Pitch Archive - The Art of Communicating

From should to would thinker

Almost everyone starts their sales and pitch stories from this simple question:

“Why should the customer choose us?”

It looks perfectly innocent. And it makes so much sense. Just list all the reasons why the customer should choose you and – boom – it’ll become perfectly obvious: they should definitely choose you.

But, here’s another question:

Why would they?

Notice how different this one feels?

Yes, sure, they should choose you, but why would they?

It’s a one-letter difference, but the answers you’ll get to this version, are so much more powerful.

→ It shifts the focus from your perspective to theirs.
→ It changes the posture from entitlement to empathy.
→ It transcends assumptions in order to arrive at understanding.

“Should” is the lazy approach that everyone takes.

It avoids facing the uncomfortable truths the “would” will surface. Truths like the gaps between what you offer and what they truly need. Or whether they even see the problem the product solves.

“Should” feels safe, but it stays in your world.
What you believe. What you value. What you assume.

“Would”, however, is curious.
It steps out of your world and into theirs.
It wonders about their struggles, their dreams, their reasons.

And when you think like that, something incredible happens:
You stop persuading.
And start resonating.

Most importantly, you’ll build something they want to say yes to — not because they should, but because they truly would.

That’s the kind of thinker who inspires action.
Who creates impact.
Who lights the path.

So, which type of thinker are you?

Keep lighting the path!

The better deal

The most lucrative pitches are not about you making a good deal. They are about the other party making an even better deal.

The better the deal is for them, the better it is for you.

As with any good relationship, the best ones are those in which both sides feel like they got the better deal.

Here’s where many pitches get it wrong:

They approach the pitch as if it was about getting the better deal. They try to impress. Paint the promises a little brighter than they really are. Frame the offer in a way that allows them to charge a little over. And use a bunch of other subtle tricks and techniques to get more out of the deal.

But in my experience, you get even better deals if you turn it around and approach the pitch differently. It’s not about getting the better deal but about being the better deal.

Can you shift your perspective from what you want to what they desire?

What would make the deal so worthwhile for the other side that they can’t believe how lucky they are?

What would be a story that sounds almost too good to be true to them, not because you overpromised but because you cared so much that it really is that good (you even underpromised)?

If you can deliver on that, if you truly are a phenomenal deal, negotiations will be very different. What previously sounded like a steep ask or a tough sell to you, might now sound like a bargain to them.

How exciting is your pitch deck?

If you’re not excited by your pitch deck, chances are your audience won’t be, either.

It’s something that has always baffled me: how far some people will go to defend a mediocre presentation with rational arguments when there’s a very simple metric to decide whether you’ve nailed it:

Does it make you feel excited?

If it doesn’t, there’s no use in arguing that it contains all the facts. Or that it’s logically structured.

If all of that is true and it still doesn’t make you feel excited, it means that your story isn’t working.

Sometimes, it’s indeed because the facts aren’t right, but in my experience it’s much more often the words people use to speak about the facts that aren’t right.

How about your pitch? Are you excited by it?

Can’t stop thinking about it

If you can manage to plant one thought in my head that I can’t stop thinking about, you’ve achieved more than most other talks.

Don’t even bother with planting a dozen thoughts until you can manage to plant that one thought in my head.

When it works and I really can’t stop thinking about it, it’s hard to believe that I wouldn’t want to know the second thought. And the third.

What’s a thought that you would like to plant in my head?

Embracing the blank stare

For some, it’s a huge source of frustration.
For others, it’s a gift.

The blank stare on people’s faces when you tell them about your great idea but they just don’t get it.

So, how is that a gift?

It’s information. It tells you that either your idea or your explanation needs improvement. Not only that. The blank stare tells you exactly where.

Pay attention to when exactly the blank stare occurs and you know where you need to improve your idea or your story.

Don’t give up until the blank stare is resolved.

But wait, there’s one exception: Your idea might not be for everyone.

Don’t waste time on optimizing your story for those who will never get it. Own their blank stare and make it even stronger for the people who you’re making it for.

Your differentiator

Being different is a by-product, not a goal.

When you treat it as the goal, “different” can easily become a trap. It deceives you to chase superficial changes like choosing quirky colors, strange slogans, or odd advertising gimmicks in hopes of being unique. Yet, these surface-level tweaks are often meaningless if they don’t tie back to something real and valuable for the customer.

This kind of different wants you to believe that by standing out in a crowd, you’ll capture attention and thrive. And you might. But there’s no guarantee that this attention will be in your favor.

The real magic happens when a business shifts its focus from “different” to “meaningful”.

When you zero in on a specific problem faced by a specific group of people and craft a solution specifically tailored to them, you’ll almost inevitably stand out for them. This customer-centric approach makes a world of difference. When no-one else provides a solution that fits so well for them, you’re obviously different. More importantly, by diving into the lives of the customers, understanding their needs, and crafting solutions that ease their pains, a business becomes a valuable asset to them. It’s about forming a connection that’s deeper than a flashy logo or a catchy tune.

Make no mistake, you might still end up using quirky colors or edgy slogans, packaging, and marketing.

But this time, it’s not just about standing out; it’s about standing out for the right reasons.

Clueless

What just happened? Did they seriously choose that piece of junk over mine?

Every detail, every nuance — mine’s miles ahead … and it’s still trumped by that amateur hour show? What a kick in the gut.

Damn it! All those nights, the endless tweaking, all the personal sacrifices—swept aside for what? Some fancy talk and smoke and mirrors? I mean, their sweet talk might impress for a moment, but it won’t hold up in the long run. Why can’t they see past the façade?

They must be blind. Or stupid. Anyone with half a brain would see mine’s the real deal. If they just looked closer, gave it a real shot, they’d get it.

Are they seriously this clueless?

====

What do you reply to this frustrated person?

They won’t know what hit them

Alright, this is it. The big meeting. I’ve got all the facts lined up, PowerPoint is flawless, and my talking points are sharp. I’m ready to persuade the heck out of them. They won’t know what hit them.

Okay, opening slide – good. I can see they’re listening. Time to ramp it up. Point one, point two, hit them with a statistic! Why do they look confused? No worries, I’ll explain it again, but faster and with more emphasis.

Wait, why is Sarah looking at her watch? And why is Mike doodling? They should be hanging on to my every word. Alright, double down. Speak louder, be more assertive.

Uh oh, I’ve lost them. They’re nodding, but it’s that empty nod people do when they’ve checked out. What went wrong? I pushed all the points, I laid out all the facts.

“Don’t persuade harder, resonate stronger.” That phrase suddenly pops into my head. My old mentor, Michael, used to say that. I brushed it off back then, but it’s ringing true right now.

I need to pause. I need to breathe. What do these people care about? What matters to them? I’ve been so focused on what I want to say that I’ve ignored what they need to hear.

Alright, shift gears.

Let’s try this again.

Slow down … tune into their frequency … and hit the right notes.

Time to resonate …

No!

In elementary sales school you learn that a prospect’s “no” is short for “not enough information”.

And so, whole armies of salesforces bombard their prospects with ever more info when the prospect has already tuned out and started to feel annoyed.

A better way is to consider the possibility that your customers are actually, you know, smart and that they might actually know what they want and need.

Sure, sometimes a “no” means that you haven’t explained it well enough or that a crucial detail was missing. But other times, a “no” really does mean “no”.

If it’s the latter, rather than adding more detail you might want to consider fixing the product or finding a better match. Only if it’s the former will tweaking your communication have an impact.

(It helps, of course, to become good at distinguishing the two.)

Charismatic founders

There’s this certain breed of super charismatic founders. You could listen to them for hours and after the meeting you’ll leave with a feeling of excitement. Their enthusiasm was so mesmerizing and that thing they were telling you about really sounded cool.

So, you feel you just have to tell your friends about it. Which you do. Well, actually it’s more that you try to tell them. Because soon you discover that it’s actually pretty hard to explain. Somehow, you can’t quite put your finger on what the point really is. What sounded so cool when she said it, sounds rather confusing when you say it.

And so, your friends don’t quite get your excitement.

Which is not your fault. Because the one thing that the founder missed was to make it easy for others to pass the message along.

They won’t be in the room when the message gets passed along. And so the message itself must be crafted such that it captivates even when others share it.

How do you make it easy for others to pass your message along?

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