Sales Pitch Shake-Up: Part One—3 Pitfalls To Pull The Plug On

The first sales pitch. It’s like walking into a lion’s den, except the lions are bored executives, and you’re armed with a PowerPoint instead of anything useful. You’ve got the product, the deck, and that dangerous cocktail of adrenaline and optimism whispering, “This is it. Today’s the day.” Then, in the blink of an eye, your prospect’s eyes glaze over like a donut, and you’re watching them mentally check out in slo-mo—probably thinking about lunch. You’re convinced—no, absolutely certain—that your product is their golden ticket, so why are they already mentally composing a “thanks, but no thanks” email? It’s the kind of experience that unleashes a gut-wrenching, confidence-slurping leech of doubt that starts murmuring—you’ve been getting this all wrong. Ignore that voice. To keep their attention, you don’t need to rewrite the rules of pitching—you just need a better way to start. After years of wading through tech startup sales pitches—both in the trenches and on the sidelines— I’ve noticed THE SAME 3 APPROACHES tripping over themselves like they're on repeat. In Part One, I’m not just breaking down why they stumble, I’m dissecting them with the kind of precision you’d use to remove a splinter. And Part Two? I’ll let you in on the one method that doesn’t just work—it sticks. 1. The Big Problem With “Starting With The Big Problem” Cue the sales pitch that’s quietly derailing most startups: “Here’s your industry’s biggest problem, and we’re the solution.” Safe bet? It’s the sales equivalent of walking into a room full of seasoned surgeons and explaining what a scalpel is. You’ll be met with blank stares because, well, they know. A Free-For-All Invitation The real issue is a lack of specificity. A generic problem definition doesn’t set you apart; it sets you up to blend in. You’ve just kicked the door wide open for Oracle, Microsoft, or even that scrappy upstart down the road to say, “Yeah, we do that too.” Congratulations, you’ve entered the commodity race where it’s all about comparison shopping—and unless you’re the cheapest or the most reputable, you’re handing over the advantage. Losing Trust Before You’ve Earned It When you lead with an overly simplistic, one-size-fits-all statement, you’re making prospects question both your understanding of the complexity their situation and your tech prowess. Imagine explaining basic mechanics to an F1 team—they already know the problem; they’re looking for someone who can offer a more sophisticated, nuanced solution. When you fail to show that depth right away, you’re one step closer to being shuffled into the “nice to meet you, but no thanks” pile. No Fire, No Focus, No Sale “Data is exploding”—sounds like a long-term challenge every industry report is tossing around, and every one of their competitors is ping-ponging around in mandatory corporate meetings. So…not an emergency. If you’re not making it crystal clear why this problem needs immediate action, your pitch becomes another bullet point on an endless to-do list that never makes it to the front burner. No urgency, no action. And your pitch? It fades into the noise as soon as the call ends. Letting Them Off the Hook, One Thought at a Time This approach also gives your prospect a dangerous gift: time. Time to convince themselves that they can live with the problem a little longer. If the stakes aren’t clear, immediate, and personal, they might think, “I get it, but I think we should sleep on it,” and just like that, your momentum vanishes, along with your chance to close. ***Or worse…***they’ll sleep on it, wake up, and conclude the problem is really serious. Serious enough to do some window shopping and look at your competitors’ offerings. 2. Stop Selling Change: Why the “New Thing” Pitch Is Already Old You know this pitch. It’s the one you half tore from your investor deck, the one that makes VCs smile and nod knowingly—“the world is shifting, and here’s our shiny new solution to lead the charge.” That works when you’re selling dreams and ten-year visions. But prospects? They’re in the trenches, battling the here and now. They need gunpowder and ammo, not promises from The Pentagon. New Isn’t Always Better—Sometimes It’s Just Riskier Novelty doesn’t necessitate value. Positioning change as the magic bullet assumes your prospects want to take that risk—spoiler alert: businesses tend to be risk-averse. They’re not waking up every morning hoping for a revolution. Change means upheaval, cost overruns, and internal chaos. Pitching the new for its own sake is a great way to spook the prospect. Another spoiler: the bigger the client, the more they hate change. Lead With “New,” And They’ll Be Wondering What’s Even Newer This approach might work when you’re up against dusty legacy systems baked into the Stone Age, but when you lean too hard on being the newest, you’re practically inviting your prospect to shop around—double-checking if you’re really the hottest option or if someone else has already stolen that crown. Suddenly, you’ve led them straight into your competitor’s waiting arms. Futurist Or Salesperson? Choose Wisely. Your prospects don’t need another armchair tech prophet waxing poetic about how the world is about to change—they’re living it. When you start sounding more like a futurist than a partner, all they hear is, “big ideas, no follow-through.” They’ll wonder if you’re the type to over-promise and then crumble under the weight of execution. They’re not looking for dazzling visions of tomorrow; they want results delivered today. If you can’t show how your solution fits into their world now, your pitch might as well be science fiction. The Procrastinator’s Dream: Change Without a Deadline Yes, the world is changing. It’s always changing. And unless you’re going to whip out a crystal ball and prove they’ll be obsolete by Tuesday, your prospect probably doesn’t care. They’ve heard it all before. Unless you’re connecting that change to something that’s hitting them square in the face right now, they’ll mentally check out. And while you’re busy painting the future, they’re scrolling through their inbox for something actually relevant. 3. Pitch or Pop Quiz? Why Asking First Gets You Nowhere Sales 101 told you prospects want to be understood. So, you kick off with the discovery pitch—jumping in with a notepad of questions, nodding like you’re their long-lost therapist. “Tell me your challenges; I’m here to listen.” Sure, you’ve set the stage, but not for yourself—you’ve handed them the mic. By leading with discovery, you’ve gone from expert to echo chamber, and before you know it, your pitch is slipping away. You’re no longer leading the conversation—you’re just along for the ride, and it’s a fast one off a cliff. Authority? Gone in 60 Seconds. Kicking off with discovery is saying, “Hey, I’m here to figure out what’s going on—mind giving me a clue?” You’ve demoted yourself from expert to errand boy, and any authority you walked in with evaporates. You’ve lost the room before you’ve even found your footing. Framing Fiasco—Letting Them Lead Blurs Your Solution Your prospect’s problem is real, but they’ve been circling it the wrong way. Their version is likely narrow, a little skewed, and probably influenced by the last half-baked solution they were sold by a competitor. By asking them to define the problem upfront, you’ve missed your chance to flip the script and nudge them into your labyrinth—the one where your solution is the only way out. Instead, you’re stuck reacting to a narrative you didn’t write. Once you’re in that story, you’re in for a game of catch-up. Stuck in Their Weeds, Not Your Strengths Open the floor to discovery too soon, and you’ll be wading through the quicksand of irrelevant tangents. Prospects love to vent about every minor inconvenience under the sun, and you’re at risk of fielding questions about things your product wasn’t even designed to address. You’re playing defense before you’ve even had a chance to attack, and your pitch is sinking fast—weighed down by everything except what you’re there to sell. The worst part? Those tangents might unearth other issues they decide to prioritize over yours. Next sales call? Pending. Same Old Script: Discovery Kills the Surprise Lead with discovery, and you’re as predictable as a rom-com ending. The second you start asking the usual questions, their brain goes to autopilot. They’ve heard it all before, and they’ve got their responses locked and ready. You’ve walked into their world without a single twist—they’re already two steps ahead and losing interest fast. By the time you hit your big reveal, they’ve mentally checked out. You’re just background noise. So… Now What? I’m not just here to trash everything you’ve been doing without giving you something better. It’s not difficult. Just start SMALL. Hone in on one tiny splinter—the one that’s been quietly irritating them (the one that YOU can get out)—and twist it just enough that they can’t ignore it any longer. How do you find that splinter? In Part Two, we’ll dig into my Paper Cut Pitch—the approach that doesn’t just grab their attention, it grabs them by the throat. Time to ditch the tired tactics and make every incision count. The first sales pitch. The first sales pitch. The first sales pitch. It’s like walking into a lion’s den, except the lions are bored executives, and you’re armed with a PowerPoint instead of anything useful. You’ve got the product, the deck, and that dangerous cocktail of adrenaline and optimism whispering, “ This is it. Today’s the day. ” Then, in the blink of an eye, your prospect’s eyes glaze over like a donut, and you’re watching them mentally check out in slo-mo —probably thinking about lunch. You’re convinced—no, absolutely certain—that your product is their golden ticket, so why are they already mentally composing a “thanks, but no thanks” email? This is it. Today’s the day. you’re watching them mentally check out in slo-mo you’re watching them mentally check out in slo-mo You’re convinced—no, absolutely certain—that your product is their golden ticket, so why are they already mentally composing a “thanks, but no thanks” email? You’re convinced—no, absolutely certain—that your product is their golden ticket, so why are they already mentally composing a “thanks, but no thanks” email? It’s the kind of experience that unleashes a gut-wrenching, confidence-slurping leech of doubt that starts murmuring— you’ve been getting this all wrong . you’ve been getting this all wrong you’ve been getting this all wrong Ignore that voice. To keep their attention, you don’t need to rewrite the rules of pitching— you just need a better way to start. you just need a better way to start. you just need a better way to start. After years of wading through tech startup sales pitches—both in the trenches and on the sidelines— I’ve noticed THE SAME 3 APPROACHES tripping over themselves like they're on repeat. In Part One, I’m not just breaking down why they stumble, I’m dissecting them with the kind of precision you’d use to remove a splinter. After years of wading through tech startup sales pitches—both in the trenches and on the sidelines— I’ve noticed THE SAME 3 APPROACHES tripping over themselves like they're on repeat. years years I’ve noticed THE SAME 3 APPROACHES tripping over themselves like they're on repeat. I’ve noticed THE SAME 3 APPROACHES tripping over themselves like they're on repeat. In Part One, I’m not just breaking down why they stumble, I’m dissecting them with the kind of precision you’d use to remove a splinter. I’m dissecting them with the kind of precision you’d use to remove a splinter. And Part Two? I’ll let you in on the one method that doesn’t just work—it sticks. And Part Two ? I’ll let you in on the one method that doesn’t just work—it sticks. Part Two one method 1. The Big Problem With “Starting With The Big Problem” 1. The Big Problem With “Starting With The Big Problem” 1. The Big Problem With “Starting With The Big Problem” Cue the sales pitch that’s quietly derailing most startups: “Here’s your industry’s biggest problem, and we’re the solution.” Safe bet? It’s the sales equivalent of walking into a room full of seasoned surgeons and explaining what a scalpel is. You’ll be met with blank stares because, well, they know. “Here’s your industry’s biggest problem, and we’re the solution.” “Here’s your industry’s biggest problem, and we’re the solution.” A Free-For-All Invitation A Free-For-All Invitation The real issue is a lack of specificity . A generic problem definition doesn’t set you apart; it sets you up to blend in. You’ve just kicked the door wide open for Oracle, Microsoft, or even that scrappy upstart down the road to say, “Yeah, we do that too.” Congratulations, you’ve entered the commodity race where it’s all about comparison shopping—and unless you’re the cheapest or the most reputable, you’re handing over the advantage. a lack of specificity a lack of specificity Losing Trust Before You’ve Earned It Losing Trust Before You’ve Earned It When you lead with an overly simplistic , one-size-fits-all statement , you’re making prospects question both your understanding of the complexity their situation and your tech prowess. Imagine explaining basic mechanics to an F1 team—they already know the problem; they’re looking for someone who can offer a more sophisticated, nuanced solution. When you fail to show that depth right away, you’re one step closer to being shuffled into the “nice to meet you, but no thanks” pile. overly simplistic one-size-fits-all statement you’re making prospects question both your understanding of the complexity their situation and your tech prowess. you’re making prospects question both your understanding of the complexity their situation and your tech prowess. No Fire, No Focus, No Sale No Fire, No Focus, No Sale “Data is exploding”— sounds like a long-term challenge every industry report is tossing around, and every one of their competitors is ping-ponging around in mandatory corporate meetings. So…not an emergency . If you’re not making it crystal clear why this problem needs immediate action, your pitch becomes another bullet point on an endless to-do list that never makes it to the front burner . No urgency, no action. And your pitch? It fades into the noise as soon as the call ends. sounds like a long-term challenge sounds like a long-term challenge So…not an emergency So…not an emergency your pitch becomes another bullet point on an endless to-do list that never makes it to the front burner No urgency, no action. No urgency, no action. Letting Them Off the Hook, One Thought at a Time Letting Them Off the Hook, One Thought at a Time This approach also gives your prospect a dangerous gift: time. Time to convince themselves that they can live with the problem a little longer. If the stakes aren’t clear, immediate, and personal, they might think, “I get it, but I think we should sleep on it,” and just like that, your momentum vanishes, along with your chance to close. This approach also gives your prospect a dangerous gift: time. This approach also gives your prospect a dangerous gift: time. ***Or worse…*** they’ll sleep on it, wake up, and conclude the problem is really serious. Serious enough to do some window shopping and look at your competitors’ offerings. they’ll sleep on it, wake up, and conclude the problem is really serious. Serious enough to do some window shopping and look at your competitors’ offerings . Serious enough to do some window shopping and look at your competitors’ offerings Serious enough to do some window shopping and look at your competitors’ offerings . 2. Stop Selling Change: Why the “New Thing” Pitch Is Already Old 2. Stop Selling Change: Why the “New Thing” Pitch Is Already Old 2. Stop Selling Change: Why the “New Thing” Pitch Is Already Old You know this pitch. It’s the one you half tore from your investor deck , the one that makes VCs smile and nod knowingly—“ the world is shifting, and here’s our shiny new solution to lead the charge. ” That works when you’re selling dreams and ten-year visions. But prospects? They’re in the trenches, battling the here and now. It’s the one you half tore from your investor deck It’s the one you half tore from your investor deck the world is shifting, and here’s our shiny new solution to lead the charge. the world is shifting, and here’s our shiny new solution to lead the charge. They need gunpowder and ammo, not promises from The Pentagon. They need gunpowder and ammo, not promises from The Pentagon. New Isn’t Always Better—Sometimes It’s Just Riskier New Isn’t Always Better—Sometimes It’s Just Riskier Novelty doesn’t necessitate value. Positioning change as the magic bullet assumes your prospects want to take that risk—spoiler alert: businesses tend to be risk-averse. They’re not waking up every morning hoping for a revolution. Change means upheaval, cost overruns, and internal chaos. Pitching the new for its own sake is a great way to spook the prospect . Novelty doesn’t necessitate value. Novelty doesn’t necessitate value. businesses tend to be risk-averse. a great way to spook the prospect a great way to spook the prospect Another spoiler: the bigger the client, the more they hate change . the bigger the client, the more they hate change the bigger the client, the more they hate change Lead With “New,” And They’ll Be Wondering What’s Even Newer Lead With “New,” And They’ll Be Wondering What’s Even Newer This approach might work when you’re up against dusty legacy systems baked into the Stone Age, but when you lean too hard on being the newest, you’re practically inviting your prospect to shop around—double-checking if you’re really the hottest option or if someone else has already stolen that crown. Suddenly, you’ve led them straight into your competitor’s waiting arms . might work when you’re up against dusty legacy systems might work when you’re up against dusty legacy systems you’re practically inviting your prospect to shop around—double-checking if you’re really the hottest option you’re practically inviting your prospect to shop around—double-checking if you’re really the hottest option Suddenly, you’ve led them straight into your competitor’s waiting arms Futurist Or Salesperson? Choose Wisely. Futurist Or Salesperson? Choose Wisely. Your prospects don’t need another armchair tech prophet waxing poetic about how the world is about to change—they’re living it. When you start sounding more like a futurist than a partner, all they hear is, “big ideas, no follow-through.” They’ll wonder if you’re the type to over-promise and then crumble under the weight of execution. They’re not looking for dazzling visions of tomorrow; they want results delivered today. If you can’t show how your solution fits into their world now, your pitch might as well be science fiction . don’t need another armchair tech prophet When you start sounding more like a futurist than a partner, all they hear is, “big ideas, no follow-through.” When you start sounding more like a futurist than a partner, all they hear is, “big ideas, no follow-through.” If you can’t show how your solution fits into their world now, your pitch might as well be science fiction The Procrastinator’s Dream: Change Without a Deadline The Procrastinator’s Dream: Change Without a Deadline Yes, the world is changing. It’s always changing. And unless you’re going to whip out a crystal ball and prove they’ll be obsolete by Tuesday, your prospect probably doesn’t care . They’ve heard it all before. Unless you’re connecting that change to something that’s hitting them square in the face right now, they’ll mentally check out . And while you’re busy painting the future, they’re scrolling through their inbox for something actually relevant. And unless you’re going to whip out a crystal ball and prove they’ll be obsolete by Tuesday, your prospect probably doesn’t care And unless you’re going to whip out a crystal ball and prove they’ll be obsolete by Tuesday, your prospect probably doesn’t care your prospect probably doesn’t care . they’ll mentally check out they’ll mentally check out 3. Pitch or Pop Quiz? Why Asking First Gets You Nowhere 3. Pitch or Pop Quiz? Why Asking First Gets You Nowhere 3. Pitch or Pop Quiz? Why Asking First Gets You Nowhere Sales 101 told you prospects want to be understood. So, you kick off with the discovery pitch —jumping in with a notepad of questions, nodding like you’re their long-lost therapist. “ Tell me your challenges ; I’m here to listen. ” Sure, you’ve set the stage, but not for yourself—you’ve handed them the mic. By leading with discovery, you’ve gone from expert to echo chamber, and before you know it, your pitch is slipping away. You’re no longer leading the conversation—you’re just along for the ride, and it’s a fast one off a cliff . the discovery pitch the discovery pitch Tell me your challenges Tell me your challenges I’m here to listen. I’m here to listen. Sure, you’ve set the stage, but not for yourself—you’ve handed them the mic. Sure, you’ve set the stage, but not for yourself—you’ve handed them the mic. You’re no longer leading the conversation—you’re just along for the ride, and it’s a fast one off a cliff Authority? Gone in 60 Seconds. Authority? Gone in 60 Seconds. Kicking off with discovery is saying, “Hey, I’m here to figure out what’s going on—mind giving me a clue?” You’ve demoted yourself from expert to errand boy , and any authority you walked in with evaporates. You’ve lost the room before you’ve even found your footing. You’ve demoted yourself from expert to errand boy You’ve demoted yourself from expert to errand boy Framing Fiasco—Letting Them Lead Blurs Your Solution Framing Fiasco—Letting Them Lead Blurs Your Solution Your prospect’s problem is real, but they’ve been circling it the wrong way . Their version is likely narrow, a little skewed, and probably influenced by the last half-baked solution they were sold by a competitor . By asking them to define the problem upfront, you’ve missed your chance to flip the script and nudge them into your labyrinth—the one where your solution is the only way out. Instead, you’re stuck reacting to a narrative you didn’t write. Once you’re in that story, you’re in for a game of catch-up . Your prospect’s problem is real, but they’ve been circling it the wrong way Your prospect’s problem is real, but they’ve been circling it the wrong way probably influenced by the last half-baked solution they were sold by a competitor By asking them to define the problem upfront, you’ve missed your chance to flip the script and nudge them into your labyrinth—the one where your solution is the only way out. By asking them to define the problem upfront, you’ve missed your chance to flip the script and nudge them into your labyrinth—the one where your solution is the only way out. you’re in for a game of catch-up you’re in for a game of catch-up Stuck in Their Weeds, Not Your Strengths Stuck in Their Weeds, Not Your Strengths Open the floor to discovery too soon, and you’ll be wading through the quicksand of irrelevant tangents . Prospects love to vent about every minor inconvenience under the sun, and you’re at risk of fielding questions about things your product wasn’t even designed to address. You’re playing defense before you’ve even had a chance to attack , and your pitch is sinking fast—weighed down by everything except what you’re there to sell. wading through the quicksand of irrelevant tangents wading through the quicksand of irrelevant tangents you’re at risk of fielding questions about things your product wasn’t even designed to address . you’re at risk of fielding questions about things your product wasn’t even designed to address playing defense before you’ve even had a chance to attack except except The worst part? Those tangents might unearth other issues they decide to prioritize over yours. Next sales call? Pending. The worst part? Those tangents might unearth other issues they decide to prioritize over yours. Those tangents might unearth other issues they decide to prioritize over yours. Same Old Script: Discovery Kills the Surprise Same Old Script: Discovery Kills the Surprise Lead with discovery, and you’re as predictable as a rom-com ending . The second you start asking the usual questions, their brain goes to autopilot. They’ve heard it all before, and they’ve got their responses locked and ready. You’ve walked into their world without a single twist—they’re already two steps ahead and losing interest fast. By the time you hit your big reveal, they’ve mentally checked out. You’re just background noise. you’re as predictable as a rom-com ending you’re as predictable as a rom-com ending You’ve walked into their world without a single twist —they’re already two steps ahead and losing interest fast. without a single twist So… Now What? So… Now What? So… Now What? I’m not just here to trash everything you’ve been doing without giving you something better. I’m not just here to trash everything you’ve been doing without giving you something better. It’s not difficult. Just start SMALL. Hone in on one tiny splinter—the one that’s been quietly irritating them (the one that YOU can get out)—and twist it just enough that they can’t ignore it any longer. How do you find that splinter? In Part Two, we’ll dig into my Paper Cut Pitch—the approach that doesn’t just grab their attention, it grabs them by the throat. It’s not difficult. Just start SMALL . Hone in on one tiny splinter—the one that’s been quietly irritating them (the one that YOU can get out)—and twist it just enough that they can’t ignore it any longer. It’s not difficult. Just start SMALL Just start SMALL How do you find that splinter? In Part Two , we’ll dig into my Paper Cut Pitch —the approach that doesn’t just grab their attention, it grabs them by the throat. How do you find that splinter? Part Two Paper Cut Pitch Paper Cut Pitch it grabs them by the throat. Time to ditch the tired tactics and make every incision count. Time to ditch the tired tactics and make every incision count.