Interesting Entrepreneur Questions for Networking

51 Interesting Networking Questions for Entrepreneurs

by Nicholas Tart on November 14, 2011 · 25 comments

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.

Ice-Breaking Questions

Here are questions to ask when you meet an entrepreneur for the first time.

  1. What’s an example of work that you do? Instead of, what do you do?
  2. What do you typically tell people when they ask you what you do?
  3. How did you come to be an entrepreneur?
  4. Why do you do what you do?
  5. 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.

  1. In the beginning, what motivated you to become an entrepreneur?
  2. Tell me about your first entrepreneurial experience as a kid.
  3. How have your entrepreneurial motivations changed since you first started?
  4. What do you consider to be your greatest achievement?
  5. What’s your most memorable experience as an entrepreneur?
  6. Describe to me the most exciting minute of your entrepreneurial journey.
  7. What does a day-in-the-life of (their name, better remember it) consist of?
  8. What’s the single most important reason for your success?
  9. What was the tipping point for your business?
  10. What do you enjoy most about what you do?
  11. What’s your least favorite part about being an entrepreneur?
  12. What’s the biggest thing you struggle with as an entrepreneur?
  13. Is there anything you enjoy more than being an entrepreneur?
  14. If you had to choose one thing, what do you think you’re the best in the world at?
  15. What’s the strangest thing you’ve ever done as an entrepreneur?
  16. How does being an entrepreneur affect your relationships with your friends and family?
  17. If you could never work again, would you and why?
  18. If you could be anything other than an entrepreneur, what would it be and why?
  19. Looking back, what’s one thing you would do differently?

Critical Thinking Questions

Only entrepreneurs know to ask these types of questions.

  1. What do you consider to be success as an entrepreneur? [tweet it]
  2. How is running a successful business different than what you thought it would be?
  3. What do you do on a daily basis to grow as an entrepreneur?
  4. What entrepreneurial hacks have you developed to stay focused and productive in your day-to-day?
  5. What things about entrepreneurship do you struggle to understand?
  6. What popular entrepreneurial advice do you disagree with?
  7. How would you like people to remember you and your company?
  8. 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.

  1. Looking back, what’s one thing you wish you understood about entrepreneurship before you ever got started?
  2. If you could offer a first-time entrepreneur only one piece of advice, what would it be?
  3. What systems have you set up in your business to help it grow?
  4. Besides money, what are your favorite ways to compensate people?
  5. What creative things do you do to develop a likeable company culture?
  6. Walk me through the ideal path you’d like someone to take to go from normal consumer to loyal customer?
  7. 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.

  1. What do you want to be when you grow up? [tweet it]
  2. What’s your favorite metaphor for describing entrepreneurship?
  3. If you had to battle a giant, what weapon would you use? It’s a metaphor.
  4. What’s your greatest fear as an entrepreneur?
  5. How do you think being an entrepreneur has turned you into a better person?
  6. 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.

  1. Do you think you’re good at what you do? [tweet it]
  2. What makes you uncomfortable?
  3. How much money do you think I could make if I started a business like yours? Instead of, how much money do you make?
  4. How much traffic do you think I could get if I created a website like yours? Instead of, how much traffic do you get?
  5. 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.

  1. 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..

Post image by: HocusFocusClick


rich November 14, 2011 at 9:02 am

i really want to get to no you more and this e-books are helping.but i want to market and make more money on my sells ,do i really need to print an complimentary card cause every time i go marketing they ask for my complimentary card.

Nicholas Tart November 14, 2011 at 10:43 am

Hey Rich! I think your complimentary cards are our business cards, right? If so, yes, I think you need complimentary cards. I get mine from and they’re only like $10-20 for 1000. You can find more info on business cards here:

Daniel November 14, 2011 at 3:12 pm


Daniel November 17, 2011 at 2:52 pm

that was a down arrow btw

Saad Khattak November 20, 2012 at 4:03 pm

Brother don’t believe on books because if you think a great entrepreneur was a great reader than i must say you are wrong.
Just take an example your teacher who teach you marketing he know all about marketing tricks but he is not an entrepreneur he must have to be because according to rules he know to become a successful business man

make your own rules to get hold on market:
1).. confidence (I can do it)
2).. be a lier (business is a race of lie)
3).. tricks (with customers)
4).. risk (behind every big success there is risk)
5).. relations (more you have relation more you will earn)

Buntu Redempter November 14, 2011 at 2:56 pm

Thanks Nick, This post will help me make awesome interview questions at

Nicholas Tart November 14, 2011 at 4:31 pm

Ah… I was wondering what you’ve been up to, Buntu! Part of the reason I created this list was exactly for that purpose. So we could get higher quality interviews to start flowing around the web. The site looks good, by the way.

Buntu Redempter November 14, 2011 at 6:28 pm

Thanks Nick, I been up to some interesting stuff including, I will be releasing my book soon as well.

Daniel November 14, 2011 at 3:09 pm

You know, I was meaning to write a good old fashioned letter to Donald Trump ,$$$$! But the problem was I didn’t know what to ask him. Thanx Nick. YO, btw, sorry i wasnt on line 4 a while

Nicholas Tart November 14, 2011 at 3:21 pm

Hey Daniel! Yeah, I’ve found that if you ask big-time entrepreneurs anything about their younger years, they like to ponder and respond. And I like the letter idea. I’ve been exchanging letters with Jim Collins, author of Good to Great, for over a year now.

Justin | Personal Growth November 17, 2011 at 9:19 am

Hi Nicholas,

You wrote a great list of interview questions here. For entrepreneurs it is all about service to others and why would some one buy your product or service compared to the “next guy.”

Can we go the extra mile or will we do the bare minimum that is expected.

Nicholas Tart November 19, 2011 at 2:00 pm

Thanks for your insight, Justin! I agree. And, most interviews are horrible because the interviewer doesn’t put any time into crafting the questions.

How do you go the extra mile with Mazzastick?

steve muldovan November 17, 2011 at 3:18 pm

I thought I downloaded 14 clicks but seem to have lost it somewhere in this machine. I love the info., but did’t get to finish it. 🙁

Nicholas Tart November 19, 2011 at 2:01 pm

Are you referring to the eBook, Get Started with Entrepreneurship?

Daniel November 21, 2011 at 2:19 pm

Of coarse, what else

Nicholas Tart November 21, 2011 at 3:49 pm

You can download web pages as .pdf files. So it could’ve been lots of things.

Steve, if you send me an email (, I’ll send you another copy.

John Moon May 4, 2012 at 10:03 pm

These are very good questions. I really liked the “what would you be doing right now if you weren’t here.” It seems like a simply question, but very thought provoking. Something I believe that every entrepreneur should ask themselves in order to figure out what they want and where they want to be. Good read!

Stacie @ May 26, 2012 at 1:42 pm

Networking questions for entrepreneurs are brilliant. I have been working on creating more interesting featured stories on my blog. This is a great guide to follow to help the process seem enjoyable and causes the audience and the guest to think.

Thank you for the goldmine of knowledge in this post.

To Your Success,

Stacie Walker
Woman in Leadership Founder

Nicholas Tart June 11, 2012 at 9:42 pm

Sure thing, Stacie! I’ve found that the quality of an interview, more often than not, comes down to the quality of questions. What type of people are you interviewing?

Stacie @ June 12, 2012 at 6:53 am

Hi Nicholas,

Nice to hear back from you! I know you are an extremely busy man.

I strongly believe in the importance of encouraging entrepreneurs, new and established, who are on the fence about starting their own business venture or who are stagnating with current business goals.

I am interviewing male and female entrepreneurs to help improve the skill set of entrepreneurs in any industry and to inspire them to build their own dreams.

The interviews will be formatted into audio podcasts. I will graduate to video podcast interviews once we have a solid system in place for our audio podcast interviews.

The 15-20 minute audio podcast will focus around any of the following topics:

Personal Development
Financial Development (business or personal)
Leadership Development
Business Building Advice (lead generation, business law, business structure, social
media,branding, etc)

I should be set up and ready to begin conducting my first podcast in two weeks. I already have a list of interested entrepreneurs that want to participate.

I am so excited!

If you know anyone that would be interested in participating, please send them my way.

I look forward to hearing back from you. Keep up the great work and continue changing lives.

To Your Success,

Stacie Walker
Woman in Leadership Founder

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