How to Make a Conversation Interesting: 8 Actionable Tips

Will Schmidt

12 min

Inside this article:

Understanding The Art of Conversation

8 Tips on How to Make a Conversation Interesting

Conversation Starters to Use

Keep Learning New Ways to Make a Conversation Interesting

Have you ever been stuck in a supremely boring conversation? Worse, have you ever felt the hot burn of embarrassment on your cheeks as you realize that you’re the reason a conversation is supremely boring?

No matter who you are, it can be hard to have interesting conversations—even the best talkers run out of steam every now and again. This is especially true in the world of sales, where being an adept conversationalist is often tied directly to your success.

After all, how many closed-won deals are you going to have in your sales cycle if you can’t even keep someone’s attention for 30 seconds? You have to learn how to make a conversation interesting, but how?

Like anything in life, the answer is practice. The good news is that opportunities to practice interesting, earnest, fun, and engaging conversations are everywhere.

Ask a customer support agent how their day is going. Chat up other people at a restaurant to see what their favorite dishes are. Find out what your mechanic’s favorite car brand is and why.

The thought of going into the world and practicing conversation skills might be second nature for some, but for others it might sound like a living nightmare. Regardless of where you fall, we’ve rounded up some actionable tips on how to make a conversation interesting.

Whether you’re building yourself up from scratch or honing an already keen edge, just remember that this is a fun exercise. And the payoff of practice can be well worth the effort for sales development representatives or account executives who depend on interesting conversations for their livelihood.

Understanding The Art of Conversation

Have you ever been talked at instead of talked with? In those situations, there’s a sender who disseminates information and a receiver who takes it in. There’s no room for conversation to happen.

That’s because conversations aren’t linear. Conversations are made up of countless threads we can pick up and run with, or drop entirely, at will. This makes them inherently multi-dimensional.

As such, a conversation can lead anywhere—you never know where it will take you. One minute you’re talking with someone about the weather, and the next minute you’re both sharing stories of your favorite international trips that fulfilled your soul.

How did you get there?

The best conversationalists know how to deftly maneuver the multiple threads of a conversation to lead from the beginning to a specific destination. There’s a subtle art to it. Here’s one potential route from Point A to Point B:

Me: “It’s very hot out today. Don’t you think?”

You: “Yea, it’s a real scorcher!”

Me: “Gosh, I’m glad I have an AC unit at home.”

You: “I can’t imagine what it’d be like to not have that today.”

Me: “You know, I was in Thailand on a meditation retreat in August with no AC. It sure made finding my center a bit more difficult.”

You: “Oh wow, I’ve always wanted to do a retreat like that! One time I went to Costa Rica for a yoga retreat and absolutely fell in love with the serenity of silence. It’s so good for the soul.”

Me: “No way! You have to tell me more. Do you have other trips coming up soon?”

If it seems simple spelled out on paper like this, I’m here to tell you that it really can be that simple in real life as well. It helps when you know where you want to steer the conversation. But you also have to remain flexible enough to chase one of many threads that can take you to a desired destination.

In the context of sales, this becomes doubly important. You know where you want the conversation to go, whether it’s booking a meeting, scheduling a demo, or getting a contract sent out.

Don’t be afraid to chase threads of interesting conversation when talking with your prospects. If you try to remain linear and force a sales pitch instead of having an authentic, interesting conversation, you may halt the entire deal.

This is something Jason Bay, Chief Prospecting Officer at Blissful Prospecting, discusses in our eBook Outbound Sales: 10 Strategies to Close More Deals in great depth. Be sure to download a free copy today and learn more.  

8 Tips on How to Make a Conversation Interesting

Like any art, the art of conversation can take time to master. Some of your success is related to learning effective communication techniques or optimizing your outbound based on the latest sales calls statistics, but there’s a lot here that depends on real-world application and practice.

You have to learn to be a good conversation partner who’s relatable, trustworthy, and interesting. To that end, we rounded up eight tips below that can help make your conversations interesting and ensure you become a great conversation partner.

1. Keep the Conversation Focused on the Other Person

People like talking about themselves. When you focus the conversation on the other person and give them an opportunity to open up, you might be surprised at just how much they decide to share. And the more they talk, the more connected they’ll feel to you.  

This doesn’t mean you should stay quiet the whole time though. That would have the opposite effect and make the conversation stale.

Drop in every now and again with small anecdotes of your own that build off what the other person is talking about. Ask probing questions to encourage them to go deeper into certain topics.

Remember that you’re in control of the conversation here. You know where you want it to ultimately lead, so make sure to subtly nudge it in the right direction as they keep talking. But also remember to be genuinely interested and curious about what they have to say.

People can smell when you’re being patronizing or inauthentic a mile away. One axiom that I always enjoy keeping in the front of my mind is this: “Every day is a school day.” If you treat your conversations with that mindset and seek to learn something new, you’ll always be genuinely interested.  

2. Find Points of Commonality and Connection

This may sound simple but it’s often easy to overlook this during conversations, especially if they’re moving fast. Undoubtedly, there will be points of common interests that naturally surface during the conversation. When they do, take the opportunity to connect over them.

For example, maybe you’re on a call with a prospect trying to book a demo to showcase your power dialer software (hey, that’s what PhoneBurner does). Along the way, they mention how much they dislike doing admin work in their CRM, and so do you.

Talk about that. Dig in deep. Explore what they don’t like about it. Relay some of your least favorite things as well. Laugh a little about both of your bad experiences.

You’ve just found common ground that’s brought you two closer together. And when the conversation comes to the point of scheduling the demo, you’re that much more connected.

3. Watch Late-Night Talk Shows

Late night talk-show hosts are some of the best conversationalists. In fact, they get paid for their ability to have interesting conversations night-in and night-out.

Naturally, talk-show hosts ask a lot of questions, mix in humor, and keep the conversation mostly focused on the other person along the interaction. You can also watch serious programs with hard-hitting interviews if that’s more your style.

Regardless, watch the mannerisms of both the host and the person they’re talking with. How are they using the tonality of their voice? Do they use specific body language to help communicate? What are they doing to connect with each other?

To put it another way, tonight’s homework: watch TV. And if you want a good laugh or some fodder for conversational humor, check out these hilarious sales memes.

4. Talk Slowly and Enunciate

Speaking fast isn’t always a bad thing, but it can be confusing for the person you’re speaking with. If you’re not present in your conversations, and you really know your stuff, you may speak so fast the other person’s head spins.

Make sure you purposefully slow your cadence down to the point where it feels almost too slow for you. I promise, you won’t be talking too slow if you do—it only feels that way. This is something you can practice by recording yourself or asking a friend to listen to you and give feedback.

The second major point is to enunciate your words. Get your mouth muscles used to pronouncing complex words with vocal warmups like:

  • Red leather, yellow leather (three times in a row)
  • You know New York, you need New York, you know you need unique New York
  • Betty Botter bought a bit of bitter butter, but the bit of butter was too bitter for the batter, so Betty Botter bought a bit of better butter

That last one is crazy, right? Oh, Betty.

All this will help you talk clearly, calmly, and confidently. That’s what people want to hear and it’ll draw them more into the conversation.  

5. Focus on the Conversation

You can ask the best questions in the world, talk confidently, and draw someone into a conversation. But if you don’t actually pay attention to what they’re saying you will fall flat on your face.

Remember: you want to be genuine and authentic in your conversations. How can you do that if you don’t pay attention?

There’s nothing worse than zoning out and realizing the other person has stopped talking and is starting at you waiting for a response. If you’re in sales, this could tank a deal faster than you can say, “I’m sorry!”. And your sales metrics will tank right along with that deal.

Draw your focus into the conversation and listen to what the other person is saying. If it helps, take notes while they talk. Do whatever you need to do in order to stay “in” the conversation with the other person.

6. Ask Personal Questions

Small talk can be frustrating and annoying if it’s too generic. Sometimes, you just don’t want to know what the other person is having for dinner tonight.

Take the opportunity at the beginning of a conversation to learn about the people you’re speaking with by asking questions about them. Focus on them by including the word “you” in your questions.

For example, you might ask:

  • What do you like to do outside of the office?
  • If you could wave a magic wand and your biggest work problem would disappear, what would it be?
  • Have you always been in your career field (marketing, sales, product, etc)?
  • Elon Musk: do you love him or hate him?

Asking for someone’s opinion is also a fun and engaging way to make a conversation more interesting. Do they have a favorite tech platform they use? How do they like to manage their work schedules? Have they read any great business books recently you should check out?

Questions like this can be extremely helpful for sales professionals after they’ve already booked an initial meeting off a cold call. These can lay the groundwork for long-term rapport and show the prospect that you’re legitimately interested in learning about who they are.

7. Ask Open-Ended Questions

If someone can answer your question with a simple “Yes” or “No,” you’re doing it wrong. These types of questions can immediately shut the conversation down.

You don’t want to be left scrambling for ways to reboot the talking or wondering how to make the conversation interesting again. Instead, prioritize open-ended questions whenever you can.  

Don’t ask: “Are you having a good day?”

Ask: “What do you love about today?”

This is also a tactic that we discuss in our eBook Outbound Sales: 10 Strategies to Help You Close More Deals. When cold calling, you need to diffuse these “Yes” questions right out of the gate in order to keep you prospect talking. Make sure to download a free copy today and learn more.

Once the other person starts talking, you can probe deeper with the five timeless journalism questions: who, what, when, why, and how:

  • Who has made their day great?
  • What happened to make today so good?
  • When was the last time they had a day like this?
  • Why do they think the day is so good?
  • How can they make sure every day is as good as today?

8. Handle Controversial Topics Delicately

Typically, there are three things people don’t like to talk about: personal finance, politics, and religion. However, there will always be one person who wants to dive into these areas and ask for your thoughts.

In some business conversations, it might be impossible to stray from things like finance and politics even. Regardless, if someone brings a controversial subject up, or they talk about something that makes you uncomfortable, be ready to pivot the conversation.

You can jump into the conversation and attempt to steer it back to your initial purpose for talking, or you can keep a few quick phrases ready to help everyone move past it. For example, you could say: “I respect your views there, thank you for sharing! But I’d like to keep us on track because we only have a limited amount of time to chat today.”

Remember, especially on sales calls, people are there to do business. Don’t be afraid to remind them of that North Star.

Conversation Starters to Use

As you’re learning new ways how to make a conversation more interesting, these following conversation starters might be able to help. Sometimes a good conversation topic sprouts from seemingly small and simple questions.

Here are a few quick questions you can fire off at the beginning of a conversation in order to get the ball rolling. Similarly, if conversation stalls you can use these to potentially reignite the chatter:

  • Tell me about yourself and your career path.
  • How is [NAME] doing today?
  • Are you working on anything exciting right now?
  • What’s your passion project at work?
  • What was the highlight of your day, week, or month?
  • What’s the best thing about working where you work?

What’s great about these interesting conversation starters is that you can align them with the initial purpose of your conversation. For B2B sales professionals, all of these can be used to push someone toward a conversation about their pain points, what their biggest priorities are, or if they need to buy new products or service.

Keep Learning New Ways to Make a Conversation Interesting

Whether you’re a natural talker, or if you’re a quiet individual, the best thing you can do to ensure conversations stay interesting is practice. Head out into the real world and talk with people, try asking new questions to your friends, and work on your active listening skills.

The more you talk, the better your conversation skills will become. That, in turn, can drastically help improve your ability to snare someone’s attention on a cold call, nail your demo presentation, and maintain lasting relationships with a prospect that leads to a signed deal.

Before you know it, you’ll be showing younger sales reps who join your team how they can make a conversation interesting themselves. And if you’re interested in learning more about how to apply these tips to your sales function, be sure to download a free copy of our eBook Outbound Sales: 10 Strategies to Close More Deals.

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