How to Make Great Conversation and Close the Deal

Want to close more deals? Become a master of conversation.

6 Min
December 9, 2022

In the world of sales, conversations are the foundation. Yet even expert conversationalists can find themselves lacking in motivation or gusto. And as any good salesperson knows, keeping the prospect’s interest is paramount.

If you’re sweating your next call, you’re reading the right article. Cold calling isn’t easy. Fun, inspiring, and interesting conversations that can lead to new opportunities and closed deals are possible. It starts with practice. Regardless of where you’re at in your career, just try to have fun with this. Good conversation is the key to building rapport and trust with your prospect.

Let’s look at 7 ways you can enhance your conversation skills and close the deal.


1: First Impression Matters

2: Practice Active Listening

3: Weeding out Prospects

4: Organic Questions

5: 2 Ears, 1 Mouth

6: Open-ended Questions

7: Practice!

Ok. Let’s dive in.

#1: First Impression Matters

Once your prospect picks up the phone, the clock is ticking. What you say and how you say it in those first moments can make or break your impression on the person. What you don’t want to do is try to pitch right away or bombard the potential client with education or information up top. You also want to avoid those targeted questions that are deeply personal, yet offer no real value or insight. Questions like, “What keeps you up at night?” or “What are you struggling with?” are only going to meet with hostility and cold responses. No one is going to open up to someone that soon, especially a stranger.

Here’s what you do instead: show what you bring to the table right away. One way to do this is to start the sales conversation with an opener that lasts around 30-90 seconds (your elevator pitch). In it, you’ll make your pitch with relevant information, real-life problems you’re witnessing in your field, or another piece of data that’s going to resonate with your prospect–this may be niche.

Once you make your pitch with the relevant data to back it up, the person will warm to you because they feel like you speak their language. You’re at their level and filling a gap they didn’t even know they had. This shared insight will earn you that sales conversation that goes under the surface and leaves room for growth in the conversation.

Another great approach is small talk. An interesting conversation is bi-directional where they learn something about you and you learn something about them. If you share your favorite things, they are more likely to share their favorite things. Make sure to ask great follow-up questions to keep them engaged. It’s important to read their body language if you are in-person or on a video call. Not everyone thinks small talk is relevant to an interesting conversation. Read the room and react accordingly.

Some small talk conversation topics:

  • Favorite TV shows or books
  • Hobbies in common
  • Bucket list items
  • Common ground
  • Role models
  • Former coworkers you both know

#2: Practice active listening

An engaging conversation can close a deal and also make someone’s day. How? With engaging conversation. The first rule to starting an engaging conversation is to consider the other person and keep it simple (KISS rule). Save the Emmy speech for the bathroom mirror because it won’t close the deal. Your potential client probably already tuned out, if they haven't already hung up the phone. Also, avoid a ton of momentum up front and the plateau towards the middle. You want to bring the same energy throughout and if anything, raise your energy towards the end.

Write down your conversation starters and key topics you want to discuss. This will help keep the conversation going if things start to stagnate. Active listening requires you to listen to their response and then ask great follow-up questions. A common mistake people make is thinking through what they want to say, while they should be listening to the other person talk.

Once you’ve demonstrated that you know what they’re going through and dealing with, you can ask follow-up questions that get them to talk about their challenges. Once you get your prospect to open up emotionally, the conversation will be easier. If your prospect shows signs of defensiveness or disengagement, throw out another interesting insight of your pitch to keep their attention. It’s ok to have a few awkward silences. Oftentimes, this is when someone is thinking about their answer. Give them the time to think before jumping in to speak.

#3: Weeding out prospects

In a sales call, qualifying your prospect for your product or service is just another step along the way to closing the deal. Unfortunately, half of the time, your prospect won’t be qualified. Instead of aiming for a perfect audience for what you’re selling, aim for a snug fit.

Approach your prospect with curiosity to find out if they’re qualified to be your customer. If they aren’t sure or are on the fence about working with you or giving you their money, then you can honestly reply that you’re not sure either and would like to ask some further questions to figure that out if that’s alright with them. This way, the control is back in your hands and you’re asking the questions to see if they’re a good fit.

Determining a prospect’s fit doesn’t mean you need to disqualify people if they’re being a little tough or difficult at the beginning of the call. If someone just doesn’t want to talk, that doesn’t mean they’re not buying what you’re selling. Taking them through a series of clarifying questions can help both parties make an informed and autonomous decision. If it’s not a good fit, great. You’re one step closer to finding someone who is.

#4: Organic Questions

Sure, you want to have a set of qualifying questions at the ready for the person on the other end to determine if they’re a good fit–we just spent a few minutes going over that–or a few seconds if you’re a speed reader. But you’ll need to make some time for what we like to call organic questions. Organic questions are non-GMO, fresh from the brain, and spontaneous bursts of insight that will help form your conversation. Both systematic and spontaneous questions complement each other.

Listing your questions like a robot won’t solve anything and will only bore whoever is on the receiving end. Plus, you’ll miss out on a chance to get to know them deeper and sharpen your sales pitch.

When you’re forming your sales conversation, use your pre-planned questions as the foundation, and then implement the organic questions. You can do this by asking people to clarify what they mean, unpack something they said, or just extrapolate on what they’re already talking about (“tell me more!”). Less robot, more human.

Here are a few you can start using to make the conversation interesting and engaging. Keep these at the ready as quick follow-up questions.

  • Can you tell me more about that?
  • What’s the outcome of that?
  • How have you tried to solve this?
  • What happens next?
  • Who else does this impact?
  • Can you give me an example?

#5: 2 Ears and 1 Mouth

The best salespeople, the most seasoned ones at least, will know that listening is the differentiator between a closed deal and just a conversation that is sort of eh. Great salespeople don’t give monologues, they don’t throw up information, and they don’t give their comedy routine. What they do is realize that the conversation is a two-way street and the prospect is both driving the car and the passenger. They talk about 65% of the talking while the prospect does the other 35%. It’s a dialogue. You were given 2 ears and one mouth. Use them in the same ratio.

After presenting a key point, it’s best to pause and let that sink in. You’ll want to really give some pause after a prospect responds as well as after you ask a question. This can feel like an awkward silence, but it’s ok. If you find yourself talking too much, take a step back. Ask a question. Then listen. If you want a sales conversation that closes the deal, just sit back and breathe. Listen to what they’re saying and dig into the details with the great follow-up questions we listed above.

#6: Ask Open-Ended Questions

Open ended questions can be good conversation starters or they can keep the conversation going. Use them to create more interesting conversations. Here are some you can start with.

  • What challenges are you facing that you’d regret not solving six months from now?
  • Help me understand the most nagging challenges with X?
  • How would you rank this priority?
  • How have you tried to solve this in the past? Why do you think that didn’t work?
  • What effect does that have on the business?
  • What are the downsides of not solving this?
  • Who else does this impact and to what extent?
  • What do you imagine a solution would look like?
  • Why do you think you haven’t found the solution yet?
  • What are some ways you think our solution would benefit you?
  • What is holding us back from moving forward right now?
  • What is the most important thing for your business?

#7: Practice!

The more you practice making calls and having good conversations, the better you will become. The best way to have more conversations, is to make more phone calls and connect with more potential buyers.

That’s where AutoReach comes in. We take away all the manual steps of dialing so you can focus on having better conversations with decision makers. Combine our outbound dialer and you newfound conversational skills and you’re bound to close more deals.

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