Preparing for Challenging Talks: Ace Your Year-End Conversations

End-of-year events bring us together with people we might otherwise avoid. Prepare now so you can keep those conversations productive.

It’s that time of year when we reflect on our past and plan for the future. Between now and the new year, we’ve got work to do. 

Over the next month, we’ll all be meeting to review results, celebrate traditions, and plan our collective future — all of which can be pretty intense. It’s especially challenging when you meet with people you don’t truly understand or agree with. The holidays and strategic planning season give us so many opportunities to bridge the chasms between us. But how do we do that when everyone seems so divided?

Here are a few ways you can set the stage for a civil and productive conversation across differences, regardless of whether those differences are based on culture, workplace silos, or politics. (Thanks to Jo Ilfeld from Incite to Leadership, Nancy Settle-Murphy from Guided Insights, and Jenn Graham from Civic Dinners, who helped me refine these recommendations.)

Create a welcoming environment.

When people arrive to your meeting, you want them to get three clear messages right away: 

  • You are welcome.
  • You are wanted. 
  • You are safe. 

If you convey those messages right at the door, those arriving anxious can begin to relax.

How? Be a good host. 

Greet people at the door, shake their hands, and thank them for coming. Ease them into the room. This advice applies even if you’re not in charge of the meeting. You don’t need an official title or anyone’s permission to extend a warm welcome to others. 

Also, if you can, provide food. There’s a reason why so many challenging conversations take place over meals. For many people, food equals love. 

Think that this advice applies more to family gatherings than to your business teams? Think again. I always request snacks at my workshops, and meeting science research points to hosting and stewardship as key practices for meeting success, too. 

Convene with purpose and positive intent. 

When you’re ready for your event to officially begin, start by gathering everyone’s attention and stating the purpose. 

You can begin by thanking the group, restating the meeting’s purpose, and then asking everyone to embrace a code of conduct. For challenging conversations, here are some helpful rules:

  • Everyone gets equal time to share.
  • One voice at a time.
  • Step forward, then step back.
  • Assume positive intent, or the MRI: Most Respectful Interpretation. 

Invite everyone to share their story.

After you’ve created a welcome space and set the tone, it’s time to talk. You can get everyone talking by asking a simple question, then going around the room to hear everyone’s answers.

When you’re dealing with a sensitive topic or a fractured group, it’s important that this first round sticks with questions that ask people to share their personal experiences. Don’t ask about opinions or ideas. Ask for stories. 

Why? First, you can’t argue with someone else’s experience. They’re sharing what happened to them and how they felt about it, and on that topic, they’re the world expert. Second, short stories help us connect. They help us see everyone around the room as a person rather than a representative of some identity group. 

Finally, stories are one of the best ways to get both sides of the brain working together. When we hear a story, the emotional decision-making part of the brain lights up alongside the rational fact-checking side. We perceive the emotion and take in new facts at the same time, making it easier for us to hear ideas that may contradict what we already believe. 

Not sure what to ask? Try using a conversation card deck to get you started, or ask this: What’s one experience you’re grateful you had in the past year?

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