10 Foolproof Ways to Make Small Talk Unforgettable

Imagine you‘re at a networking event or sales kickoff. You spot your dream client or new coworker across the room. You know you need to make a strong first impression to build a relationship with this key contact.

So you walk up, armed with a smile and a firm handshake. "Hi Sarah, I‘m Mike! How are you?"

"I‘m good thanks, how are you?" she responds.

"I‘m great!"

… Cue the crickets. 🦗🦗🦗

We‘ve all been there. The dreaded chitchat stalemate. Where do you go after "How are you?"

According to a study by [Source], the average person has over 50,000 conversations per year. And research shows that [X%] of those conversations start with some version of "How are you doing?"

But just because this greeting is ubiquitous doesn‘t mean it‘s effective. In fact, a survey by [Source] found that [Y%] of people find the question "How are you?" to be insincere and irritating when used by someone they don‘t know well.

The problem is, if you don‘t have a thought-provoking follow-up ready to go, the discussion can quickly turn into a meaningless exchange of pleasantries. And that first interaction is critical—you may not get another chance to connect with that person.

So how can you turn forgettable small talk into unforgettable rapport-building? It all comes down to a skill I call "conversational threading."

What is Conversational Threading?

Conversational threading means actively listening for tidbits you can use to weave a robust dialogue. It‘s about tugging on different strands of information and seeing where they lead.

When you "thread" a conversation, you:

  1. Make an observation or ask a question
  2. Listen intently to the response
  3. Ask a relevant follow-up question

Threading allows you go deeper on a particular topic and uncover uncommon commonalities. According to the book Click: The Forces Behind How We Fully Engage with People, Work, and Everything We Do by Ori and Rom Brafman, finding rare common ground is one of the most powerful ways to instantly click with another person.

The authors explain a psychological concept called "schema breaking." In essence, our brains are wired to pay special attention to things that deviate from our normal script or pattern.

So by definition, to spark engagement you need to shake people out of autopilot and break free from the "How are you?" script. Luckily, a few simple shifts in your approach to small talk can help you do just that.

10 Foolproof "How Are You?" Follow-Ups

The next time you‘re tempted to default to discussing the weather, try one of these threads instead:

1. "Working on anything exciting lately?"

This open-ended question is a perfect way to get the other person talking about their passions and priorities. It gives you valuable intel about what makes them tick.

Listen for hints about goals they‘re working towards or challenges they‘re facing. Is there a way you could help them based on what they share?

2. "What‘s the best thing that‘s happened to you this week/month/quarter?"

Prompt the person to reflect on recent positive events in their life. This primes the conversation for an optimistic tone and can lead to energetic discussions.

Sharing "highs" also builds psychological safety and trust. If they open up about something personal, be sure to respond with empathy and care.

3. "[Your company] has been making a lot of exciting moves lately. What‘s your take on [recent announcement or industry trend]?"

Show you‘ve done your homework by referencing a timely company or industry event. This communicates that you care about their business and want to swap insights.

Based on how they respond, look for opportunities to showcase your knowledge and credibility too. Just be sure not to one-up or steamroll— keep the focus on their perspective.

4. "I saw your post about [hobby/interest]. Tell me more!"

In the age of social media, it‘s easier than ever to spot conversation fodder. Bringing up someone‘s extracurricular passions is guaranteed to get them talking.

Express genuine curiosity about what energizes them. How did they get into that hobby? What do they love about it? When you show interest, they‘ll be excited to share.

5. "What‘s the last great book/article/podcast you consumed?"

Swapping recommendations for content is a fun way to bond over shared interests. It also gives you a glimpse into how the person learns and what kind of information they find valuable.

Come ready with your own recommendation to keep the thread going. Offer to send a link to your favorite episodes or readings on the topic after your chat.

6. "What‘s your biggest priority these days?"

Asking about someone‘s focus invites them to share what‘s top of mind. It could be a project they‘re leading at work, a skill they‘re developing, or a personal goal.

Lean in and ask follow up questions to better understand their motivation and game plan. Knowing their priorities can help you spot ways to add value.

7. "What do you love most about what you do?"

It‘s easy to bond over shared passions. Prompt the person to gush about the parts of their job that jazz them up. What lights them up? What impact are they proud of?

Research shows that discussing positive experiences can increase energy and engagement. Savor the good emotions and be their hype man.

8. "On a scale of 1-10, how [adjective] are you feeling today? What would make it a 10?"

Throwing out an unexpected scale injects some playfulness into the conversation. Pick an adjective that matches the vibe: energized, caffeinated, TGIF, etc.

Their rating will clue you into their headspace and the follow up question will get them fantasizing about brighter possibilities.

9. "Working on anything outside of work that you‘re excited about?"

Jobs are just one slice of people‘s identities. Show you‘re interested in them as a whole human, not just a job title. Inquire about passion projects, side hustles, volunteer gigs, etc.

Exploring their outside interests adds color and dimension to your understanding of what drives them. You may uncover shared values that strengthen your bond.

10. "What‘s one thing I should know about you?"

Give the other person the mic and let them share what they think is important for you to know about them. This could be a motto they live by, a formative story, a fun fact, etc.

How they answer will give you a glimpse into how they view themselves. Listen for values and beliefs that you align with.

The 3 Tenets of Make-‘em-Love-You Small Talk

Now that we‘ve covered what to say, let‘s talk about how to say it. No matter which follow-up questions you use, be sure to adhere to three core principles:

1. Be interested, not interesting

The top mistake people make in conversations is trying too hard to be clever and impress the other person. But research shows we build stronger connections when we focus on being interested rather than interesting.

You can demonstrate interest by asking thoughtful questions, listening intently, and seeking to understand the other person‘s experiences and opinions. Suspend your own agenda and get curious about their world.

2. Practice active listening

Active listening means being fully present and focused on understanding the message behind the words. It‘s the difference between waiting to talk and seeking to comprehend.

Some active listening techniques:

  • Paraphrase what you heard back to them
  • Ask clarifying questions
  • Notice body language and tone
  • Minimize distractions and maintain eye contact
  • Respond with empathy and care

When you make someone feel truly heard and understood, you lay the foundation for a genuine connection.

3. Give generously

The best conversationalists look for ways to add value to others. Maybe that‘s sharing a resource, making an introduction, or offering a piece of advice.

Approach small talk with a mindset of generosity. Instead of worrying about what you‘ll get out of the interaction, focus on what you can give. Even just offering a sincere compliment can be a meaningful deposit in the relationship bank.

According to the norm of reciprocity, we feel compelled to repay kindness. So when you lead with generosity, you trigger a virtuous cycle.

Small Talk That Leads to Big Outcomes

Mastering the art of small talk can have a major impact on your professional success and personal fulfillment. Let‘s explore some of key benefits:

Boost Your Likability

People do business with people they like. Period. In one experiment, a group of MBA students were instructed to conduct a mock sales meeting. The students who spent just a few minutes engaged in small talk before diving into their sales pitch were rated as more likable and trustworthy than those who launched straight into their spiel.

Expand Your Network

Every big opportunity starts with a small connection. According to HBR, a larger, more diverse network is associated with greater career success and faster advancement. Cultivating your conversational skills allows you to connect with people outside your immediate circle and open up new doors.

Increase Your Influence

The ability to engage and inspire others is a hallmark of great leaders. After all, leadership is the art of motivating people to act towards achieving a common goal. Being able to build quick rapport is key for getting people to embrace your vision and rally behind your cause.

Close More Deals

People are more likely to buy from reps they have a good rapport with. A study by Gong.io found that the sales reps with the highest win rates spent on average 8% more time building rapport than their peers.

Devoting a few extra minutes to small talk allows you to build familiarity, find common ground, and establish trust—the foundational elements for influencing behavior.

Your 7-Day Small Talk Challenge

If the idea of making idle chitchat still fills you with existential dread, fret not. Like any skill, riffing on pleasantries takes practice.

Here‘s a simple 7-day challenge to help you sharpen your conversational chops:

Day 1: Compliment a stranger on their cool t-shirt or unique accessory
Day 2: Ask a coworker what the best part of their weekend was
Day 3: Offer to help someone in a small way and see where the conversation leads
Day 4: Notice one new detail about a place you go every day
Day 5: Reveal an unexpected fact about yourself when someone asks how you are
Day 6: Ask a follow-up question anytime you‘re tempted to say "That‘s nice"
Day 7: Make a quirky observation to spark a fun conversation

Keep a journal of the responses you get and the way each micro-interaction makes you feel. Getting in daily reps will reprogram your brain to see small talk as a fun opportunity to learn and connect rather than a chore.

Make Your Mark

Small talk doesn‘t have to be shallow. With the right mindset and techniques, even a quick exchange can be the start of a meaningful connection.

By skipping the temptation to go through the motions when someone asks "How are you?", you open the door to more rewarding interactions. Each conversation is a chance to make your mark and move your relationships forward.

So get out there and start threading your way to unforgettable connections. One "How are you?" at a time.

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