Tips for Crafting Sales Questions

Top reps ask 4x more implication questions than average ones. Here’s why SPIN Selling still works. Most reps jump straight into pitch mode. They ask a few surface questions, then start talking features. That’s not selling. That’s presenting. SPIN flips the script. It gets the buyer to sell themselves. Start with Situation questions. Learn their current state, but keep it short. Experienced reps ask fewer of these than you’d expect. Move to Problem questions. Uncover what’s not working. Where they’re stuck. What’s costing them time or money. This is where small deals get won. But for complex sales, you need more. That’s where Implication questions come in. Show the consequences of inaction. What does this problem cost them? How does it affect other areas? What’s the revenue impact? Top performers ask these 4x more than average reps. They build urgency without being pushy. Finally, Need-Payoff questions. Let the buyer articulate the value. How would solving this help? What would the impact be? Why is this important? When they say it, they believe it. Here’s the key insight: Buyers don’t just want you to solve their problems. They want to understand why solving them matters. SPIN gives you the framework to guide that conversation. Not through charm. Not through pitch decks. But through the right questions in the right order. Save this framework. Use it on your next discovery call. Watch how fast urgency builds.

One question can close more deals than your best pitch deck. Last month, I watched a $250K deal flip in a single sentence. The rep didn’t share a slide. He asked one question and the buyer completely reframed the problem. Most reps obsess over the answers they’ll give. Elite reps obsess over the questions they’ll ask. A well-placed question can: Expose an unseen risk Reframe the problem in higher-stakes terms Make the buyer realize the cost of doing nothing We started tracking the impact of this shift. Just training reps to ask better questions increased our win rate by 27% in 90 days. Examples: ❌ Instead of: “What challenges are you facing?” ✅ Ask: “If this problem is still here in 6 months, what does that cost your business?” ❌ Instead of: “What would success look like?” ✅ Ask: “If you could only fix one metric this quarter, which one changes everything?” Great selling isn’t about pushing harder. It’s about pulling the truth to the surface. 💬 What’s one question you’ve asked that instantly changed a deal?

The Art of Asking Questions in Sales In sales, success doesn’t come from delivering a perfect monologue of product data. It comes from asking the kinds of questions that disrupt the status quo, uncover unmet needs, and inspire action when “good enough” feels safe. Research from IQVIA shows that 50–70% of pharmaceutical sales calls end with no action. Not because the products lack value, but because we often fail to uncover why the prescriber should care enough to change. My First Lesson in the Power of Questions The first model I was ever trained on was SPIN Selling, which stands for Situation, Problem, Implication, Need-Payoff. At the time, I thought it was just a framework to memorize. But I quickly learned it was really about guiding customers to discover answers for themselves. I still remember an early call with this concept: instead of leading with product features, I asked about the situation of patients, uncovered problems with adherence, explored the implications of delayed outcomes, and then asked: “How would it change your practice if those barriers were removed?” The physician paused, leaned in, and said: “That would make all the difference.” He wasn’t convinced by me, he had convinced himself. Our trainers used to joke that their goal was to give us “SPIN in our spine.” Since I learned the model over 30 years ago, I’d say they succeeded. Why It Still Matters Today- Questions challenge inertia. They spark curiosity where routine has taken hold. Questions reveal patient impact. They shift the focus from “my drug” to “their patients.” Questions build credibility. Data informs, but questions engage. The Bottom Line Before your next call, prepare not just your talking points, but your asking points. The best reps don’t pitch. They probe. They don’t push products. They find problems and solve them. Because the goal of sales isn’t to be a “product pusher.” It’s to be a problem finder and a problem solver.

Two of the WORST questions you can ask on a sales demo: "Does that make sense?" "What questions do you have?" Those don't sell. They just fill the silence. ✅ 10 demo questions that move deals forward: "How are you doing [X workflow] today?" (Ask right before you demo the feature → creates contrast between today vs your product.) "How does that compare to how you're doing it now?" (Ask right after the demo → reinforces contrast, locks in value.) "To what extent do you envision this being useful in your situation?" (Gets them imagining themselves using your product.) "How do you see your team using that?" (Solid for decision makers who buy but don't use.) "To what degree is this resonating so far?" (A mid-point pulse check. Much better than "any questions?") "To what extent do you see that solving [problem they shared earlier]?" (Closes the loop between pain → solution.) "What benefits do you see showing up in your world from this?" (Gets them to voice the benefits out loud.) "Where do you want to double-click with a few questions?" (Same intent as "any questions?" but phrased as a pattern interrupt.) "It seems like that resonated—what challenge in your business makes that hit home?" (When you strike a chord, this uncovers gold.) "It seems like this isn't resonating—where am I missing the mark?" (When you're off track, this pulls you back on track.) The difference? The first two questions put the spotlight on you. The 10 above put the spotlight on them. That's where selling happens. P.S. These 7 strategies will help you CLOSE more deals in a GTM crisis: https://lnkd.in/d_DkYTSH

Stop asking discovery questions like - What's your budget? - What's your timeline? - Who's the decision maker? - What are your decision criteria? - Are you looking at other solutions? They make prospects feel interrogated. ↳ And add zero value throughout the sales process. Start asking discovery questions like • If we solved (insert problem), what would be the impact for you & your team? • What's an ambitious but attainable timeline for go-live? • Are we okay missing that date - and what would be the consequences if we do? • Who else needs to be involved to get this on the radar of the executive team? • What are must-haves vs. nice-to-haves for you when it comes to choosing a new solution? • Have you taken a look at what else is out there? 2 key takeaways: 1. Discovery is not an interview. ↳ It's a process of guiding the buyer in their decision process. 2. Buyer experience is a differentiator. ↳The more value you add during the sales cycle, the more deals you will close. What else would you add?👇

Average sellers ask questions to get information. Standout sellers ask questions to create emotion. Here are 3 examples to help you make this shift ⤵ 1/ Confidence: This feels like, "Oh wow, they really know their stuff." → For prospects feeling in over their head / don't know where to start. Q: “Most people overlook X, which always turns out to be key. So let's start there — to what extent have you already explored X?” 2/ Empathy: This feels like, "Finally, someone who gets me.” → For prospects who are standoffish, or misunderstood. Q: “Is there something about this issue that others you’ve explained it to just don’t seem to understand?” 3/ Calm: This feels like, “Ah, I can finally catch my breath.” → For prospects feeling anxious, like they’re always falling behind. Q: “Oh wow, you’re further ahead than what I’m used to seeing. What have you already tried, that seems to be working?” We could go on, but the idea is to always ask: 1/ What’s happening in my prospect’s life? (e.g. layoffs inside their team) 2/ What negative emotion is this causing? (e.g. anxiety, fear, uncertainty) 3/ What’s the opposite, positive emotion? (e.g. hope, indispensability) Then, ask accordingly. Release & replace. Hope you can give it a shot this week,

Inspired by a conversation on our SalesWomentoring WhatsApp community… One of our members said: "I wish I could observe some of you in action to catch the finer nuances of a conversation, learn, and implement." So we made a cheat sheet. Because when prospects shut down your questions, It’s not about you - it’s about how you asked. 👇 𝐀 𝐦𝐢𝐧𝐢-𝐠𝐮𝐢𝐝𝐞 𝐨𝐧 𝐩𝐫𝐨𝐛𝐢𝐧𝐠 𝐰𝐢𝐭𝐡𝐨𝐮𝐭 𝐩𝐮𝐬𝐡𝐢𝐧𝐠: 1. Earn the Right to Ask Before you question - share value. ✅ “We’ve helped [industry] teams improve [metric] without a big overhaul. Mind if I ask something to see if this is relevant?” 2. Use Softeners Questions feel better with buffers. Try: • “I’m wondering…” • “Would it be okay if I understood…” ✅ “Would it be okay if I asked how you currently budget for this?” 3. Be Conversational, Not Clinical ❌ “What’s your biggest pain?” ✅ “Many [role]s I meet are stretched managing [X]. That happening for you too?” 4. Try the 3R Formula: Relate – Reflect – Redirect “You mentioned expansion. That usually means onboarding chaos. How are you managing training?” 5. Don’t Pitch Yet. Be Curious. ✅ “What’s been the trickiest part of [task] lately?” 6. Ask Future-Focused Questions ✅ “Where would you like this to be 6 months from now?” ✅ “What does a win look like this quarter?” 7. Offer Options, Not Open Blanks ❌ “What’s the challenge?” ✅ “Is it hiring or retention that’s harder right now?” 🎯 Bonus Tip: Tone > Technique Confidence doesn’t mean pressure. Lead with calm curiosity - it earns more trust than any script. Want more behind-the-scenes tips like this from real women selling in real rooms? Join our next session or drop into the comments👇 PS: Special thanks to Supneet Kaur Kohli, Vidhya Rekha Archana Patel for inspiring this one!

The best AEs ask killer discovery questions. Here's my top 10: Notice: They're all focused on priorities and challenges. (That's not a coincidence!) 𝗧𝗵𝗲 𝗕𝗲𝘀𝘁 𝗗𝗶𝘀𝗰𝗼𝘃𝗲𝗿𝘆 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀: 1. "You mentioned X. Would you say that's the most important thing you're looking to accomplish with a solution like ours?" Always seek to understand their number one priority. 2. "Appreciate you sharing, Jill. Sounds like X is a priority. Curious if you could share more about that?" Have a real conversation (ie actively listen) and ask follow up questions. Don't just use a checklist for discovery. 3. "Thank you for running me through everything, Jill. I work with a lot of clients in your situation. Usually, X and Y are the biggest priority for them. Is that the same for you?" Leverage your experience and subject matter expertise to give options. 4. "When you say X is a challenge, what do you mean by that exactly?" Never take an initial challenge shared at face value. Dive deeper always. 5. "One thing I'd like to understand is what's most important to you. Would you mind walking me through your evaluation criteria? Are there 1 or 2 things that really stand out as the most important for you and your team?" 6. "When it comes to [process] who else on your team is involved? And have they mentioned anything being a challenge around that?" Don't just ask questions about your prospect learn about their team too. 7. "For your [other decision maker] what would you say is the biggest priority for them in this evaluation?" Great question for uncovering priorities/challenges of key stakeholders. 𝗠𝘆 𝗕𝗶𝗴𝗴𝗲𝘀𝘁 𝗧𝗶𝗽𝘀: 1. Write down your favorite questions when it comes to discovery and uncovering the challenges and priorities of your prospect. 2. For each product you sell write down the most common challenges you solve and the questions you ask to see if your prospect is experience them too. 3. Review your discovery calls and give yourself an honest assessment on how well you uncover the priorities and challenges of your prospect. 4. Have your manager review a call specifically for uncovering challenges and priorities on a discovery call. What's your biggest tip when it comes to discovery? - Mike 👉 Get The Best Sales Newsletter delivered straight to your inbox for FREE: https://lnkd.in/g-dHTj7s

I ask stupid questions on purpose. Here’s why they work. People are wired to give surface-level answers. “Smart” questions get rehearsed responses. But “stupid” questions? They force prospects to slow down, think deeper, and reveal insights they wouldn’t have shared otherwise. Here are my go-to questions that help me uncover pain points, create urgency, and close deals: 1. "Why hasn’t anyone solved this before now?" → Reveals past frustrations and hidden roadblocks. If they’ve tried solutions that failed, this tells me where others went wrong. 2. ''Why is this even a problem?'' → It forces prospects to verbalize their pain. If they struggle to answer, maybe it’s not urgent, or they haven’t fully thought through why they need a solution. 3. "What would a perfect solution look like for you?" → Instead of pitching, I let them describe their dream outcome. They often give me the exact playbook for closing the deal. 4. “What’s the worst thing about your current process?” → A bit awkward, but this cuts through polite answers and gets straight to the raw frustration. 5. “What happens if you don’t make a change?” → This shifts the focus from “nice-to-have” to “must-fix.” It makes them confront the cost of inaction. 6. “Why are you trying to solve this now if it’s been a problem for a while?” → Uncovers the trigger that made them act today instead of a year ago. Their answer gives me leverage. 7. “What’s your biggest ‘aha’ moment since we started talking?” → Helps me gauge if I’ve added value, or if they’re just being polite. Bonus: Always ask ‘why’ as a follow-up. If I don’t understand something, I don’t pretend. I just ask “why?” again. It’s simple, but it gets to the root of their thinking. Simplicity is a superpower in sales. What’s your go-to ‘stupid’ question? #sdr #coldcalling #sales  

Want to Keep Prospects Engaged? Use These 8 Game-Changing Questions Most salespeople struggle to keep prospects interested during demos. The result? Missed opportunities to build trust and close deals. Here’s what works instead: 1) Don’t Assume Their Use Case ↳ Ask: “What else comes to mind about how you’d use this?” - Helps them picture how it fits into their daily workflow. - Uncovers additional ways your solution can help. 2) Focus on Team Impact ↳ Ask: “What would this let your team do differently?” - Highlights how your solution makes their work easier. - Reveals which changes matter most to them. 3) Understand Their Priorities ↳ Ask: “How important are these insights to you?” - Identifies if this is a must-have or a nice-to-have. - Gives you a roadmap to align with their goals. 4) Explore Current Challenges ↳ Ask: “Can you tell me how you’re doing this now?” - Exposes gaps in their current process. - Sets the stage to showcase why your solution is better. 5) Highlight the Value ↳ Ask: “How would you handle this without this feature?” - Makes them visualize the extra effort without your tool. - Reinforces the benefits of your solution. 6) Assess Business Impact ↳ Ask: “What effects does this problem have on the business?” - Links their challenges to team or company performance. - Helps you understand their pain points on a larger scale. 7) Determine Urgency ↳ Ask: “How big of a deal is this problem for your company?” - Gauges whether solving this issue is a priority. - Helps you qualify their readiness to act. 8) Compare and Contrast ↳ Ask: “How does this compare to what you’re doing now?” - Encourages them to evaluate your solution objectively. - Makes it clear how your offer stands out. Salespeople who ask these thoughtful questions keep prospects engaged—and uncover the insights they need to close the deal. Here’s the key takeaway: - Don’t just present. Ask, listen, and adapt. Curious about how these questions can transform your approach? Let’s discuss in the comments! #SalesSuccess #B2BSales #CloseDeals #EngageYourProspects #DemoTips