Team Icebreaker Activity: Making Caring Conversations Easier
At a time when so many people crave compassion and meaningful relationships, this simple team icebreaker opens the door to deeper trust. Whenever we use compassionate conversation starters in a leadership development program or an executive retreat, you can feel an instant shift in the energy of the room. One reason this activity works so well is that each member of your team gets to choose the icebreaking prompt THEY want.
No one is put on the spot. Everyone chooses what they want the team to know about them.
The other day, I sent these questions out in advance of an executive team-building session. I ran into one of the executives at breakfast at the hotel before the meeting. She said, “I’m so excited about our time together today, and I know exactly what I need to say. She sure did, and I could see the entire team hanging on every word.
Another executive was new to the team. He exhaled deeply and smiled as he read through the options. He answered the question:
“What are you grieving most from this last year?”
He told us about the death of his young friend (he was young too) and the impact that had on his approach to life. That conversation didn’t take long– but I could tell that vulnerability accelerated his human connection to the team.
There’s a reason that Gallup includes “I have a best friend at work” as a cornerstone question in their employee engagement survey. When people feel connected at a human level, they’re more productive, more engaged, and tend to stick around.
Why Deeper Conversations Build Stronger Teams
Have you been in this situation before? Someone casually asks, “How was everyone’s weekend?” And the replies are quick and shallow:
“Good.”
“Yeah, same here.”
“Not much, just chilled.”
Meanwhile, someone on your team—let’s call him Kevin—is silently struggling. He’s thinking, “My weekend was rough. My kids are sick, my wife is overwhelmed, and I’m running on fumes. But I don’t want to bother anyone with my problems.” So he says, “Same,” and you move on to the work.
Kevin doesn’t get the help he needs, and you miss an opportunity to show your team you care.
This is where practicing deeper conversations makes all the difference. It’s not about turning your team into a therapy group; it’s about creating a space where real connection feels normal and safe. When people feel seen and supported, they bring their best selves to work—and to each other.
Compassionate Conversation Starters to Help Your Team Connect
These conversation starters work great as a quick warm-up to a remote meeting or as part of a speed-connecting session at a virtual kick-off.
You can share the conversation starters in advance, or distribute at the start of the meeting. The magic in his team icebreaker is that it makes it feel safe to be vulnerable. Because each human gets to choose what they disclose.
Of course, it’s not just the one conversation that makes a difference. These questions can help your team form a habit of being a bit more real with one another. And after a while, they won’t need a conversation starter to start a more compassionate conversation.
So here they are. I’ve also attached the exercise from our team development playbook to make it easy to download.
Questions to help people connect after a tough year
- What has been one source of inspiration or strength for you this year?
- If you had a one-word mantra to describe your approach to this year, what would that be?
- As you reflect on the turbulence of this past year, what makes you proud?
- What are you grieving most from this past year?
- What are you learning about yourself?
Conversation starters to help your team learn more about one another
- One thing you don’t know about me that might surprise you is __________.
- On weekends I love to ___________.
- Some of the people most important in my life are __________
- One thing I’m really looking forward to outside of work is ______________
- If money were no object and I could pick any career I wanted, I would love to be a professional _________.
Conversation starters to help your team celebrate and encourage one another
- Who on this team was particularly helpful to you this year? Why?
- What do you appreciate most about working on this team? Why?
- What kind of recognition do you find most meaningful?
- One idea I have for us to be more supportive of one another is __________.
- Next time we accomplish something big, I think we should celebrate by ____________(insert realistic idea here).
Probes to encourage your team to share their concerns
- One thing I’m worried about is ____________
- I don’t think we’re spending enough time talking about __________
- My biggest hope for this year is ____________ and my biggest fear is ____________.
- If there was one thing that could derail our team’s success this year, what would that be?
- At a personal level, I’m most worried about __________
click to download sample conversation starters
Of course, once the team has some regular practice with some of these conversation starters, you can also invite your team to BYOQ (Bring Your Own Question), Inviting them to consider a compassionate probe that would serve the team.
Your turn. What are some of your best practices to encourage your team to connect at a deeper level?
Whew, that gallup point about a “best friend at work” slapped me. Puts words to what I’ve been feeling since I started here 10 months ago. I’m the only caucasian female at my job. All the other females and the majority of the males are hispanic. Some caucasian males. Feel like a fish out of water in regards to culture, language, food, politics, even the neighborhoods where we live. I love my job, but def don’t have a relational friend here. I’m also HR, so there’s also that ‘barrier’ that keeps people at a distance, even though I try hard to be real and connect. Makes me want to cry, but then I’d ruin my makeup and it’s too early in the day for that! Lol.
Thank you for these questions. I feel they can be useful here. Love all your articles!
Kelly, thanks so much for sharing your experience and preserving your makeup! I’ve also worked in an environment like you describe and, while it’s not easy, that experience of being the “other” is so valuable from an HR and leadership experience, isn’t it? It takes time to build trust – especially when common shared experiences don’t align, and these questions are indeed a great place to start. Thank you for your work and commitment to human-centered leadership!