The best thing about conversation, and feedback, is that it enables the other person to gain a fresh perspective through ‘fresh eyes’.  You never know who you will meet at a networking event, what new things you might learn and how you might be able to help someone.

These questions will give you a great starting point as you venture into feeling more comfortable starting conversations. Remember… conversation (and networking for that matter) is like a muscle… the more you exercise it the stronger it becomes.

Best Conversation Starters

  1. How did you get started in your business?  Everyone loves to talk about their baby – their business baby that is.
  2. Who’s your ideal client?  If they haven’t nailed down who they really want to serve, their avatar, then this question will make them think.
  3. Who do you need to connect with?  Everyone needs to meet someone. 
  4. What aspect of your business are you most proud of?  There might be a certain sector, division, project, idea or concept that is performing really well and they might like to talk about it. 
  5. How can I help you grow your business?  Similar to question #3, but the answer may be broader than just who they need to connect with?
  6. What makes your approach to the industry different?  This is where a little bragging comes in to play.
  7. What’s your biggest challenge? Is there someone I know that might be able to help you with that?  The second part of the question is obvious, that’s why you are asking it. Sometimes just stating that you are willing to connect them with someone who might be able to help, shows that you care enough to help and that you are a true connector. 
  8. What advice would you give someone just starting in your business?  Everyone wants to feel as though their knowledge and wisdom matter; in fact it does. Many people have a great deal of tips in their toolkit that will benefit others.
  9. What one thing would you do with your business if you knew you could not fail?  This question is a loaded one – one that people will take a moment to ponder before answering. It’s every person’s dream!
  10.  Describe the strangest or funniest incident you’ve experienced in your business.  A little humor is a good thing and these stories are often ones you can share! Everyone has a war story.
  11. What do you enjoy most about your profession?  This question elicits a good, positive feeling.
  12. What significant changes have you seen in your industry through the years?  For a seasoned professional, who has the battle scars to prove it, this is their question.
  13. What do you see as the coming trends in your industry?  I love this question. It elicits great responses from new and seasoned business people alike.
  14. What have you found to be the most effective ways to promote your business?  This is such a positive question. They are not likely to share their secrets but sage advice that you can likely share with others.
  15. What advice would you give another entrepreneur? From one entrepreneur to another, there is usually some sage advice to pass on.  It’s one of those ‘If I knew then what I know now’ type of questions.


  1. What one sentence would you like people to use in describing the way you do business?This can be a tough question to answer and one that may require some thought. They will likely stop and think really hard before answering this question.  Not a typical question, but one that is worth its weight in gold – for both of you! 
  1. What activities do you like to do outside of work?  This opens up a tonne of conversation, from travel, to sports, to recreation and more.

Networking and the art of conversation is a journey. Like I said earlier, conversation and networking are like muscles you use in exercising, the more you use them the easier it gets. Have fun and don’t forget to leave your comments. What’s your favorite conversation starter question and why? What’s your biggest challenge in starting conversations?

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Deb Alcadinho is the owner of Your Brand Power and Westshore Women’s Business Network (WWBN). She works with business and professional women to develop their personal brands to help them gain their competitive edge and stand out in a crowded marketplace, increasing revenues and their branding. WWBN provides a networking platform, training and business development for business women to connect, inspire, learn, grow and succeed.