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Your goal as a sales rep shouldn’t just be to close deals. You exist to help prospects achieve their goals.
But you can’t help people if you don’t know anything about them. Your prospects are more than just a number or a target. They have emotions, stories, struggles and triumphs — just like you.
If you want them to trust you enough to buy, you have to show them that you understand and care. You have to connect with them in a meaningful way.
And that’s where open-ended sales questions come into play.
What is an Open-Ended Sales Question?
Open-ended sales questions are questions that require more than a simple “yes” or “no” response. They force prospects to think more deeply about their pain points and desires. And when prospects share these answers, sellers are able to position their products and services better.
Thoughtful open-ended questions in sales also help salespeople and prospects build stronger relationships during the discovery phase. They facilitate better conversations and make prospects feel like sellers are invested in their success.
So how do you ask an open-ended question in sales? With confidence and patience.
Asking these types of questions can feel uncomfortable at first. They’re harder for prospects to answer, which means people need time to think, and silence on sales calls can be unnerving.
Lean into the silence. Give your prospects a chance to formulate an honest response.
When you jump in too quickly, you can steer the conversation in the wrong direction. And you disrupt a thought process that could have opened the door to a more focused sales process.
You can also draw confidence from your pre-call preparation. Set the stage for a great conversation by sending a note in advance about what you’re hoping to cover and what value the prospect stands to gain.
This is best done over a warm video message that puts the prospect at ease. People who are comfortable are more likely to share openly with you about their goals and pain points.
(for more coverage on the topic of video prospecting, check out our article here)
And keep in mind that the experience you deliver during the sales process really matters. You want your customers to refer you to other great potential customers down the road.
People remember when they have a comfortable buying experience – one filled with smooth and friendly conversations every step of the way.
(here’s a more in-depth read on how to ask for referrals)
With all of this context in mind, here are some of the best open-ended sales questions we use today.
7 Questions to Uncover Your Prospect’s Situation and Background
In any sales conversation, it’s important to uncover who your prospects are and how their organizations work.
Sales-qualifying questions like the ones below are the cornerstone of the sales process. They provide the framework for meaningful conversations and establish the trust you need to build relationships.
1. How many people are on your team?
Your CRM can provide basic information about your prospect’s role in their company. But when it comes to the internal structure of their team, you’re going to have to ask more questions.
Use situational questions like the one above to begin uncovering more details about your prospect and their team. This question also provides a space for you to follow up with more in-depth, structure-focused questions.
For instance, after your prospect responds, you can follow up with something like, “So where does your team of [NUMBER OF PEOPLE] fit into the sales organization of your business?”
Focusing on their team and their company structure demonstrates that you prioritize how their company functions rather than what you want to sell them.
2. Would an increase in revenue help your business? [IMMEDIATE FOLLOW-UP QUESTION]
Revenue will always be part of an organization’s bottom line. So chances are, the answer to this question will be a resounding “yes.”
The word “yes” evokes positive emotions. Encouraging your prospect to say it early on sets the tone for the rest of the conversation. And after you ask about revenue, it’s important to keep the conversation moving in that same positive direction.
Parlay your prospect’s simple answer with something like, “So where are you pacing towards your revenue goals this quarter?”
3. How did you hear about us?
This question might seem basic, but it can yield impressive results.
It guides people to consider their own story, which can reaffirm their need for a solution and uncover valuable insights for the marketing team.
4. I see you’re using [A SPECIFIC TOOL], is that right? [IMMEDIATE FOLLOW-UP QUESTION]
Your prospect’s current tech stack can reveal a lot about their goals and potential areas of opportunity for your business.
For example, if you know your prospect is using Salesforce, try something like, “I see you’re using Salesforce right now, is that right?” After they reply “Yes,” follow-up immediately by asking, “Which key performance indicators (KPIs) are you tracking?”
Or, if you’re looking for even more specific details, try something like, “Are you tracking your engagement? What are your current email open rates?”
5. What quotas or targets [DO YOU] or [DOES YOUR TEAM] have to hit?
Your prospect’s targets and quotas will impact how they envision integrating your product into their workflow. Understanding their goals can help you leverage that information. And it will put you in a better position to help them succeed.
6. Who is in charge of identifying / owning expansion opportunities?
You won’t get very far in the sales process without knowing who has the final say. And while many questions can help you uncover key decision-maker details, sometimes it’s best to be direct.
For an alternative to this question, try asking something like, “Who else should we involve in this conversation?”
7. When implementing a new tool, what does that process look like?
You need insight into internal company processes, in addition to knowing who the decision-makers are. Having an idea of how an organization implements new solutions can help you (and your prospect) create and meet reasonable expectations over the course of the buying journey.
8 Questions to Determine Your Prospect’s Pain Points
After you’ve learned more about your prospect’s background, the next questions you ask should reveal their pain points. And you’re not just trying to solve symptoms of a problem; you want to address root cause issues.
The more you know about the problem you’re solving, the more value you can add.
8. What’s the most important thing you want to get out of this meeting?
Recent sales research by Hubspot highlights that for 69% of prospects, the number one way to create a positive sales experience is for reps to listen to their needs.
This question lets buyers to “clear their plates” first. Most people struggle to listen or engage until they’ve had the chance to share their own urgent thoughts or concerns.
It also gives them a chance to share more helpful context that you can use when crafting your pitch. Plus, you can use their answer in your follow up email to show you were listening.
(here’s a blog post on more follow-up sales email templates you can use today)
9. How are you using [YOUR TYPE OF PRODUCT] in your process or workflow?
An excellent way to encourage your prospect to think about what they may be missing from their workflow is to ask them how they’re using the type of product you’re selling.
This open-ended question is also one of the best cold call opening lines that won’t piss off your prospects.
(and here’s an in-depth article on cold calling scripts and best practices)
10. What metrics do you need to see [YOUR PRODUCT] make the most impact on to determine success?
Your prospect’s answer to this question will help uncover some of the deeper obstacles they’re experiencing. It will help you better position your solution and clear any roadblocks to getting your deal done.
11. Can you tell me about who [YOU, YOUR SALES REPS, TEAM, ETC.] are / is reaching out to?
The answer to this question gives you an idea of the broader dynamics at play that could affect your ability to win the sale. The phrasing here also invites a deeper reflection that could reveal helpful insights.
12. What are you doing currently to solve this problem?
In most cases, prospects are already looking for answers to their pain points. Figuring out what they’ve tried or are already exploring today can help ensure you pitch a differentiated solution.
13. Why are we looking at this now?
Instead of asking your prospect, “Is this a priority?,” consider rephrasing the question to, “Why is this a priority now?” The switch to an open-ended variation leads to in-depth discussion, and the word “now” reinforces the notion that finding a solution is urgent.
14. How do you lose deals to competitors?
Asking about your prospect’s competitors and their lost opportunities allows you to assess where they may be falling short. Is their competition investing in something they aren’t?
It also open the door for more dialogue about how your solution can help them fill in that gap.
15. How do I help support your next steps now?
The answer to this question brings forth details that could otherwise stall the deal later in the process. Getting these blockers out now gives you more time to mitigate risk.
It also positions you as more than just a salesperson. You’re a resource or thought partner who can help solve this problem with the buying team.
6 Questions to Discover the Impact of Removing Your Prospect’s Pain Points
Guiding your prospect through the buying journey means helping them to see what you already know: your product will alleviate their pain.
The following questions focus on your prospect’s emotional and rational decision-making. You need to win both sides of the brain to convince someone to work with you.
16. What would happen if you didn’t choose our solution to solve this problem?
Emotional decision-making is based on your prospect’s feelings and expectations. According to a report by The Advertising Research Foundation, your prospect’s emotions have a strong influence over the decisions they make.
Provoking an emotional response with open-ended questions like the one above guides the rational decision-making process in your favor.
This is because your prospect understands how they would benefit directly before focusing on more rational and measurable concerns (such as budget limitations).
17. What was the last tool you implemented successfully, and what could you contribute to that?
It’s typically best to ask your prospect one question at a time. But there may be occasions when asking two-part questions makes the most sense.
In this case, if you were to ask exclusively about the last tool your prospect implemented, the answer would likely be one or two words.
But asking the additional question of why they successfully implemented that tool emphasizes (and reminds them) that integrating new tools can be an effective process that benefits them in the long run.
18. What got you excited about [YOUR COMPANY] or [YOUR PRODUCT]?
Excitement is positive; it’s contagious — use it to your advantage!
This questions steers the conversation in a positive direction and unveils your prospect’s vision for how they might use your solution.
19. How do you see your [TEAM] or [ORGANIZATION] using [YOUR TYPE OF PRODUCT]?
This question prompts your prospect to think through other people’s perspectives on your offerings. It’s a great way to turn contacts into champions who advocate for you within their own organizations.
20. Tell me what things would be different if you could [CONVERT LEADS HIGHER, GET BETTER SHOW RATES, ETC.]
This question gets your prospect to envision a better future – one that depends on your solution. It gets them excited about a possible transformation while also revealing potential issues.
21. How will being able to [PRIMARY BENEFIT OF YOUR PRODUCT] help you in your business?
Your prospect may know little about your product. Highlighting key benefits and asking your prospect how it will help them indicates you have the solution to a problem they’re facing.
4 Questions to Clarify Your Prospect’s Answers
What you ask after your initial question is just as important in your discovery process. Your open-ended questions will inevitably reveal new information that may need further clarification.
22. When you said ______, can you tell me more about that?
Active listening conveys empathy and builds trust. This question shows you are tuned into your prospect’s words and thinking hard about what their answer means.
23. What else would you _______?
Instead of asking, “Is there anything else?” try asking, “What else would you _______? Your prospect is more likely to elaborate in response to this variation.
It’s also another “plate-clearing” question that gives your prospect a chance to bring up any concerns or issues you haven’t been able to discuss yet.
24. What I heard you say is ______. Can you be more specific?
There are going to be times you need more information to continue a conversation with your prospects. Asking for more details, especially when digging into specific pain points, is vital to having a complete understanding of your prospect’s story.
25. What did you mean when you said ______?
Honesty is crucial in business transactions. Telling your prospects you don’t understand something builds trust and shows that you’re willing to speak up when something doesn’t make sense.
What Comes Next?
Using these questions should open up doors in your conversations and (hopefully) lead to more sales. The more you use them, the better you’ll get.
Quick note on how to really impress your prospects: Send meeting recaps that incorporate language your prospect used during the meeting. Share their answers back with them to show you listened and are prioritizing their goals.
We recommend doing this over a video message. A video message is a much clearer way to communicate complex information and gives your prospect something to reference that isn’t a block of text in an email.
And every time they come back to that video message, they’ll be reminded of you – your personality, your warmth, your energy. This is what makes you memorable as a salesperson.
For a deeper dive on how to send great follow-up emails, check out this post.
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