9 Non-awkward Sales Conversation Starters

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Sales Tactics : 10 min read

9 Non-awkward Sales Conversation Starters

Learning the art of conversation is a game changer for sales pros.

Many sellers believe the sales conversation kicks off with the pitch. You know, a rehearsed description of the product/service and their associated benefits, topped off with a dash of pressure to “buy now” or “book an appointment.”

In this relationship era, selling is all about connecting. And that’s where the pitch-first strategy falls apart—you’re overwhelming the prospect with information and demanding a commitment.

Selling isn’t about pushing product. It’s about creating an emotional environment that gets a person to open up. Once you’ve set the psychological scene, you can gently lead the buyer from a friendly introduction to a signed contract.

Below, we’ll look at some conversation starters and best practices designed to improve your sales calls. And no, they don’t involve weather or the local sports team.

What conversation starters should accomplish:

The best sales calls are personable, yet professional. Often the challenge lies in striking a balance between the two. So long as the conversation stays within “safe for work” territory and doesn’t include a high-pressure pitch, you should be okay.

Ideally, your first interaction should help you identify your prospect’s goals and what you can do to help make reaching those goals a bit easier.

When you hang up the phone, you should have the following information:

  • Does the prospect need the product/service?
  • Does it fit their budget?
  • What factors affect their decision?
  • Is this person the decision-maker?

With that in mind, write down what you hope to get out of the conversation, so you can build your questions around a specific goal.

Research before you call.

This seems obvious, but you should never go into a sales call without knowing who you’ll be talking to. If someone picks up and they “have some time to talk,” you need to be prepared with a few personalized questions.

If this prospect is in your CRM, great—you’ll already have some information on hand, such as lead source, an initial email, or evidence they downloaded a lead magnet. Obviously, these CRM clues provide some context, but you’ll need to do some digging on your own to get a sense of who you’re talking to.

Google the company your prospect works for and learn more about what they do. This will give you some foundational knowledge to ask about the buyer’s role and where you can add value.

You can learn a lot from someone just by reviewing their LinkedIn page, too. Here, you’ll see things like connections and job experience, but also hobbies and passions. Do you have mutual connections? If so, bring that up to establish some familiarity right off the bat. It’s these extra steps that inform the questions you ask.

In this example, you’ll see that Jason has spoken at a lot of events and has included some articles in his bio. Here, you might mention that you’ve seen him speak at NYU or that you both went to school in North Carolina.

If you don’t have any commonalities, read one of the blog posts and ask him what he thinks about a related topic:

how to start a sales conversation based on linkedin info

That said, it might be a bit awkward to ask questions about a prospect’s pottery hobby without letting them know that you checked their LinkedIn profile, so tread lightly here.

Prepare to ask open-ended questions.

There are questions you can quickly reply to with a simple yes or no: “Do you want to save time?” Or, “Do you want to make more money?” These don’t qualify as conversation starters.

According to Harvard Business School, people who ask more questions are more likable. So make like a journalist and ask questions that follow the five Ws — why, when, who, what, and where.

the 5 Ws of asking questions.

These types of questions naturally keep conversations going and keep dead-ends at bay. And, if you are genuinely interested, your prospect will instantly feel like they matter.

How many questions should you ask?

Unfortunately, there’s no magic number when it comes to how many questions you should ask. We will say this, don’t approach your sales conversation like a checklist, otherwise, your prospect might feel like they’re being interrogated. A conversation is a back and forth, and the goal is to make this enjoyable for the prospect so that they want to talk to you again.

Gong.io found that asking a bunch of questions at the top of the call (note the beginning of the call timeline for average performers) made prospects feel as though reps were reading questions from a list, not listening to problems:

By contrast, top performers approached their questions in a balanced, natural manner. This way, the focus is on the conversation, not the script.

Now, let’s switch gears a bit and look at some non-awkward conversation starters that build rapport and uncover pain points.

1. How long have you lived in X city? How do you like it?

This is an excellent general question that helps you gauge how a prospect responds to an initial attempt at banter. Are they distracted or do they seem shy? Does this launch your conversation partner into a whole saga about how they ended up in San Francisco after growing up in New England and bouncing around the globe for 10 years.

In either case, this is a smart way to get a sense of who you’re dealing with and allows you to tailor your approach based on this personality barometer.

2. How long have you worked in your current role?

A get-to-know-you question of sorts, asking "How long have you been doing X?" gets the ball rolling. It might sound a little vanilla, but there are a couple of benefits to asking a question like this.

One, it’s a fairly basic question that allows you to drill down into specifics. People love talking about themselves, so you can milk this one with some add-on questions, like how did they get started in their role and did they plan on working in this field.

Two, you can easily steer that conversation toward challenges and pain points your product/service will potentially solve.

3. What do you like most/least about your role? 

By asking this question, reps can get a prospect to open up about what they like and dislike about their job. As this happens, reps should take note of their pain points and keep them talking.

For example, the prospect might say they hate spending time entering invoices. They’d rather focus on face-time with clients. That’s where you ask, “What solutions are you using to manage invoices?” And, “How is x solution working?

It’s open-ended—you’re listening to the buyer as they share what they don’t like about work. From there, you can present your solution.

4. Can you tell me more about what you’re planning this year?

This is kind of a broad question, but it’s useful for probing deeper which makes it an excellent sales conversation starter.

Say the buyer tells you they’re planning on an expansion or a product launch. From there, you might ask questions that tease out an immediate need. For instance, “What do you need in order to make this launch successful?” Or “What challenges do you anticipate as you grow?

Find out where you can make their lives easier by sequencing your questions to uncover where your solution can add the most value.

5. What does your typical day look like?

Similar to the what do you like most or least about your job question, but a little more specific. This question gives you a sense of what X role at X company actually looks like.

This question does two important things. The first being that it shows the customer that you’re serious about understanding what they’re all about. Secondly, this question uncovers inefficiencies.

If they tell you they’re spending too much time on spreadsheets or social media, you can show them how your solution helps them solve this problem, so they can spend more time doing what they love.

6. What are you looking forward to right now?

You could frame this in a couple of different ways. One option is, asking some variation of “What’s ahead for your business?” Or, if you’ve established some rapport, you can keep it open-ended.

The benefit of this conversation starter is it can go in any direction. The prospect can talk about a project they’re working on or share that they’re expecting a new baby, or gearing up for a trip to Europe. In any case, their answer opens the conversation further, allowing them to share something (anything) they feel passionate about.

If it veers off course, ask them a follow-up question that bridge the gap between the personal and the professional.

7. What are you reading right now?

Maybe this isn’t the ice breaker you’d lead with, but asking the prospect what they’re reading is a good way to establish some commonalities. You might find you like similar authors or you both recently finished the same book. Which, from there allows you to ask for book recommendations or ask what kinds of industry publications they like to read.

Additionally, this question can segue into a discussion about how a book or article relates to a workplace issue or a potential strategy.

Sure, there’s always the possibility that the prospect isn’t reading anything. Another option is asking where the buyer typically seeks out industry information or answers to their problems. In this case, there’s an opportunity to learn more about the prospect’s knowledge about your solution.

8. I’ve never heard of that. How does it work, what is it?

Let them educate you. This is a nice way to let your prospect talk about themselves, which according to Psychology Today, gives us a “neurological buzz.”

During your conversation, take on the role of student and use this opportunity to learn from the prospect. Obviously, you’re the expert when it comes to your product/service, but feel free to let your guard down and let your curiosity take over.

Other questions you can ask here are, “What is the ideal outcome, here?” Or, “How does x connect to y?” When people feel that someone wants to hear what they have to say, they’ll be more likely to open up.

9. How do you like the vendors you’re working with?

Yes, this particular question addresses the competition, but you’re going about it indirectly. Find out what solutions your prospect is currently using—it doesn’t have to be your competition either.

If they mention a specific product, ask how it works, what they would change, and so on. Here, you don’t want to go in for a quick sale; instead you’re listening for areas where you can genuinely be helpful.

Embrace the empathy statement

One of the easiest ways to foster a genuine connection with a prospect is through empathy statements. As you go through your questions, listen for opportunities to show prospects that you care.

  • So, if I’m hearing you correctly, you’re having x problem while trying to achieve y?
  • I think you might find x solution helpful in this situation
  • What about (current solution) do you think needs to improve?
  • May I make a suggestion?
  • I’d love to dig into this a bit more. Do you mind if I ask a few more questions?
  • I can definitely answer those questions for you, but feel free to stop me at any time.
  • Is it ok if we review everything we’ve covered so far?
  • Is your current solution working for you?
  • That is frustrating, what do you think would help reduce stress here?
  • Can you tell me more about (challenge/pain point)?
  • I appreciate your time

When you’re asking open-ended questions like “How do you like the vendors you’re working with?” the prospect might reveal that they’re dealing with an issue with on-time deliveries or their software is missing a key feature. Here, you’ve got an opportunity to jump in and say something like, “I think you might find x solution helpful in this situation.”

Non-awkward conversation starters are subjective

Finally, it’s worth pointing out that conversation starters aren’t uniform or strict. An awkward sales conversation starter is one that feels wrong coming out of your mouth.

Focus more on how you “sequence” your questions, asking follow-ups as prospects reveal more information. It’s more about creating an honest, human connection than fixating on a canned set of questions.

For more ways to level up your sales strategy, register for our free on-demand webinar. In it, we’ll cover the 7 Habits Reps Need to Crush Their Quota.