The difference between a meeting that goes somewhere and one that stalls out often comes down to the questions you ask. Closed questions — "Are you happy with your current vendor?" — invite one-word answers and kill momentum. Open-ended questions invite the prospect to talk, reveal what actually matters to them, and give you the information you need to close.
Field reps have an advantage here. When you're sitting across from someone, you can read body language, notice hesitation, and follow up in real time. You're not competing with their inbox or hoping they'll respond to a follow-up email. You have their attention — but only if you use it well.
This article covers 20 open-ended sales questions organized by where they fit in a typical field sales conversation: building rapport, uncovering needs, qualifying the opportunity, and moving toward a close. Each question is designed for face-to-face meetings where you can see the prospect's reaction and adapt accordingly.
Open-ended questions can't be answered with a simple yes or no. They require the prospect to think, explain, and share context. The difference matters:
The first invites a one-word answer. The second invites a conversation.
Effective open-ended questions typically start with:
The goal isn't to ask questions for the sake of asking. It's to uncover information that helps you understand whether this prospect is a fit, what they actually need, and how to position your solution in terms that matter to them. The open-ended questions examples below show how to do this at each stage of a field sales conversation.
Inside sales reps work with limited signals — tone of voice, maybe video if they're lucky. Field reps sit across the table. You can see when a question lands, when the prospect leans in, when they hesitate before answering.
This creates opportunities that don't exist over the phone:
You can go deeper. When a prospect gives a surface-level answer, you can follow up immediately: "Tell me more about that." In person, they're more likely to elaborate than they would on a call.
You can read the room. Body language reveals what words don't. If they tense up when you ask about budget, you know to tread carefully. If they light up when discussing a specific challenge, you know where to focus.
You can adapt in real time. A phone script is linear. A field meeting is dynamic. The right open-ended question at the right moment can take the conversation somewhere you didn't plan — often somewhere more valuable.
You have undivided attention. They're not checking email or muting themselves to talk to someone else. When you ask a thoughtful question, they're present with you in a way that rarely happens remotely.
The questions below are designed for this context — face-to-face meetings where you have the opportunity to listen, observe, and respond.
Not every question fits every meeting. Use what works for your situation.
The first few minutes set the tone. These questions establish that you're interested in them as a person and a professional, not just running through a pitch.
1. "What's top of mind for you right now when it comes to [relevant area]?"
This question surfaces their priorities immediately. You're not assuming anything about why you're there — you're inviting them to tell you what matters most. The answer tells you how to frame the rest of the conversation.
Field tip: Watch their body language. If they give a vague answer or seem distracted, they may not have an urgent need. If they lean in and give specifics, you've hit on something that matters.
2. "I noticed [something specific in their office/facility] — can you tell me more about that?"
Being on-site gives you context no phone call can. An industry award on the wall, a whiteboard full of project notes, a piece of equipment you recognize — these are conversation starters that show you're paying attention and give the prospect something concrete to talk about.
Field tip: Arrive a few minutes early and observe the lobby, their office, or the facility. Look for awards, photos, product displays, or anything that signals what they care about.
3. "Since I'm here, would you mind giving me a quick tour of your operation?"
This is a field-only question. Walking together breaks the formality of sitting across a desk. People open up more when they're moving, and showing you around puts them in the expert role — which builds trust.
Field tip: Let them lead. Ask simple questions as you walk — "How long have you been in this space?" or "How big is the team?" Keep it light. The real discovery questions come later.
4. "What's changed in your business recently that's affecting how you work?"
This question surfaces recent shifts — new leadership, lost deals, growth pressure, market changes — that create urgency. Change often means pain, and pain means opportunity.
Field tip: If they mention a recent change, probe deeper. "Tell me more about that" or "How has that affected your team?" That's often where the real pain lives.
Discovery is where field sales shines. These questions help you understand what the prospect actually needs — not what they think they need, and not what you want to sell them.
5. "What's the most challenging part of your current [process/approach]?"
Direct and effective. This question surfaces pain points without assuming you know what they are. Let them tell you what's broken.
Field tip: When they answer, watch where their eyes go. If they glance at a specific area of the office or toward a colleague's desk, there's a story there. Follow up: "I noticed you looked over there — is that related?"
6. "Can you show me how your team currently handles [specific area]?"
Don't just ask them to describe it — ask to see it. This is a field-only advantage. Watching a process in action reveals inefficiencies, workarounds, and pain points they've stopped noticing because they're so used to them.
Field tip: Take notes on what you observe, not just what they say. "I noticed your team had to switch between three screens to complete that — is that typical?"
7. "If you could change one thing about what I just saw, what would it be?"
After you've observed their process, this question lands harder. They're not describing a hypothetical — they're reflecting on something you both just witnessed. It makes their answer more concrete and actionable.
Field tip: Reference something specific you observed. "You mentioned that step takes longer than it should — if you could fix that, what would it save you?"
8. "What happens when [their current process] breaks down? Can you give me a recent example?"
Asking for a specific example forces them to go beyond generalities. You'll hear real stories with real consequences — time lost, customers frustrated, deals missed — that you can reference later.
Field tip: Listen for emotion. When they describe a recent failure, note their tone and body language. That's where the real pain is.
9. "How is this problem affecting your bottom line — or your team's day-to-day?"
This question quantifies the pain. Vague problems get vague priority. But when they say "We're losing two hours a day to this" or "It's costing us deals," you have the foundation for a business case.
Field tip: If they give a general answer, ask for specifics. "Roughly how much time does that cost per week?" or "What does that mean in lost revenue?" Numbers make the problem real — and make your solution easier to justify.
10. "What have you tried before to address this? Can you show me what didn't work?"
Asking to see failed attempts — old tools, abandoned processes, dusty equipment — gives you insight no phone call can. You'll understand why they failed and how to position your solution differently.
Field tip: If they show you an old solution that didn't work, ask: "What would have made this successful?" Their answer tells you exactly what they're looking for this time.
Not every meeting becomes a deal. These questions help you understand whether this prospect is a real opportunity — and what it will take to move forward.
11. "Who else here should be part of this conversation? Could we grab them for a few minutes?"
This is a field-only power move. Instead of asking for a future meeting with stakeholders, ask to include them now. You're already on-site — make the most of it.
Field tip: If they hesitate, offer a low-commitment option: "Even a quick five-minute intro would help me understand their perspective." People are more likely to say yes to a brief interruption than a scheduled meeting.
12. "How do decisions like this typically get made here? Who would I need to meet with?"
Understanding their process helps you navigate it. You'll learn who holds budget, who influences the decision, and what hoops you'll need to jump through — so you can plan your next steps accordingly.
Field tip: If they're vague, ask: "Walk me through the last big purchase like this — how did that get approved?" Real examples reveal the real process.
13. "What would need to be true for you to move forward — and what can I show you today that would help?"
This question surfaces criteria AND offers to address them on the spot. You're there — if they need a demo, a reference, or more detail, you can provide it immediately rather than scheduling another touchpoint.
Field tip: Come prepared with materials, case studies, or a demo you can pull up on the spot. Being ready to answer "Can you show me?" is a field rep advantage.
14. "What's driving the timeline here? Is there an event or deadline I should know about?"
Urgency determines priority. If there's a hard deadline — a board meeting, a contract renewal, a seasonal push — you know how to pace the deal. If there's no timeline, you may be educating rather than selling.
Field tip: Watch how they answer. Confident and specific ("We need this done before Q3") means real urgency. Vague and hesitant ("Sometime this year, maybe") means you're early in their process.
15. "To make sure I'm proposing something realistic — what budget range are you working with?"
Budget questions can feel awkward. Framing it as "making sure I propose something realistic" positions you as helpful, not pushy. If they hesitate, offer a range: "Companies like yours typically invest between $X and $Y. Does that align with what you're thinking?"
Field tip: In person, you can read hesitation that you'd miss on a call. If they pause or shift uncomfortably, pivot: "We can figure out the exact numbers later — I just want to make sure I'm in the right ballpark."
The end of the meeting determines what happens next. These questions surface remaining concerns, confirm alignment, and set up clear next steps.
16. "Based on what we've seen and discussed today, what concerns do you have about moving forward?"
Referencing what you've "seen" anchors the conversation in shared experience. You walked their floor, watched their process, met their team. This makes objections more concrete and easier to address.
Field tip: If they raise a concern, address it on the spot if you can. "Let me show you how we've handled that for other customers" — and pull up a case study or demo right there.
17. "I'm sensing some hesitation — what's holding you back?"
Being face-to-face means you can read hesitation that inside reps miss. Use this question when body language tells you something words aren't. The answer is often more honest than you'd expect.
Field tip: This question only works if your tone is genuinely curious, not accusatory. Lean back, soften your voice, and give them space to answer honestly.
18. "Based on everything you've shown me today, which of these problems do you see our solution fixing first?"
This asks the prospect to prioritize — and grounds the conversation in what you've observed together. It's a soft close that confirms alignment and often reveals which pain point matters most.
Field tip: If they point to something specific you saw during the walkthrough, you've found your hook for the proposal.
19. "What can I do while I'm here to help you move this forward internally?"
You're on-site — use it. Maybe that means meeting another stakeholder, leaving materials with a specific person, or doing a quick demo for someone who just walked by. This question surfaces what would actually help, not what sounds polite.
Field tip: Ask what they'll need to sell this internally. "Do you need a one-pager, a pricing summary, or something you can forward to your team?" Give them the ammunition to champion your solution.
20. "Before I leave — what's the one thing I should follow up on first?"
This is better than "what's the next step?" because it's action-oriented and acknowledges you're about to leave. It forces them to prioritize and gives you a clear, immediate action item.
Field tip: Write their answer down in front of them. It shows you're taking it seriously and creates a subtle commitment on their end.
Asking open-ended questions is only half the equation. How you ask — and what you do with the answers — matters just as much.
Going too deep too fast. Jumping straight into budget and timeline questions before building rapport kills momentum. Warm them up first.
Not actually listening. If you're thinking about your next question while they're answering, you'll miss what matters. Take notes, make eye contact, and follow up on what they actually said. Using a voice-to-CRM tool after meetings can help — you focus on listening during the conversation, then capture details via voice note on the way out.
Asking "why" too often. "Why did you do that?" can feel accusatory. Soften it: "What was the thinking behind that decision?"
Accepting surface-level answers. When they give a vague response, dig in: "Tell me more about that" or "Can you give me an example?" The gold is usually one question deeper.
Talking more than listening. Top-performing reps typically spend more time listening than talking. If you're doing most of the talking, you're pitching, not discovering.
The best field reps don't pitch — they listen. Open-ended questions are the tool that makes listening productive. They turn one-sided presentations into conversations, surface information that closed questions miss, and help you understand what the prospect actually needs rather than what you assume they need.
The 20 questions above are a starting point. The real skill is knowing when to use them, how to follow up based on what you hear, and when to go deeper versus when to move on. That comes with practice — but it starts with asking better questions.
Ready to make sure the insights from those conversations actually make it into your CRM? Request a demo and see how Leadbeam helps field reps capture meeting details without the data entry.
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