Sales Discovery Tips

I watched a CEO fire his entire sales team last month "They're not hitting numbers. We need fresh blood" Six months earlier, I had warned him this would happen The real problem wasn't his sales team It was his onboarding process New customers were churning within 90 days because they never properly implemented the product The sales team kept filling a leaky bucket But he wanted "closers" not "customer success strategies" Here's what most companies get catastrophically wrong about sales growth: - They obsess over acquisition while neglecting retention - They celebrate closed deals but ignore customer lifetime value - They hire more salespeople instead of fixing broken systems I've spent 10 years rescuing companies from this exact death spiral. The pattern is always the same: - Sales targets increase - Quality of customers decreases - Churn accelerates - Desperate discounting begins - Margins collapse - Team gets blamed and replaced - Repeat until bankruptcy The solution isn't mysterious, but it requires courage: - Stop chasing new logos for 90 days - Audit your entire customer journey - Ask departing customers uncomfortable questions - Fix the leaks before adding more water That CEO who fired his team? His replacement team is now struggling with the exact same issues Meanwhile, his competitor grew 100% last year with a smaller sales team but a robust customer success program Revenue isn't just about closing deals It's about creating sustainable value that customers can't imagine living without Fix the system, not the symptoms P.S. If you need help with your sales, send me a message

I’ve been in sales for 17 years and managed 100s of AEs. This profession is so full of bad advice and it took me ages to find my mentors. Here are 9 things I wish someone had told me years ago… 1. Buyers Close Deals, Not You It’s easy to obsess over sales meetings. But the real magic happens in buyers' internal meetings—those you’re not invited to. Align your actions with the critical steps THEY need to build consensus. Don't sell. Enable them to buy. 2. Your Sales Process is Meant to Be Broken On that note, your role is not just to execute your process but to offer ‘Project Management Services’ to your buyers’ process. Your process is there to offer a good foundation to build on, but it only covers 5-17% of your buyers’ process. 3. Calendar Overload = Illusion of Control Weekly champion syncs feel great, but the truth is—you’re probably not moving the needle much. If you fail to equip buyers between calls with the right tools or content, you’ll discover your “champion” isn’t championing. Help them build momentum internally—24/7. 4. Budget is Almost Never the Deal-Breaker Stop asking about budget on the first call. It is rarely a reason to qualify out. No buyer only spends on pre-allocated line items. “No budget” simply means “No Justification” to create one for the value you’ve been able to convey. 5. Accessing Stakeholders is NOT Enough Multithreading is not about having many people on your calls/emails. That’s a vanity metric. It’s about building separate relationships to support their specific needs/requirements/concerns. That’s what truly moves the needle. 6. Executives Hate Deep Discovery on Calls Structured deep discovery doesn’t work well in executive calls. You must lead with stories, teach them something new, and let a conversation develop. They have zero patience. If you try to have long conversations first, they’ll tune off. 7. You’ll Fail 99% of Outbound Intro Calls if You Treat Them Like Inbound You lead with discovery on Inbound but lead with insights on Outbound—It’s OK to use slides if they serve the discovery. It’s even OK to demo before you have all the pain points figured out. As long as it all serves the discovery. 8. Drop the ‘Perfect Discovery’ Fantasy A perfect disco only works in a role-play. Try it in real life and you'll end up with no next steps. Worry less about your framework, and more about having a meaningful conversation around ‘why do anything’, ‘why now’, and ‘why you’. The rest only helps you and can come later. 9. Speed is Your Biggest Easy ‘Hack’ to Drive Urgency Nothing cuts down deal cycles like dictating a fast rhythm of communication. Received an email? Answer from your phone right away. Talking next steps? Offer a call tomorrow. Discussed timeline/MAP? Recap that on every follow-up. —— Don’t make it harder than it has to be. Make mistakes. Learn from them. But always learn from other people’s mistakes first. P.S. Check out Aligned-the tech I wish I had https://lnkd.in/dwX_Zizk

In 27 months, we grew Retention.com from $1M-$13M ARR with only 1 salesperson (me) doing 1,000's of sales calls. Here are my 10 biggest pieces of advice for any startup who wants to book and close more sales calls: 1. Ask for 15 mins, but book 30 When booking a meeting outbound, you have a better shot at getting a meeting by asking for 15 mins than 30. You may have piqued their interest but with a busy schedule, they are going to weigh learning about your business vs their time. Ask for 15 but send a meeting invite for 30.  If they can’t do the full 30, they will let you know, but from my experience, this rarely happens. 2. Tell your story People remember a story more than a product  Figure out your short story that you can tell prior to getting into the product pitch. How does your story connect to your business / product? 3. 5X5 Pitch Keep your product deck for your initial call to 5 slides / 5 minutes and make sure you answer any of the common questions you get from prospects. You can always book a follow up call to share more detail once you hook their interest. 4. Always Be Pitching Take control of the call and the sales cycle. You will only learn what does and doesn’t work by actually pitching.  5. Tell a customer story Again, people remember stories more than they do stats. Tell a story of a customer before implementing your product and the business outcome after implementing it. Don’t just talk numbers. Talk about how people felt, what they said, etc. 6. Create Urgency Attach an incentive if the deal is done by the end of the week or month.  (Example: 20% more credits or a 15% discount)  This also sets you up well for follow up as it now makes them feel like you are on their team to try and help them get the deal in for their benefit. 7. Land and expand We all want to close the big ACV deals, but the truth is most buyers don’t want to make a big commitment without seeing how your product works. Find a way to get them on for a small $ amount, with the plan to expand if the product meets their expectations. 8. Opt-Out Period Reduce buyer friction by offering a 90 day opt out period if you are trying to close 12 month agreements. It shows confidence that your product will drive the results you say it will. 9. Deck Recap Create a 1-2 pager highlighting the most important parts of your sales deck that you can send via email after every call (even if they don’t ask for it). The prospect won’t remember all details from the call, so this gives them something to look back on and will help sell internally if other stakeholders are involved. 10. Video for FAQs Create short form talking head video answering all FAQs. This will add value in your follow up, show you listened to the questions they had and that you care about making sure they understand the answers. It also helps internally as others will likely have the same questions as the person on the phone. Have questions about how to book/close more calls? AMA anything 👇

You’re on a discovery call. The conversation is flowing. Suddenly the prospect drops this question: “How are you different from your competition?” Your first instinct? Probably to jump in and explain: “We’re the only ones who…” “We have the best…” “Clients who work with us say…” But here’s the problem: when you’re explaining you’re convincing. And no one wants to be convinced. Why? Because prospects know you have an agenda. Of course, you’re going to put your best foot forward. Talk about your wins. Showcase your edge. But to them, it feels… self-serving. So what’s the way out? Instead of convincing, shift to understanding. Understanding starts with meeting them where they are—acknowledging what’s likely swirling around in their head. Like this: “I’m sure you’ve seen a lot of similar solutions, all promising the same thing. It’s tough to tell what really sets anyone apart.” And then—pause. You’re not selling. You’re empathizing. You’re showing them you get it—that you’re not just another salesperson with a rehearsed pitch. Here’s the magic: once people feel understood, they’re far more open to hearing you out. From there, you shift the focus away from you and toward them. “Different means something unique to everyone. Do you mind me asking, what does it mean for you, based on what you’re trying to achieve but haven’t yet?” And then you listen. Not with an agenda. Not with a mental checklist of what you’re going to say next. You just listen. Because your job isn’t to cram their head full of information about why you’re the best. Your job is to draw out their story. Why? Because people don’t buy because they understand you. They buy because you understand them. Buyers have the answers. Sellers have questions.

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 😁

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?👇

🔮 Four Levels Of Customer Understanding (https://lnkd.in/eJFghrDe), how to think of underlying reasons for user behavior, hidden motivations, root causes and the different layers of reality that are often overlooked in product design — from what people say to what they think or feel to what they actually do to reasons why they do it. By Hannah Shamji and Helio. 🤔 What people do, say, think and feel are often different. 🚫 Assumptions and hunches rely on most obvious reasons. ✅ But most obvious reasons rarely paint the full picture. ✅ People don’t always cancel because they actually want to. ✅ Pricing is never the only reason why people don’t buy. 🤔 Customers often don’t realize why they made a decision. ✅ We built understanding by studying 4 levels of reality. ✅ Level 1: “What we tell others”, unreliable, opinions, hearsay. ✅ Level 2: “What we tell ourselves”, interviews, debrief, surveys. ✅ Level 3: “What we actually do”, task analysis, observation. ✅ Level 4: “Why we do it”, task walkthroughs, context, interviews. Level 1 is most unreliable, and barely brings good insights. Often people imagine and say things that don’t necessarily represent real reasons for their behavior. They rather explain behavior through the lens of how a customer perceives it, or wants it to be perceived. The real magic happens on higher levels. But they require right questions, interviews and observations and, most importantly, user’s trust. So ask people to walk you through their daily routine. Explain to you where your product fits in their life. Observe how they complete their tasks in their environment. Study where they lose time, repeat actions, hover but don’t click, or click and then go back. Don’t ask them to speak loudly. Pay attention to when they scratch their neck, or raise their eyebrows. Smile, or laugh, or look worried. Many companies speak about “validation”. Yet validation often means accepting and confirming existing assumptions. As Hannah Shamji writes, instead, we should diagnose existing behavior without any preconceived notions or affiliations. So don’t validate — research instead. The hardest part is understanding customer’s real motivations — and the only way to get there is by building a sincere, honest and trustworthy relationship. A relationship that feels right. One that customers can wholeheartedly engage in. Once your customers really care and want to help, getting to real understanding will be much, much easier. (Leaving useful resources in the comments below due to LinkedIn link policy ↓)

I lost 22 of my first 23 opportunities when I first joined Gong. I focussed on our 10+ competitors and learning every unique feature we had. Since then, my win rate shot up and it all centers around one principle: 𝗖𝗵𝗮𝗹𝗹𝗲𝗻𝗴𝗶𝗻𝗴 𝘀𝘁𝗮𝘁𝘂𝘀 𝗾𝘂𝗼. Before any selling is effective, you need to deeply understand their problem. You need strong mutual buy-in on 'why change.' 6 non-negotiables for me to uncover: 𝟭. 𝗜𝗱𝗲𝗻𝘁𝗶𝗳𝘆 𝗮 𝗰𝗼𝗺𝗽𝗮𝗻𝘆-𝘀𝗽𝗲𝗰𝗶𝗳𝗶𝗰 𝗼𝗯𝗷𝗲𝗰𝘁𝗶𝘃𝗲 How to ask: ↳ "Gong aside, what are the top 2-3 strategic priorities you're most focussed on." ↳ "What company-specific objective does Gong align most to, in your eyes?" Example: ↳ New product being launched 𝟮. 𝗔𝗿𝗲𝗮 𝗼𝗳 𝗢𝗽𝗽𝗼𝗿𝘁𝘂𝗻𝗶𝘁𝘆 𝗜𝗱𝗲𝗻𝘁𝗶𝗳𝗶𝗲𝗱 𝗪𝗶𝘁𝗵𝗶𝗻 𝗜𝘁 How to ask: ↳ “For this new launch, through your lenses, what's the biggest single risk to making this a success?” Example: ↳ Sellers are all over the place demoing + messaging it 𝟯. 𝗧𝗵𝗲𝗶𝗿 𝗖𝘂𝗿𝗿𝗲𝗻𝘁 𝗦𝘁𝗮𝘁𝗲 How to ask: ↳ "What metric is that most affecting today?" ↳ "Where is that at today?" Example: ↳ 20% win rate 𝟰. 𝗧𝗵𝗲𝗶𝗿 𝗜𝗱𝗲𝗮𝗹 𝗦𝘁𝗮𝘁𝗲 How to ask: ↳ "In an ideal world, where would you want to get that to?" Example: ↳ 25% win rate 𝟱. 𝗤𝘂𝗮𝗻𝘁𝗶𝗳𝘆 𝘁𝗵𝗲 𝗥𝗢𝗜 How to ask: ↳ "If you bridged that gap, have you done the math on what that would be worth? Example: ↳ Growing 5% in win rates, is worth $2M / annually 𝟲. 𝗪𝗵𝗮𝘁 𝘁𝗵𝗲𝘆'𝘃𝗲 𝘁𝗿𝗶𝗲𝗱 𝘁𝗼𝗱𝗮𝘆 𝗮𝗻𝗱 𝘄𝗵𝘆 𝘁𝗵𝗮𝘁 𝗱𝗼𝗲𝘀𝗻'𝘁 𝘄𝗼𝗿𝗸. How to ask: ↳ What have you already done to try and solve that? Example: ↳ Having managers sit in on more calls which has been time intensive. You won't uncover all 6 of these on the first call and that's okay Build on each and uncover them through the entire cycle Discovery is a never-ending process Not just a sales stage 😁 P.S. Join 700+ sellers who've grabbed my full discovery blueprint: https://lnkd.in/dmYbzPGi

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

When we dissect discovery calls, we hear this same motion almost every time - the buyer opens up about what they need, which prompts the seller to meet them with exactly how they can help. Perfect, right? Nope. We are SO eager to hear something that we can solve that we don't pause to ask the critical question - why? ***We know what you need, we don't know why you need it.*** What's the business pain? What's the cost of inaction? How much does this one issue impact dozens of people, dozens of times/day? How does this impact your goals for the year ahead? Is this enough of pain point that it's worth the trouble of changing? What's the monetization associated with the pain? Why is it important to change now? Have you tried to tackle this change before? And so on... Toss a sticky on your laptop and simply pause when you hear what they want. This is your moment to... differentiate significantly better qualify this opp get a host of details that will help you figure out how to best solve their challenges understand if you're talking to the right team ...and up your odds of advancing this opportunity #samsales