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

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 😁

Gong just announced last week they blew past $300M in ARR. WOW. In 2016, I started at Gong as the 2nd US employee at $200k ARR. 20 SaaS sales tips I learned during my time in that storybook growth journey: 1. Money follows pain. Stop selling benefits. Start selling pain relief. You'll close more. 2. WHO matters more than WHAT. If you're talking to the right person: But you have bad sales technique? You can still win. If you're talking to the wrong person: And have great sales technique? You lose. 3. Don't multi-thread. Single-thread with multiple people. Break people out into 1:1 meetings. Stole this from Krysten Conner. 4. Don't multi-thread too much. Looping in the wrong people can kill your deal. Get the blend of people just right. No, IT doesn't always need to be involved. 5. Great cold emails don't talk about your product. They talk about pain. They look like a page from your buyer's diary. 6. Follow up. Fast. Some sellers take days to follow up. They don't want to seem desperate. Stop it. This isn't dating. Speed sells. 7. The secret to enterprise deals: Pick the deals you can win; then win the deals you pick. 8. Build your business acumen. It makes your sales techniques 2x as effective. Without acumen, you're hollow. 9. Don't seek approval. Seek to solve problems. Big difference. Don't grovel. 10. Buyers don't buy because of ROI. ROI doesn't drive purchases. Emotion does. They simply need ROI to justify the purchase. 11. There are two winners in each deal: The seller who won. The seller who ejected from the deal early and didn't waste time. 12. "Continuity of power" is the ultimate metric. Getting access to power is one thing. Getting a 2nd or 3rd meeting with power is entirely different. Only sellers with sharp acumen get the latter. 13. Great sales calls start with planning. Don't wing it. 14. Voice tone matters. Stop inflecting up. Inflect down. It sets an equal tone. 15. Become a master wordsmith. Words trigger mental pictures. Mental pictures trigger emotions. Emotions trigger actions. Actions close deals. 16. Don't negotiate price too early. It should be the last thing you do before the deal closes. Anything else is too early. 17. Talk about money like it's nothing. Quote a $600,000 proposal with a straight face. That's a super power. The best salespeople have a casual attitude about money. The worst salespeople freak out when they talk numbers. 18. Selling is a set of skills. Not a personality trait. 19. Use the same words your buyer uses. Stop paraphrasing. Stop putting your own twist on things. Use their words. 20. Always know the next step. Bad news: If you don't know what next step you'll suggest? You're wasting that sales call. Selling is an act of leadership. So lead. P.S. Master every aspect of SaaS sales with a FREE trial of pclub.io here: https://lnkd.in/gzF2YwKt

Most sales calls fail… in the first 2 minutes. Not because of: • Poor pitching • Weak closing • Bad pricing The real mistake? Rushing to give solutions before understanding the problem. That's why: • Quick solutions get ghosted • Fast proposals get stuck • Rapid responses get ignored The best closers know— Deep understanding wins more deals. ← Read this again. Go slow if you want to go fast. You need to earn trust before a sale can happen. All clients want: • To be seen • To be heard • To be understood So when you prescribe solutions or jump to conclusions without understanding where they've been, what they've tried, where they're going, what their fears are, what an ideal partner experience might be like, your solutions might be falling on deaf ears. Duh! Doesn't everyone already know this? Knowing and doing are two different things. Sad to say, I've witnessed too many people in sales scenarios: ask "checklist questions" (the kind where you go down a list and the answer doesn't seem to matter), ignore obvious signs of "I'm not ready to move forward" and bulldoze ahead, and not listen with empathy or understanding of what the prospect is going through. The sales call winds up being just a lead-up to asking for the sale. If this is what you're doing, why go through the charade of feigning like you care? Just ask for the sale up front. What's the alternative? The answer is the question. Get good at asking questions. Big. Beautiful. Questions. Next. Learn how to listen. What is the client saying? What aren't they saying? What else could this mean? Then, ask good follow up questions. It's how you demonstrate, what they say matters. Say: "I'd like to loop back and ask you to unpack what you said about (x). I want to know more." What is one of your favorite, beautiful questions that you love to ask in the sales/discovery conversation with prospects? How do they respond? Let's build a list for everyone to benefit. Don't forget to save and share this post for later reference. #salestraining #smallbusinessadvice #smallbusinesstips #getmoreclients

There’s an AE on my team that hits 200% of quota. Consistently. 🤯 Here’s her secret:  She asks the hard questions. 1. “You mentioned [date] as a goal. What’s driving that timeline, and is that date firm?” Verifies whether the timeline is real or aspirational. 2. "Based on what you’ve seen so far, is there anything that’s giving you pause about moving forward with us?” Invites honest feedback to surface objections early. One of my favorites. 3. “How does our solution compare to others you’re evaluating?” Tests competitive positioning and whether you're the frontrunner. 4.“Who else on your team needs to feel good about this before a decision is made?” Instead of just jotting down names and objections, she builds pages in Aligned to address concerns. That way, when new stakeholders join later, all the context is already waiting for them. 5. “If [insert key stakeholder] were here, what concerns would they raise?” Forces your champion to think on behalf of other decision makers. Great way to learn real objections. 6. “Have you ever purchased something like this before? What did that process look like internally?” Surfaces potential red tape or hidden decision criteria. 7. “What needs to happen between now and [target close date] for this to actually happen?” Pushes them to co create the buying journey and surface risk. 8. “When you picture this going live, what’s the ideal outcome for your team in the first 90 days?” Surfaces their definition of success. These questions do 3 things: – Build trust. – Surface the real decision process. – Give you everything to close/won the deal. 🎯 Bonus Tip: She doesn’t just ask the hard questions, she operationalizes them in Aligned. Here’s how… https://lnkd.in/gs7Gt5Rd That’s how you turn discovery into closed/won deals. - Mike G

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 👇

Selling into a Fortune 50 company isn’t a straight shot—it’s a multi-threaded, high-stakes game where you have to win over three completely different audiences at the same time. 👑 C-Suite (aka "The Big Picture People") – They care about risk, revenue, and competitive advantage. If your pitch doesn’t tie back to a business outcome, it’s dead on arrival. Keep it short, strategic, and dollar-driven—they have about 30 seconds before they mentally check out. 🧠 Technologists & Strategists (aka "The Architects of the Future") – These folks are your deal-makers or deal-breakers. They want to know if your solution fits their long-term IT roadmap, scales, and won’t become next year’s tech debt. If you can’t show how your product integrates seamlessly with what they already have, you’re in for a long road. ⚙️ Practitioners (aka "The Ones Who Actually Use the Thing") – These are the engineers, security teams, and network admins who will either champion your solution internally… or fight it tooth and nail. If your product makes their lives easier (less manual work, better automation, no fire drills at 2 AM), they’ll become your secret weapon in getting the deal done. 🎯 The Trick? Selling to All Three in Parallel. C-suite? Tie it to revenue and risk. Technologists? Prove it’s a strategic fit. Practitioners? Make their job easier. The best enterprise salespeople aren’t just selling—they’re orchestrating. Every great deal is won at multiple levels. How do you navigate selling to different stakeholders? Drop your best tips below! ⬇️ #EnterpriseSales #TechSales #StrategicSelling

When I was in sales, the hardest question was: “Which accounts are actually worth my time?” We had CRMs full of companies and contacts, but no real way to know who was in-market. So we spent hours digging through filings, news, and social posts – hoping to find a signal. Even the best reps could only cover 30 to 40% of the accounts they were assigned. The rest was just wasted opportunity. That’s changing with AI. I have been talking to our customers and even our own reps at HubSpot about how they are using intent data to drive better prospecting. And it is dramatically different. Here is what I am seeing great reps do: Spot demand before it’s obvious. They are using AI to scan job postings, funding announcements, press coverage, even community chatter, to flag the accounts most likely to buy. Qualification is completely different with intent data. Make conversations personal and relevant. Reps are using AI to get alerts the second an account shows intent, like visiting a pricing page right after a funding round. And they are using sequences to send out relevant emails that feel personal. This is what intent-based qualification and prospecting looks like. Salespeople can not only cover more accounts, they can connect with each account in a deeper way. One sales leader we connected with told me: “What used to take 20 hours a week in research now takes one. And we’re seeing better responses than ever.” Prospecting used to be guesswork. With AI, it’s precision.

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?👇