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Conversation Starters to Help Groups Open Up

A handful of online learning sessions with expert facilitators Amy Climer and Chad Littlefield added a few more tricks to my repertoire. The two modeled a handful of get ‘em talking techniques and conversation starters that I’ll be happy to replicate at my next session, live or online! Hopefully, they’ll do the trick for you too.

First Words: The Sooner the Better

Chad credited Priya Parker, author of The Art of Gathering with saying, “If you can get people to use their larynx in the first 5-7% of the gathering, they’re more likely to use it in the rest of the 95% of the event.” The challenge for facilitators, therefore, is to get people to speak as quickly as possible in any meeting or gathering where participation is essential. Here are a few tips to help make it happen:


Tell the group you’re all going to try to “break Zoom.” Invite everyone to unmute themselves. Then, when you say, “go,” ask everyone to say hello at the same time, in whatever language you prefer. 3-2-1-GO. If you’re meeting in person, you can try the same thing. Say “hello” to the group and insist on a greeting back from everyone. If the group is too quiet, say “That was lame, let’s try it again!” Alternatively, make it a game, performance-style: “When I say ‘hey’ you say ‘ho.’ Hey … Ho… Hey … Ho.”


Polling tools can make it super easy for every person to engage. Additionally, the facilitator and participants get a snapshot of the whole group. For further give and take later in the session, the facilitator can refer back to the survey/polling results or ask the participants to reflect on the results.


Ask participants to find and open the Chat field. Start with an easy question in Chat. For example, you might ask, “What is one of your favorite topics of conversation.” NOTE: any time you ask for a “favorite,” be sure to say “one of your favorites,” as that makes questions much easier to answer.

Regular Chat

Either, have everyone respond and “send” their response when they’re ready.

Chat Storm

Instead of sending responses when each person is ready, try a “chat storm” instead:

  1. Set-up: Tell participants NOT to send their replies immediately. Rather, request that they write their answer to the questions, but don’t hit “send” until you give the go-ahead. Pause, then say, “3-2-1-GO!”  When responses are in, ask everyone to review the Chat and identify another person’s response that they are naturally curious about. Ask one participant to unmute and ask that person a question about their response.
  2. Why storm?: The advantages of a chat storm include: 1) its fun factor; 2) the lack of distraction when thinking about your own reply; and 3) an opportunity for participants to interact with one another.
Chat Networking

If, at some point during the session, you invited participants to type in their title and organization. Later on, you might encourage them to take a moment to look up and down the chat for someone whose profile intrigues them. Welcome them to consider that person a secret buddy. Moreover, at the end of the session, suggest that participants share their LinkedIn profiles, in case they want to connect with those buddies down the road.

Going Deeper: Diving into More Meaningful Conversation

After getting folks to utter their first words and make basic connections, you might look for ways to deepen the conversation — online or face-to-face. You can accomplish this with a thoughtful question, image, or quotation. Because the success of your effort may lie in the prompt that you use, take time to consider it fully or draw from a deck of carefully curated questions such as the UNZIP-it! Decks or WeConnect Cards.

Use Images

Images, photographic or illustrated like Climer Cards, can also lead to wonderfully rich conversations. As Daniel Pink, NYT best-selling author, said, “If a picture is worth a thousand words, a metaphor is worth a thousand pictures.” Indeed, images and metaphors – comparisons between two things that aren’t alike but have some things in common – are incredibly powerful because they allow speakers to:

  • Weave several different ideas together
  • Engage creative thinking
  • Bring more nuance to an idea
  • Go deeper more quickly

Poignant Prompts for Image-based Conversation Starters

While a good selection of images will do most of the work, these prompts will help participants draw the most out of them:

  • For Team Development: Pick a card that represents… (or is a symbol or a metaphor for…)
    • … a change you want to make
    • Your definition of… (conflict, teamwork, etc.)
    • A wish you have for our team
    • A hope you have for our company’s future
    • Where we are in our project
    • How you feel when you’re on your way to a team meeting
    • Who you are in our team
  • For Evaluations: Choose an image that reflects how you feel you’re doing in your job; a career aspiration; a change you want to make professionally
  • For Icebreakers: Pick an image that represents…
    • A quality you’re proud of
    • Something you recently learned about yourself
    • A quality or experience that will help you succeed in the session
  • For Connections: Pick an image that represents…
    • Your connection to the content…
    • A question you want to ask someone else
  • For Session Reviews… Find an image that relates to one idea you’d like to hold on to a month from now or year from now

Facilitation Tips and Tricks

A few more quick reminders, to enhance your gathering and promote the exchange of ideas:

  • Be clear with instructions: Say, for instance, “In 1 minute, share your name, which image you selected and why (watch the time and use the whole time, not just a quick one-word answer)”
  • Make starting easier: Suggest an easy way to determine who should speak first (i.e. person with the shortest hair)
  • Add context: For any prompt or question, remember you can always add a context (i.e. If asking about goals, feel free to specify … at work; …at home; …during this session)
  • Get creative: If you have a set of questions you love and a set of images, pair the two together.

Give People an “Out”

Before launching into a conversation starter exercise, with the hope of deep conversation, be sure to set expectations and remind them that they always have complete agency in terms of how they answer a question. Explain, “You have 100% choice in how you answer a question. When you see a question or prompt, you can reply in any way that feels safe:

  • Share “lite” or frivolous answers
  • Delve into deeper, self-reflective answers, or stories
  • Take a pass
  • Choose a different question

Form Small Groups

Many feel more comfortable sharing in small, more private, and intimate groups. Whether you’re gathering in person or online, it’s easy to structure activities to facilitate small-group sharing.

Building Community

With so much talk about the epidemic of loneliness and crises in mental health, the more we can do to share more honestly and more deeply with our fellow humans, the better. Let’s take time to use questions to build relationships, understanding, and community. Thanks to Amy Climer and Chad Littlefield for their inspiration!

Read More on Conversation Starters

How Deep Will You Go?

7 Tips for Formulating Great Questions

Choosing What to Share


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