How to Be a Better Conversationalist Pt. 2

Four critical conversation skills

Conversation is one the riskiest things we do every day. 

Every disclosure is a bet, each question a gamble. But these small risks have enormous payoffs. Genuine connection, friendship, understanding—even love—are possible rewards.

In part one we covered conversational styles. We learned that no style or ethic is inherently better—but compatibility matters. When styles align naturally, conversation flows with the ease and smoothness of a dance. But what happens when they clash?

When your styles are at odds, you have to rely on strategy and skill.

The hidden architecture of conversation

But why are clashes in conversation style so uncomfortable in the first place? In Every Conversation Counts, Riaz Meghji writes there are three unspoken questions beneath every interaction:

1. Are you listening to me?

2. Do you care about me? 

3. Can I trust you?

When styles misalign, these fundamental needs go unmet. And it’s painful! When a declarative speaker’s enthusiasm is unmet, they feel dismissed. When there’s no space to contribute, an invitational speaker feels forgotten. When the conversation feels off, speakers can’t build trust and care.

This hidden architecture is important to understand because it shifts the stakes. You’re not just working on your conversation skills, you’re growing your capacity for human connection. It's not just about learning to speak differently—it's about learning to recognize and respond to these basic human needs, regardless of style.

Like any game of chance, conversation requires both luck and skill. While we can't control our conversation partner's style, we can develop the skills to bridge the gaps.

Four Critical Skills

These are the top techniques I’ve seen are most lacking and easiest to upskill quickly.

1. Recognize and create openings

In the improv dance of dialogue, a great conversationalist can recognize, no matter the style, an opening to take the floor.

In the article Good Conversations Have Lots of Doorknobs, Adam Mastroianni calls these openings conversational affordances, or “doorknobs”—opportunities to join the conversation that you can take hold of. 

“Physical affordances are things like stairs and handles and benches,” he writes. “Conversational affordances are things like digressions and confessions and bold claims that beg for a rejoinder.”

For declarative speakers, the challenge is learning to build these doorknobs into your natural enthusiasm—creating space for others to join your energy. For invitational speakers, it's about learning to recognize these doorknobs when they're offered, and gathering the courage to grasp them.

(see final section for more doorknob examples)

2. Show genuine curiosity

Research shows that curious people create faster, closer bonds—even during small-talk. Genuine curiosity builds intimacy. When you feel your conversation partner is genuinely interested, you don’t have to wonder “do they care?” 

To be curious, though, you must hold an inherent belief. You must trust every conversation has something to teach you. One chance meeting can change your life! Paths are branching at every encounter! This belief keeps you open, hopeful, seeking.

Curiosity can be a character trait—but it’s also a learned behavior. Psychologist Todd Kashdan, pioneer of the five-dimensional curiosity scale, defines curiosity as a "mechanism of action" rather than a fixed state of mind. Curious people ask questions, offer “doorknobs,” and seek novelty and intellectual pursuits in common with their conversation partner. Check out Kashdan’s research to see where you fall on the 5D scale.

Cultivate a curious mindset by looking for things in common, seeking novel points of view, exploring your partner’s areas of expertise.

Admittedly, it’s hard to be curious about a boring topic. But you have a secret weapon. The easiest way to stimulate genuine curiosity is to look for stories. 

3. Look for stories

Storytelling is a fascinating function of evolutionary biology. Unlike small talk, stories are very information dense. A short anecdote about someone’s grandmother can reveal layers about their family, history, and value system. Stories also operate on a chemical level. Narratives release oxytocin, increasing memory retention and empathy, making people feel more trusting and compassionate.

When your conversation partner shares a story, you’ve stuck gold. Stories energize the exchange and pump up oxytocin. As they tell their story and see your genuine curiosity, they feel heard, valued, and reassured they can trust you.

But how to find the story?

Literally just ask: If your partner shares an interesting fact or funny detail (a doorknob!), you can just ask: “What’s the story behind that?” Simple and inviting.

Share first: Build trust by offering a brief, related story first, and invite them to reciprocate. “I just moved to the Bay too! I got my car stolen in the first month, haha. What was your move like?” 

The Three Ts

This is a framework adapted from Rian Meghji’s Every Conversation Counts. Look for trails, transitions, and triumphs and ask them to elaborate:

Trails: Look for insights into their journey or life path. Phrase your question with “how” and “why” to draw out stories.

• "How did you find this career path?" ; "Why did you change your mind about that?"

Transitions: Ask for stories about life changes or milestones.

• "What was the hardest part about moving to a new city?" ; "How has your routine changed since becoming a parent?"

Triumphs: Highlight achievements, or challenges they’ve overcome. (People love flattery!) Ask for specific moments of emotional depth.

• "Wait, you wrote a book? That’s amazing! What was the process of getting it published?”

• "You built an app in less than a month? So impressive! What’s the problem you’re proudest of solving?"

4. Self-disclosure

Most conversations begin with boring questions—“How was your day?” “What is your job?”—and that’s okay! Your goal, however, is to slowly raise the stakes, moving toward deeper emotional wagers. To truly connect, both conversation partners must “self-disclose”—aka offer personal experiences and feelings.

Meta-analyses show self-disclosure increases feelings of closeness and social attraction. By sharing more about yourself, you turn up the hedonic tone, building trust as you both feel heard and understood. 

Reveal personal feelings to a stranger? Sounds scary, yes. But evidence shows it’s more pleasurable and less awkward than we fear. This study from 2021 found we reliably overestimate the awkwardness and underestimate the happiness we’ll feel after having deep conversations with strangers.

source

The researchers found participants “felt less awkward, and created more connectedness” during their deep conversations than predicted, and it replicated across seven experiments. Interestingly, the study’s “deep” questions were very similar to the “36 questions that lead to love”.  

The now-renowned set of 36 questions was developed in 1997 by researcher Arthur Aron. The experiment built intimacy so successfully that two participants were married six months later.

Mandy Len Catron, the writer of the viral NYT article, explains it this way: the questions “accelerate intimacy” by rocketing past the superficial talk that holds us back. “We all have a narrative of ourselves that we offer up to strangers and acquaintances, but Dr. Aron’s questions make it impossible to rely on that narrative.” Find the list of questions on page 15 of the original study here.

These 36 questions work because they give a structured, methodical approach to the give-and-take of self-disclosure. By alternating between sharing and listening, they create a balance that fosters trust and mutual understanding.

However, be advised that these magic questions are a self-disclosure speed-run. In most situations I don’t recommend launching past “What do you do for work?” into “What is your most terrible memory?” Balance is key—share enough to build trust without overwhelming your conversation partner. There is a tipping point where self-disclosure veers into over-sharing or trauma-dumping.

Closeness thrives on the gradual and reciprocal exchange of personal experiences. As trust grows, you raise the stakes together, venturing into deeper, more rewarding emotional territory.

Reasons conversations fail

Conversational skills give you more finesse and confidence, but not every interaction is a win. It’s important to recognize common failure modes. 

Fear of rejection

• Fear of rejection stands in the way of every real human connection. It’s a defense mechanism and a paradox: by holding back self-disclosure to avoid social pain, we also block the intimacy we crave. Every time we speak, we gamble with vulnerability—but it’s a risk we have to take. (See awkwardness study above and anxiety below).

Egocentric questions

• Do your questions always redirect to your own interests? To borrow from Mastroianni: “Enough of me talking about stuff I like. Time for you to talk about stuff I like!”
  Genuine curiosity is an outward-facing beam. You can offer personal interjections to build rapport and signal understanding—but these should illuminate your partner’s contribution, not redirect to you every time.

One-upping 

• This one is especially toxic. One-upmanship looks like this:

  • "I've been really stressed at work lately." 

  • "Stressed? You have no idea. My workload is absolutely insane right now..."

  You may think you’re sympathizing, but it makes the other person feel dismissed. Reframe your contribution by replacing competitiveness with empathy and an invitation to elaborate. Something like this:

  • "I've been really stressed at work lately." 

  • "Dude, I feel you, I’m underwater too. How are you managing?"

Anxiety

• Anxiety cripples our ability to communicate authentically. Instead of staying present and connected, we spend mental energy on anticipating and overanalyzing. This one is so hard to unlearn. All I can offer is trite but true: you gotta practice. 
  Research finds that preparing a few questions in advance actively reduces anxiety. Exposure therapy works, too—and fast. This study found that people reduced anxiety talking to strangers in one week. 

  
  Also, be reassured that people like you more than you think. Research finds we all suffer from the “liking gap” illusion. Researchers found that “people systematically underestimated how much their conversation partners liked them and enjoyed their company.” The study authors reassure us that most people are “liked more than they know.” 
  Use this knowledge as a psychological safety net. Bring your curiosity, share your stories, and trust that human connection is more forgiving than your anxiety insists.

Advice based on your conversation style

Now for some quick-fire advice tailored to your conversational style and ethic. Check out the full article on finding your conversational style here.

Declarative Style (when talking to invite/wait)

• Build more doorknobs: Catch yourself when you start "Well, in my experience..." → Pause and ask "How has that worked out in your experience?"

• Ask for elaboration: Catch yourself when you feel excited to share a similar story → "Wait, how did you handle that moment?"

• Avoid one-upping: "That's nothing, I once..." → "What was the hardest part of that for you?"

• Mirror and reflect: Catch yourself planning your next story → Summarize what you just heard: "So what I'm hearing is..." "If I understand correctly..."

Invitational Style (when talking to declarative)

• Grasp more doorknobs: Catch yourself asking your third question in a row → "You know, what you're describing reminds me of..."

• Offer self-disclosure: Catch yourself nodding and saying "That must be hard" → Share a time you faced something similar

• Show enthusiasm: Catch yourself being purely reactive → Articulate your excitement: "That's fascinating because..."

Interrupt Ethic (when talking to invite/wait)

• Show curiosity: Catch yourself saying "Oh! That reminds me of a question..." → Add "...but finish what you were saying first"

• Practice giving space: Catch yourself finishing their sentence → Count to 2 before speaking

• Encourage storytelling: Catch yourself rapid-fire responding → Ask "What's the story behind that?" 

• Add value before switching: Catch yourself changing topics → First validate their point: "That's important because... and it reminds me of..." 

Wait Ethic (when talking to declarative/interrupt)

• Practice interjecting: Catch yourself holding a relevant thought too long → Flag it briefly: "I want to come back to what you said about X"

• Grasp more doorknobs: Catch yourself thinking "I'll wait my turn" → Look for conversational affordances like digressions or bold claims to join in

• Take non-verbal cues: Catch yourself waiting to be explicitly invited → Jump in when you hear energy dropping, or look for non-verbal invitations (eye contact, open palms, tilt of the head)

• Signal engagement differently: Catch yourself staying respectfully silent → Use brief verbal affirmations ("mm-hmm", "yes!") to show active listening

When you show genuine curiosity, create openings, seek stories, and calibrate self-disclosure, you're not just improving your conversation skills—you're increasing your chances of the biggest reward: connection, care, belonging.

The most skilled conversationalists aren't those who have choreographed moves—they're the ones willing to take small risks, moment by moment, to build trust and understanding.

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Welcome to Season 3 of The Ick! The social rulebook has been rewritten in our post-pandemic world—and it's left us wondering, “Am I doing this right?” With help from psychologists, linguists, and social scientists, season 3 of The Ick is creating a modern field guide to social etiquette and decoding the hidden architecture of human connection.

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