Compassionate Conversation Starters: How to Help Your Team Connect More Deeply

These conversation starters make caring dialogue a bit easier.

For most teams, having genuine caring conversations takes practice. It can feel easier to keep the conversations light, particularly if that’s your team culture.  But at a time when people are longing for compassion and connection, taking the conversation a level deeper can make all the difference for your employees’ mental health, as well as for building deeper trust. These compassionate conversation starters are a great way to normalize going a level deeper, so it’s easier for anyone to start a conversation when they need it most.

Why practicing going a bit deeper matters

Have you ever experienced a scene like this?

Someone asks, “How was everyone’s weekend?”

And the responses are quick and casual.”Ahh, good, man.” “Yeah, mine too.” “Did you do anything fun?” “Not much, you know … just chilln’.”

And, one guy, let’s call him “Kevin” is sitting there thinking:

“You know, my weekend was pretty crummy. My three kids have the croup. We are worried it’s COVID, so none of our family could help. And my wife is pretty sick too. I’m extra worried about her, because she’s already under so much stress. No one got much sleep. I know, we’ve got this important presentation today, so I got in early, but honestly, I’m pretty much toast and could use some extra help.

But instead, he says, “Yeah, you know. Same.”

His body language is telling you something’s not quite right, but you don’t want to pry. So you move on to the work at hand. Kevin doesn’t get the support he needs, because he’s too afraid to ask.

The Best Way to Get Better at Deeper Conversations is to Have Deeper Conversations

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.

I’m not suggesting that these conversation starters will suddenly turn every member of your team into besties, but a regular cadence of real conversation makes it easier to bring up the tough stuff as needed.

In my last role at Verizon, I led an entirely remote team. It could have been a really lonely job for all of us.

One day, my boss observed, “It’s amazing to watch how close your team is to one another. You can tell that they truly care and enjoy one another. And, so much laughter. Not to mention, you’re getting it DONE! How do you all do that?”

The truth is, I give all the credit to my team.  As the leader, I just had to create to space to make these conversations possible.

When we were able to be together, we shared meals and talked about the hard stuff. We made it okay to not be okay on the team. People felt like they could pick up the phone and just vent to one another without judgment. They asked what they could do to help—and then did.

I want that for you and your team too.

So here are a few conversation starters that can help.

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 entire list of conversation starters and invite each team member to pick one to answer. Or you can rotate through a question of the day or week.

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.

Questions to help people connect after a tough yearWhat 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 anotherWho 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 concernsOne 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 __________

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?

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