious innovation and eventually an industry leader too.

10. Are You Happy, and Would You Change Anything?

Business isn’t just about money. It’s about happiness too. You know what they say: If you do something you love, you’ll never work a day in your life. That’s not so easy to cultivate once your passion becomes your actual job and starts to feel a whole lot like work.

A great question for entrepreneurs is, "Are you happy?” The answer can tune you in to the true struggle of the work-life balance and can offer advice to help you stay grounded, happy and healthy as your company continues to grow.