{"id":"unconventional-client-pitch-tactics-38462","slug":"unconventional-client-pitch-tactics-38462","title":"Unconventional Pitch Tactics That Actually Win Clients","description":"What happens after you find the hidden pocket in the AI market — how do you actually win the work? This episode climbs a ladder of unconventional client pitches, starting with the mild (no slides, one page, a pre-mortem) and rising through live demos, recorded support calls, physical props, and a human pretending to be the AI behind a folding screen. Each rung gets more effective and more dangerous, and the top of the ladder is a tactic that either wins the room or ends your career. If you pitch AI work to clients — or sit on the other side of the table — this one is for you.","excerpt":"From ditching slide decks to wheeling in a day's worth of paper — a ladder of pitch tactics, from mildly odd to career-ending.","pubDate":"2026-10-18T11:04:30.362Z","tags":["professional-communication","generative-ai","ai-agents"],"heroImage":"https://files.myweirdprompts.com/covers/unconventional-client-pitch-tactics-38462.png","podcastAudioUrl":"https://episodes.myweirdprompts.com/audio/unconventional-client-pitch-tactics-38462.m4a","podcastDuration":"20:56","episodeNumber":6090,"transcript":"Corn: A consultant walks into a boardroom with forty slides, and the client checks his phone on slide three. Somewhere in the same city, a different consultant walks in carrying a cardboard box, says nothing, and puts it on the table. Everyone looks at the box.\n\nCorn: That's the territory today. We did the hidden pockets in AI careers not long ago, and Daniel's follow-up is about the moment after you've found the pocket, which is the pitch. Unconventional ways to present to a client and win the work. And he wants a ladder of them, starting with the mildly unusual and climbing all the way up to the kind of tactic that ends a career, or at least ends the meeting. Which means the man in the chair is the same man as last time, because nobody has stood in front of more strangers asking for things than Hilbert.\n\nHerman: Herman Poppleberry, and I'd like it on the record that I brought a deck.\n\nCorn: To a podcast.\n\nHerman: It's only nine slides. That's under the Kawasaki limit.\n\nHilbert: Put the deck down, Herman. The deck is the bottom of the ladder. The deck is the floor the ladder is standing on.\n\nCorn: So rung one is no slides at all.\n\nHilbert: Rung one is that you arrive and the screen stays off. That alone. In a room where the last four people plugged in a laptop and spent two minutes looking for the right cable, the man who doesn't plug anything in has already won the first two minutes.\n\nHerman: It has respectable ancestry, too. Bezos banned slide decks from Amazon's senior meetings in an email in two thousand four. His argument was that a narrative memo forces better thinking than twenty pages of bullet points, and the meetings there famously start with everyone reading the memo in silence for the first twenty minutes or so.\n\nCorn: Twenty minutes of silence. You'd last about four, Herman.\n\nHerman: I would last the full twenty. I'd just be reading it faster than everybody else and looking up.\n\nHilbert: You don't need twenty minutes. You need one page. You hand it over, you say read this, and you sit there. Silence is the most unusual thing you can bring into a sales meeting. Everybody else fills it. The client is braced for you to talk at them, and you don't, and they read. The page has three things on it. What's broken. What it costs them each month. What you'll do in the first fortnight.\n\nHerman: I'll defend the deck for a second, though. Some clients want the deck. They want something to forward to the person who wasn't in the room.\n\nHilbert: Then the page is the thing they forward. A page survives forwarding. A deck forwarded without the man who made it is forty pictures of nothing.\n\nHerman: Fair. Corn, would that work on you? If someone sat down across from you and handed you one page and went quiet?\n\nCorn: I'd read it twice, because I'd assume it was a trick. Which is the same thing as paying attention.\n\nHilbert: Rung two. You open with how the project dies.\n\nHerman: The pre-mortem. That's Gary Klein's technique. Before a project starts, you tell the team to imagine it's a year from now and the thing has failed, and then everyone writes down why. Klein wrote about it in the Harvard Business Review, and he leaned on earlier research suggesting that imagining the failure as already having happened makes people noticeably better at naming the causes. Something on the order of thirty percent better.\n\nHilbert: In a pitch it does something else as well. Every other consultant who comes through that door tells the client how well it will go. You say, here are the four ways AI projects die at companies like yours. The pilot nobody uses. The bot that tells a customer the wrong refund policy. The bill. The one person who understood it leaving. And here is what we do about each one. The client has been lying awake about at least two of those. Now you're the only person in the building who has said them out loud.\n\nCorn: You're selling the cure by being the only one who admits the disease exists.\n\nHilbert: You're the doctor who mentions the side effects. People trust him more. They don't know why.\n\nHerman: There's a risk, which is that you talk them out of the project.\n\nHilbert: Then it was a project you shouldn't have won. Better they change their mind in the meeting than in month four.\n\nHerman: Rung three, then, if we're climbing. I've got a guess at it.\n\nHilbert: Go on.\n\nHerman: You build the thing before the meeting.\n\nHilbert: You build the thing before the meeting. You take what's public. Their website, their help pages, their price list, the questions people ask about them online. You put a small assistant on top of it. It takes an evening now, that's the whole shift in this business. And when they ask what it would look like, you don't describe it. You turn the laptop round and say, ask it something about your own company.\n\nHerman: The famous version is Dropbox. Before the product was finished, Drew Houston posted a short demo video, a few minutes long, showing it working. The beta waitlist reportedly went from about five thousand people to around seventy-five thousand practically overnight. Nobody was signing up for a pitch. They were signing up because they'd watched the thing do the thing.\n\nCorn: And the first question they ask the demo is the one it gets wrong.\n\nHilbert: Always. Which is the best moment of the meeting, Corn, because now you explain why it got it wrong, and how you'd fix it, and you've stopped being a salesman and started being the person who knows how it breaks.\n\nHerman: That links back to the evaluation pocket, really. The demo getting one wrong is your opening for the testing work.\n\nHilbert: It's not an accident. Leave one wrong on purpose if it doesn't find one by itself.\n\nCorn: That's rung three and a half, and it's already a bit morally ambiguous.\n\nHilbert: It's a demo. Every demo is morally ambiguous.\n\nLarry: Running out of ways to stand out? Introducing Rung of the Month, the subscription box that delivers a brand new unconventional pitching tactic to your door, every thirty days, whether you have a client or not! Starter members receive one prop, slightly pre-pitched. Professional members receive two props and a laminated card reading I have deliberately not brought slides. Executive members receive a live prop, which may not survive the post. Every box includes a sealed envelope of authentic pre-mortems, failures guaranteed! To cancel, simply present a twenty minute pitch to our cancellations committee explaining why you deserve to leave. The committee does not read slides. The committee does not read memos. The committee meets in silence. Rung of the Month. You're already on the ladder.\n\nHerman: I have one of those. The live prop arrived in March and it's still in the bathroom.\n\nHilbert: Rung four. Bring the client's customer into the room.\n\nHerman: Bezos again, slightly. There's the old story about the empty chair in Amazon meetings, the seat left open to stand for the customer who isn't there.\n\nHilbert: An empty chair is too polite. Bring the actual customer, in the form of a recording. Before the meeting you ring their own support line. Three times. At lunch, in the evening, and on a Friday afternoon. You record what happens. Then in the meeting you play it. The hold music. The menu with nine options. The voice that says your call is important. And then you say nothing, and you let the managing director listen to his own company not answering him.\n\nCorn: That's a wonderful way to be thrown out of a building.\n\nHilbert: It's a coin toss. Half of them throw you out. The other half go very quiet and ask how fast you can start. I don't pitch to the first half anyway.\n\nHerman: I'd actually put that on a higher rung than you have. You're playing their failure back to them in front of their own staff. That can humiliate somebody who'll then quietly kill your contract.\n\nHilbert: That's why you ask for the meeting with the person above the one responsible for the phone.\n\nCorn: The ladder has an org chart built into it.\n\nHilbert: Every ladder does.\n\nHerman: Corn, where are you on this one? Brilliant or cruel?\n\nCorn: Both, which is why it works. If I were the client I'd hate you for a day and hire you by Thursday. I'd never invite you to anything again, but I'd hire you.\n\nHilbert: Rung five, and now we leave the respectable part. The object.\n\nHerman: Props.\n\nHilbert: Something they can't ignore and can't throw away. Herman, you'll know the mosquitoes.\n\nHerman: Bill Gates at TED in two thousand nine. He was talking about malaria, he said malaria is spread by mosquitoes, opened a jar, and let some loose in the auditorium. His foundation said afterwards they weren't carrying anything. Accounts differ on how many there were, the organisers said only a few, but the point was made. He'd said that more money went into baldness drugs than malaria research, and then he made a room full of very rich people feel slightly bitten.\n\nCorn: The only TED talk with a genuine call to action.\n\nHilbert: That's the principle. Make the problem physical. If you're pitching document processing to an insurance company, you don't show a slide that says forty thousand claim forms. You hire a trolley, you go to their own post room, and you wheel in one day's paper. Put it on the boardroom table. Leave it there. Say, this is Tuesday.\n\nHerman: That's actually good. I was expecting it to be worse.\n\nHilbert: It gets worse. The Airbnb founders.\n\nHerman: The cereal. In two thousand eight, broke, they designed novelty cereal boxes for the American election, Obama O's and Cap'n McCain's, sold them for forty dollars a box, and by Chesky's own account raised about thirty thousand dollars. It's part of the story of how they got into Y Combinator. Paul Graham reportedly figured anyone who could sell forty dollar cereal could survive.\n\nHilbert: So the leave-behind is merchandise of their own problem. For the insurance company, a cereal box. Claims Flakes. The back of the box is a maze, and the maze is their actual approval process, every step, drawn properly. There's no way out of the maze. That's the joke, and also the finding.\n\nCorn: Is there a toy in the box?\n\nHilbert: A tiny rubber stamp. It says pending.\n\nHerman: I'd buy that.\n\nHilbert: Everyone would buy it. That's the problem with it. The marketing department will want to know who made it and then you'll be doing cereal for three years.\n\nCorn: That's a hidden pocket of its own.\n\nHilbert: Rung six. You become the product.\n\nHerman: Oh, I know what you're going to say. The Wizard of Oz.\n\nHilbert: Say it, then, you're going to anyway.\n\nHerman: It's a real technique in interface design, going back to IBM in the eighties. You test a system that doesn't exist yet by having a human hidden behind it, pretending to be the computer. The user types, a person in the next room types the answers back, and you learn how people would actually use the thing before you've built it.\n\nHilbert: In a pitch, you sit behind a screen. A real one, a folding one, the kind from a hospital ward. The client's staff type questions into a laptop on the table. You answer them, from behind the screen, as the assistant you're proposing. In a flat voice. And you only use the information they'd actually give the system. If they haven't given it the refund policy, you say I don't know. After fifteen minutes you fold the screen away.\n\nCorn: And the room realises it's been chatting to a consultant in a cupboard.\n\nHilbert: The room realises the system is only as good as what they put into it, which is the most useful thing they'll learn all year. And they've seen you being patient for fifteen minutes. Nobody else they've met in this field is patient.\n\nHerman: That's genuinely the best one so far, and it's also the one where you're crouching behind hospital furniture.\n\nHilbert: The best ones usually involve crouching.\n\nCorn: We're at rung six and things have stayed technically legal. When does that change?\n\nHilbert: Rung seven. You turn them down.\n\nHerman: The reverse pitch.\n\nHilbert: You do the full meeting, you ask all the questions, and at the end you say you don't think you can take them on yet. You list three things they'd need to fix first. Their data's in nine places. Nobody owns the project. The budget is for a demo, not a system. You stand up and you leave. You leave the list.\n\nCorn: And then you wait by the phone looking casual.\n\nHilbert: You wait about nine days. They fix one of the three, and they ring you, because now they want to prove to you that they're worth it. You've turned a pitch into an audition, and they're the ones auditioning.\n\nHerman: That one makes me nervous. It assumes you can afford to walk away. Plenty of small consultants can't.\n\nHilbert: You can afford to walk away from the ones who were never going to pay. The trick is you were always going to lose those. You're just losing them sooner and on your own terms.\n\nHerman: I'll take half of that. Corn, would you do it?\n\nCorn: I'd do it once, by accident, because I'd gone slowly and they'd lost interest. And I'd call it a strategy afterwards.\n\nHilbert: That's how most strategies start.\n\nCorn: Rung eight. I'm assuming we're now in reputational damage.\n\nHilbert: Rung eight. The pitch is delivered by your AI, and you attend as its assistant.\n\nHerman: You're joking.\n\nHilbert: An avatar. Your face, your voice, a cloned voice, on the big screen, presenting. You sit at the side of the room with a notebook. When it says something wrong, you raise your hand and correct it, politely. When the client asks it a difficult question, it says that's a great question for my human colleague, and turns, and you answer. You're the man who manages the machine. That's the job you're selling.\n\nCorn: There's a version of you in the meeting that's more confident than you are.\n\nHilbert: There's a version of all of us that's more confident. Mine has never been asked to leave a building. And the thing about it is, they'll remember it for ten years. Whether they hire you is a separate matter. Nobody forgets the man who brought himself.\n\nHerman: There's real risk in that one beyond the novelty, though. Half of what makes a client trust a consultant is the feeling that the person is fully present. You're deliberately putting a machine between yourself and them.\n\nHilbert: Some clients want exactly that. They want to see the machine. The ones who don't, you'll know within a minute, because they'll keep looking at the man with the notebook instead of the screen.\n\nCorn: Rung nine.\n\nHilbert: Rung nine is the one I wouldn't do. Not anymore. You hold the pitch somewhere it can't be ignored. The client's own car park. A table and two chairs and a flask, set up at seven in the morning in the space next to the managing director's. When he arrives, you're there, you stand, you say, I have nine minutes, and you show him one page.\n\nHerman: That's ambush.\n\nHilbert: It's ambush, Herman. Ambush with a flask. It worked twice for a man I know. The third time security moved the table and he kept pitching, standing up, to the barrier.\n\nCorn: Did the barrier go up?\n\nHilbert: The barrier went up for the managing director. Not for him.\n\nHerman: For the record, that is the rung where you start being talked about, and not in the way you'd want.\n\nHilbert: Every rung above six, people talk about you. The question for the consultant is which story they'll tell. The one with the trolley of paper gets told at their Christmas party as a good story. The one with the car park gets told to the security company.\n\nHerman: I'd like to bring this back down to earth for a second, because I think there's a pattern under the whole ladder, and it's the useful part. Every rung that works does one of three things. It shows rather than tells. It makes the client's own problem physical, the paper, the hold music, the maze. Or it turns the power round so the client is the one doing some persuading. The rungs that fail are the ones where the stunt is about the consultant.\n\nHilbert: Twelve.\n\nHerman: Sorry?\n\nHilbert: Twelve. You said the Amazon meetings start with twenty minutes of silence. It's closer to the length of the memo. Six pages at the speed most of those people read is twelve, perhaps fifteen. Nobody sits for twenty, they're finished by twelve and pretending to reread the appendix.\n\nHerman: I'll take twelve.\n\nHilbert: I only know because I tried it on Waterford County Council. Not the memo, the silence. I needed a roundabout renamed. There was a roundabout at the end of my road, four exits, and it had no name, and the delivery vans couldn't find me, because the sat nav called it unnamed roundabout and turned them back toward Dungarvan. The council's roads department had a man called Desmond Phelan who dealt with naming. Senior executive officer. He had a rule that he would hear any member of the public for exactly nine minutes, on the first Tuesday of the month, at a desk on the second floor, next to the photocopier. So I prepared. I wrote one page. Three things on it. What's broken. What it costs. What I'll do in the first fortnight. I handed it to him and I sat there, and I said nothing. Desmond read it. Desmond read it again. Then he said, Mister Flumingtop, you've used four of your nine minutes being silent. And I said yes. He didn't know what to do with that. Nobody had ever handed the minutes back. He gave me the roundabout on the spot, subject to a public consultation, and the consultation is the part that went on.\n\nCorn: How long did it go on?\n\nHilbert: Fourteen months. I had proposed calling it Flumingtop Cross. There was an objection from a man two doors down, Gerry Kinsella, who kept geese, and wanted it named after his oldest goose, which was called The Bishop. He did his pitch in the car park. He brought the goose. He brought The Bishop to the council offices in a cat basket, on a Tuesday, and he stood in the space next to the county manager's car from seven in the morning. Herman, there's a little click on your end, every time you say Bishop, you're closing your mouth on the mic, I'll take it out later. He stood there until the county manager arrived, and The Bishop got out of the basket, and that was more or less the end of the consultation. Desmond rang me himself. He said, Mister Flumingtop, your page was very good, and the goose was in the minutes. The roundabout is called Bishop's Cross. There's a sign. The vans still go to Dungarvan, because nobody updated the sat nav, but now they go to Dungarvan past a sign with a goose on it. I couldn't use the council's laser pointer either, the button sits too far down for a claw, so I'd brought my own page. Gerry didn't need a laser pointer. He had a goose.\n\nHerman: That's the car park rung working, though. That's the one you said you wouldn't do.\n\nHilbert: It worked for Gerry. I'm not Gerry. I don't have the goose.\n\nCorn: The car park works if what you bring into the car park can't be argued with.\n\nHilbert: The Bishop died in two thousand nine. The sign is still up. Desmond retired and the new man answers emails in under a day. I wrote to him in August about the sat nav. He wrote back in four hours and said the roundabout has always been called Bishop's Cross, and asked if I'd like to submit a page.\n\nHerman: Four hours. That's a council that learned something from a goose.\n\nCorn: Whatever the council learned, there's something in that for Daniel past the poultry. Every tactic that worked on this ladder, the silent page, the trolley of paper, the hold music, even the goose, put something in the room the client couldn't argue with. Most pitches are arguments, and people defend themselves against arguments. They don't defend themselves against their own Tuesday sitting on the table.\n\nHerman: And the gap between a story they tell at the Christmas party and a story they tell the security company is about one rung, so it's worth knowing which rung you're on before you climb it. Thanks, as ever, to our producer Hilbert Flumingtop, who kept the levels tidy through all of this.\n\nCorn: This has been My Weird Prompts. If you've enjoyed this one, a review on Spotify helps other people find the show.\n\nHerman: We'll be back soon.\n","showNotes":"There's a moment after you've found your niche in the AI market when you have to walk into a room and ask for the work. Most people bring forty slides. The episode argues that's the floor of the ladder, not the top.\n\nRung one: arrive and keep the screen off. Hand over a single page — what's broken, what it costs monthly, what you'll do in the first fortnight — then sit in silence while they read. Rung two: open with how the project dies. A pre-mortem, where you name the four ways AI projects fail at companies like theirs, positions you as the only person willing to admit the disease exists.\n\nRung three: build the thing before the meeting. Take their public website and help pages, stand up a small assistant, and let them ask it about their own company. When it gets something wrong, that's the best moment in the room — you stop being a salesperson and become the person who knows how it breaks. Rung four: record their own support line at lunch, in the evening, and on a Friday, then play it back to the managing director and say nothing.\n\nThen it gets stranger. Bill Gates released mosquitoes at TED to make malaria physical; the equivalent is wheeling one day's worth of claim forms into the boardroom. The Airbnb founders sold forty-dollar novelty cereal to stay alive. Rung six is the Wizard of Oz technique — a human hidden behind a folding screen, answering as the proposed assistant, saying \"I don't know\" when the data isn't there. And rung seven is the one that ends careers: turning the client down.","promptSanitized":"Follow-up to the episode on hidden pockets in AI careers, with Hilbert as the expert again: highly unconventional strategies for client presentations and pitching in AI consulting, as an escalating ladder from slightly unusual tactics to downright bizarre and potentially reputation-tarnishing ones, with genuinely useful ideas mixed in with the absurd.","transcriptUrl":"https://episodes.myweirdprompts.com/transcripts/unconventional-client-pitch-tactics-38462.md","url":"https://myweirdprompts.com/episode/unconventional-client-pitch-tactics-38462/","_links":{"self":"https://myweirdprompts.com/api/episodes/unconventional-client-pitch-tactics-38462.json","html":"https://myweirdprompts.com/episode/unconventional-client-pitch-tactics-38462/","audio":"https://episodes.myweirdprompts.com/audio/unconventional-client-pitch-tactics-38462.m4a"}}