The art of the sales conversation starter


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You pick up the phone and dial your prospect. In the moments between the first ring and when they pick up, you experience a few unpleasant emotions: anxiety, fear, doubt, lack of confidence. The whole conversation may have already taken place in your head inside of just a few seconds. And the imagined outcome may be iffy.

That’s what sales calls feel like—even to seasoned pros, never mind a small business owner trying to up their hustle. 

The fact is that selling is hard. And that first call may be the most important and significant moment in any sale. 

The problem with most first sales calls is exactly that: they’re sales calls. The salesperson comes on too strong. They focus on the close rather than solving a problem. And their idea of building rapport doesn’t reach much further than asking about the weather. 

So of course, sales calls get a bad rap. 

But they still work. In fact, they’re still the most effective channel for selling

We know how hard that first call can be. So we’re here to help. In this post, we’re going to show you how to make that first call fantastic by covering these topics: 

Want to close more deals? Download this free outbound playbook to learn more.

📱 Get your team pitching, prospecting—and closing—with this free guide.

🎉 Enjoy!

Prep work

Sure, you can put your Bluetooth headset on and start dialing people right away. But you’ll probably end up burning otherwise valuable leads or spinning your wheels looking for the right person to speak with. You can’t go in without knowing anything and expect people to be receptive—research is a must. The good news is that it’s relatively easy to do your research if you know what to look for. You won’t even need any special sales software at this point.

Find your prospect

If you’re selling to a business, use LinkedIn to find out who you should be speaking with at that company. Simply search for the company’s profile, click on “People,” and use the search field to find the individual with the title that you need to speak with.  

RingCentral LinkedIn Profile


Know your prospect

Once you’ve identified them on LinkedIn, take note of their location, how long they’ve been in the role, content they’ve shared, awards they’ve won, or anything else relevant. Look them up on Twitter and Google for more insight into who they are and what they’re interested in. 

Look for what you have in common

The easiest way to turn a stranger into a friend is to find out what you have in common. Look for connections you have in common: a state or country you grew up in or the college you attended. These small, seemingly unrelated commonalities can help turn a cold call into a conversation, and that makes it a whole lot easier to start selling. 

A word of caution: keep it high level and professional. Knowing their childhood pet’s name isn’t only unnecessary, it’s kind of creepy too. 

Sales conversation starters, part 1: ice breakers

Congratulations. You’ve picked up the phone, dialed, gotten through the gatekeeper, and have your prospect live on the phone. What now? 

First, introduce yourself. 



Do you have a few minutes to chat? 

Assuming they say yes (and many will), avoid the temptation to dive right into the pitch. Instead, ask a few softball questions. They’ll help you build rapport and even reveal a bit about the prospect’s personality. Here are some examples:

I noticed that you’re relatively new to New York. How do you like it so far? 

If you’ve been to New York, or wherever it is they live, you’re opening the door to a conversation about your shared experiences there. They can talk about what they like and dislike about the place—weather, traffic, restaurants, you name it. This gets them talking and gives you a better understanding of what kind of person they are. 

I see you’ve been at COMPANY for X time. What do you like most about your role? 

Again, you’re tailoring your questions to the prospect. That tells them that you know who you’re speaking with and that you’ve done at least a bit of research. It also opens the door to learning more about their role and what their challenges are. 

I noticed that you were recently recognized for AWARD/ACHIEVEMENT. Congrats! What was that like? 

Here, you’re appealing to their ego. People enjoy being recognized for their professional achievements, so they’ll appreciate that you took notice. Questions like this can help you learn more about their challenges and goals without directly asking about them.

Create conversation—just get that ball rolling. Use these as a starting point, and you’ll almost certainly think of a few follow up questions. As you listen to what the prospect says, identify ways your product may be able to address a problem, make something easier, or even just relate to them and their experiences. 

Sales conversation starters, part 2: probing questions

At this point, you’ve established trust with the person you’re speaking with. The conversation is moving smoothly. You’ve learned a bit about them, where they’re from, and what they do (even if you already knew those things from your research). You may have even shared a laugh or two. 

But, you both know that it’s still a sales call. 

Had you started with probing questions, there’s a good chance the call would have ended right there. But you’ve graduated from being a potentially disruptive interruption to a welcome one. To move things forward, you’re going to have to learn more about their challenges and goals. The good news is, at this point, you can be more upfront about asking about them:

What are your biggest goals this year? 

Very straightforward. Where are they now versus where do they want to be down the road? What is the must-do task they face? This question is important because it gives you a complete view of their aspirations, and makes it easier to identify how your product can help your prospect get there. 

What are your biggest challenges? 

Reaching goals is all about addressing pain points and overcoming challenges. Knowing what those pain points are will, again, reveal so much about how you might be able to help. Tailor your product or service to their challenges instead of talking about yourself first and trying to fit their story into yours. Use this question to uncover problems and needs that they may not be able to address currently. 

What would help you reach the goal/overcome the challenge? 

Your prospect may or may not know the answer to this question. But in asking them, you’re looking for ways that your product can accomplish what they’re up against. 

Take notes. Ask follow-up questions based on how they reply. Resist the urge to respond to every answer about how your product solves that problem. Listening, not pitching, is the key to winning here. You’re trying to see the prospect’s big picture. And that’s going to make it easier to demonstrate the value your product or service can deliver. 

Pitch lightly

If you’re lucky, your prospect has identified a problem and they’re eager for someone (maybe you!) to help them solve it. But most of the time, you’re only beginning to understand what their world looks like and how you might be able to help. Instead of going straight into the pitch, think about other ways you can suggest value without coming on too strong. 

For example: 

“That’s really interesting. One of my customers at COMPANY was experiencing a very similar issue. We were able to help him solve it using X, Y, and Z.”

The response demonstrates the value of the product and allows the prospect to understand how the results were achieved—but without being pushy. 

From here, consider wrapping things up and talking about next steps. 

“I know you’re tight on time. But I think I can help you with this. Could we schedule another meeting to go over it in a bit more detail?”

If you can’t close the deal right away (and that’s okay), getting that second meeting should be your primary goal. What you learn now through these questions will make it easier for you to build a strong case that a second conversation is worth having. 

7 tips on how to sell like a pro

Beyond asking a few ice breakers and probing questions, the following tips can help you improve the way you approach and interact with your prospect. 

1. Know what’s happening in your prospect’s industry.

Was there a recent IPO, merger, or acquisition in their industry? A big product launch that’s attracting a lot of buzz? Knowing the who, what, when, where, and how of what’s happening in their industry can go a long way in not just creating conversation topics, but also understanding their challenges and how you may be able to help. 

2. Listen. And then listen some more. 

Salespeople who listen more than they talk tend to close more deals. But listening is more about learning than simply not talking. By listening to what your customer tells you, you’ll uncover important cues—a challenge, a need, or a professional point of view—you’d otherwise miss by listing off a bunch of features and benefits. 

Listening allows you to identify the problem and align your talking points to what your prospect has expressed. Suddenly, you’re solving a big problem they’re struggling with instead of selling them something they’re not sure they need. 

3. Know when to keep calling—and when to move on.

According to Velocify, more than half of prospects who convert require six calls to make contact. So, there’s a lot to be said for being persistent. On the other hand, instead of giving you a clear-as-day “no” response, some people will say “it’s not a great time” and postpone meetings into perpetuity. 

If you’ve reached out a number of times with no luck, there’s no shame in assuming the prospect isn’t currently interested. Consider reaching out to them in a quarter or two—circumstances and needs change. 

4. Don’t be too casual. (Or too professional.)

So, what’s considered casual and professional? That depends on who you’re speaking with. Be friendly and polite, but use the first few questions to determine the kind of tone the prospect is using. Do they seem relaxed and easy-going? Then be easy-going, too. Are they speaking in a business formal way? Then you may want to button up the way you speak to them. People tend to like people who are similar to them, so within reason, try to mirror your prospect’s tone. 

5. Go easy.

Trying to close too quickly can easily shut down the conversation before it even starts. Consider your first call an opportunity to test the waters: make contact, build rapport, explain who you are, and touch on how you may help. At this point, you probably haven’t given yourself enough time to truly consider their challenges. If there’s an opportunity to provide real value, say so, and schedule another call where you can dive into how in more detail. 

6. Avoid jargon.

You’re the product expert. But the customer probably isn’t. If you’re using language that’s specific to your field, you’re going to lose the prospect fast. So avoid using uncommon acronyms and industry jargon in favor of straightforward language they understand. This makes your customer far more receptive to what you’re saying and puts you both on equal footing. 

7. Leave them with something.

Your first sales call with a prospect will usually be just an intro and light conversation. When you’re wrapping up the conversation, be sure to get an email address so you can leave them with something—a case study, eBook, blog post, or webinar invitation. Something for them to check out and mull over. It’s also a great gateway to a second conversation. Here’s an example: 

Wrapping up a conversation, leaving a report for customers to check out

Tools that make selling easier

Selling is challenging work. These sales apps can make finding leads, making calls, and keeping your prospects and customers organized infinitely easier. 

🤔 Are you thinking about purchasing a new sales app? What should you consider during the buying process?

👀   Get this free guide to purchasing the right sales apps for your business.


A business phone system

Even if you’re just a small business, having a business phone system is always a good idea—especially if you’re making sales calls and getting lots of inbound calls. Having one can make even a small team look like a big well-oiled machine with features like:

  • Multiple business numbers if you need them
  • Cloud support so you can make calls from any device using the internet
  • Video meetings in HD
  • Text and MMS messaging

If your team is growing, you might even look for more advanced features that make it easy to coach and save time while you’re selling. Here are a few things to look for when you’re shopping for a phone system to support your team’s goals and encourage effective teamwork

  • Call monitoring: So that managers can quietly listen in on calls with new sales reps to keep them on track. 
  • Call recording: So you can capture conversations, find opportunities for coaching, and even examples of great selling!
  • Salesforce integration: If you use Salesforce, this makes it easy to log calls you make right into Salesforce without toggling apps. 

LinkedIn Sales Navigator

LinkedIn is a great platform for identifying prospects. But if you want to turn up the lead generation dial, LinkedIn Sales Navigator makes it even easier to find leads with automatic lead recommendations, notification of job changes, and a bunch of social selling features that can complement your pick-up-the-phone-and-dial strategy. 

LinkedIn Sales Navigator

So. Many. Leads.


It’s not free, but there is a week-long free trial available to see if it’s right for you. Learn more about LinkedIn Sales Navigator here

A customer relationship management (CRM) platform

Keeping track of your customers can quickly become overwhelming. A CRM makes it easy to organize customer names, titles, challenges, goals, where you left off, and when you should follow up again. Pricing varies and can get quite high amongst some of the bigger names in the CRM industry. But for small businesses, there are lots of free and affordable options that should meet most, if not all of your needs. AgileCRM is one of them, and an added perk is that it integrates with communications tools like RingCentral to keep all of your sales calls and conversations in one place:

Agile CRM platform

AgileCRM is easy to use and integrates with RingCentral to help you keep all your sales conversations organized.


Wrapping up your first sales conversation

That first call is the hardest because it’s your one and only opportunity to make a good impression, but it’s well worth the effort to do well. 

It sets the stage for the rest of your relationship and helps the prospect see you as someone who solves problems—instead of someone who calls you up every quarter looking to ink a deal. 

Do your research, be friendly, ask smart questions, and demonstrate value. It’ll help you establish trust and pave the way to success. 

Originally published Mar 10, 2020, updated Feb 25, 2021

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