I see it all the time when I’m being sold to: the rep has a script, maybe a pitch deck, and some “value prop” bullet points ready to go. What they don’t have? A real conversation. I was the same way at the outset of my career, spending those early calls talking at the prospect instead of learning about them. Not surprisingly, it wasn’t very effective.
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Since then, I’ve learned that the best sales conversations are built around questions, not pitches. In fact, recent research from Salesforce shows that 82% of B2B buyers want reps who act as trusted advisors, which means leading with curiosity and listening more than you talk. That’s where open-ended questions come in.
The right question doesn’t just get a prospect talking — it gives you the raw material you need to position your solution in a way that actually matters to them. Below, I’ll share how I structure my questioning process, the types of open-ended sales questions I’ve found work best, and 20 questions I actually used to turn cold calls into real opportunities.
Tables of Contents
- What makes a good open-ended sales question?
- How to Create a Good Line of Questioning
- Open-Ended Questions for Sales
What makes a good open-ended sales question?
A good open-ended sales question does three things:
- Invites a story, not a yes/no answer. If a question can be answered in one word, it usually kills momentum. For example, “Are you happy with your current vendor?” Get a “yes” and you just hit a wall even the Kool-Aid man would struggle with. But “Tell me about your experience with your current vendor” invites the prospect to talk about both highs and lows, and it gives you some room to work with.
- Shows you’ve done your homework. I’ve found that prospects open up faster when I demonstrate I know something about their business. Asking, “Why did you expand into [market] last year?” shows I did some preliminary research and respect their time.
- Builds trust by focusing on them. When I ask about a buyer’s goals, challenges, or process instead of talking about my product or service, it signals that I’m more interested in helping than selling. That shift in tone makes prospects more willing to share real insights.
At the end of the day, the best open-ended questions don’t feel like an interrogation. They feel like the start of a partnership.
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How to Create a Good Line of Questioning
The biggest mistake I see new reps make is going too deep, too fast. Prospects need to warm up before they’ll talk about priorities, budget, or timelines. Here’s how I structure a line of questioning.
1. Start with general open-ended questions.
I usually begin by asking about industry trends. We’re living in an incredibly dynamic and tumultuous period, where technology is shaking up nearly every industry and shifting geopolitical winds are creating both uncertainty and opportunity. The news isn’t always good, but prospects are living it, and in my experience, they want to talk about it.
2. Gauge the lead’s interest as they answer your initial questions.
Pay close attention to how much detail they give. Short, guarded responses often mean I haven’t earned trust yet. Longer answers mean I can dig deeper.
3. Ask early on how the company evaluates new products and services.
This is one of my go-to questions because it reveals their buying process and decision-makers. I’d rather know upfront if they require an RFP, committee review, or sign-off from a procurement specialist than waste weeks chasing someone with no buying authority.
4. Always ask about the budget.
I’ve learned the hard way that avoiding budget questions just delays the inevitable. You don’t need a hard and fast number, but an operating window is essential. I’ll usually phrase it like: “When you’re considering solutions like this, what kind of budget range do you typically set aside?”
5. Close by establishing follow-up steps.
Even if the prospect isn’t ready to buy, I establish a clear next step. Whether it’s scheduling a follow-up call, getting an introduction to another stakeholder, or asking for permission to check back in next quarter, explain what you’re going to do and then do it without fail. Lots of things in sales will be outside your control, but this isn’t.
Below are 20 open-ended questions I use regularly. After each, I’ll add a note on why it works and how I’ve applied it in real conversations.
Open-Ended Questions for Sales
- Can I ask you some questions about your business?
- Could you tell me about your business?
- You specialize in X. Why did you choose that niche?
- What trends in your industry are shaping how you operate today?
- What are your goals for the next [3, 6, or 12] months?
- What does your boss hope to accomplish in the next year?
- How does your company evaluate new products or services before buying?
- If nothing changes in the next 6-12 months, what’s the risk?
- Tell me about your average day. How would this solution impact your daily work?
- What's holding your team back from reaching your goals?
- Was budget a barrier in solving this problem previously?
- Why is this a priority for you now?
- Who are you doing business with now and why?
- Is there anyone else you think I should speak with?
- What is the business problem you're trying to solve?
- What are the priorities for your business/team this quarter?
- What are your biggest obstacles?
- What events are you attending this year?
- Where do you see the biggest opportunities for growth?
- When is a good date to follow up?
1. Can I ask you some questions about your business?
If the prospect has come to you, you don’t need permission to start working through some discovery questions. For any cold outreach, whether it’s a phone call, email, a message on social media, or a conversation at a networking event, I like to get permission early and signal that I’m there to learn, not pitch.
2. Could you tell me about your business?
It sounds simple, but I’ve had prospects I thought would stonewall me share 10+ minutes of background from this one question.
Pay attention to the things they talk about, but try and note what’s not being said as well. It can take some practice (and often industry specialization) to spot what the speaker is omitting, but if it’s on your mind you’ll pick it up quicker than you think.
3. You specialize in X. Why did you choose that niche?
I love this question because it taps into human nature. People really enjoy sharing their expertise, and we all tend to be better at things we naturally enjoy. Get the prospect to share that spark of enthusiasm and they’ll not only share valuable information, it will be a fun conversation for you both.
4. What trends in your industry are shaping how you operate today?
I like to ask this early because it shows that I’m curious about their world, not just interested in winning their business. It also helps me identify external forces like regulatory changes, labor shortages, or new technologies that might be driving decisions. For example, when I asked this question to a regional construction firm, they immediately brought up staffing challenges.
Fortunately, digital marketing is about attracting new talent just as much as it is winning new customers. Knowing that was a top priority helped us not only close the deal but deliver the exact solution they needed.
5. What are your goals for the next [3, 6, or 12] months?
I ask this early to align my solution with their roadmap. For example, if my product takes six months to generate the kind of results that the prospect wants to see in three months, I should make sure someone in customer success is aware of the outsized expectations.
On the other hand, if the buyer is looking to achieve a goal but not for another year or two, they might just be kicking tires and wasting time.
6. What does your boss hope to accomplish in the next year?
Prospects don’t operate in a vacuum, and even CEOs have priorities that come from external sources like boards and key shareholders. This question uncovers those pressures and helps you understand what’s actually prompting the conversation.
In addition, it helps you understand exactly what the buyer is looking for out of your solution.
7. How does your company evaluate new products or services before buying?
This question has saved me countless hours. Want to reveal the buying process and who holds the keys? Just ask. Knowing where to target your limited capacity is key in sales, and it’s important to be respectful of the prospect’s time as well. Making sure you’re talking to the right person is just common sense.
8. If nothing changes in the next 6-12 months, what’s the risk?
Most sales opportunities end in no decision, which is why I like this question. Far from being pushy, it helps prospects confront the cost of inaction. Either doing nothing is risky and likely to cost them, or it’s not particularly dangerous and there’s very little chance I’m selling anything.
In one conversation I had with a manufacturing firm, the prospect admitted that their outdated digital presence might cause them to be overlooked for a major contract opportunity coming down the pipeline. Once the risk was voiced out loud, the project not only became urgent, but it had a deadline.
Free Guide: 101 Sales Qualification Questions
101 Questions to Ask Contacts When Qualifying, Closing, Negotiating, and Upselling.
- Budget Questions
- Business Impact Questions
- Competitor Questions
- And More!
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9. Tell me about your average day. How would this solution impact your daily work?
This question is one of my favorites because it moves the conversation from abstract benefits to real, tangible impact.
Any time you can prove your product or service will save the buyer a) money or b) time (and thus money), you’ve immediately got the wind at your back. If they’re having trouble making the connection or are skeptical of your ROI calculations, ask about a typical day and do some back-of-the-envelope math right in front of them.
10. What's holding your team back from reaching your goals?
If you know the prospect is dealing with certain obstacles, I’ll use this question. If they’re high functioning and could very well be achieving their assigned goals, I might alter it slightly to something like “What are the biggest constraints on your team?”
There’s always room for improvement, and some version of this question uncovers pain points the prospect might not have fully articulated yet.
11. Was budget a barrier in solving this problem previously?
If the prospect says yes, it’s time to do some more digging. You may be able to position your solution as a more cost-effective alternative, but only if you know what the buyer was previously paying or the amount they were quoted.
In any case, the question can help surface budget issues if they weren’t especially transparent during the initial line of inquiry. The budget has the power to hamstring deals at the last minute — but only if you let it.
12. Why is this a priority for you now?
Timing is everything in sales. This question uncovers the “trigger event” behind the project, whether it was a missed deadline, a lost opportunity for the prospect, or a firestorm that created headaches far enough up the ladder to warrant a solution. There’s a reason the conversation is happening, and it’s up to you to find out what that reason is. This question is just one approach I use.
13. Who are you doing business with now and why?
It doesn’t matter if the prospect mentions a vendor offering a solution to a completely unrelated problem, this question helps me understand their decision-making criteria.
Is that vendor the cheapest, the most technologically advanced, the most respected, or the most accessible? Are they local, global, or did a salesperson on their team just play golf with the right VP? If you can find out how the buying company does business, you can play to that as much as possible.
14. Is there anyone else you think I should speak with?
This is one of my favorite questions because it acknowledges the reality of B2B sales: very few deals are made by a single person. Gartner reports that the average B2B buying group for complex solutions now includes 6-10 decision makers. Whether you’re dealing with 10 buyers or two, I’ve often found that my initial contact is happy to point me toward their colleague in finance, operations, or IT who also needs to weigh in.
I once asked this question on a call with a mid-level marketing manager, and she introduced me to the CFO, who became the real champion of the deal. Without that handoff, I would’ve been spinning my wheels.
15. What is the business problem you're trying to solve?
Prospects sometimes get caught up in features, whether they’re better dashboards, cleaner integrations, or a nicer UI. The key is to tie them back to the real business challenge. I use this question to ground the conversation.
For instance, a client once spent 10 minutes describing how frustrating their current CRM was. When I asked about the bigger problem it was creating for the team, he admitted missed revenue targets were the real issue. That shift turned our conversation from “better software” to “hitting growth goals.”
16. What are the priorities for your business/team this quarter?
Annual goals are important, but quarters drive urgency. I’ve closed more deals by aligning with a Q2 or Q3 initiative than by trying to fit into a vague year-long strategy.
For example, I once worked with a construction firm that needed a new web presence before a regional trade show. Asking about their quarterly priorities helped me understand that timeline, and we won the project because I showed we could deliver just in time when it mattered most.
17. What are your biggest obstacles?
I keep this one in every meeting, and give people plenty of space to think after I ask it. Often, they’ll reveal something deeper than the surface-level frustrations that may dominate a lot of the conversation.
In my experience, the insights they reveal after some careful, uninterrupted thought are actually the ones that drive buying decisions compared to the day-to-day annoyances that are often top of mind in any job.
18. What events are you attending this year?
I like this question because it adds a human touch and opens the door for casual rapport. If a prospect mentions a conference I know, I can reference sessions or even suggest grabbing coffee there.
In one case, a prospect mentioned they’d be at a local industry trade show. I made a point of attending too, and that in-person conversation sealed trust much faster than Zoom ever could. In a world where the default has largely become digital interactions, those in-person moments are still difference makers and I prioritize them over just about everything.
19. Where do you see the biggest opportunities for growth?
This is a forward-looking question, and I use it to shift the tone from “problem solving” to “possibility building.” Prospects light up when they talk about growth.
I had a talent development client who told me their biggest opportunity was expanding into a new industry, and that single answer changed how I framed our work together. I showed how our digital strategy could leverage their existing experience and help them break into that vertical, and it resonated immediately.
20. When is a good date to follow up?
Closing without a next step is like leaving a race without crossing the finish line. Whenever possible, I try not to end a call until I’ve got something on the calendar. That often means stopping five minutes early to set a time instead of talking up until the last minute when the prospect has a hard stop. A set date avoids the dreaded “I’ll get back to you” limbo, and a follow-up date that’s two months out is miles better than none at all.
From Curiosity to Closing
Over the years, I’ve learned that open-ended questions aren’t just some technique — they’re the foundation of consultative selling. When I show genuine curiosity, prospects reward me with insights I could never get from a pitch deck. Fortunately, I love learning about all kinds of different businesses and the challenges they face.
I almost never close a deal on the first call, but by asking better questions, I always leave with more trust, more understanding, and a clear next step. If you trust the process, you’ll get to a close one conversation at a time.
Editor's note: This post was originally published in June 2014 and has been updated for comprehensiveness.
Free Guide: 101 Sales Qualification Questions
101 Questions to Ask Contacts When Qualifying, Closing, Negotiating, and Upselling.
- Budget Questions
- Business Impact Questions
- Competitor Questions
- And More!
Download Free
All fields are required.
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