Why do you want to be an entrepreneur?
It’s a simple question, but the answer could determine whether you succeed or fail in business. A strong why keeps entrepreneurs focused and willing to push through inevitable challenges when they pop up. Yet still, many aspiring entrepreneurs jump in without fully understanding their motivations, leading to uncertainty, burnout, and often, failure when they face adversity.
The best entrepreneurs don’t just take action. They ask the right questions first. This helps shape your mindset, clarify your strategy, and uncover blindspots before they become obstacles.
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In this article, we’ve put together 15 questions to ask experienced entrepreneurs. The aim is that you will use them to find the answers you need to start your entrepreneurial journey. They will help you define your purpose, map out your next steps, and prepare for the realities of building a business.
Let’s dive in.
Mindset & Personal Development
Before you step into the world of entrepreneurship, you need the right mindset. Being an entrepreneur demands resilience, adaptability, and a willingness to go beyond your comfort zone. The most successful business owners aren’t just skilled at what they do, they understand how to think, learn, and grow despite the odds.
The following questions will help you develop the mindset necessary to thrive as an entrepreneur and identify areas you need to work on.
1. What motivated you to start your business?
Every entrepreneur has a reason for taking a leap into business ownership. Over half of small business owners start their ventures to be their own boss. For many, the financial opportunities are the main motivators. Unlike a nine-to-five, entrepreneurial businesses offer potentially uncapped earnings, but that’s not guaranteed.
Understanding your core motivation is crucial. It fuels your drive and serves as a compass during difficult moments. It gives you a strong enough why to keep going when you otherwise might give in.
2. How do you handle fear and uncertainty?
Entrepreneurship is inherently filled with uncertainty and risk. While your mindset can go a long way in preparing you to face challenges, you need to be realistic and craft strategies to make sound decisions under pressure. This is a valuable lesson to learn from successful entrepreneurs, especially those in your niche.
When you study businesspeople, you unearth various coping strategies.
Many preach embracing action over inaction, encouraging you to take decisive steps. Others recommend developing a risk management framework to evaluate potential paths based on a set of criteria, like cost, feasibility, and risk potential.
You never know when a mishap, financial issue, or an accident might happen so learn from fellow entrepreneurs on how to handle this uncertainty.
3. What habits or routines contribute most to your success?
Social media gurus have convinced the masses that a morning routine is key to success in life, but how true is this? The reality is that different methods work better for different people. That said, consistency is essential. When you take on tasks methodically with a routine, you create a data set that you can analyze and tweak to fit your specific needs.
Habits that entrepreneurs often praise include waking up early, regular exercises, goal setting, continuous learning, and evening reflection. It’s best to have an idea of habits and routines before talking to an entrepreneur.
4. What’s the biggest misconception about being an entrepreneur?
Let’s face it, entrepreneurship is romanticized and far too often viewed as a fast track to wealth and autonomy. In most cases, this couldn’t be further from the truth.
Entrepreneurs are made, not born. Sure, some people might be more inclined to take risks or follow a passion, but many successful businesspeople have honed their abilities through continuous learning and adaptation.
Understanding misconceptions is crucial for aspiring entrepreneurs. Recognizing the realities and watching out for pitfalls, like unlimited freedom or getting rich quickly, helps you set better expectations.
5. What skills do you think every entrepreneur should develop?
Alt: Networking is a crucial part of being an entrepreneur. Here is a breakdown of your network | Source: Harvard Business School
Entrepreneurs wear many hats. Having diverse skills is an absolute must, but what are the most important competencies?
According to Harvard Business School, practical skills like financial literacy, networking, public speaking, openness to feedback, and pattern recognition are key. These may not be what you want to hear, but these skills can get you far in business.
One of the more recent trends for companies is big data integration. This is where you connect data from multiple sources to unlock key insights for your business. The takeaway here is that you need to understand a little bit about every aspect of your business to be able to gain the most valuable insights that can inch your company forward in the right direction.
Go into a meeting with an entrepreneur who has these ideas prepared. Ask them to discuss them and break down the core competencies in their own words. This is where you’ll get the juiciest details.
6. How do you define success in entrepreneurship?
There have been plenty of studies on entrepreneurship, uncovering valuable insights. However, most studies define success with specific criteria in mind and then discuss the importance of each component to entrepreneurs. This is limiting as it prevents entrepreneurs from delving into their definitions of success and success criteria.
By asking people for their own take on success, you unearth the gold.
For some, success means financial independence, which is understandable and straightforward. But, others may view success through impact, measuring it by positive change or the number of people they employ.
Success isn’t one-size-fits-all. Hearing other interpretations helps you come up with your own definition, which you can take with you as you start your own business.
Practical Steps to Building a Business
At some point, every entrepreneur has to move from thinking to doing. Execution separates ideas that remain dreams from businesses that thrive.
Building a business is about making informed decisions, adapting to challenges, and taking risks with purpose. This step is often the main difference between success and failure as an entrepreneur.
7. What’s the first step someone should take before starting a business?
Aspiring entrepreneurs rush to build websites, create logos, and launch their products before they even know if there’s a real demand for them. This can be effective. Any setbacks serve as teachings that may be necessary on their journey.
But, it’s not efficient. The first step to building a successful business isn’t branding; it’s validation.
Talking to potential customers, tasting ideas in the real world, and gathering honest feedback will save you time and money. Take Sara Blakely, the founder of Spanx, the clothing company that helps outfits fit better. She started by cutting the feet off her pantyhose and wearing them to see if they worked, saving money before developing an expensive prototype.
This is just one side of the coin. Ask ten different entrepreneurs how to start a business, and you’ll get ten different answers. That’s why the question is so valuable.
8. How did you come up with your business idea?
Every successful business starts with a spark of inspiration. Some entrepreneurs spot a market gap, others build on personal frustrations, and some stumble upon an opportunity by accident.
Look at Hamdi Ulukaya, founder of Chobani. He came across a classified ad for an abandoned yogurt factory. Instead of dismissing it, he saw an opportunity, bought the facility, and introduced Greek yogurt to the U.S. market. It’s now a billion-dollar company.
For freelancers and creatives, ideas are often born out of necessity, like recognizing a demand for better client relationships or spotting inefficiencies in an industry and designing a service around it.
Asking this question can open your eyes to how entrepreneurs recognize and seize opportunities.
9. How do you approach pricing your products or services?
Pricing is tricky for entrepreneurs. It’s easy to undercut yourself in the beginning when you lack confidence, but this can be detrimental in the long run.
Pricing can determine the type of clients you attract. Price too low and you bring in bargain hunters; too high and you might price yourself out of the market.
In most cases, your strategy will be industry-specific. For example, when selling products, you generally price items in relation to the competition.
However, in a totally different sector, such as law, legal firms like Baumgartner Law structure fees around contingency models. This means clients only pay if the firm secures compensation.
Don’t be afraid to ask for grizzly details and take ideas that relate to your industry and audience.
10. What’s been the most effective marketing strategy for your business?
Marketing is one of those all-encompassing terms that can mean a wide variety of things depending on the industry. Nowadays, innovative marketing strategies are often what elevate entrepreneurs to a new level, whether it’s paid ads, email campaigns, or otherwise.
Marketers have more tools than ever to promote their products and services. This doesn’t mean you need to use them all. Sometimes, simple strategies work best.
For example, GoKenny personal injury lawyers use hyper-targeted local marketing to ensure their services are seen by the right people at the right time. And, it works.
Asking about marketing strategy doesn’t just give you ideas, it also inspires you to think outside the box.
11. What’s one financial mistake you made early on, and how did you fix it?
Every entrepreneur has a financial misstep story; these lessons are goldmines for starting out.
For example, you often hear of people mixing personal and business finances in the early stages.
This practice can lead to accounting nightmares and potential legal issues that necessitate emergency lawsuit loans, from companies like Tribeca.
By hearing how others overcame financial mistakes, you can avoid making them in the first place. If you don’t get a good answer, pry a little more.
Overcoming Challenges & Long-Term Growth
Every entrepreneur will inevitably face setbacks. But what separates those who thrive from those who fold is how they handle challenges and adapt over time. Growth doesn’t just mean scaling the business; it’s about learning from mistakes, making smarter decisions, and staying in the game when things get tough.
This final set of questions will help you uncover the lessons that experienced entrepreneurs have learned the hard way.
12. What’s the biggest challenge you’ve faced as an entrepreneur?
This question doesn’t need much explaining. When you ask the right person, you will learn about the real struggles business owners face as well as the creative solutions they employ to overcome them.
Many entrepreneurs face massive financial challenges, from a lack of funding to unforeseen problems like the pandemic and from personal accidents to supply chain issues. Understanding them prepares you for the inevitable.
13. How do you deal with competition in your industry?
Competition is a given in any industry, whether you’re a tech startup or an established injury law firm. Seasoned professionals in your industry can show you proven ways they’ve managed to stand out and succeed despite fierce competition.
For instance, some entrepreneurs focus on highlighting their unique strengths rather than mimicking competitors. As Oleg Shchegolev, co-founder of SEMrush, advises, “Stop watching the competition and think for yourself.”
Others emphasize the importance of understanding your customers and competitors to identify market gaps and position yourself more effectively.
14. How do you prevent burnout while running a business?
Statistically, entrepreneurs work more than other professionals. Going your own way demands long hours and relentless dedication, making burnout a real problem. Finding out how your peers avoid this may be the difference maker in having a long and prosperous career.
Work-life balance is something most professionals strive toward, but is it realistic when you have lofty goals? Whatever way you look at it, you’ll need self-care practices to keep up a demanding lifestyle, which is something seasoned entrepreneurs can help you with.
15. What’s one lesson about entrepreneurship you wish you had learned sooner?
Jeff Bezos, founder of Amazon, emphasizes the importance of embracing failure as a learning tool. Oprah Winfrey highlights the significance of following your passion and purpose. Elon Musk cites resilience and perseverance as requirements for enduring hardships and pushing through challenges.
Gaining similar insights from like-minded businesspeople will help you anticipate challenges, make better decisions, and navigate your entrepreneurial path with clarity.
The Right Questions Lead to the Right Answers
Entrepreneurship isn’t about having all the answers. It’s about knowing which questions to ask. By learning from those who’ve already walked the path, you can avoid common mistakes, gain valuable insights, and build a business with confidence.
Whether you’re just getting started or refining your approach, seek mentorship, stay curious, and don’t be afraid to take calculated risks.
For more insights on freelancing and entrepreneurship, explore Millo and continue shaping your journey.
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