A conversation is only as good as the questions that you ask.
And a good conversation with an important person will go a long way towards accomplishing just about anything with your business.
To make networking more interesting and fruitful, I put together a list of 51 thought provoking questions to ask entrepreneurs.
Here are questions to ask when you meet an entrepreneur for the first time.
- What’s an example of work that you do? Instead of, what do you do?
- What do you typically tell people when they ask you what you do?
- How did you come to be an entrepreneur?
- Why do you do what you do?
- What would you be doing right now if you weren’t here?
Get to Know Them Questions
These questions will help you get to know them so they’ll warm up to you.
- In the beginning, what motivated you to become an entrepreneur?
- Tell me about your first entrepreneurial experience as a kid.
- How have your entrepreneurial motivations changed since you first started?
- What do you consider to be your greatest achievement?
- What’s your most memorable experience as an entrepreneur?
- Describe to me the most exciting minute of your entrepreneurial journey.
- What does a day-in-the-life of (their name, better remember it) consist of?
- What’s the single most important reason for your success?
- What was the tipping point for your business?
- What do you enjoy most about what you do?
- What’s your least favorite part about being an entrepreneur?
- What’s the biggest thing you struggle with as an entrepreneur?
- Is there anything you enjoy more than being an entrepreneur?
- If you had to choose one thing, what do you think you’re the best in the world at?
- What’s the strangest thing you’ve ever done as an entrepreneur?
- How does being an entrepreneur affect your relationships with your friends and family?
- If you could never work again, would you and why?
- If you could be anything other than an entrepreneur, what would it be and why?
- Looking back, what’s one thing you would do differently?
Critical Thinking Questions
Only entrepreneurs know to ask these types of questions.
- What do you consider to be success as an entrepreneur? [tweet it]
- How is running a successful business different than what you thought it would be?
- What do you do on a daily basis to grow as an entrepreneur?
- What entrepreneurial hacks have you developed to stay focused and productive in your day-to-day?
- What things about entrepreneurship do you struggle to understand?
- What popular entrepreneurial advice do you disagree with?
- How would you like people to remember you and your company?
- When I tell people about how I met you, what would you like me to say?
Seeking Wisdom Questions
This is where you start asking probing questions to get their best advice.
- Looking back, what’s one thing you wish you understood about entrepreneurship before you ever got started?
- If you could offer a first-time entrepreneur only one piece of advice, what would it be?
- What systems have you set up in your business to help it grow?
- Besides money, what are your favorite ways to compensate people?
- What creative things do you do to develop a likeable company culture?
- Walk me through the ideal path you’d like someone to take to go from normal consumer to loyal customer?
- What’s the best business idea you have that you’ll never use?
Creative Entrepreneurial Questions
Here are a couple creative entrepreneurial questions that are fun to ask.
- What do you want to be when you grow up? [tweet it]
- What’s your favorite metaphor for describing entrepreneurship?
- If you had to battle a giant, what weapon would you use? It’s a metaphor.
- What’s your greatest fear as an entrepreneur?
- How do you think being an entrepreneur has turned you into a better person?
- How do you think being an entrepreneur has hindered you from becoming a better person?
If You Dare Questions
Ask these questions at your own risk.
- Do you think you’re good at what you do? [tweet it]
- What makes you uncomfortable?
- How much money do you think I could make if I started a business like yours? Instead of, how much money do you make?
- How much traffic do you think I could get if I created a website like yours? Instead of, how much traffic do you get?
- In the few minutes that I’ve been talking with you, what are your impressions of me?
Call to Action Question
If you started the conversation with a goal in mind, which you should’ve, this is where you get what you want.
- I want to help you. How can I?
That’s it. That’s the million dollar question. It’s the difference between being a “remind-me-who-you-are-again” and making a lasting impression on someone.
Helping others is the only way you’ll get what you want in life.
So… How can I help you? I want to know what you struggle with so I can help.
Update: Since publishing this post, I co-founded a simple freelance marketplace called AwesomeWeb. If you’re a freelance web designer or developer and you need more clients, find out more and sign up here.