Conversational Qualification: 60 Open-Ended Questions You Can Use in Sales Calls and Emails
Explore 60 questions you can ask in emails or calls to qualify leads conversationally
Great sales conversations don’t start with pitches.
They start with questions.
That said, it can’t be any question. The best salespeople ask open-ended questions that guide the conversation, uncover real needs, build trust and rapport, and give insight to help sales teams adjust pitches in real time.
We’ll be taking a closer look at which questions you can ask and how to ask them so that your B2B outreach hits the sweet spot.
Why open-ended questions matter
In a perfect world, you’re able to walk into every sales call or email already knowing your prospect’s needs and pain points.
Unfortunately, reality isn’t so kind. Most decision-makers don’t broadcast their problems and challenges on social media.
That means you have to discover their pain points during a conversation. And that’s exactly where open-ended questions come in handy.
By asking open-ended questions, you can:
- Get detailed, thoughtful answers that share more context and a better shot at tailoring your value proposition to your prospect’s needs
- Discover pain points, priorities, and objections that your precall research might’ve missed
- Get your leads to talk about what matters to them so you can guide conversations without seeming pushy
- Make prospects feel heard so you can build trust and strengthen rapport
Think of open-ended questions as a steering wheel that allows you to direct the conversation like you would a car. But crafting the right question isn’t always easy.
What makes a good open-ended sales question?
Before diving into sales questions, here’s a quick primer on the differences between open-ended and closed-ended questions.
| Open-ended questions | Closed-ended questions | |
| Begins with… | What… Why… How… Could you tell me more about… | Is/Are… Do/Did… Would/Will… Could/Can… Was/Were… Have… Which… Who… When… Where… |
| Examples | What challenges are you facing in your current process? How do you evaluate new tools and vendors? Could you tell me more about how you deal with this? | Are you currently using a solution for this? Do you have a budget for this project? Would you like a follow-up demo next week? |
In short, closed-ended questions limit the conversation and can be answered with one word, usually “yes” or “no”. Open-ended questions open up the conversation and need more than one word for a good answer.
A good open-ended sales question checks three boxes:
- It targets the prospect’s priority or pain point
- It creates space for a detailed answer
- It moves the conversation forward
The third point can be particularly tricky as moving the conversation forward isn’t about the question itself, but about its broader context, like when and how you ask it during a sales conversation. And when timed right, they can act as momentum builders to push your prospect from curiosity to commitment.
60 open-ended cold call questions
We’ve grouped open-ended questions by their timing and purpose in a sales conversation, starting with rapport-building and finishing with post-closing questions.
Rapport-building questions
Rapport-building questions are essentially icebreakers.
They can feel like small talk, but they lower the prospect’s defenses and set a friendly tone:
- How’s your week going?
- Saw you’ve been with [Company] for a few years. What’s kept you there?
- I noticed your team just expanded. How has that impacted your day?
- Out of curiosity, how did you get into the [industry] space?
- Looks like you’re based in [City]. Has the market been as crazy there as we’re hearing?
- What’s been the most exciting project on your plate lately?
Asking these questions instead of cutting straight to the chase might seem counterintuitive. However, they disarm prospects by shifting focus away from the pitch. Once you get them to talk casually, they’re more likely to open up to your next questions.
General discovery questions
General discovery questions are exactly what they sound like. Their purpose is to understand your prospect’s current situation, needs, priorities, and context before you suggest a solution.
They fill any gaps in your lead research by tapping into important details:
- Could you walk me through how your team currently handles [problem area]?
- What goals is your team focused on this quarter?
- Why are you considering [a competitor solution] for that?
- How are things going with [their current vendor]?
- How much of a say does your team have in decisions like this?
- What’s been the biggest challenge to solving [problem] so far?
General discovery questions help you map out the best way to tailor your pitch for this person. You learn about their pain points, priorities, decision-making processes, and biggest challenges, so there’s no need to guess. Asking these questions also shows the prospect that you care about them.
Qualifying or prospecting questions
You can use qualifying questions if you need to find out the lead’s buying intent, urgency, authority, and budget:
- What attracted you to [solution]?
- How big of a priority is fixing this, compared to other goals?
- What budget could you possibly allocate for solving this problem?
- When you consider buying a new [product category] for your team, what other decision-makers will have to approve this purchase?
- What happened when you tried solving this in the past?
- What kind of timeline are you working with to get [solution] in place?
Prospecting questions help you make certain you’re talking with the right person: someone who can become an actual customer. You’ve probably scored your leads in advance, but it never hurts to double-check as things might’ve changed within the company (and information found online may be wrong).
Impact or benefit-driven questions
You’re talking with an actual decision-maker, and you already know their current situation. However, people buy on emotions, not logic. Impact questions can get them to emotionally buy into the outcome of adopting your product.
Here are a few impact questions:
- If you could solve this issue tomorrow, what would that mean for your team?
- What would improving this process free you up to focus on?
- How would fixing this affect your revenue or KPIs?
- What would happen in the next three months if you couldn’t solve this issue?
- If this works exactly as you want, how would things change in your company?
- What kind of results would make this a no-brainer for your leadership?
These questions shift the focus to the benefits of your solution. Instead of waiting for a pitch, the prospect will start selling themselves on the value of your product.
Near future questions
If a prospect appears hesitant, you can strengthen the emotional appeal of your solution with questions about the near future:
- Let’s say this problem’s off your plate. What does that free you up to do next?
- How would your typical day look if this ran the way you wanted?
- What would the ideal version of this process look like for your team?
- If your current roadblocks disappeared, what’s the first thing you’d go after?
- What does ‘done right’ look like for you six months from now?
- If nothing stood in your way, how would you build this from scratch?
These might seem like you’re asking the lead to merely fantasize about the future. But in truth, these questions help people visualize outcomes and make them more open to change as their mindset shifts from status quo to possibilities.
Clarifying questions
Clarifying questions excel at focusing the conversation and digging deeper into a specific topic of the sales call. If all’s gone well, the lead’s hopefully given you a decent amount of new information to work with, but there’s always room to improve your understanding.
Here are some clarifying questions you might try:
- When you say “it’s a bit messy,” can you give me an example of what that looks like day-to-day?
- You mentioned your current tool is not reliable. What kind of issues are you seeing?
- Can you walk me through what happened the last time you tried to solve this?
- What exactly do you mean by “we’re not ready yet”: timing, budget, or something else?
- You said leadership was hesitant. What’s their biggest concern right now?
- Just so I understand, when you say “we want to improve efficiency,” what’s the metric or outcome you’re targeting?
Ask clarifying questions to find important details that you need to fine-tune your pitch. One or two clarifying questions show that you care, but too many of them can tire and annoy prospects.
Objection-handling questions
Prospects voice objections when there’s something specific they ended to be sold on. After all, they’re still on the line and haven’t hung up on you.
Discover the true obstacles with objection-handling questions:
- May I ask why you feel like it’s bad timing?
- When you say it’s too expensive, what are you comparing it to?
- Sounds like you’re happy with your current setup. What’s working well for you?
- What reservations do you think other stakeholders might have?
- What would need to change for this to be a priority for your team?
- Why do you think this tool will be challenging to master?
With these questions, you can keep the conversation going when the lead pushes back. Instead of arguing, you further explore their situation and discover something you can use to persuade them.
Closing questions
When it’s time to wrap up the call, do it with closing questions:
- How are you feeling about what we’ve discussed so far?
- What concerns should we tackle before moving forward?
- What does your ideal next step look like from here?
- What would you need to see to feel fully confident in saying yes?
- What would make this a clear win for your team?
- If we got started this month, what would that rollout look like on your end?
Closing questions test commitment without pressure. They help gauge where the prospect stands, reveal any last-minute concerns, and give both sides clarity.
Post-closing questions
Post-closing questions help lock in commitment after the prospect says “yes.”
Here are some examples:
- What does a successful first 30 days look like for you?
- What’s the best way to keep communication flowing?
- What’s the one thing you’re most excited—or nervous—about with this rollout?
- Anything we should avoid, based on past vendor experiences?
- How do you want to measure success during the rollout?
- What should we know about your internal processes before we start?
These questions show you’re still engaged after the sale and set the tone for smooth customer onboarding.
Relationship expansion questions
After wrapping up the sales conversation, you can still take a moment to explore new opportunities within the prospect’s organization or test the waters for a cross-sell or upsell opportunity.
That’s what relationship expansion questions do:
- What’s one area we haven’t touched on yet that could use support?
- What else is your leadership team focused on that we might be able to support?
- If we could remove another bottleneck for you, where would you want us to start?
- What’s next on your roadmap that we should be aware of?
- What other tools or teams would you need this to integrate with?
- What other initiatives are happening this year that connect to this problem?
These questions uncover unmet needs within the company, offering more opportunities to grow your deal.
How to create a good line of questioning
To hook prospects from the start and keep their interest, you need to ask your questions with the correct technique. It’s just as important as the right order to form a strong line of questioning.
Start broad, then narrow down
Ask general questions at the beginning of your discovery calls. Then proceed with more specific ones.
For example, you can start by asking, “How are you currently approaching [area/problem]?”
Then narrow down with: “What have you tried so far to fix that?” or “What’s been the biggest challenge with that approach?”
Listen more than you speak
Sales calls are just as much about listening as they are about talking.
Don’t rush prospects if they fall silent. Allow them to pause and let them talk more. Echo the key words from their response in your next question. For instance, if they mentioned issues with their current vendor, ask what kind of issues they’re having.
Show curiosity
When your prospect drops a sudden insight, follow up on it.
For example, if they bring up a recent change in their organizational structure, ask what triggered it. This kind of inside information might hold the key to closing a deal.
Gauge the lead’s interest
This is much easier done on video calls, where you can read the prospect’s tone, facial expression, and body language.
When they lean in, ask a deeper follow-up question. If they seem distracted or impatient, ask whether it would be better to continue the conversation another time.
Ask about evaluation criteria
It’s vital to find out what they would consider a success, so that you can explain how your product can do exactly that.
Word your question to sound something like this: “When you evaluate products and services that do [X], what outcomes matter most?”
Ask about the budget
As you go through lead qualification, you must make certain they can afford your product. Be respectful and subtle, asking something like, “How do you usually go about budgeting for new solutions?”
Establish the next set of steps
Before wrapping up, you should get the prospect to agree to the next step, such as a follow-up call or a sales demo. For that, it’s okay to ask closed-ended questions like, “Would it make sense to set up a follow-up call?” or “Does next Wednesday at 10 a.m. work for you?”
Example line of questioning
A line of questioning for a cold call might include three steps that gradually build engagement:
- Initial question: “How do you currently handle customer onboarding?”
- Follow-up question: “What kind of delays or bottlenecks do you see in this process?”
- Final question: “If you could change one thing about it tomorrow, what would that be?”
From the final question, you can transition to your pitch, explaining exactly how your product can fix that “one thing” the prospect most wants to change.
Fitting open-ended questions into your scripts becomes easier with practice. However, take care to avoid certain things from the start.
Common mistakes to watch out for
Mistakes during a B2B sales discovery call could cost you a deal.
Here are a few pitfalls you might want to keep in mind when asking questions.
Accidentally asking a closed-ended question
Sales calls are challenging because they’re happening in real time, and you need to think on the spot.
That’s why you might accidentally ask “Are you happy with your current tool?” instead of “What’s working well with your current tool?”
Unfortunately, the first question can be answered with a yes or no, and can kill momentum or shut the door early.
To avoid this mistake, practice your call as many times as you need to get it right every time.
Asking too many “why” questions
“Why” questions demand special caution because they can easily come off as blaming the prospect, especially if you accidentally use the wrong tone.
Think: “Why did you choose this tool?” or “Why aren’t you looking for an alternative?”
Replace “why” with “how” or “what” whenever possible.
- What led to that decision?
- How did that impact your team?
An occasional “why” question is okay, as long as it doesn’t sound accusatory.
Skipping follow-up questions
Follow-up questions can fall victim to the human tendency to cut corners.
If a prospect says, “We’re frustrated with our current system,” and you simply move on, you’ve missed an opportunity.
Instead, ask a follow-up question:
- What specifically frustrates you about it?
- How does that affect your daily work?
The skill of jumping at the opportunity to learn important details comes with practice. That means you’ll have to make lots of, or at least rehearse, actual sales calls to get this part right.
Asking too many questions
Rapid-fire questions overwhelm people and turn discovery calls into interrogations. A good rule of thumb is to ask five to seven questions during a call:
- One or two rapport-building or general discovery questions
- Two to three prospecting, benefit-driven, or objection-handling questions
- One or two closing questions
It’s okay to go slightly above that with clarifying questions about what the prospect just told you, but aim to keep the total number under ten.
In cold emails, you should keep questions shorter than in calls, and ask no more than one question per message.
Asking generic questions
Generic questions like “Tell me more about your business” get vague, useless answers. Instead, fine-tune your questions to extract exactly the info you need, such as “How are you tracking performance across remote teams right now?”
By making your questions more specific, you can ask fewer of them and still get a solid grasp of the lead’s situation and sales qualification.
Using the wrong tone
Overly formal or robotic phrasing often comes off as inauthentic or confrontational, killing trust. Aim for a friendly tone and simple, everyday language.
Wrong tone (too formal and cold): “Can you elaborate on the deficiencies of your CRM system?”
Better: “What’s not working for you with your current setup?”
Failing to give enough time for an answer
After asking your question in a phone or video conversation, take a pause.
Silence is your friend.
It means the prospect is processing your question and wording their answer. If you fire off your next question too fast, you sound worked up and like you’re not paying attention.
Failing to keep questions on topic
A question that comes out of nowhere feels off. Connect it to what the prospect has just said: “You mentioned delays in approvals. What causes that?”
This last part is one of the hardest to nail, as you’ll have to adjust questions on the go. Luckily, our AI sales assistant can help you quickly master the skill of asking open-ended questions.
How AiSDR helps you ask smarter questions
AiSDR does more than just automate outreach.
You can use AiSDR to find and conversationally qualify leads who match your ideal customer profile.
This means you can configure the AI to ask meaningful open-ended questions that surface a lead’s pains, priorities, and level of urgency.
Whether it’s through emails, LinkedIn messages, or cold call scripts, AiSDR asks questions that aren’t just filler. They’re strategic, based on an analysis of firmographics, buyer signals, and social activity.
The cold call script generator will even include tailored, insight-driven questions you can use as talking points to uncover objections and guide the conversation.
