Discovery Call Conversation Techniques

I’ve done 350+ discovery calls in the past 3 years and closed 7+ figures in contract value. I always structure my 1st call in the same 5-step format: Great sales is nothing more than a structured approach to help prospects make a decision. It shows them that I’m understanding and have their best interest at heart. I consider sales to be part of the service. It’s consulting. Here's how my discovery calls look: 𝟭. 𝗚𝗲𝘁 𝗧𝗵𝗲𝗶𝗿 𝗦𝘁𝗼𝗿𝘆 I want to find out as much as possible about them. My goal is to understand their journey & personality, and also make them feel heard & understood off the bat. They talk, I shut up. If they jump straight into business, I gently steer them back. ___ 𝟮. 𝗔𝗻𝗮𝗹𝘆𝘇𝗲 𝗙𝗶𝘁 Next, I dive into their business model, bottlenecks, and top goals: • Who’s your ICP? • What do you offer? • What’s your marketing status quo? • etc. I figure out if a collaboration makes sense and whether they need our help or something else entirely—like coaching, a new tool, a different vendor, or just advice on improving their current setup. ___ 𝟯. 𝗜𝗻𝘁𝗿𝗼𝗱𝘂𝗰𝗲 𝗠𝘆𝘀𝗲𝗹𝗳 I recap what they’ve shared and then introduce myself. Here, I try to mirror how they shared their story: • what topics did they focus on? • how far back did they go? • what did they highlight? At the same time, I look for similarities between us to create relatability. Then at the end, I explain what I do on a high level. ___ 𝟰. 𝗞𝗲𝘆 𝗧𝗵𝗲𝘀𝗲𝘀 & 𝗥𝗼𝘂𝗴𝗵 𝗕𝘂𝗱𝗴𝗲𝘁 𝗥𝗮𝗻𝗴𝗲 From there, I introduce the 3 key theses they need to believe for us to work together. • Thesis 1: The decisions we make are influenced by the people we trust and the content we consume. • Thesis 2: Content helps build relationships & trust at scale. • Thesis 3: Content is an infinite game If they're not aligned with this thesis, it usually indicates we're not a fit. At the same time, I also discuss the rough budget range to make sure we're on the same page about expectations early on. ___ 5. 𝗕𝗼𝗼𝗸 𝘁𝗵𝗲 𝗡𝗲𝘅𝘁 𝗦𝘁𝗲𝗽 If it feels like a fit, I lock in a follow-up call right then. I never leave this for later—it just adds uncertainty and hassle. If it’s not a fit, I still try to offer value—maybe I send some free resources or give advice. ___ 𝗕𝗲𝘀𝘁 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗲𝘀 𝗜 𝗙𝗼𝗹𝗹𝗼𝘄: • I call out any elephants in the room. • I recap what they say to confirm my understanding and give them a chance to add details. • This also helps me process what they’ve shared. • I always leave room for their questions. • Their needs are #1 priority. #b2bsales #founderledsales #consultativesales

A rep called me frustrated. "I ask all the right questions, but they clam up after 10 minutes. Discovery feels like pulling teeth." I listened to her last call. She was doing everything "right" according to most sales training. Except for one thing. She was treating discovery like an interrogation instead of a conversation. Here's what I told her: Stop trying to get everything in 30 minutes. You're not a police detective gathering evidence. Instead, go deep on what matters most → their pain. Three questions that changed her entire approach: "What's driving this to be a priority right now?" "What happens if you don't solve this in the next 6 months?" "How is this impacting you personally?" Notice something? No questions about budget. No stakeholder mapping. No buying process. Just pain. Deep, emotional, get-them-talking pain. Here's what happened on next call: Prospect spent 20 minutes explaining their challenges. Shared things she never heard before. Got emotional about the daily frustration. Old Rep would've panicked: "I didn't get the buying process info!" New Rep said: "Based on everything you've shared, this sounds complex. Let's schedule another call to walk through how companies typically solve this." Prospect immediately agreed. Why? Because she proved she understood their world. The follow up call? Prospect brought their boss. Shared budget range. Outlined their evaluation timeline. All because the first call was about them, not about her information gathering checklist. Look, I get it. Sales methodology says you need certain data points. But prospects don't care about your methodology. They care about feeling understood. When you nail the pain, everything else flows naturally. The reps's close rate went from 18% to 29% just by changing her discovery approach. Same questions. Same product. Different mindset. Sales VPs: teach your reps to be consultants, not interrogators. The reps who master this thinking close bigger deals because they uncover the real emotional drivers behind every purchase decision. Ever noticed how your best discovery calls feel more like therapy sessions than sales calls? Strange, isn’t it? 😎 — How 700+ clients closed $950 million using THIS 6 step demo script: https://lnkd.in/eVb32BUx

i tracked my last 100 discovery meetings at Distribute. The deals i closed all do the EXACT same thing: i ran the meetings like a hostage negotiator, not a salesperson. Not a sales rep. They assume everything will explode. But orchestrate like i was directing a Oscar winner. After 1000s of discovery calls at Outreach, Taplio, and 3 other ventures, here's the playbook that turns strangers into signatures: 1. The Pre-Game Stalk ==> (T-minus 2 hours) LinkedIn deep dive + their last 10 press releases + their competitor's latest moves + their CFO's Twitter complaints = ammunition Found a CEO complaining about missing Q3 targets. Opened with: "Saw you missed Q3. Here's how 3 companies fixed that exact revenue gap." Had their attention in 8 seconds. 2. The Opening Hijack ==> (Minutes 0-3) Them: "So tell us about your company..." Me: "I will. But first—I spent 2 hours studying your business. I have 3 hypotheses about why you're here. Mind if I share them? You can tell me if I'm completely wrong." Right 87% of the time. Memorable 100% of the time. 3. The Reverse Discovery ==> (Minutes 3-15) Don't interview them. Diagnose them. "Based on your job postings, you're scaling SDRs but your close rate is tanking. That means either bad leads or broken handoffs. Which one's killing you?" They lean forward when you know their shit better than they do. 4. The Competitor Landmine ==> (Minute 20) "Quick question—are you talking to [Competitor]?" If yes: "Good. They're great at X. We're better at Y. Here's a 90-second breakdown of who chooses who and why." If no: "Good. They wouldn't solve your specific issue anyway. Here's why..." Either way, you just poisoned the well. 5. The Price Anchor Drop ==> (Minute 25) "Before we continue—this is expensive. We're talking $200-500k expensive. Should we keep talking?" The weak disappear. The real buyers get serious. Your pipeline gets cleaner (yay) 6. The Homework Test ==> (Final 5 minutes) "I'm sending you 3 things: 1. ROI calculator with YOUR numbers 2. 8-minute demo video of YOUR use case 3. One-pager your CFO will actually read (use Distribute for this) If you actually look at these, we'll have a second meeting. If not, we'll both save time. Deal?" People who do homework buy. People who don't were never buyers. —— Most reps run first meetings like job interviews. Begging for approval. Praying for next steps. Top reps run them like doctors. Diagnose the disease. Prescribe the cure. Let them decide if they want to live. Your close rate will thank you.

Most discovery calls feel like an interrogations. Question. After question. After question. “What are you measuring?” “What is it today?” “Where do you want it to be?” “What happens if you do nothing?” “What’s the value of the difference?” Prospects leave lighter, but none the wiser. Want to disrupt the status quo? Bring a point of view that rattles the tray. Look at Enzo Avigo, CEO at June.so. He doesn’t just ask founders about churn. He says, “Your activation metric is lying to you.” Then drops a new lens that reframes the whole dashboard. Suddenly SaaS leaders see a problem they didn’t even have a name for. And June is the only company talking about the cure. You can do the same in discovery calls. Step one: expose an assumption. “Most teams treat last touch attribution like gospel.” Step two: swap in a sharper frame. “The problem is data shows that first‑encounter moments predict revenue far better.” Step three: invite them into the story. “Would you be open to hearing a different perspective on how teams capturing those moments and CAC by up to 30%?” Now you’re not probing; you’re teaching. You’re the guide who names the monster hiding under their bed and flips on the light so they can finally see it. Questions still matter. But when they ride shotgun with a clear point of view, you stop sounding like every other rep and start sounding like the partner who rewrote the playbook. That’s how you win. Not by gathering answers, but by giving people a new question they can’t stop asking themselves

After running 600+ discovery calls over the last 3 years here’s whats obvious Most reps still treat discovery like a script not a conversation 🤷♂️ Thats why deals stall, go dark or never even get off the ground I’ll be honest Early in my career “discovery” felt like just another step in the process Go down the list, ask the questions, move on But every time I did that it backfired → Deals slipped → Buyers went silent → I’d get feedback like “just not the right time” or worse no reply at all It wasnt until I flipped the script that things changed Discovery became the make-or-break moment Not the “qualification round” Not the interrogation Its where trust is built or lost Where you either see the real problem or chase the wrong one So I got obsessed with the basics How do you make discovery feel like a conversation not an interview? Here’s what actually works → 𝗗.𝗜.𝗦.𝗖. 𝗳𝗿𝗮𝗺𝗲𝘄𝗼𝗿𝗸 (my not so secret weapon) → D: Discover their world “Whats on your plate right now?” “Whats the big picture for your team?” → I: Identify pain, real pain “Whats slowing you down?” “If you could wave a magic wand what’s the headache you’d get rid of?” → S: Scrutinize decision & landscape “How do you usually tackle stuff like this?” “Anyone else who needs to be looped in?” → C: Clarify success + next steps “What does a win look like here?” “What would make this call worth your time?” I started setting expectations up front “This isnt a pitch. I’m just here to see if there’s an actual problem worth solving together” and closed with clear next steps always What happened? Deals stopped going dark People opened up (sometimes with things they’d never told a vendor before) And my pipeline became real. Full of opportunities that wanted to talk 146 folks tuned in to my Sell Better session with Will Aitken today and the messages after? “Thanks for the great talk!” “Learned a lot & got some great take aways” “I love how you use video for your recap!” The right discovery call doesnt feel like a step in the process. IT is the process So if you’re stuck running scripted calls try making it a conversation Try asking questions you actually care about the answers to Because that’s what opens the door Curious Whats your go to move to make discovery feel human? Drop a comment or DM me if you want the full D.I.S.C. deck or just want to jam on sales process. Always down to talk shop

If I had to choose only ONE question to ask during discovery conversations when I'm trying to rip and replace an incumbent, it would without a doubt be this one: "What is it about your current solution that makes you not love it a hundred percent?" Here's why it works (IMO): "What don't you like about your current vendor?" triggers defensiveness. They may have been the ones who bought the thing. Admitting they hate it feels like admitting they made a mistake. "What challenges are you facing?" gets bullshit answers. They've said it in six other vendor calls this month. But "what makes you not love it a hundred percent?" gives them permission to be honest without requiring them to trash anyone. Nobody loves anything completely. There's always friction. Always something slightly off. And when you create space for that admission, they can open up. So that's my one question. That said, the important stuff is what happens next. After they answer, resist the urge to pitch whatever you're selling. Go deeper instead. - "Tell me more about that." - "How long has that been going on?" - "What have you tried so far to fix it?" The second and third layers are where the REAL pain lives. Surface answers get surface deals. Deep answers get signed contracts. Here's a quick discovery framework that builds on this whole idea: Call it the 3x3 model. 3 types of questions. 3 layers deep on each. 1. Situational questions to establish context. - What does your current workflow look like?  - Who's involved?  - What tools are you using today? Now go three layers deeper: - What's the process?  - Who owns it?  - How long has it been this way? 2. Gap questions to uncover friction. - What's not working the way you'd want?  - Where do things break down?  - What takes longer than it should? Again, go three layers deeper: - What's the gap?  - What's causing it?  - What has that cost you? 3. Future state questions (to help reveal the buying vision). - If this worked perfectly, what would change?  - What would you be able to do that you can't do today?  - What would success look like in six months? Aaaaaand again, go three layers deeper: - What's the goal?  - Why does it matter?  - What happens if you don't get there? Each layer doubles the value of the insight. Situational questions tell you what exists. Gap questions tell you what hurts. Future state questions tell you what they'll pay for. That's the whole game.

I've listened and coached over 3,785 calls over the last few years. Here's what makes a good first call: 1. The sales rep or founder is seeking to understand the world the prospect lives in. Systems, people, workflows. Pains within those. The impact of pain on other parts of the business. This is priority no. 1 for any good sales call. 2. The call has structure. There's a framework at the start of the call that sets a mutual outcome for both prospect and rep/founder. Time check. People check. The purpose of the call. The ideal outcome for the prospect. Then permission to discuss next steps if outcome is met. 3. There are pain-based probing questions. The way this happens differs from call to call. But the most typical ones I've seen are either menu-option pain questions that a prospect chooses from. Or a "walk me through" type of question to better understand workflows, then a follow-up around "where are things breaking down?" 4. When pain is present, the best reps/founders dwell in it for a while. They'll ask follow-on questions. They'll ask for specific examples. They delay solutioning. The try to go as deep as they can into the pain they've found. 5. The solutioning part of an intro/disco call rarely takes more than 30% of the allotted call time. It's tailored to what was uncovered in discovery. The rep/founder doesn't show everything. They have a structure for demoing the right stuff. They avoid training a prospect on what features exist + how to use them. They repeat the context + problem, share capabilities gained, then show specific workflows for how to solve the pain. 6. There is a solid next step conversation with an attempt at discovering the decision process. This is usually 10-15% of the allotted call time. The best reps/founders don't rush this. And the very best ones book another meeting before leaving the call. My biggest takeaway with good calls - they all sound different, but feel the same. The components of the call never change, from rep to rep, product to product, industry to industry. Founders - learn what a good call looks like, and think through these components. Just doing this, slightly better than what you're doing now, will have a major impact on deals moving forward. The first call is the most important call. It happens 100% of the time. So spend the bulk of your upskilling here.

One of the worst ways to handle discovery: (I know because I've done it) Treating it like an interrogation. Asking back to back questions. Not breaking it up with conversation or context. I used to run through my list of questions like a robot. Check, check, check. Getting my answers, but missing the actual conversation. The prospect would start giving shorter responses. Their energy would drop. And I'd wonder why I wasn't getting any real insights. Sound familiar? Here's the easy way to fix this: 1. Repeat back what they said "It sounds like there’s a ton on your plate, so you don’t have time for __. How is *competitor* supporting you with that?” 2. Ask second-layer questions Not just "What's your biggest challenge with ___?" but "What do you feel like is keeping you from reaching that revenue goal?" 3. Share relevant context "That's interesting - we've seen similar issues with other customers in your industry. Here's what we've learned..." 4. Show genuine curiosity "That's surprising to me. Can you tell me more about why you don’t think ___ is working well?" The difference is dramatic. A few weeks ago, I had an initial demo that completely transformed because of this approach. The prospect told me what their revenue goal for this year is. Instead of just noting it and moving to my next question, I paused. "That’s an ambitious goal. What exactly are you putting in place to achieve that?" I was genuinely curious to know. What followed was a 10-minute conversation that revealed: - What they currently have in place (what’s working, and what’s not) - Their current program ROI (which was alarming for us both) - Their micro goals (that make up the overall revenue goal) - Lack of capabilities with current vendor - Their exact pain points Gold mine. Had I just flown through questions, I would have missed it all. After our conversation, she followed up with the SDR, "thanks so much for reaching out, we had such a great conversation!!" Great discovery isn't about checking boxes. It's about creating a conversation where prospects feel heard. Where they're comfortable sharing the real story. Not just the surface answers. The best sellers aren't the best questioners. They're the best listeners. What discovery technique has made the biggest difference in your sales conversations?

Your discovery questions are terrible because they produce predictable answers. "What's your biggest challenge?" "What keeps you up at night?" "What's your goal this year?" Prospects have answered those questions 100 times already. The best discovery questions make the buyer stop and think. Here are 10 of my favourites and why they work: 1. What changed in the last 90 days that made you take this call? - This is my favorite discovery question. - Because buyers don't wake up one morning and randomly book demos. - Something changed: A missed target, a new leader, a budget shift or a customer complaint. - Find the trigger and you'll usually find the real opportunity. 2. What happens to your team in 6 months if this stays the same? - Most reps talk about pain. - Top reps uncover the cost of inaction. - If there's no consequence, there's usually no urgency. 3. Walk me through how you handle this today. - Not: "What tool are you using?" - Actually walk me through it, step by step. - This is where you understand manual work, bottlenecks, spreadsheets, workarounds and hidden frustrations. 4. What have you already tried and why didn't it work? - This question saves months. - You immediately learn: What they've tested? What they hated? What failed before? - And what you should avoid pitching. 5. Six months after we go live, what's true that isn't true today? - This forces buyers to define success. - In their words, not yours. - Those answers become your future ROI story. 6. Walk me through how a decision like this gets made. - Don't ask: "Who's the decision maker?" - Ask about the process. - The process reveals the people, the reverse rarely works. 7. If you had to rank your top 3 priorities for the quarter, where does this fit? - Everything sounds important on discovery calls. - Very few things are actually urgent. - This question helps separate the two. 8. If we agreed on terms tomorrow, what happens next on your side? - A real buyer and a real champion knows. - Someone who says "I'm not sure" usually doesn't control the process. 9. Who else are you evaluating and what's pulling you toward them? - The second part matters. - Most reps ask who, but very few ask why. - The "why" tells you what buyers actually care about. 10. What's the worst-case scenario if you choose the wrong vendor here? - This is where the real risk shows up. - Not company risk or personal risk, but the fear nobody talks about. - And those are often the real reason deals stall. One last thing: Don't ask all 10. Discovery is a conversation, not an interrogation. Pick the questions that fit the situation. Then listen longer than feels comfortable. Most prospects will tell you exactly how to win the deal if you stop trying to pitch and start trying to understand. — Follow Noam for more AI × Sales systems.

Gong analyzed 42,945 closing calls to figure out what actually closes deals. I just read their research. It changed how I think about sales. Here's what they found: (spoiler: not your closing tricks) 1) Successful vs Unsuccessful Closing Calls Are Identical: → Same talk-to-listen ratio → Same no. of questions asked → Same interactivity level (speaker switches/min) → Same everything You can’t spot a win or loss just by the convo 2) Discovery Calls? Totally Diff: → Talk-to-listen ratio: huge gap between won/lost → Questions asked: direct correlation to deal success → Interactivity: winning demos are 2x more interactive → The trajectory is set here, not at closing 3) Asteroid Principle: → A tiny asteroid shift when far from Earth, changes everything → Once in the atmosphere: too late, outcome sealed → Early sales process: buyer perceptions in flux, easily shaped → Late sales process: solid perception; locked preference: point of no return → Closing tricks don't help 4) Competitive Mentions: → Discuss competitors early: increases win rate → Discuss competitors at closing: decreases win rate → Early: you set the rules of the game in your favor → Late: you're trying to convince against choosing the competition  → Competitive deals won with discovery techniques, not closing techniques 5) The ONE Difference That Matters: → Topics the prospect raises during the close call → Successful closings: buyer asks- SLAs, implementation, customer success, pricing details, long-term partnerships → These are "pre-purchase jitters" = buyer is ready, wants reassurance → Unsuccessful closings: buyer isn't asking these because they're not ready → It’s about the prospect’s readiness not the seller’s technique 6) Your Job on Closing Calls: → Don't close: Lead → Don't push, manipulate or pressure → Lead through emotional hurdles → Provide authentic reassurance → Clear confusion  → Show long-term commitment through behavior → Be decisive & recommend the right path → This is a mode of operation 7) What You Control: → Frame their problems & define their buying criteria early → Shape their perceptions while they’re flexible → Set competitive positioning before others  → Ask questions that uncover real needs → Drive interactive dialogue in early demos → Build trust upfront 8) The Math: → 1M+ calls & 42,945 closing calls studied → Near 0 behavioral diff between won vs lost closing calls → Huge behavioral diff in early-stage calls → Result: deals decided early, executed late 9) Implementation: → Focus on mastering discovery instead of closing tricks → Train reps on early-stage conversations → Record + analyze discovery calls, not closing calls → Fix talk-to-listen ratio early → Ask more questions in discovery (direct driver of success) → Build interactive demos (2x more ping-pong = 2x more wins) The deal is won in discovery; the closing call just exposes the result. Hours spent on closing tactics vanish. Hours spent mastering discovery compound.