Holiday conversations: AI as a tool in navigating tense gatherings

AI can offer an emotional intelligence boost when holiday gatherings get tense. Some guiding prompts to stay thoughtful, accepting, and confident during the inevitable tough discussions.

Bringing this week’s post to you on Wednesday because who reads on a holiday 🦃

The day is upon us. Tomorrow, 300 million Americans (or something like that) walk into situations that feel tense from the moment the car door opens. Feasts, family, and the potential for fraught conversation can bring emotional weight — the kind that sneaks right by you until it comes out as something entirely unintended.

It was hard to come up with this week’s topic, but with all of that ahead of us, it became the perfect time to tap into what AI can bring to our EI arsenals (EI = emotional intelligence).

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Key Takeaways:

• Emotional intelligence can be practiced, and AI can be an outstanding tool to help prepare for challenging environments

• Prompts can help develop strategies for managing conflicting opinions, bridging generational gaps, and navigating awkward silences

• By using prompts, you can rehearse specific scenarios, reduce anxiety, and encourage thoughtful and confident communication

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Here’s what we can (and can’t) control

It’s a pretty short list, but also a hugely powerful one. The only thing we can really control is ourselves. Which really boils down to our reactions, both verbal and internal.

Odds are you know how you want to react, but that intention is competing with a lot of things, like:

• Confirmation bias or favoring information that aligns with our beliefs and rejecting that which doesn’t. If we think someone is bringing this bias to the metaphorical table, they probably think we are as well.

• Emotional contagion, which sees negative emotions spread in group settings. One raised voice doesn’t have to turn into two.

• Generational identity theory and the historical events that shape the worldview of a generation. What feels universal to you might seem baffling or even alienating to another.

And the tools we have in our corner are things like the social facilitation effect (warm tones help everyone feel at ease), cognitive ease (the power of simple and familiar topics) and nonverbal cues (eye contact, smiling, or an open posture).

Make no mistake, we can prepare. And I submit AI can be one of the strongest tools to do so. Consider this: If you can name what you’ll be facing and have a plan to stomach the dread, there will be a cornucopia of moments to foster empathy, connection, and growth. See what I did there?

Here’s what we’re going to be facing

Some of the biggest things you might be dreading are: conflicting opinions, generational gaps, and uncomfortable silences.

We’ll talk about each of these one-by-one, each with a prompt that can help you dig into specific scenarios you might be wringing your hands over.

Let’s start with…

Contentious and conflicting opinions

Nothing is guaranteed to stall dinner faster than what happened in early November. And that’s just politics — there’s also parenting, sports teams, and for the especially unlucky, Taylor Swift and Travis Kelce. These discussions can spiral quickly, and ‘no politics at the table’ isn’t the answer.

Below is a prompt you can use to prepare ahead. Drop in your contentious scenario of choice, and it will help you to drum up how you can keep your air of empathy and respect without caving in. A few example scenarios:

• “Some of my family voted for a candidate who I strongly disagree with in the election”

• “Members of my family have taken to bandwagon thinking that supports/villifies Palestine (or Israel) but don’t have a great understanding of the situation”

• “My family has a very strong stance on X thing that hasn’t been proven”

I want you to help me navigate contentious family conversations by brainstorming empathetic yet firm responses that align with my beliefs. Your goal is to equip me with strategies to communicate effectively, preserve relationships, and maintain my values.

The goal is to:

1. Balance empathy with self-assurance, ensuring conversations remain constructive even in emotionally charged situations.
2. Provide responses should aim to preserve positive relationships without compromising my core values.

-- Scenario START --
[You can describe a specific family conversation you’d like help with. E.g. some of my family members voted for a candidate who I strongly disagree with in the election]
-- Scenario END --

Given my specific scenario, you will provide me strategies to help me with the following.

Empathetic Responses:

* Suggest responses that demonstrate understanding and empathy toward the other person’s perspective.
* Include language that acknowledges emotions, respects the other person, and shows active listening.

Standing Firm:

* Offer strategies to assert your beliefs or boundaries in a respectful and calm manner.
* Avoid overly confrontational language, focusing instead on phrases that express confidence and clarity.

Reflection and Tools:

* Suggest ways to de-escalate tension, such as reframing the conversation, finding common ground, or redirecting the focus.
* Recommend tools or phrases to disengage gracefully if the conversation becomes unproductive, while maintaining dignity.

The best things about this prompt are 1) it will help you find the words to respond gracefully while 2) standing firm in your own beliefs.

Generational gaps

The difference between rotary phones and TikTok is a cultural divide. Bridging these gaps demands active effort and patience.

The following prompt can help you role-play scenarios responding to generational criticisms with curiosity instead of defensiveness. A few example scenarios:

• “Older generations of my family constantly share the conviction that young people are lazy”

• “Younger generations act like I should know about new technologies and seem offended when I ask more about them”

I want you to help me role-play scenarios where I practice responding to generational criticisms with curiosity rather than defensiveness. The goal is to: 

1. practice fostering understanding through curiosity and open dialogue, rather than allowing criticism to lead to defensiveness or conflict 
2. maintain positive family dynamics while feeling confident in my ability to communicate my own beliefs and boundaries respectfully

-- Scenario START --

[Provide me with a scenario where a family member of a different generation offers a criticism or opinion on something I’ve done or beliefs I hold.]

-- Scenario END --

Given my specific scenario, you will help me using the following instructions.

Curiosity-Based Responses:

* Encourage me to respond with curiosity rather than immediately becoming defensive.
* Your responses should help me explore the reasoning behind the criticism in a non-confrontational way.
* Frame questions or remarks that invite further explanation from the other person

Active Listening Techniques:

* Offer advice on how to actively listen, such as repeating back key points or showing empathy with verbal nods.
* Encourage me to reflect the criticism back to the other person to show that I understand their viewpoint before responding.

Maintaining Calm and Respect:

* Guide me on staying calm and respectful, even if the criticism feels unfair or outdated.
* Provide examples of responses that assert my beliefs without escalating the conversation (“I see things differently, but I respect where you're coming from”)

Reframing the Situation:

* Suggest ways to reframe the situation in a positive light, making potential conflict into an opportunity for growth or learning.
* Recommend ways to express how the conversation makes me feel without being defensive (“I feel that we’re approaching this from different angles, but I’m happy we’re having this conversation”)

In particular, this prompt is going to encourage curiosity. It’ll potentially even help you find similarities where you thought there were only differences.

Uncomfortable silences

At every table, there’s a moment when the conversation lulls and everyone fills their mouth with mashed potatoes. The real key is this: don’t panic.

Use AI to role-play awkward scenarios and practice ways to jump-start conversations. For example:

• “I have a cousin who is an aloof teenager and tends to answer in monosyllables”

• “My grandparent who tells the same long-winded story for the fifth time”

• “My cousin only ever talks about raising their kids and I’m never sure how to make conversation about other things”

I want help role-playing awkward conversations with someone I might find difficult to talk to. The goal is to rehearse how to start conversations confidently, without overthinking or self-judging.

The goal is to:

1. practice starting conversations naturally and confidently
2. minimize my internal anxiety or self-judgment within the moment.

-- Provide Details START --  

[Share information about the person you’d like help talking to (e.g., a colleague, family member, or stranger).]

-- Provide Details END --

Please follow the below instructions.

Conversation Starters: 

* Suggest simple, natural ways to begin the conversation, such as open-ended questions, compliments or light humor

Overcoming Overthinking: 

* Offer tips to reduce anxiety, like: Breathing exercises to relax.
* Help me establish re-assuring thoughts (e.g. "It’s okay not to have all the right words.")
* Offer ways to handle silence without stressing, such as pivoting with a new topic

Maintain Natural Flow: 

* Keep the conversation going with follow-up questions
* Provide tips to stay present, focusing on the other person’s response

This prompt is great because it can kickstart ideas about how to keep conversation going. But more importantly, it helps battle the overthinking or self-judgment that thrive within those awkward silences.

Some prompts to spark better conversations

Want some more basic prompts that’ll help in navigating large gatherings? We have some of those too. Here are prompts that can be used to:

Reframe disagreements

Help me navigate a potential disagreement by generating 10 open-ended, curiosity-driven questions.

The goal is to invite thoughtful dialogue and encourage understanding rather than confrontation.

For example:
* 'What experiences have shaped your views on this topic?'

De-escalate tension

Brainstorm a list of calming phrases or empathetic responses I can use to de-escalate tense holiday conversations. 

Focus on language that acknowledges emotions and redirects the discussion toward a more positive or neutral topic.

Learn about a different generation

Provide key milestones, cultural moments, or trends for people born between the years of {YEAR_START} and {YEAR_END}.

I want to understand their perspective better. I intend to use this knowledge to find common ground and connect with members of different generations.

YEAR_START = "1950"
YEAR_END = "1970"

Build bridges with shared knowledge

Generate a list of 15 conversation starters that highlight similarities between past and present. The goal is to find common ground and create meaningful connections.

For example, how technology has evolved over time or shared family traditions that have changed.

Generate icebreakers

Create a list of 25 lighthearted and fun icebreaker questions I can use at holiday gatherings. 

These should be general enough to spark laughter or curiosity without making anyone uncomfortable.

As an example question: 
* 'What’s the funniest holiday memory you can remember?'

Brainstorm nostalgia

Help me come up with 10 conversation topics that evoke nostalgia and tailor them to my family. 

For example: 
* asking about favorite childhood holiday traditions
* memorable family trips
* classic movies or music everyone loved together

Ease your own nerves

I need 10-20 tips to help me keep conversations flowing naturally during the holidays. Include tips for all of the following:

1. re-entering a stalled conversation
2. handling moments of awkward silence
3. staying calm when I feel nervous.

A note of thanks

I wanted to take a moment to thank everyone who opens up this newsletter on a weekly basis. I couldn’t be more thankful that you give me your attention, support what I’m trying to do and stay open to learning and trying new things. Have a great holiday, all!