Layered Questioning Strategies for Sales Professionals

Coffee is for closers. That line, and the toxic bravado behind it, needs to go. The best consultants and salespeople don’t sell. They start with one simple question: “Why?” And The Wolf of Wall Street is not a how-to sales guide. It’s a cautionary tale soaked in ego and adrenaline. Glengarry Glen Ross? Same thing. A masterclass in manipulation and moral bankruptcy, yet somehow these warped tactics, fast talk, pressure plays, "always be closing" still show up in sales training, and yes, recruitment floors. The recruitment industry, like it's close cousin real estate, is littered with outdated tropes: “Sell the pen.” “ABC: Always Be closing.” “Dominate the room.” Say whatever it takes to close the deal. These tactics are not just outdated. They’re shallow. Real influence doesn’t come from how well you pitch, post, or promote. It comes from how well you listen and whether what you say is backed by substance. Take “Eddie,” a self-proclaimed million-dollar biller with stories spanning Manhattan, London, and beyond. Mate, we all know it’s smoke and mirrors. A performance. You aren’t Brisbane’s own James Bond. The truth? -- The best salespeople don’t push. They pull. -- They don’t dominate the room. They open it up. -- They don’t talk more. They listen better. But not just any questions. They ask the ones no one else dares to. The ones that peel back assumptions, uncover motivations, get to the root of the problem. Most people ask what. Good people ask how. The best ask "why." Why? Because “why” changes the conversation. It unlocks purpose. Invites honesty and builds trust. “Why did that matter to you?” “Why do you feel that way?” “Why” is a shortcut to the truth. I remember sitting in a team meeting years ago. Nick, a sharp and well-respected colleague, was pitching a cost-saving plan that completely missed the mark for our customers. Instead of challenging him directly, I just kept asking “Why?” Five times. Eventually, he paused, and concluded there were better, more customer-focused options. That’s the power of better questions. Not to trap someone, but to help them see more clearly. When you lead with curiosity, you’re building connection. You’re showing someone you care about them, not just the transaction. And that’s where trust happens. That’s what actually drives referrals, sales, and loyalty. Take it from me, someone who spent +20 years getting this wrong. It turns out that the sale is just the byproduct. The real win? Be the person who gets it. Who listens when others talk. Who connects instead of convinces. Be the person who gives it all away for "free." Because you know it will come back around anyway. So next time you’re in a conversation, sales or otherwise, ditch the “pitch script.” Get curious. Ask better questions. Go where others don’t. And above all, ask "Why?" The real magic in winning the deal, doesn't happen when you sell. It happens when you understand. Enjoy the coffee.

Prospects aren’t targets. They’re humans. Humans respond best when they feel understood, not convinced. The best salespeople know how to make others feel heard. When you ask a question, then another question, then another unrelated question, discovery calls can feel like interrogations. If you don’t listen and instead rapid-fire scripted questions, it feels like you’re not genuinely interested in the response but rather focused solely on your agenda of quantifying pain so you justify your solution. If people don’t feel understood, they’re not going to trust what you recommend. The way out? Ask fewer questions on discovery calls. Go deeper. Like a therapist: “What’s on your mind?” (Inbound.) “How's it going?” Mute. (Digging deeper) “Afraid to dial?” (Digging deeper) “It’s like the phone is a cactus.” Mute. (Digging deeper) “What else?” Mute. “There are so many sales trainers. What prompted you to call us?” “What's the real challenge?” (Digging deeper.) “What's your perspective on why that is?” “If you're looking back 6 months from now, what has to have happened for you to feel really happy with your progress?” (Digging deeper.) “How so?” Don't ask a digging deeper question if you're not curious about the answer. When people feel understood, you build trust. And in a world of similar products, trust is why people choose you. Seller’s don’t have the answers. Buyers do. The seller’s job is to draw them out. Learn the gentle art of making others feel understood here: https://lnkd.in/eVfUevmz

Your challenger training may have taught your reps to start fights they can't finish. You spent $50K on a sales methodology. Flew in consultants. Ran workshops on "constructive confrontation." Then your AE challenges a buyer's assumption and gets hit with: "Actually, we've been doing this for 15 years and know our business better than you do." What happens next? They fold. Apologize. Start pitching features. Because you taught them to throw punches, not take them. The big thing about challenger selling is that it only works if your reps can handle the emotional backlash that comes with disagreeing with prospects. And many of them can't. Which, to be clear, isn't necessarily their fault. They just haven't been provided any psychological resilience training. Before you teach reps to challenge assumptions, teach them to: 1. Expect emotional resistance as validation rather than rejection. When a buyer gets defensive, that means you hit something real. Most reps interpret pushback as "I said something wrong" instead of "I said something that matters." Train them to lean in: "It sounds like this is something you've put a lot of thought into. Walk me through your current approach." 2. Master the "third question" technique. Most reps ask one question, get pushback, then retreat. Encourage your reps to have the confidence to dig deeper. - First push: "That's an interesting perspective. What's driving that approach?" - Second push: "And how long have you been using this process?" - Third push: "What metrics are you tracking to measure success?" Each question shows you're genuinely curious, not just challenging to challenge. 3. Practice the uncomfortable pause. When buyers push back hard, it's natural to try and fill silence with backpedaling. Just let the tension breathe, people! Count to three. Then ask: "What's working well about your current approach?" 4. Reframe resistance as qualification data. Every objection tells you something about their pain tolerance, decision-making process, or internal politics. If they can't handle being challenged in discovery, they DEFINITELY can't handle change management post-sale. To be clear, challenger selling works. It just works better when your reps can handle the emotional backlash that comes with disagreeing with prospects. Don't let your reps crumble at the first sign of friction. Train the psychology first. The methodology second. In a world where every rep has the same playbook, resilience is the real differentiator.

The biggest mistake in sales isn't your pitch. It's asking the wrong questions. This CIA-inspired method will help you close more deals: Most salespeople obsess over what they'll say instead of what they'll ask. Elite closers know your questions control the conversation. The right questions guide prospects toward buying naturally, while the wrong ones kill deals before they start. I learned this the hard way. For years, I wasted time on "rapport" questions about weekend plans and vacation spots. They felt safe but went nowhere. But former CIA agent Andrew Bustamante revealed a better approach: "Conversation Maps" where agents plot interactions before they happen. Elite salespeople create similar decision trees. Each question has a purpose - uncovering needs, revealing pain, or qualifying prospects. Nothing is random or just fills silence. Ask questions that make buyers feel powerful, not powerless. When buyers feel stupid, they don't buy. Questions that are easy to answer but reveal critical information. Questions that help them articulate their needs clearly. Here's how to build your Conversation Map: 1. Identify 3-5 critical decision points before calls 2. Plan paths based on possible answers 3. Focus on questions revealing what they truly value 4. Prepare follow-ups that make them feel understood With mapped questions, you guide without pushing. After each conversation, review which questions resonated, where the conversation stalled, and what unexpected turns appeared. Then adjust accordingly. The power of Conversation Mapping isn't just closing more deals. It frees you from anxiety about what to say next. It gives customers freedom to make confident decisions. Most sales advice dies in the trenches. Scripts collapse. Objections blindside you. But when you own the conversation, you win. More in the comments 👇:

I stopped asking "What are your priorities?" in sales calls. I'd get generic, unhelpful answers each time. I ask these instead: 1. What are the top 3 metrics you're measured on this quarter? ↳Knowing their key performance indicators reveals what truly matters. 2. What's keeping you up at night about hitting those goals? ↳Their biggest fears and challenges point to where you can create value. 3. Where are you currently losing revenue or leaving money on the table? ↳Quantifying the cost of inaction builds urgency for change. 4. Have you explored other solutions before? What didn't work? ↳Understanding past failures helps you differentiate and avoid the same pitfalls. 5. What would a successful outcome look like for you in 6 months? ↳Aligning on their definition of success guides your solution positioning. 6. Who else is impacted by this issue across the company? ↳Identifying all stakeholders ensures you bring the right people into the process. 7. What's your budget range for addressing this? ↳Getting a sense of investment appetite upfront avoids wasted time. 8. What's your decision-making process and timeline? ↳Mapping the path to a decision keeps the momentum going. 9. What concerns do you have about moving forward? ↳Surfacing objections early allows you to directly address them. 10. How will you measure ROI if we're successful? ↳Defining ROI metrics upfront justifies your pricing and business case. Vague, open-ended questions lead to vague, unhelpful answers. Get specific, and you'll uncover the insights to truly understand the buyer's situation. --- Repost ♻ to help your network with this important skill Comment “SEQUENCE” below if you want me to send you 13 email sequences that sell like crazy. 

Your sales calls are failing, and you don’t even know why.  Most professionals focus on what they offer. Features, benefits, pricing. But the real magic happens when you start asking why.  I’ve trained B2B professionals on LinkedIn at over 300 corporates, and helped them generate millions in B2B leads, and there’s one thing I see over and over... ... deals are lost because the right questions weren’t asked.  So, here are 5 “Why” questions that top closers ask during client intake:  1. Why this?      ↳ Does the client truly understand their problem, or are they just exploring options?      ↳ Ensures your solution is actually the right fit—before wasting time.  2. Why now?      ↳ No urgency = no deal. This question filters out tire-kickers who aren’t ready to buy.      ↳ Reveals the real driver behind their interest, whether it’s pain, opportunity, or pressure.  3. Why us?      ↳ Forces the client to convince themselves that you’re the best fit.      ↳ Exposes whether they actually know your unique value—or if they need more proof.  4. Why not in-house?      ↳ Identifies if they see the value in outsourcing or if they’re just curious.      ↳ Helps frame your offer as the smarter, faster, or more cost-effective solution.  5. Why not wait?      ↳ Pressures them to confront the cost of inaction.      ↳ Helps you understand if they’re truly committed—or if this is just a wishlist item.  Asking why doesn’t just give you answers. It gives you control. It tells you if they’re serious. If they understand their own problem, and if they see YOU as the right solution.  Most sellers talk too much. The best ones ask the right questions.  Which “Why” question do you use the most in sales calls? PS: I hit the 30,000 connection limit so I can't accept new connections without kicking somebody else out. Therefore I will not accept default ones, only personalised ones that make me smile.