26 Rep-Approved Conversation Starters, and Why They Work So Well

Most sales conversations likely start the same way.

Rep: “Hey, how are you? Thanks for taking the time to speak today.”

Prospect: “No problem. I’m doing well. And you?”

Rep: “I’m doing pretty well. I can’t believe the weather you guys are having!”

Prospect: “Yeah, it’s pretty nuts. But it comes with the territory.”

And ... now what? A sales rep’s job is to get from “How’s the weather?” to “Who do I send the contract to?”, and it’s not easily done. Veteran salespeople can navigate this journey with ease, but for younger reps, the transition is more difficult.

Below are 26 phrases sourced from real sales reps you can use to steer the conversation toward the sale.

1) What are your goals?

By identifying the prospect’s goals, sales reps can tailor their presentation to address those specific objectives.

2) What’s your story?

Asking about the prospect’s story can provide key details into what matters to them and why this prospect chose the career path they did.

3) How did [prospect’s industry or job] become a passion of yours?

This question can help you understand what the motivating factors are behind your prospect’s career choice, which can help the salesperson position their product to align with the prospect’s interests.

4) What would you most like to achieve professionally in the next year?

You can ask this question to learn which direction your prospect is aiming to take their team. Armed with this knowledge, you can begin to explore how your product fits into that future and can help make those goals a reality.

5) What’s the biggest problem preventing you from achieving your goals?

Asking this question allows your prospect to control the conversation and explain their most pressing business pain. Once you’re aware of their priorities, you can begin working on a strategy with your prospect.

6) How do you plan to solve [your biggest pain point]?

Asking this question allows the prospect to explain their strategy in their own words. This will show you their level of expertise and provides an opening for you to provide advice. It’s also an opportunity for salespeople to begin positioning their their product as part of the strategy.

7) What made you leave [previous company] to work here?

You can find this out from basic LinkedIn research, and this question helps determine what matters to the prospect professionally.

For example, if a prospect left because the company wouldn’t adapt to new technology, the salesperson can show how their product is easy to learn and integrates with a multitude of tools.

8) What’s your favorite part of the job?

This question helps salespeople determine what gets prospects most excited and how their product can make that experience better.

9) What’s your least favorite part of the job?

This is a subtle way of asking about a pain point without explicitly using the term. Many prospects who are directly asked about “business pain” won’t know what to say; this question puts it in more concrete terms.

10) I noticed [X article] you wrote / shared, what made you write / share it?

This is an easy way to give your prospect a little ego boost,  but more importantly, you’re inviting your prospect to speak about a topic they care about. This allows a conversation to develop naturally about the prospect’s concerns, and opens the door for follow-up questions.

11) Did you notice [industry thought leader] wrote [blog post] yesterday?

By asking a question about a shared interest, the rep can spark a debate or conversation with the prospect and gain insight into their opinion on specific topics. As an added bonus, research shows people are more likely to trust someone they are similar to.

12) On a day-to-day basis, walk me through your responsibilities.

This provides you with two critical pieces of knowledge: Is this the person that most benefits from your product and are they likely to see its value? If your prospect’s day-to-day responsibilities don’t align with your product, it’s best to move onto another prospect in the company.

13) Do you ever find yourself over your head with [pain point]?

Just because a pain point exists doesn’t mean it’s high on a prospect’s priority list. This question taps into how much the pain actually costs the prospect in lost productivity, money, and more.

14) What were you looking for when you downloaded this resource?

The beauty of inbound leads is that you don’t need to hunt for a pain point. Asking an inbound lead why they downloaded a resource is a natural starting point, which leads directly into a conversation about what the prospect wants to improve in their business and how this resource helps.

15) Why did you decide to take this phone call?

This question alerts the rep to what exactly the prospect is looking for and how interested they are in the product.

16) What do you think makes your business unique?

By asking this question, salespeople can determine what matters most to their prospects and can bring it up during the sales process to provide value.

17) How can I make this process easier and better for you?

Instead of trying to search for unique ways to provide value, ask what the prospect is looking for directly. You can now personalize your sales process to ensure it aligns with your prospect’s expectations.

For example, your prospect might enjoy asking clarifying questions but salespeople she’s spoken with in the past have dominated the conversation. Now, you can be especially careful not to make that mistake.

18) What is it you think we do?

This question changes the conversation because salespeople can use it to confirm or correct the buyer’s assumptions while providing insight they might not have.

19) Name the three most important tasks you have to complete today.

Similar to asking about day-to-day responsibilities, you can determine how hands-on your prospect is and whether or not they will experience the value of your product.

20) What is something you do every day that is critical to your success?

Understanding the most critical part of a prospect’s job helps salespeople understand if their product is either a solution to a pain point or a contributor to what they’re already having success with.

21) What is on the top of your priorities list this year?

If your prospect could only accomplish one thing this year, what would it be and how could your product contribute to that goal? Armed with this knowledge, salespeople can explain how their product can contribute to that plan.

22) What's the biggest challenge you've faced this year?

A prospect’s biggest challenge is usually caused by (or is) their biggest pain point. Salespeople can begin to advise the prospect on how to address it and begin to build trust.

23) Do you anticipate any changes to the business in 2016?

Changes to company-wide strategy are a sign of goals and pain points the business plans to solve for in the year ahead. Does the company plan to expand? What about downsize? Will they enter a new market?

24) What are your top priorities for Q1 in 2016?

Another way to ask #23, this question narrows the rep’s focus to their prospect’s individual situation.

25) What's a day in the life of [prospect’s name] like?

How much time is this prospect spending at work? Do they have any hobbies? This information is key to understanding what matters to the prospect and how they prioritize their tasks on a day-to-day basis -- and an opportunity to build some rapport.

26) Tell me about 2015. What went well? Where do you want to improve?

Without having to directly ask what went wrong, reps can use this question to probe into the prospect’s highs and lows where they need to do better.

Getting a prospect from “How are you?” to “We accept VISA.” is no easy task. For some reps, getting the conversation started is incredibly simple. For others, it requires a little more work. By using any of these 26 phrases, reps can begin shifting the conversation from the weather toward the actual sale.