Pitch Archive - The Art of Communicating

The devil’s cute advocate

There are two ways to play the devil’s advocate game: the serious way and the cute way.

The cute way goes like this: Think of an objection to your idea. Be proud that you thought of that objection. Come up with some reply (mostly anything will do). Check the box and move on to the next objection.

The cute advocate is a low effort way of reassuring yourself that you’ve made some due diligence. It’s not so much meant to challenge your idea but more to soothe your conscience. It easily happens when you’re overly confident of your idea – which is when we tend to not take objections too seriously.

The serious way is very different. It’s a high intensity effort to question every little detail and make it your goal to spot even the tiniest of loopholes. You play the devil’s advocate with even more passion than you have for your own idea. You get joy out of crushing your idea. That’s why you don’t settle with your first reply. You keep on challenging it. Try to uncover contradictions. Find all the false assumptions …

The serious way can feel devastating. At times, you may feel like giving up because really, the devil’s advocate is right, your idea is just a huge pile of nonsense.

Which of course it isn’t.

Guess which of the two approaches leads to better ideas?

The players who prefer the cute version might appear to be more confident at times. And they might get away with it in the short run. But if you’re interested in making a difference, you might be better off if you didn’t try to be right but started to get it right instead.

The overlooked part of pitch preparation

When you’re pitching an idea, the actual pitch presentation is only part of the conversation. Sometimes a small part. And yet, it often gets all of the attention in the preparation process.

It’s just as important to prepare for the Q&A part. But how do you do that, given that you don’t know what actual questions are going to be asked?

My favorite way is to play the devil’s advocate game and to do it rigorously. Choose someone on your team to challenge your idea in every possible way and have an actual conversation.

Here’s the crucial part. You have to play it seriously. It’s easy to be satisfied with the first reply that pops into your mind and just check the box. Resist that urge and play it seriously! Challenge that reply again.

And when you’re done, repeat the whole process. Again and again. Changing roles in every cycle.

You will never need most of the situations you’ve gone through in that process. But remember that in order to appear as though you didn’t have to prepare, you gotta be prepared 10x.

Winning pitches

When you’re pitching an idea …

… clear beats clever.
… tangible beats sensational.
… plain English beats jargon.

I have yet to see an exception to this rule.

The slickness of a great pitch

A great pitch doesn’t succeed because it’s slick. It succeeds because it’s clear. Slickness is a side-effect of clarity.

With clarity comes slickness, not the other way around. You can design a super slick pitch deck that’s utterly confusing, has no clear message, and remains vague about the actual plan.

But make it super clear and it’ll be hard to make it ugly.

Copying the slickness is tempting. But copying the clarity is way more useful. But that – of course – means doing the work.

The good news is that once you’ve done the work, you won’t need to copy the looks anymore. You’ll automatically arrive at a tone that’s uniquely appropriate for you idea.

Persuading people

The moment you try to persuade your customer you essentially admit that …

i) either you don’t fully understand what really matters to them or
ii) you don’t trust your product to deliver on what matters to your customer.

(Or both, obviously.)

If you fully understand your customers’ needs and desires and if you also trust in your product to deliver on that, then you won’t need to persuade. You only need to make them see by telling a true story about your product.

Because once they see it, it becomes totally obvious: This is the product that serves my needs. They’d be fools not to buy it, right?

That’s why it’s so much easier to start with that story in mind and build your product so it delivers on that story – rather than the other way around.

When you first build the product and then go looking for a story, you might end up discovering that it’s, well, not that great a fit after all. Hence, the need for persuasion techniques.

But when you do it the other way around, then all it takes is to speak with clarity.

Open doors

Two very different ways to create an offer:

No. 1: Leave as many doors open as possible and make sure that there’s something in it for everyone even if that means that it’s not perfect for any specific person.

No. 2: Close as many doors as possible and make sure that it’s perfect for one specific person even if that means that it doesn’t appeal to most.

Which one do you choose?

PS: There’s no right or wrong here. It’s a choice. But it’s best to make it a conscious choice.

What’s the boldest promise you can make?

I’m speaking of bold promises that you actually intend to keep.

I mean, it’s easy to make bold promises when you don’t intend to keep them, right? It’s also easy to keep little promises when they are not bold at all.

It’s the combination that is hard: Make a bold promise and confidently keep it.

Bullshitters don’t care about keeping promises. That’s why they are so good at making bold promises. Their sole concern is to get the deal and they will promise you anything that will make you more likely to sign it.

People who care for the cause, on the other hand, struggle at the other extreme. Too often, they shy away from making bold promises because they want to be 100% certain to be able to keep them. Which leads them to only ever make the littlest of promises.

But too often that’s a way of hiding. Hiding from the work that would be required to keep a bolder promise.

The sweet spot is to make a bold promise (possibly even one that scares you) and work hard to keep it.

The key difference is this: For the bullshitter, the deal is the end of the story. For people who care, it’s the beginning.

The customer will only know after the deal.

Don’t leave them to the bullshitter. In the customer’s best interest you need to be able to compete with the bullshitter. You know their game. Change it! Not by making smaller promises but by making bigger efforts to keep bold promises.

The right idea in the wrong meeting room

Some pitch situations quickly turn into a status game.

The pitching party feels high status because they feel like they’ve really nailed it and have an extraordinarily brilliant product. It’s going to change the world (which might be true).

The decision maker feels high status because they get to decide about the proposal and they want you to know that they have the final say. They are extraordinarily brilliant in identifying trends (which might be true).

Inevitably, both desires for higher status clash when one of the parties makes a claim that the other just must dispute – because, well, they know it better (which might be true).

The world, however, couldn’t care less about who’s right and who’s not. Or about who’s in charge and who’s not. They care about which ideas see the light of day. And so, the right idea in the wrong meeting room likely isn’t worth much when the parties have status as their top priority.

Change happens easier if we ban status from the meeting room.

If the other party doesn’t see it that way, you might be better off looking for a different partner.

Pitching to the masses

With Apple’s massive success over the years, it’s easy to miss that Apple’s greatest pitches were not to the masses.

Quite the opposite. Many observers dismissed the iPod initially (“A Firewire interface?”). Many ridiculed the iPhone initially (“No keyboard?”). Many laughed at the MacBook Air initially (“No DVD drive?”)

Steve Jobs embraced that fact. Knowing that he couldn’t sell a billion iPods right from the start, he didn’t even try to.

He didn’t speak to the masses. He spoke to the people who got it. Those who care for the same things Apple cares about.

That’s a crucial insight to understand the “reality distortion field”. This term was crafted by people who “didn’t get it” to make fun of the people who “did get it”.

Of course, what really happened was that Jobs intentionally resonated strongly with what mattered to the latter while – again: intentionally – dismissing the rest.

Jobs didn’t bother to make everyone fall in love. He gave the fans a reason to love the new product. He gave them a reason to be a proud early adopter. He gave them the feeling that Apple understood their struggles and built a solution that smoothly solves them.

And then, the fans spread the word. Slowly. The iPod took years to become a mass phenomenon.

What matters to your fans and how can you speak their language so clearly that it appears to outsiders as a reality distortion field?

Would you like tea or coffee?

A simple decision, isn’t it? Well, you have no idea.

Let’s have some fun with it and pretend we would have to decide in a meeting. Obviously, we’ll need a PowerPoint to discuss the matter, right? Quickly, we arrive at 10 slides highlighting all of the important aspects, like so:

Slide 1: Title slide with presentation title (“Advantages and disadvantages of proceeding with tea vs. coffee”), name of presenter, their department, date, location, at least five logos
Slide 2: Agenda
Slide 3: Sales distribution of tea and coffee during the last 6 quarters, broken down by region. Underneath: comparison with other drinks such as hot chocolate and various juices
Slide 4: Mission statement for the coffee choice, market analysis including target group breakdown
Slide 5: Composition of ingredients (unfortunately, though, the font is so tiny that you can’t read anything) plus certificates from food testing institutes
Slide 6 & 7: The same for tea
Slide 8: Customer satisfaction rating and award for the most creative brand campaign 2021
Slide 9: Classification in the brand range with different flavor additives, variants, sizes and special promotions
Slide 10: Summary
Bonus slide 11: “Thank you for your attention”

All of this followed by an intense discussion to repeat the arguments a couple of times.

All of this without ever asking the question plainly: “Would you prefer tea or coffee?”

I’m positive that quite a number of meeting room presentations fit that description rather well.

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The devil’s cute advocate

The overlooked part of pitch preparation

Winning pitches

The slickness of a great pitch

Persuading people

Open doors

What’s the boldest promise you can make?

The right idea in the wrong meeting room

Pitching to the masses

Would you like tea or coffee?

Spread the Word

Dr. Michael Gerharz

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