Fresh off a victory lap from selling my first startup, I waltzed into Skytech Corp’s palace of a headquarters, feeling invincible. I was on cloud nine, or maybe cloud ten? But let’s face it, when you’ve just sold a company, you kinda feel like the LeBron of the business realm, slam dunking left and right. Well, that day, instead of slam dunks, I felt like I airballed in front of the entire stadium. Imagine this: sleek boardroom, all eyes on yours truly, and I’m laying out our next big thing, pouring my essence into every word. The result? A symphony of silence. Six suits looking at me like I’d just rapped Shakespeare in Klingon. Ouch.

So, let’s dive deep, my friend. I want to unwrap this cringe-worthy day layer by layer, not for you to have a good laugh (although, feel free if you want) but to gift you with some nuggets of wisdom that changed the game for me. And guess what? These nuggets could be game-changers for you too, whenever you’re trying to sell an idea, product, or even just yourself.

Setting the Stage: Managing Expectations

Alright, so here’s the rub: before you can captivate an audience, you’ve got to understand their playground and set the damn rules. Yeah, I know, it sounds as basic as Business 101, but trust me, it’s often overlooked, and boy, can it bite you in the ass.

The Art of Pre-empting – Picture this: You’re psyched about this epic movie everyone’s raving about. You grab your popcorn, snuggle into the comfy theater seat, the movie starts, and… meh. Why? Simple. Overhype. See, that’s what happens when folks don’t manage expectations. So, when you’re showing off your stuff, keep it real. Don’t underpromise just so you can shock and awe, but also, don’t build it up so much that any result falls flat. It’s kinda like salsa dancing – it’s all about that right balance, baby.

Mind-Reading for Dummies – Oh, c’mon, don’t kid yourself. No one’s freaking Professor X from X-Men. You can’t read minds. But, what you can do is eliminate the guesswork. Wanna know a pro-tip? Drop breadcrumbs. Yeah, you heard me. Tease ’em a little. Send out a brief, a snippet, a freakin’ meme even – just give them something to gnaw on before the main course. That way, they have a sense of what’s coming, and there are no nasty surprises.

Setting the Tone: Formal vs. Freestyle – This one’s a riot! I still cringe remembering when I rocked up to a formal meeting in my lucky SpongeBob socks (don’t judge). Know your damn audience! Corporate moguls? Probably best to leave the novelty socks at home and brush up on the latest stock market trends. Startup geeks in Silicon Valley? Hell, rock those socks and throw in a hoodie while you’re at it.

So, the moral of this part of my messed-up story? Manage expectations like you’re herding cats. It’s tricky, requires finesse, but when done right, man, it’s pure magic.

Talking the Talk: Translating Your Brilliance

Look, you’ve got the big brains and the goods. No doubt about that. But what’s the point if your audience needs a damn Rosetta Stone to decipher what you’re selling? Let’s dive into how you can make sure your brilliance doesn’t end up lost in translation.

Speak their Love Language – I ain’t talking ’bout cuddles and sweet nothings. It’s about tapping into your audience’s vibe and language. So, you’re pitching to tech nerds? Drop that lingo like it’s hot. Slinging a concept to marketing mavens? Hit them with those metrics and stats. The idea? Make your message slide smoother than a buttered-up otter down a slide. Get fluent in their jargon, pick up on their pet peeves, and for heaven’s sake, avoid those buzzwords that make them roll their eyes!

Building the Bridge: Relating to THEIR World – Here’s where it gets real. You’ve got your story, and it’s a damn good one. But what’s even cooler? Weaving your narrative into theirs. You’ve got to find that common thread. If your product’s gonna change their game, show them how. Paint a picture, vivid and clear, where you bridge the gap between what you offer and what they freaking need. It’s all about making your world mesh seamlessly with theirs. No square pegs in round holes, alright?

Managing the Misfits – Oh boy, the tough crowd. We’ve all been there. They’re the skeptics, the naysayers, the “prove-it-to-me” peeps. Look, not every pitch is gonna be met with a standing ovation. Sometimes, you’ll face a room colder than a polar bear’s toenails. That’s when you pull out the big guns – clarity and simplicity. Leo da Vinci hit the nail on the head: “Simplicity is the ultimate sophistication.” Trim the fluff, laser-focus on the essence, and serve it up neat.

In essence, it’s like this: you can be the sharpest tool in the shed, but if you’re not speaking the same language as your audience, you’re just background noise. So, tune in, resonate, and make sure your brilliance hits the right notes.

Crafting the Connection: Familiarity in Presentation

Alright, hotshot, let’s get one thing straight. You remember that one jingle from when you were a kid, right? The one that’s still stuck in your head, even after all these years? Why? ‘Cause it’s familiar. And, let me spill the beans, the power of familiarity, when done right, can be your ticket to nailing that presentation or pitch.

Déjà vu isn’t Always Bad – We humans, we’re funny creatures. Throw something completely alien our way, and we might just go running in the opposite direction. But give us a vibe, a feel, something that tickles the back of our memory? That’s the sweet spot. The trick isn’t to regurgitate what they already know but to weave in elements that resonate. Think of it like this: new song, but with a sample from a classic. It feels fresh yet familiar. That’s your mission.

Pushing Boundaries (But Not Too Far) – Taking risks is cool, no doubt. But there’s a fine line between edgy and “Whoa there, buddy!” You’ve got to give your audience a glimpse of what lies beyond the horizon, not shove them off the cliff into the unknown. Innovation is brilliant, but if it’s too out there, you’ll lose your peeps. You want them intrigued, on the edge of their seats, not bolting for the exit.

Being Relatable vs. Being Revolutionary – Let’s shoot straight: If you’re coming in hot with something revolutionary, you need to ground it. If your idea’s zooming at warp speed, you’ve gotta throw down some anchors for your audience. You can’t just hand grandma a VR headset and throw her into a virtual world without a guide. Introduce your rad ideas, but link them back to something they can grasp. Relate to their world, then lead them to yours.

Remember, it’s not about dumbing it down. Hell no! It’s about framing your brilliance in a way that’s approachable. Give them a little taste of home, a sprinkle of the known, before you whisk them off to see the wizardry of your world. By the end of your pitch, they should feel like they’ve been on a journey, not like they’ve been hit by a freight train of “what the heck was that?”

Alright, tiger, ready to jump into the deep end of relationships and pitching? I promise it’s less about moonlit walks and more about sealing the deal. Let’s roll!

Relationship 101: The Core of Every Pitch

So, let’s get this party going. Now, I’ve been around the block a time or two, and if there’s one universal truth in this business gig, it’s this: People don’t buy products, they buy relationships. Hell, they buy you. It sounds corny, but stick with me.

Beyond Business: Building Trust – How many times have you bought something because of the person selling it? A charismatic car salesman, a friendly barista recommending a new coffee, or even your buddy convincing you to watch that new Netflix show. It’s all about trust, my friend. If you’ve been ghosted after a pitch, pause and reflect. Did they buy into you? Did they trust you? Relationship-building isn’t about knowing the specs of your product inside out. It’s about remembering that your client’s kid just won the soccer championship or that they’re an absolute freak for Italian food. Is it schmoozing? A bit. But it’s genuine schmoozing. Keep it real, keep it pro, and for Pete’s sake, don’t cross into the creepy zone.

Collaboration > Dictation – Gone are the days of “I talk, you listen.” We ain’t in a lecture hall. We’re in the era of synergy, baby! If you want to get anywhere in this fast-paced biz world, you’ve got to switch gears from dictator to collaborator. Don’t just spill your brilliance, make room for theirs. Heck, if they walk out feeling like the idea was partly theirs, you’ve hit gold. Why? ‘Cause everyone wants to feel heard. Everyone wants to be part of something bigger. It’s not just about ego-stroking (though, let’s be real, who doesn’t love a bit of that?). It’s about creating something epic, together.

Redefining Feedback: Constructive > Destructive – Alright, squad, real talk. Criticism stings. No one likes to hear that their baby, their brainchild, has flaws. But would you rather have spinach in your teeth and no one tell you? Feedback is your mirror, showing you the good, the bad, and the “oh hell no.” Don’t be the guy who tosses shade on every idea. Instead, be the rockstar who’s all about solutions. Celebrate the dunks, learn from the airballs, and remember, it ain’t personal. It’s growth.

There’s a reason they call it the “art” of pitching. ‘Cause, just like any masterpiece, it’s nuanced, it’s layered, and it’s unique to the creator. Relationships, trust, collaboration — these aren’t buzzwords, they’re the foundation. And if you master this? Well, you’re not just pitching anymore. You’re connecting, you’re resonating, and heck, you’re winning.


Let’s bring it home. Pivoting expectations isn’t about conjuring up some magical formula or doing a secret handshake with potential clients. Nah, man, it’s more like jamming at a concert – you vibe, you dance, and you resonate.

Let’s do a quick rewind. That day at Skytech Corp – when I waltzed in, all swagger and confidence, thinking I was about to bring the house down? I might’ve missed the mark on the presentation, but the lessons? Priceless. More valuable than any MBA or snazzy seminar. Because, at the end of the day, it’s not about how much you know, but how well you can connect.

Life, business, presentations – it’s all a dance, right? Sometimes you lead, sometimes you follow. Sometimes you’re smooth as hell, and other times you’re tripping over your own feet. But, dude, even if you fall, you get back up and keep dancing. The key is reading the room, feeling the rhythm, and adjusting your moves accordingly. The art of winning your audience isn’t locked in fancy slides or jargon-filled monologues. It’s in the soul, in the authentic human connection.

Each section we dove into, whether it was setting the stage, speaking the language, crafting connections, or building relationships, all circles back to one core concept: being genuine. It’s about listening just as much as talking, about sharing stories and embracing feedback, and, most importantly, about being real.

Now, if you’re feeling overwhelmed, thinking, “Damn, how do I put all this into action?”, don’t sweat it. Baby steps. Each time you prep for a presentation, or a pitch, or heck, even a casual chat over coffee, think about the connection. How are you making your listener feel? Are they intrigued, engaged, invested? Are you resonating with their needs, their desires, their goals?

And remember this: in the grand scheme of things, one botched presentation or one unimpressed audience ain’t the end of the world. It’s a stepping stone, a learning curve. Hell, if I let every misstep or goof hold me back, I’d still be stuck in my parents’ basement jamming to 90s tunes (which, let’s be real, still slap).

So, my friends, next time you’re gearing up for that big pitch, presentation, or power move, take a deep breath, channel your inner superstar, and pivot those expectations. Embrace the lessons, cherish the connections, and above all, keep the authenticity game strong. You’ve got this. Now, go out there, set the world on fire, and remember – it’s not about perfection; it’s about connection.

About the Author: Geoffrey Byers
Geoffrey is one of the world's foremost Designers. He is also a Serial Entrepreneur, Author, Speaker, and Mad Scientist. Hypothesis-Driven experimentation is his love language.