25 [Meaningful] Conversation Starters

How many times do you initiate a conversation with someone using the weather as your topic? Do you dread networking events and extended family get-togethers because of the required small talk chit chat?

Discussing the weather is so easy. It’s also not very exciting. Unless there’s an earthquake. Or a tsunami.

It can be challenging to find ways to connect with someone you may not know very well, or someone you haven’t seen in a long time. The good news is when you do, your conversation can make an impact on that person and shazaam, the relationship grows more interesting.

Even when talking to a high school or college student wouldn’t you like to think of something to ask a teenager other than “What do you want to major in?”

With all the texting, emailing, tweeting, instagramming and multitasking, (heaven forbid we actually pick up the phone!) a meaningful conversation these days is about as common as temperatures below the 90s in Charleston summer.

But what is more delicious than getting below the surface of a person and finding out their special qualities? With one meaningful conversation (and it doesn’t have to last 2 hours) you can make a friend for life. It’s exhilarating to find out you’re not the only one who was dreadfully homesick in college or loves all things lemon.

You can totally avoid eye-glazer, soul-numbing questions. These conversation starters are quirky enough to provoke stimulating and memorable conversations, EVEN with teenagers. (These were tested on nearby teen daughters.)

They are designed for the business audience: clients, prospects, employees and people you meet in networking events. These conversation starters also make fabulous ice breakers! You can vary these questions to suit any conversation partner in any situation. So long, awkward moments.

But wait, there’s more!

You can also deploy these at your next family vacation. You will love the looks on their faces when you ask the unexpected-and-provocative question.

And one more thing! They are great questions to discuss with the best conversation partner of all: yourself! I’m still working on #7.

25 [Meaningful] Conversation Starters

1.What is a piece of really bad career advice you received? Did you know it at the time or did you find out later?

2.What do you most enjoy in your daily work?

3. How is your work in reality compared to what you thought it would be?

4. If you could start your career over, what single decision would you have made differently?

5. What is your best tip for keeping up with people in your community or network?

6. How do you measure your success?

7. Who, from the present or past, would be your ideal mentor?

8. What is a meaningful compliment you’ve received lately?

9. Who is your style icon?

10. Have you read anything lately that impressed you deeply? Please share!

11. Have you ever been so grateful for something that years later, you’re still grateful for it?

12. Please tell me something about you that is not in your official bio.

13. How do you get your best ideas? (Followed by “How do you keep track of them?”)

14. If you could magically have the time and money for this, what kind of advanced degree program would you enroll in?

15. What was your worst project that you can remember?

16. Do you think elegance is relevant to business today?

17. What was your favorite part of today?

18. Outside of work, what are you an expert on?

19. Do you consider yourself an extrovert, introvert or ambivert?

20. Have you ever attended a workshop that blew your expectations out of the water?

21. What is your favorite way to celebrate a big win?

22. How would you describe your communication style?

23. Have you ever won an award? What was it for?

24. If you were a writer, what kind of book would you author?

25. Do you have any unusual family traditions?

Feel free to add to this list by commenting below.

Laura Camacho is obsessed with communication as a tool for building bridges and careers. She believes all conversations should be carried out with style and enthusiasm. And a presentation is just a special sort of conversation. Read her weekly posts at www.mixonian.com. She’s up for hire for quirky communication workshops and private coaching.