Sales Discovery Tips

Yesterday I had a call with a VP of Enablement And what she shared, blew my mind. "We fed Ai our top rep's calls," she said. "What we discovered changed everything." I had to know more. Her company: 400+ rep SaaS org The problem: Only 3 reps consistently hit 150%+ of quota The question: What makes them different? So they ran an experiment. Fed 6 months of call recordings into Ai. Top 3 performers vs everyone else. "Find the patterns," they told it. 45 minutes later, her entire enablement strategy was in the trash. Here's what they discovered: Discovery #1: Top reps talk 28% LESS Average rep: 64% talk time Top performers: 36% talk time But when they do speak? Surgical precision. Discovery #2: They "lose" more deals Top reps disqualify 41% of opportunities in discovery. Average reps disqualify 12%. Her reaction: "We've been teaching reps to save every deal. Our best reps are doing the opposite." Close rates tell the story: Top reps: 68% Everyone else: 24% Discovery #3: The 17-minute rule No top performer mentions product features before minute 17. Not once in 6 months of calls. Instead, they talk about: - The prospect's competition (38% of discovery) - Industry disruptions (29%) - Personal career goals (21%) - Team dynamics (12%) "We train feature-benefit from day one," she told me. "Our best reps ignore it completely." Discovery #4: They use one phrase repeatedly "The best companies in your space are..." Appears 4.2 times per call for top reps. 0.3 times for everyone else. Always followed by strategic silence. Prospect fills the gap every time. Discovery #5: Their follow-up is backwards Average rep: "Here's what we discussed" Top rep: "Here's what your competitor just announced" Top reps lead with market intelligence. Never with meeting recaps. She showed me what happened next: They rebuilt everything. Scrapped their 40-slide onboarding deck. Threw out their talk tracks. Redesigned training from scratch. New approach: Week 1: Master strategic silence Week 2: Practice disqualification Week 3: Industry intelligence training Week 4: Competitive positioning No product training until week 5. But here's what really got me— "The hardest part wasn't changing the training," she said. "It was convincing leadership that everything we believed was wrong." Her parting words: "If you're not using AI to audit your top performers, you're training your team to be average." She's right. We assume we know what works. We document what we think happens. We scale the wrong behaviors. Meanwhile, top performers are breaking every rule. And crushing quota doing it. CSOs, here's your assignment: Pick your top rep. Feed their calls to AI. Prepare to be shocked. What "best practice" would AI prove wrong in your org?

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?👇

I've spent 10 years perfecting the art of discovery calls: - reviewed over 2,500 discovery recordings - analyzed millions of discovery calls with AI - personally run (estimated) 3,000 disco calls Here's 5 of my best discovery call tips for 2023: 1. Discovery is a process. Not an event. It’s not a STAGE during the sales cycle. It’s a process. Your buyer’s situation is in flux. If you do “set it and forget it” discovery, you lose. Bad salespeople treat discovery as “check the box." They "front load" discovery. Great salespeople do continuous discovery. Don't set it and forget it. 2. The best discovery CREATES value. It makes buyers THINK. "Most" discovery CONSUMES value. It merely gathers info. Yes, you need to uncover things. But if that's ALL you do? You build a transactional relationship. Don't settle for transactional. Settle for transformative. - challenge your buyer - diagnose the cause of issues - make them consider new angles $500k+ earners do that. 3. Uncover the 'need behind the need.' For whatever reason: Most buyers share surface-level info. I'm not sure why. I suspect it's just how humans crystallize thoughts. Try asking this: "Thanks for sharing that. Do you mind if I ask what's going on in your business that's driving that to be a priority to begin with?" Or, ask them to take you back in time. Your buyer once had a meeting with colleagues to discuss the issue they're trying to solve. That triggered them to reach out to you (among other actions). Ask them about that: "I have to assume you had a meeting with colleagues where you discussed the issue, and agreed to act on it. What did that meeting sound like?" There's gold behind that question. 4. Re-validate everything. Never assume that what you uncovered remains true. Priorities change. Buyers’ needs are transient. When things change, you’d better know. If you followed the last tip, you’ll uncover priorities. But if you treat discovery as “set it and forget it," you’ll miss. Here’s how to re-validate: Start every follow up sales meeting with this: "What’s changed since the last time we talked?" 5. Phrase questions to get LONG answers Hate it when buyers answer with one-word responses? It sucks. According to data, successful salespeople get LONG answers to questions. Here’s how: SIGNAL to your buyer that you want a long response. Do that by phrasing your questions the right way. Start your question with one of these phrases: - help me understand... - walk me through... - talk to me about... This phrasing signals that you want your buyer to answer in depth. You’ll get richer answers. I'm out of space. If you want more, let me know? Until then, know this: Questions are the most powerful tool you have to sell. I spent 10 years collecting the best sales questions in a Google Doc. I tested them. I refined them. Now you can use them. Here's the mega list sales questions: https://lnkd.in/g-VRcCsq

For my first 16 years in tech sales, I averaged 240K/year W2 income. In my last 4 years, I averaged 720K/year. In order to triple my income, I had to change my sales approach entirely. Here's what I changed: I started using a new approach that I now call Yo-yo selling: 🪀 Yo-yo selling emphasizes starting at the executive level, conducting thorough discovery within the organization, and then returning to the executive with a tailored business case. Like holding a yo-yo, you are constantly in communication with the Executive Sponsor and updating them as you collect information and conduct deep discovery lower down in their organization. You are literally going up and down the organization, but always taking everything back to the Executive Sponsor to surface your findings along the way. Here's a breakdown of the framework: 🎯 𝐈𝐚𝐧 𝐊𝐨𝐧𝐢𝐚𝐤’𝐬 “𝐘𝐨-𝐘𝐨 𝐒𝐞𝐥𝐥𝐢𝐧𝐠” 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 This strategy involves a three-step process: 1. Start at the Top (Executive Engagement) Initiate contact with a senior executive to understand their most pressing challenges, the reasons behind the need for change, and the consequences of inaction. If your solution aligns with their needs, secure their sponsorship for further discovery within their organization. To secure the Executive Meetings, it's essential to create a tailored POV (point of view) on where you think you may be able to help them based on your initial research of their highest level goals and priorities. Chat GPT has made this research a LOT faster now. 2. Conduct In-Depth Discovery (Middle Management) Engage with department heads and key stakeholders to uncover the day-to-day challenges they face. Focus on understanding their processes, pain points, and the implications of current inefficiencies. Gather direct quotes and insights to build a comprehensive view of the organization's needs. 3. Return to the Executive (Present Findings) Compile the insights gathered into an executive summary and business case. Present this to the executive sponsor, highlighting how your solution addresses the identified challenges. Tailor your demonstration to focus solely on relevant aspects that solve their specific problems. 🚀 Why It Works 1. Accelerates Sales Cycles: Engaging executives early ensures alignment and expedites decision-making. 2. Builds Credibility: Demonstrates a deep understanding of the organization's challenges and showcases a tailored solution. 3. Facilitates Internal Buy-In: By involving various stakeholders, you ensure that the solution meets the needs of all parties, increasing the likelihood of adoption. I'm pleased to share that that Yo-yo selling was recently awarded as a Top 15 Sales Tactic of All Time by 30 Minutes to President's Club, and I received a cool plaque for entering the 30MPC Hall of Fame. Since I have no chance of entering the Hall of Fame for my baseball or golf game, this is a nice consolation prize 😁

Your prospect says: "We need a new sales platform because we want to grow the business." What happens next determines whether you're average or elite. AVERAGE REP: "Great! Let me tell you about our features..." (You’ve ALREADY lost if this is how you answer) (Let’s watch an elite rep handle this now…) ELITE REP: "Grow the business?" [waits in silence] PROSPECT: "Yes, we need to increase revenue by 30% this year." ELITE REP: "Why is hitting that 30% target so critical right now?" PROSPECT: "We need it to secure our Series C funding." ELITE REP: "What would missing that target mean for the company?" PROSPECT: "We'd have to delay expansion and possibly cut headcount." ELITE REP: "And for you personally, what would it mean to secure that funding?" PROSPECT: "My equity would finally be worth something. Plus, I'd prove to the board they made the right choice promoting me to CRO." ELITE REP: "So if I understand correctly, you need to grow 30% to secure Series C funding, which would both protect your team from layoffs AND potentially make your equity worth seven figures while cementing your position as CRO. Is that right?" PROSPECT: "Exactly. So how can you help us?" THIS is the difference between qualification and transformation. After coaching thousands of reps, I've found that most never get past the first layer of discovery. They treat prospects like a checklist rather than an onion. The fortune is in the follow up questions. My CHAN Code for ethical influence has three simple steps: 1. Ask an open-ended question 2. Go DEEP with the RIM framework (Relevance, Impact, Motive) 3. Repeat back as a question for understanding When you master this process, you transform "we want to grow" into concrete business and personal impact that makes it impossible for prospects to ghost you. The hardest territory to manage isn't your CRM. It's the six inches between your prospect's ears. — Sales reps… want me to break down the Wolf of Wall Street’s B2B discovery session? Go here: https://lnkd.in/gPT-Qprv

Every sales leader I talk to at the moment is struggling with some version of the same issue. The symptoms are different, but the underlying cause is the same. - Sales cycles elongating - Deal slippage - Prospects not showing up to meetings - An uptick in ghosting - Poor forecast accuracy - A drop in deal volumes - A drop in conversion rates What's actually happening out there in Buyer land? I've been delivering win-loss reviews for B2B companies around the world since 2011 and I'm seeing buyer behaviours I've never observed before... Let me break down some of them quickly for you and share some guidance on how to use these lessons to your advantage: Trend #1: Risk has jumped up the decision tree in order of importance, to the very top of the list for many clients, even more so when it's a new vendor. Action: Go deeper on risk in your discovery conversations, recognise that risk is both organisational and personal...find ways to better manage, mitigate and share risk with your clients...Be the low risk option. Trend #2: Value for Money, Responsiveness and Cost are consistently selected as the most important decision criteria by many clients. Action: Responsiveness should be an easy one to get right, but many sellers are stretched too thin right now...do less, but do it better. Trend #3: Change in Strategic Direction is the most frequently cited reason for customers coming to market for a new solution at the moment. Action: Try to reverse engineer this reason, to understanding what caused this change in direction and what it actually means for the business. These are your keys to the kingdom, when building a rock solid business case. Trend #4: Feedback from Peers and Colleagues has emerged as the most trusted information source for almost all respondents. Action: Case studies and customer references are losing their luster...find ways to tap into the trust which prospective clients have in their own peer network, as a way to unlock deeper connections and build trust. Trend #5: Customers are demanding more detail in the proposal documents, tender responses and business cases which they are receiving. Action: Put in the work, avoid the cookie-cutter responses, find your win themes and weave them in, share the detail they need to make an informed decision. I haven't got a crystal ball, so I can't tell you if/when the pendulum will swing back the other way, from a buyer behaviour perspective. What I can tell you with a high degree of certainty is that prospective customers have raised the bar, in terms of their expectations from their vendor partners. It's our job now to to elevate the preparation, patience and professionalism of B2B sellers everywhere, to meet these changing needs and maintain our relevance to the customers we serve.

After 214 closed deals, here are my top 6 disco questions (no 4 saved my last deal) If you don’t go deep on pain, you don’t close. You just build pipeline that looks good- and goes nowhere. This happened to me in one of my 1x1s with my manager. He asked me, what is their pain? I answered, they are "chasing receipts". My manager: “this is no pain, this is process description. Dig Deeper." Of course, this deal went nowhere. So I stopped settling for surface-level answers. 𝗔𝗻𝗱 𝘀𝘁𝗮𝗿𝘁𝗲𝗱 𝗮𝘀𝗸𝗶𝗻𝗴 𝘁𝗵𝗲𝘀𝗲 6 𝗾𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 𝗼𝗻 𝗲𝘃𝗲𝗿𝘆 𝗱𝗶𝘀𝗰𝗼𝘃𝗲𝗿𝘆 𝗰𝗮𝗹𝗹: 1. “𝗪𝗵𝗮𝘁 𝗵𝗮𝗽𝗽𝗲𝗻𝘀 𝗶𝗳 𝘁𝗵𝗶𝘀 𝗽𝗿𝗼𝗯𝗹𝗲𝗺 𝗶𝘀𝗻’𝘁 𝘀𝗼𝗹𝘃𝗲𝗱 𝗶𝗻 𝘁𝗵𝗲 𝗻𝗲𝘅𝘁 3 - 6 𝗺𝗼𝗻𝘁𝗵𝘀?” → Why it works: It surfaces urgency or kills the deal early. What to listen for: Real impact, deadlines, strategic goals. Use it when: The prospect says “it’s annoying” or “not ideal.” 2. “𝗪𝗵𝗼 𝗲𝗹𝘀𝗲 𝗶𝘀 𝗳𝗿𝘂𝘀𝘁𝗿𝗮𝘁𝗲𝗱 𝗯𝘆 𝘁𝗵𝗶𝘀 𝗶𝗻𝘁𝗲𝗿𝗻𝗮𝗹𝗹𝘆?” → Why it works: Pain spreads across teams. Use it to multithread. Follow-up: “If this stays broken, how does that affect their targets?” 3. “𝗪𝗵𝗮𝘁 𝗮𝗿𝗲 𝘆𝗼𝘂 𝗱𝗼𝗶𝗻𝗴 𝘁𝗼𝗱𝗮𝘆 𝘁𝗼 𝗺𝗮𝗻𝗮𝗴𝗲 𝘁𝗵𝗶𝘀?” → Why it works: Shows how painful the workaround is. If they say: “Spreadsheets,” “Manual work,” “Email chains” → Dig in: “How much time does that take weekly?” 4. “𝗪𝗵𝗮𝘁’𝘀 𝘁𝗵𝗲 𝗰𝗼𝘀𝘁 𝗼𝗳 𝗸𝗲𝗲𝗽𝗶𝗻𝗴 𝘁𝗵𝗶𝗻𝗴𝘀 𝘁𝗵𝗲 𝘄𝗮𝘆 𝘁𝗵𝗲𝘆 𝗮𝗿𝗲?” → Why it works: Forces them to quantify pain. Prompt with: - Lost time - Delayed reporting - Missed revenue - Frustrated teams 5. “𝗪𝗵𝘆 𝗶𝘀 𝗻𝗼𝘄 𝘁𝗵𝗲 𝘁𝗶𝗺𝗲 𝘁𝗼 𝗳𝗶𝘅 𝘁𝗵𝗶𝘀?” → Why it works: Helps you understand if this is just interesting or a priority. If unclear: “What changed recently that made this worth looking into?” 6. “𝗪𝗵𝗮𝘁 𝗸𝗶𝗻𝗱 𝗼𝗳 𝗽𝗿𝗲𝘀𝘀𝘂𝗿𝗲 𝗱𝗼𝗲𝘀 𝘁𝗵𝗶𝘀 𝗽𝘂𝘁 𝗼𝗻 𝘆𝗼𝘂 𝗮𝗻𝗱 𝘆𝗼𝘂𝗿 𝘁𝗲𝗮𝗺?” → Why it works: Emotional pain matters - especially with CFOs and decision-makers. Follow-up: “What would change for you if this were off your plate?” The result? - More urgency - Fewer slow deals - Better qualification = More real business cases that close My take: Most reps hear one pain point and jump to the demo. But the best AEs slow down - and dig deeper. If there’s no pain, there’s no deal. And if there’s no urgency, it’s your job to find it—or walk. What's your best follow-up question when someone says “Yeah, it’s a bit annoying”? Let’s build a stronger discovery toolkit below. Happy Monday y'all. JBTHE(backonstockholm)AE PS. Want my demo prep sheet? Comment DEMO below.

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

Hey Salespeople: Do you truly understand the Challenger sales methodology (teach, tailor, take control)? It does not mean being aggressive. TEACH – Provide insights that challenge the prospect’s current thinking and help them see an unrecognized problem or opportunity. This approach positions the salesperson as a trusted advisor rather than just a vendor. Example: Instead of just pitching accounting software, show a CFO data revealing they're spending 40% more time on compliance than industry peers, costing them $200K annually in labor inefficiency. TAILOR – Customize the conversation to align with the prospect’s industry, company priorities, and individual stakeholder concerns. Example: When speaking with the IT Director, focus on integration and security features; with the CFO, emphasize ROI and cost reduction; with end-users, highlight ease of use and time savings. TAKE CONTROL – Taking control involves guiding the sales conversation confidently, addressing objections proactively, and steering the prospect towards a decision. This doesn't mean being aggressive, but rather being assertive and value-focused Example: After demonstrating value, saying "Based on what we've discussed, I recommend starting with our enterprise package at $85K annually. To hit your Q3 goals, we should begin implementation within three weeks. Does your team have the authority to move forward, or should we include someone else in our next conversation?"

Here's a naughty lil secret about discovery in mid-market and enterprise deals. Many of us were taught that the purpose of discovery is to understand the customer's needs, so we can map our solution back to those needs and show how we can help. Here's the fatal flaw in that theory. If we're asking our customers to tell us their needs, chances are, they're telling our competitors the same thing. So, the odds that our solution will be meaningfully different than our competitors are slim. As a result, customers commoditize us around the one area they CAN tell a difference. Price. How could we approach discovery instead? Here is my 5-step process: 1 - Build a hypothesis on what the company trying to achieve, and seek to understand what you're missing as an outsider. *Find this in CEO letter to shareholders, interviews with the Founder, CEO guest appearances on podcasts, etc.. Bring it to the call, and frame it as, "As an outsider - this is what it seems like the business is trying to achieve. But, what have I missed?." 2 - Be curious about HOW that stakeholder currently believes/assumes they will accomplish that goal, and ask HOW they formed that opinion. *Example: Company's goal is to 4x subscription revenue by 2025. To do so, CRO believes they must hire more SDRs and raise activity targets. CRO believes these are the right needs, because this approach worked at his/her last 3 companies. 3 - Introduce evidence that contradicts those beliefs/assumptions. *This is your reframe. Our goal isn't to tell them they're wrong. It's to introduce an enemy to that belief/assumption that breaks it. Key is to make it so you aren't attacking the person, but rather, exposing them to something environmental that makes 1+1 = 3, not 2. 4 - Give them a formula to calculate the implications of continuing with their current approach. *This is NOT an ROI formula. That's what happens IF they change. This is about COI (cost of inaction). What happens if they don't change? 5 - If you've piqued their curiosity, suggest that they collect the inputs needed to calculate the size of the pain, and bring those to the next call. Don't assemble or sell the solution yet. Just agree that we'll explore the size of the pain together, to see if this is even an area worth exploring. Discovery shouldn't feel like death by 1000 questions, or a qualification exercise so that we can pitch our stuff. It should feel like two colleagues exploring a problem together. TLDR: When approached this way, discovery convos are one of the best places to drive a competitive wedge. Not around our product. But, around our ability to be a strategic partner to how the prospect thinks about their own business. (PS - if you're planning your 2025 sales kickoff, this is one of the sessions I love to teach)