Try the Conversation Diamond to flex more effective choices in heated conversations

8 Tools to Help to Navigate Tense Holiday Dinners

Winning the Holidays with better Conversation Design

Daniel Stillman
5 min readNov 18, 2022


Family Dinner and an Argument

The holidays are coming, and with them often come long, large and heavy dinners and potentially, uncomfortable conversations that can spill over into open battle.

I want to give you some quick tips so you and your whole family can enjoy a nice dinner together. If you really want to dive in, get some free chapters from my book Good Talk, all about how to design conversations that matter.

Eight ways to avoid a holiday dinner Battle

1. Drink Less

All of the tips below take effort and mental agility, so skip a round or two so you have the emotional resources to manage yourself.

Also, eat a snack before you go if it helps calm and center you.

2. Slow the conversation down

The space between one person talking and another is generally about 200 milliseconds. That’s really fast — barely a breath! It takes us about 600 milliseconds to even think of the beginning of a response, let alone a well-considered one.

SO TAKE A BREATH before responding to anything. THEN:

3. Dodge Questions and Provocations

“SO! Are you two having kids or what!?”

“Are you going to vote for Sleepy Joe in 2024?!”

“Isn’t it a disaster what’s happening at our borders!?”

Research shows that if you don’t want to answer a question, the best way is to deflect it by answering it with another question, ideally one that’s relatively on-topic and somewhat humorous.

“Do you mean Human Kids? Or Baby Goats?“

“Is it 2024 yet?!”

“Isn’t it a disaster that I can’t have another slice of PIE!?”

Any question will do, actually…it will redirect attention, de-escalate the tension and give you time to breathe.

4. Take Winning Off the Table

Taking Winning off the table is the first principle of The Better Arguments Project.

The truth is, Facts don’t change Minds.

So ask yourself — if facts don’t change minds, why am I trying to argue with my Racist Uncle about the existence of Structural Racism?

Taking winning off the table is an INNER MOVE. It’s not something you say or do outwardly …it’s something you do, inside, from your being. Taking winning off the table turns down your internal temperature, which means you can more easily keep the conversation from boiling over.

Once you make that inner move, you can take another tip from the Better Arguments Project:

5. Prioritize Relationships and Listen Passionately

Listening deeply is both an inner and an OUTER MOVE and so, it’s something you can attempt to act out, even if you feel reluctant.

You *can* fake it until you make it.

Not talking, making eye contact, nodding and small sub-vocalizations like “mmm…” “ahh-huh…” and “really?” can buy you some time, space and grace.

Try going past simple active listening and use the Listening Triangle instead. It’s based on a Harvard Business Review article about managing polarized workplaces and I wrote about it more deeply here.

The Basic Steps of the Listening Triangle.

  1. Ask a real, powerful question.

“So, Uncle Oz, I hear that your thinking about abortion rights has evolved over time. Tell me about that.”

2. Listen Deeply.

3. Actively Listen, ie, paraphrase and confirm that you got it right.

“SOOO…Uncle Oz, you think that a woman, her doctor AND local politicians should ALL be part of the conversation about what to do about a potential pregnancy? Did I get that right?”

4. Re-ask. Don’t move on to another topic. Shift your question just a little bit to dive one step deeper and help triangulate your understanding of the person’s position.

“Do we need a local politician on call in the hospital or…?”

It can be hard to do but if you lean in, keep a straight face and dive in, it can be quite bracing.

Note: The Listening Triangle is much easier to use if you really care about the person and your relationship with them.

If you truly want to understand what makes Uncle Oz tick and have more empathy, you could also try…

6. Tell me a Story about…?

If it feels to draining to fake the Listening Triangle, try asking a story-driven question.

“Tell me a story, Uncle Oz, about how you first started feeling this way about this issue.”

Stories activate our empathy AND get our conversation partners to be reflective.

Asking for stories also means they might talk a bit longer, which means you get to do less work in the conversation… and again, buy yourself time!

7. Take Poll vs Digging in

We all (mostly) still believe that democracy is a good idea, so, use it to keep the conversation focused on topics everyone wants to talk about.

Uncle Roy might enjoy provoking Liberal Snowflake Tears by talking about how we should MAGA, or Aunt Susan might enjoy educating everyone about the impending climate disaster…but not everyone wants to engage in those conversations.

Reframe the conversation with a poll rather than reacting to the bait.

“That’s a really worthwhile question/topic/issue…I’ve got lots of thoughts on it and I’m sure you do, too.

But…I’d love to make sure we talk about something that can include the whole table. Would folks like to weigh in on this topic or would you rather us all talk about something else….?”

8. Remember that you have choices

In EACH moment of a conversation, you can react to the bait being dangled in front of you OR you can reflect and deflect with listening and questioning.

You can also just be silent and hold space.

Each turn you take (or don’t) is a choice.

I find it’s helpful to keep the Conversation Diamond in mind when I’m stepping into a challenging situation to remind myself that I can start a new conversation if I want, or reframe the current one.

I am in control of my choices.


Try the Conversation Diamond to flex more effective choices in heated conversations

You can slow the conversation down and make a conscious choice.

And leaving is sometimes the best choice. That “leaving” can be literal, or just conversational:

“I don’t want to talk about that.”

You can always quote James Baldwin as you opt out:

“We can disagree and still love each other unless your disagreement is rooted in my oppression and denial of my humanity and right to exist.”

— James Baldwin

Happy Holiday Conversations Everyone!