Most sales reps think discovery is about asking questions. They’re wrong.
Real B2B sales discovery is an excavation. You’re not just collecting information; you’re uncovering the motivations, fears, constraints, and dynamics that will either make or break your deal.
The difference between reps who consistently hit quota and those who struggle often comes down to this single skill: asking sales discovery questions that reveal what prospects actually need, not just what they say they want.
In fact, top performers’ discovery calls are 76% longer than those of average performers.
Why Good Discovery Questions Drive Better Sales Outcomes
Good sales discovery questions do more than gather information; they fundamentally change the trajectory of your deal by building trust, uncovering hidden needs, and creating urgency that didn’t exist before the conversation.
First, you’re demonstrating expertise and genuine interest in your prospect’s business, which separates you from competitors who launch straight into product pitches.
Second, you’re gathering the intelligence needed to craft a solution that actually fits their unique situation, reducing objections later in the sales cycle.
Third, you’re helping prospects clarify their own thinking—often, they haven’t fully articulated their challenges until you ask the right questions.
The data backs this up. Sales teams that excel at discovery consistently see higher win rates, larger deal sizes, and shorter sales cycles because thorough B2B sales discovery eliminates surprises. You know the stakeholders, the budget reality, the decision criteria, and the competition before you present. You know because they told you.
10 Questions You Should Ask in the Discovery Phase
The ideal number of questions to ask on a discovery call is between 11 and 14 targeted questions, according to Gong’s analysis of over 519,000 B2B sales call recordings; however, the difference between average and exceptional B2B sales discovery isn’t about asking more questions. It’s about asking the right ones.
We listed the 10 discovery questions you should be asking:
“What specific goals are you hoping to achieve this quarter?”
This sales discovery question cuts through the noise and gets straight to what matters most right now.
You’re aligning your solution with your prospect’s immediate priorities and business rhythm by focusing on quarterly goals.
This question uncovers whether they’re thinking about growth, efficiency, cost reduction, or something else entirely—giving you the context to position your offering as a bridge to their desired outcomes.
The beauty of this question is that it reveals both ambition and urgency. When prospects share their quarterly targets, they’re essentially giving you their success metrics. You’ll understand what they’re being measured on, which means you can demonstrate ROI in terms they actually care about.
Pro tip: Listen for the difference between “nice-to-have” goals and mission-critical objectives. The language they use—words like “must,” “critical,” or “we’re being evaluated on this”—tells you everything about purchase urgency.
“What’s slowing you down right now?”
This is one of the most powerful B2B sales discovery questions because it reveals pain in real-time. Instead of asking about hypothetical problems, you’re focusing on active friction—the obstacles your prospect is wrestling with today.
Learning to uncover your prospects’ pain points is fundamental to success. This question surfaces operational bottlenecks, resource constraints, technology gaps, and process inefficiencies that are costing them time and money.
What makes this question so effective is its simplicity. The casual phrasing makes prospects feel comfortable sharing frustrations they might not disclose in response to more formal questions. You’ll often hear about problems they haven’t even fully articulated to themselves yet, which positions you as a trusted advisor rather than just another vendor.
Pro tip: After they answer, resist the urge to immediately pitch your solution. Instead, ask “How long has this been an issue?” to gauge pain severity and decision urgency.
“What happens if this challenge isn’t resolved?”
This sales discovery question transforms abstract problems into concrete consequences. It forces prospects to confront the actual cost of inaction—lost revenue, missed opportunities, SDR burnout, competitive disadvantage, or regulatory risk.
When buyers articulate these consequences themselves, they’re building their own business case for change. This question is particularly powerful in B2B sales discovery because it shifts the conversation from features and pricing to business impact.
You’re no longer selling a product; you’re helping them avoid a future they don’t want. The emotional weight of consequences often outweighs the logical appeal of benefits, making this a critical inflection point in discovery.
Pro tip: Listen for phrases like “we can’t afford to” or “we’re at risk of losing”—these signal high-stakes scenarios that justify premium pricing and expedited timelines.
“What have you tried so far to fix the problem?”
This question is intelligence gold. It reveals your prospect’s problem-solving history, budget allocation, internal capabilities, and what hasn’t worked. You’ll learn about competing solutions they’ve tested, workarounds they’ve built, and why previous attempts failed.
This information helps you avoid suggesting something they’ve already rejected and positions your solution as the missing piece they haven’t found yet.
Understanding their previous attempts also shows you how sophisticated they are as buyers. Have they tried quick fixes, or have they invested in comprehensive solutions? This tells you about their commitment level and helps you calibrate your approach.
You’ll also discover if they have sunk costs or existing vendor relationships you need to navigate.
Pro tip: If they’ve tried multiple solutions without success, probe deeper: “What did those approaches miss that you’re looking for now?” This helps you differentiate immediately.
“Who else is involved in making this decision?”
In B2B sales discovery, understanding the buying committee is non-negotiable. This question maps the decision-making landscape—the influencers, approvers, end-users, and potential blockers.
You need to know if you’re talking to the economic buyer, a champion, or just someone doing preliminary research. Each role requires a different conversation and different information. This sales discovery question also uncovers the dynamics of their organization.
You’ll learn about departmental priorities, competing agendas, and who holds veto power. Armed with this information, you can build a multi-threaded strategy that addresses each stakeholder’s unique concerns and motivations, dramatically increasing your win rate.
Pro tip: Don’t just collect names and titles. Ask, “What’s most important to [title] when evaluating a solution like this?” to understand each stakeholder’s individual decision criteria.
“How does this issue affect other departments or teams?”
This question expands the scope of impact beyond your primary contact’s world. In complex B2B environments, problems rarely stay contained—they ripple across organizations.
When you uncover these cross-functional consequences, you transform a departmental purchase into an enterprise priority, often unlocking larger budgets and executive sponsorship.
This sales discovery question also helps you identify additional champions and stakeholders you should be engaging. If the marketing team is struggling because of a sales operations problem, you now have potential allies who can advocate for your solution. You’re building a coalition of supporters who all benefit from solving the issue.
Pro tip: Use this information to craft a business case that speaks to multiple departments. When you can show how your solution creates value across silos, you become strategic rather than tactical.
“What are your expectations from a solution like ours?”
This question reveals what “good” looks like from your prospect’s perspective. You’ll discover their must-haves versus nice-to-haves, their assumptions about what’s possible, and potential misconceptions you need to address.
Sometimes prospects have expectations you can’t meet—better to know that now. Other times, they’re expecting far less than you can deliver, giving you an opportunity to exceed expectations and create wow moments.
In B2B sales discovery, managing expectations early prevents disappointment later. This question also helps you understand if they’ve done their homework about solutions in your category, or if they need more education about what’s possible. Their answer guides how you structure your presentation and proposal.
Pro tip: If their expectations seem unrealistic, don’t immediately shut them down. Instead, ask, “Help me understand what would happen if you achieved that?” to uncover the underlying need.
“What would success look like six months after implementation?”
This sales discovery question gets prospects to visualize a positive future state with your solution in place. You’re learning about their definition of success in concrete, measurable terms.
Do they measure success by revenue growth, cost savings, time efficiency, user adoption, or customer satisfaction? Their answer becomes the foundation of your value proposition and success plan.
This question also separates dreamers from serious buyers. Prospects who can articulate specific success metrics have thought through the change management and have stakeholder buy-in.
Those who give vague answers might need more time and nurturing. You’re qualifying both the opportunity and the timeline.
Pro tip: Document their success metrics verbatim and reference them throughout the sales cycle. In your proposal, show exactly how you’ll help them achieve the outcomes they described.
“What’s been the biggest frustration with vendors in the past?”
This is your roadmap for differentiation. Past vendor frustrations reveal deal-breakers and must-haves that might not surface otherwise.
Maybe they’ve been burned by poor implementation support, surprise costs, unresponsive customer service, or overpromised features. When you understand these pain points, you can proactively address them and position your company as the antidote to their bad experiences.
This B2B sales discovery question also builds trust. By asking about frustrations, you’re acknowledging that vendor relationships don’t always go smoothly and demonstrating that you want to do better.
Prospects appreciate the candor, and it opens the door for honest conversations about concerns they might have about working with you.
Pro tip: After they share, explicitly address how your company handles that issue differently. “I hear you. Here’s specifically how we approach implementation to avoid that problem…”
“What would make this a no-brainer for you to move forward?”
This is perhaps the most direct sales discovery question you can ask—and one of the most valuable. You’re essentially asking prospects to tell you how to close the deal. They’ll reveal price expectations, decision criteria, timing considerations, and any remaining concerns.
Some will tell you exactly what they need to see in a proposal; others will surface objections you didn’t know existed.
This question works because it frames the conversation around removing obstacles rather than pushing a sale. You’re positioning yourself as a partner trying to make their decision easier, not a vendor trying to extract a signature. The responses you get will help you craft a proposal that speaks directly to their decision-making process.
Pro tip: Use this question near the end of discovery, once you’ve built rapport. If they can’t answer it, they’re not ready to buy—which is valuable information that saves you from wasting time on an unqualified opportunity.
Avoiding Common Mistakes in Discovery Calls
Even experienced sales professionals fall into predictable traps during B2B sales discovery. Recognizing these mistakes is the first step to eliminating them from your process.
The interrogation trap: Rattling off sales discovery questions one after another without building on responses makes prospects feel like they’re being interviewed rather than having a conversation.
Discovery should feel collaborative, not like an inquisition. After each answer, acknowledge what you heard, dig deeper with sales follow-up questions, and share relevant insights that demonstrate you understand their world.
Premature solution mode: The moment a prospect mentions a problem, many salespeople jump into pitch mode. Resist this urge.
If you present solutions before fully understanding the situation, you’ll miss critical context and appear more interested in selling than helping. Complete your discovery before positioning your solution.
Talking more than listening: Your prospect should be talking 60-70% of the time during discovery. If you’re dominating the conversation, you’re gathering information too slowly and missing valuable insights.
Your job is to ask thoughtful questions, listen actively, and probe deeper—not to showcase your product knowledge prematurely.
Skipping the painful questions: Many salespeople avoid asking about budget, decision-making authority, or competition because they fear it seems pushy. But avoiding these topics leads to stalled deals and wasted time.
Frame these sales discovery questions professionally: “To make sure I’m proposing something realistic, what budget range have you allocated for this?” Professional buyers expect and respect direct questions.
And if you ever face the “You’re pretty expensive” objection, remember this:
Failing to confirm understanding: Never assume you understood correctly. Paraphrase what you heard and confirm: “So if I’m hearing you right, your biggest concern is… Did I get that right?”
This prevents miscommunication and shows prospects you’re truly listening, building trust in the process.
Not taking detailed notes: You won’t remember everything. Take thorough notes during discovery, or better yet, record the call (with permission). These notes become the foundation for your proposal, follow-up emails, and internal discussions.
They’re also invaluable when you need to bring new stakeholders up to speed later in the sales cycle.
Bottom Line
The stakes are too high for surface-level discovery.
Every hour spent on an unqualified deal is an hour you could have invested in a winner. Every misunderstood requirement becomes an objection later. Every missed stakeholder becomes a blocker who appears out of nowhere to derail your deal.
But when you truly get what drives your prospect’s business, solving their problems becomes the easy part. That’s when selling stops feeling like convincing and starts feeling like collaborating.
