Conversation Skills

The art of flowing, engaging dialogue.

Anatomy of a Great Conversation

A good conversation has:

Balance: Both people contribute roughly equally
Flow: Natural transitions between topics
Engagement: Both people are interested and present
Connection: Some level of understanding or rapport
Closure: Appropriate ending

Conversation Starters

Small Talk

Purpose: Warm up, establish rapport, find common ground

Common topics: - Weather ("Nice day today!") - Shared situation ("How about that traffic?") - Neutral observations ("I like your shirt") - Safe questions ("How was your weekend?")

Small Talk Isn't Pointless

It serves important functions:

Breaks the ice
Establishes friendliness
Tests receptiveness
Finds conversation threads to pull

Opening Strategies

1. Observation + Question - "I noticed you're reading [book]. How are you liking it?" - "That's an interesting [item]. Where'd you get it?"

2. Compliment + Follow-up - "Great presentation! How long did it take to prepare?" - "I love that idea you mentioned. Can you tell me more?"

3. Shared Context - "So how do you know [host]?" - "Have you been to one of these events before?"

4. Light Opinion Question - "What do you think of [neutral topic]?" - "Have you tried [place/thing]? I'm thinking about checking it out."

Conversation Starters to Avoid

❌ Overly personal ("How much do you make?") ❌ Controversial ("What's your political view on...") ❌ Negative ("I hate these events") ❌ Complaining ("Traffic was terrible") ❌ Too intense ("What's your biggest regret?")

Maintaining Conversations

The Threading Technique

Pull on "threads" the other person offers:

Them: "I just got back from Seattle."

Threads available: - Travel ("How was the trip?") - Seattle specifically ("First time there?") - Why they went ("What brought you to Seattle?") - Coming back ("Glad to be home?")

You: Pick one thread and pull

Example

Them: "I'm a teacher, but I used to work in tech."

Threads: - Teaching (What grade? Subject?) - Previous tech work (What kind? Why switch?) - The transition (How was that change?) - Comparison (How do they compare?)

The Pendulum Approach

Conversation swings back and forth:

Them → You → Them → You

Their story: "I went hiking this weekend"

Your response options:

Question (keep focus on them): "Where did you go?"
Relate (brief, then return): "I love hiking! Where did you go?"
Share (shift to you): "I went hiking too! I was up at..."

Balance these: - Mostly questions = interview - Mostly relating = competitive - Mostly sharing = self-centered

Good ratio: 2 questions : 1 relate : 1 share

Active Contribution

Don't just respond—contribute:

Passive: - Them: "I'm thinking about getting a dog" - You: "Oh, cool"

Active: - Them: "I'm thinking about getting a dog" - You: "That's exciting! What kind are you considering?"

Or: - You: "That's exciting! I grew up with dogs. Have you had one before?"

The Five W's

Use journalist questions: - Who: "Who introduced you to that?" - What: "What's that like?" - When: "When did you start?" - Where: "Where did this happen?" - Why: "What drew you to that?" (softer than "why") - How: "How did you get into that?"

Topic Transitions

Natural Transitions

Association: - "Speaking of [topic], that reminds me..." - "On a related note..."

Contrast: - "On the flip side..." - "Completely different topic, but..."

Expansion: - "Building on that..." - "Along those lines..."

Awkward Transitions

Sometimes you need to switch topics:

Explicit: - "Can I ask you about something else?" - "Changing gears for a second..." - "Random question..."

Callback: - "You mentioned earlier that... I'm curious about that"

When to Let Topics Die

Not every topic needs to be extended:

Signs a topic is dead: - One-word answers - Lack of follow-up questions - Checking phone or looking around - Long pauses - "Yeah..." with trailing off

How to move on: - Don't force it - Try one more thread - If still dead, transition - Sometimes silence is okay

Conversation Balance

Monitoring Balance

Check periodically: - Who's talking more? - Who's asking more questions? - Whose topics are we discussing?

If unbalanced: - Too much you: Ask them a question - Too much them: Share something relevant - All their topics: Introduce something new

The Spotlight

Think of conversation as a spotlight:

[You] ←→ [Them]

Good conversations pass the spotlight:

Holding it: You're talking, they're listening Passing it: You ask a question or invite their input Receiving it: They're talking, you're listening Returning it: They ask you something

Spotlight Hogs

Some people never pass the spotlight. If you:

Keep trying to pass it (ask questions)
They keep taking it back (don't ask you anything)
After 10 minutes you've barely spoken

→ Either accept this dynamic or exit the conversation

Depth Levels

Conversations exist at different depths:

Level 1: Rituals

Greetings and goodbyes
"How are you?" "Fine, you?"
Weather and traffic

Level 2: Facts

What you do
Where you're from
Neutral information sharing

Level 3: Opinions

What you think about things
Preferences and tastes
Judgments and evaluations

Level 4: Feelings

How you feel about things
Emotional reactions
Vulnerabilities

Level 5: Core

Values and beliefs
Fears and dreams
Deep personal information

Navigating Depths

Early in relationship: Stay at Levels 1-2 Building trust: Move to Level 3 Closer connection: Venture to Level 4 Intimate relationships: Level 5 is appropriate

Match Their Depth

If someone shares Level 4 (feelings), respond at Level 4

Don't respond to vulnerability with facts: - Them: "I'm feeling really overwhelmed" (Level 4) - Bad: "What's on your schedule?" (Level 2) - Good: "That sounds really hard" (Level 4)

Conversation Challenges

Challenge 1: Awkward Silences

Why they happen: - Topic exhausted - Both thinking - Discomfort - Lack of rapport

How to handle: - Don't panic—some silence is fine - Count to 5 before jumping in - Observe them (comfortable or uncomfortable?) - Introduce new topic if needed - Sometimes just acknowledge it: "Well, we covered that thoroughly!"

Challenge 2: Interruptions

If you interrupt accidentally: 1. Stop immediately 2. "Sorry, go ahead" 3. Let them finish completely 4. Return to your point only after

If they interrupt you: 1. Pause 2. Let them finish 3. Either: Return to your point ("As I was saying...") 4. Or: Let it go if the moment passed

If they interrupt repeatedly: - More assertive: "Hold on, let me finish" - Hold up finger (pause gesture) - Keep talking briefly to reclaim - Accept that some people just do this

Challenge 3: Controversial Topics

When they arise: 1. Assess: Is this worth engaging? 2. If no: Deflect politely 3. If yes: Engage respectfully

Deflection strategies: - "I don't know much about that" - "That's not really my area" - "I try not to discuss [topic] at [setting]" - "Let's talk about something else"

Engagement strategies: - Ask questions to understand their view - Find common ground where possible - Disagree without attacking - Know when to disengage

Hot Topics

Politics, religion, money, sensitive current events:

Rarely appropriate with acquaintances
Needs high trust to navigate
Easy to damage relationships
Usually okay with: Close friends who share values or can disagree respectfully

Challenge 4: One-Sided Conversations

If you're doing all the talking: - Ask them a question - Create space for them to speak - Stop and wait - "But I've been talking a lot—what about you?"

If they're doing all the talking: - Try to interject politely - Ask if you can share something - Use body language (lean back, break eye contact briefly) - If chronic: Limit time with this person

Challenge 5: Boring Conversations

If you're bored: - Try to find an interesting angle - Ask deeper questions - Introduce new topic - Or politely exit

If they seem bored: - Check engagement cues - Ask if they want to talk about something else - Don't take it personally - It's okay to end the conversation

Conversation Enders

Graceful Exits

Why you might exit: - Natural end point reached - Time constraints - Want to talk to others - Not enjoying it

How to exit politely:

1. Reason + Future - "I should get going—early day tomorrow. Great talking to you!" - "I need to check in with my friend. Let's catch up later!"

2. Appreciation + Close - "This was really interesting. Thanks for the conversation!" - "I enjoyed hearing about [topic]. Take care!"

3. Introduction - "You should meet my friend [name]. Let me introduce you..." - (Then you can slip away after introductions)

4. Honest - "I'm going to mingle a bit. Enjoy the event!" - "I need to grab some food. Good seeing you!"

Exit Signals

Prepare for exit by: 1. Wrapping up topic: "Well, sounds like you've got that handled" 2. Body language: Step back, break eye contact 3. Verbal cue: "Well..." or "Anyway..." 4. Looking around: Glance at others or exit

Don't Over-Explain

You don't need a lengthy excuse:

❌ "My stomach has been bothering me and I think I need to find a bathroom..."
✅ "I need to head out. Great talking with you!"

Advanced Techniques

Callback Humor

Reference something from earlier in the conversation:

Earlier: Talked about their fear of birds Later: "Watch out, there's a pigeon!" (light joke)

Builds rapport and shows you were listening.

The Bookend

Start and end on the same note:

Opening: "How's the new job?" Middle: Various topics Closing: "Hope the job continues to go well!"

Shows attentiveness and provides closure.

The Gift

Give them something useful: - Recommendation ("You should check out...") - Introduction ("I know someone who...") - Information ("I read that...")

Makes you valuable and memorable.

Practice Exercises

Exercise 1: Thread Identification

Listen to conversations (or podcasts) and identify: - What threads were offered? - Which threads were pulled? - Which were ignored?

Exercise 2: Balance Timing

In your next 3 conversations, time: - How long you talk vs. them - Aim for 50/50 (±10%)

Exercise 3: Depth Tracking

Note what depth level each conversation reaches: - Level 1, 2, 3, 4, or 5? - Did it match the relationship?

Exercise 4: Exit Practice

Practice graceful exits: - End 3 conversations early (but politely) - Try different exit strategies - Notice how people react

Next: Social Cues - Learn to read the subtle signals in interactions