6 Ways to Keep the Conversation Going

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Tristen Taylor
Tristen Taylor



52% of sales leaders say conversations are one of the most important productivity metrics to track. So whether you're negotiating with a prospect or just having a quick chat with another professional — the way you keep that conversation going can be the difference between a lost opportunity or your next closed-won deal.

sales rep using tips on how to continue a conversation for an engaging interaction

But sometimes, it's easier said than done. Ideally, your conversations will lead to lasting relationships — but you may need help finding more to say to avoid forcing the conversation.

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In this post, we'll give you our best tips to help you carry out more productive, meaningful conversations that can turn a simple chat into an important connection.

How to Keep a Conversation Going

1. Find common ground in small talk.

Diving into the sale at the top of your conversation can come off as pushy. Instead, you're better off greeting them and starting the conversation with a point of relatability, like small talk. This type of talk can be simple, harmless topics of discussion like:

  • Bringing up the latest sports event
  • Asking if they've seen [insert recent big movie]
  • Asking for recommendations on local attractions
  • Inquiring about how they chose their career
  • Finding out if you share any hobbies or interests

These minor talking points help you to share more of your personality and trustworthiness without the pressure of an immediate sales pitch.

Pro Tip: Keep in mind that small talk is just that — small. Keep it sweet and avoid overly invasive questions regarding more personal matters like where someone lives, their family, religion, or politics out of respect for their privacy.

2. Use open-ended questions.

Asking open-ended questions can make for particularly productive conversations. As you get to know who you're talking to, let them guide the story-telling and encourage them to go more in-depth with questions like:

  • “Tell me more about…”
  • Why do you feel this way?”
  • How did you come to this conclusion?”
  • “How can I support you?”

Pro Tip: Keep your "yes" or "no" questions to a minimum to keep the conversation from being cut short. You're chatting to learn more about a person, not pressing buttons on a robot.

3. Use compliments or positive reinforcement throughout dialogue.

Never underestimate the power of praise. When you can hold a conversation with complimentary language throughout, the person on the receiving end will be much more inclined to hear more from you.

For example, if your prospect has done a lot of research on your offering, weave subtle compliments throughout your responses, such as:

  • "It's great that you've done so much research. I'd love to answer any questions you have."
  • "Meeting enthusiastic people like you is one of my favorite parts of the job."
  • "I appreciate that you took this time today to review the details. I hope you found what you were looking for."

Pro Tip: There’s a fine line between complimenting and excessive flattery. Prospects know your real intention is to sell to them, so don’t focus too hard on buttering them up. Your product or service should speak for itself.

4. Engage in active listening.

Active listening is one of a salesperson's best assets. Every prospect you meet has unique problems, circumstances, and needs that have led them to seek out your business — and hearing them out allows you to understand and capitalize on those factors. Effective active listeners cover these best practices:

  • Approach each dialogue with a goal to learn something.
  • Let the other speaker talk and make sure to fully understand what they’re saying.
  • Nod your head or signify that you comprehend or follow the conversation.
  • Listen to the words of the speaker and encourage them to tell you more.

Pro Tip: Active listening will also help you to personalize your solution to your prospect's needs. This can make them feel like more of a priority, making them more likely to want to do business with you.

5. Remember that your body language speaks, too.

If I'm talking with someone who looks uninterested, distracted, or busy with a different task, I'll usually take it as a hint that they'd like the chat to end soon. But sometimes, the person on the other end doesn't even know that their body language is giving this signal.

To avoid sending mixed signals and make sure to:

  • Maintain a healthy amount of eye contact.
  • Face the person you're speaking to, or angle your chair toward them if seated.
  • Refrain from phone use or excuse yourself to answer an important, time-bound message.

Pro Tip: You don’t have to stare the other person down throughout the entire conversation — just give them the attention you would want in return so they know their words are valued.

6. Learn to talk through an objection to a solution.

When speaking to a potential customer, you can often tell when they have reservations about your product or service. It's your responsibility to let them know their options, especially since 60% of customers say no four times before saying yes.

Patrick Downs, a former PandaDoc Sales Enablement and Training Manager, discusses how to speak to prospects with reservations in this HubSpot Academy interview.

Downs emphasizes that when you listen to a potential customer’s fears,you need to lean into their words, acknowledge the objection, and guide them to the right solution.

Pro Tip: You have to be very careful navigating a conversation where the prospect has already voiced doubt. Refrain from dismissing the customer's objections and highlight a different solution as a big takeaway of the discussion. Let them do with that information what they will — applying too much pressure could make them abandon the sale altogether.

Ways to Keep the Conversation Going

Now that we’ve gone through our best tips, take this list of our biggest takeaways you don’t want to forget.

ways to keep the conversation going

Don't Put a Stop to the Conversation Just Yet

Holding a productive conversation doesn’t have to be a hassle, sometimes it just comes down to core principles and a willingness to pay attention to the person on the other end. Communication is a vital tool that every sales rep relies on, so with practice, you can make your future conversations a breeze.

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