So…30 Conversation Re-Starters

awkward conversation

We’ve all been there: in a conference room with colleagues or clients we’ve met less than a handful of times waiting for a meeting to begin. The standard greetings have died down leaving a potentially awkward silence in the room. Or, we’re at a networking event and the group of three we were mingling with quickly became a pair when the mutual contact walked away and we’re left scrambling for ideas to keep the conversation going.

“Quick! Pick up the conversation and keep it going,” you tell yourself. But how? What do you say? Meet the conversation re-starter, a question that is likely to spur at least a few minutes of banter and knowledge-revealing information about the other person, helping you build rapport, create a relationship, and walk away with details to help you remember them by. Keep in mind that conversation re-starters are only effective if you follow up with the response to keep the conversation going. For example:

You: Where is your office located?
Respondent: Our office is in Wicker Park, but our headquarters are in New York.
You: Wow, there are so many great restaurants in Wicker Park, what a great neighborhood to work in. I recently went to Piece Pizza – have you been?
You: I used to live in Wicker Park. And, I visited New York in January. Have you visited the headquarters?

Here’s a list of 30 conversation re-starters for the next time you find yourself saving the fumble and running for the end-zone instead of dropping the ball (or letting the dead ball lie untouched).

These questions don’t ask for professional help or expertise.
They’re rooted in curiosity.
They are not yes/no questions in an attempt to keep a conversation going, versus a series of yes/no questions you may get stuck in again.
They’re not politically or religiously-oriented.
They’re not too personal (reducing the risk that you seem nosy or invasive).


  • What do you enjoy the most about your role and company?
  • What is most challenging about your role?
  • What new projects are you working on?
  • What projects have you worked on lately that you’re most proud of?
  • What tools do you use to keep track of your clients, projects, schedule, travel plans?
  • How big is your company/team?
  • Where is your office located?
  • What’s the latest at your company, anything new and exciting?
  • I do X for my company, who’s the best person to connect with at yours for X?
  • What kinds of clients do you work with (size, industry), any that I would know?

Industry News, Current Events

  • I just heard X company released X, do you think it will take off?
  • What new apps, technology have you discovered lately that you’re excited about?
  • What networking events or conferences have you attended that you recommend? What did you like about them?
  • What are some of your favorite industry blogs, or influencers to follow on Twitter?
  • What are new trends in your industry?
  • How is your company different from your competitors?
  • How is your industry changing as people become more mobile and social?
  • What technologies do you use to keep in touch with team members and partners and meet remotely?

Casual, Social

  • What do you recommend for lunch/happy hour around here?
  • What do you recommend for the best (food type) in the city?
  • What are you listening to these days?
  • What did you do this past weekend/what are your plans for this weekend?
  • Which social media channels do you use personally and for business?
  • Are you an iPhone person or an Android person?
  • What’s your favorite way to stay connected, LinkedIn, email, Twitter?
  • What team are you rooting for in X game? (if not obvious)
  • Where did you go to college?
  • Where are you from originally?
  • How do you enjoy the city outside of work?
  • Where is the last place you traveled to/any travels coming up?

How do you keep conversation going once it seems to die down? What are your conversation re-starter ideas to add to this list?


Image: iStockphoto

About The Author

Rebecca Otis is the Content/Social Media Manager at Digital Third Coast, a digital marketing agency that helps businesses find and connect with customers through SEO, PPC, and content and social media. You can find Rebecca on Google+, Twitter, and LinkedIn.