How to Make a Conversation Interesting: 8 Actionable Tips

Will Schmidt

April 23, 2024

15 min

Table of Contents


  • Being a great conversationalist directly impacts sales success—and practice makes perfect. Seize every opportunity to engage in interesting, fun conversations.
  • Conversations are not linear; they can lead anywhere, offering endless topics to explore. The best conversationalists are goal-oriented but flexible enough to let things unfold organically.
  • Focus your conversations on others, find common ground, and use open-ended questions to keep engagement high. Incorporate humor, slow down your speech, and genuinely listen to improve conversation quality.
  • Avoid controversial topics delicately and use specific conversation starters to ignite or sustain dialogue.
  • For sales conversations, the right tools can be just as important as the right strategies. Try PhoneBurner for free today to see how it can improve call quality for your sales team.


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 sales, where being an adept conversationalist is often tied directly to your success.

Fortunately, mastering the art of conversation is a skill you can hone with practice, even during everyday encounters. Whether it's a casual chat with a customer support agent or a deeper discussion with a friend, every conversation is an opportunity to sharpen your skills.

We’ve rounded up some actionable tips on how to make a conversation interesting to help get you started. Use these tips to improve the quality of your sales calls and the conversations you have in your daily life.

How PhoneBurner Improves Conversation Quality

The tips below will help you in any conversation—but if you’re looking for tools that make a measurable difference on your sales calls, PhoneBurner can help.

We designed our platform to help reps have more high-quality conversations with prospects. Here are some of the features that help most:

That’s just a taste—PhoneBurner is loaded with features that help you learn more about your leads and reach them seamlessly so you can have more meaningful interactions. Start your free trial today to give your phone calls an instant boost.

Sales rep engaged during conversation

Understanding the Art of Conversation

Conversations are not just exchanges of information; they're dynamic and multi-dimensional. Great conversationalists understand this and navigate through various topics effortlessly, creating rich and engaging experiences.

Before you try the tips we’ve listed below, remember the following:

  • Conversations aren’t linear; they can lead anywhere. You’ll need to be comfortable letting things unfold organically, even if things don’t seem to be going exactly the way you imagined.
  • It’s important to enter conversations (especially sales calls) with a goal in mind—but you also need to stay flexible.
  • Conversations have multiple threads, any of which can be a viable road to the destination you want. If you try to remain linear and force a sales pitch instead of having an authentic, interesting conversation, you may lose your lead.

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. Download a free copy today to 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. Here are eight easy tips you can start using now to make yourself a stronger 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. Here are some tips for striking the right balance:

  • 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.
  • Remain 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 & 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 interest that naturally surface during the conversation. When they do, take the opportunity to connect over them. Here’s an example:

  • Say you’re on a call with a prospect trying to give them an overview of 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.

Sales rep watching late night talk show to practice conversation skills

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 during the interaction. Watch the mannerisms of both the host and the person they’re talking with—then ask yourself the following questions:

  • 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 & 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 that the other person’s head spins.

Try to 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.

Sales rep genuinely listening during phone call

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’ll 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 staring 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 it.

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. Take the opportunity at the beginning of a conversation to learn useful information about the person 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?

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

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 your prospect talking.

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.

Engaged sales rep starting conversation with prospect

Conversation Starters to Use

As you’re learning new ways to make a conversation more interesting, the 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 services.

Keep Learning New Ways to Make a Conversation Interesting

Whether you’re a natural talker or quiet by nature, 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 remember: the right tools are just as important as the right strategies. Try PhoneBurner for free and see how it can make it easier to make your conversation skills work for you on sales calls.


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