Last week, I was standing on stage at the Build a Better Agency Summit, talking about a topic near and dear to every agency owner’s heart: how to build better, more effective pitch decks to overcome buyer skepticism to win more pitches and sell bigger ideas.
The room was full. The energy? Electric. And somewhere in the middle of that talk, we got to the part I call “the language of influence.” It’s where we drill into the idea that words matter. But even more than the words themselves, how you say them separates a forgettable pitch from a winning one.
Flash forward a few hours—I’m on the flight home, reviewing an agency's new pitch deck. You know the kind: sharp design, engaging copy, solid strategy. Honestly, it was a pretty good deck, but as I scrolled through my notes to prepare my analysis, one comment kept popping up like a flashing red light at every intersection. One slide after slide, bullet point after bullet point, I had written one word:
How?
The more I looked at it, the more I realized—‘how’ was the thread unraveling the whole pitch.
Because in sales, especially in a pitch, “how” can be your best friend or worst enemy. It all depends on timing, tone, and context.
The Good “How”
Let’s start with the version of “how” we all want to hear:
How do you do that?
When a prospect says this early in a conversation, it’s gold. They’re curious. They’re leaning in. This kind of “how” is an invitation—a signal that your idea has sparked something. That they’re picturing it in their world. That they want to believe.
And it’s your job, in that moment, to walk through the door they just opened. Show them, don’t tell them. Use a story. Use analogies. Validate their curiosity by making the complex feel simple and the impossible feel inevitable.
This kind of “how” means you’re gaining traction. You’re building trust. You’re being seen as the expert, the guide, the one who gets it.
The Bad “How”
But let's flip the coin. If you’re in the middle of your pitch, laying out your recommendations, your campaign, your big idea… and they stop and say:
How would that work?
That’s not curiosity. That’s skepticism
That’s a sign you didn’t lay the yellow brick road. You didn’t map the journey clearly enough for their brain to follow it. You've left the information loop open. Chances are you spoke in superlatives vs telling details. And now, instead of leaning in, their cognitive load just spiked. They’re working harder to understand than they should be.
Neuroscience tells us that when people work too hard to understand something, they remember less of it. And B2B Decision Labs found that the less is more approach reduces your credibility with prospects, making overcoming buyer skepticism more difficult.
In other words, a skeptical “how” often means they’re not buying what you’re selling. They’ve gone from “this sounds great” to “prove it.” Or worse, “I’m not sure I believe you.”
That’s not a pitch anymore. That’s a trial. And guess who’s on the witness stand?
Why It Happens
So why does the bad "how" show up?
The three most common reasons I see in my work helping agencies create more effective pitch decks:
- You skipped steps. You jumped from problem to solution without mapping the journey in between. You showed the outcome, but not the process.
- You used insider language. Acronyms, jargon, frameworks that make sense to you but not to them. You made them feel dumb—and people don’t buy from those who make them feel dumb.
- You didn’t build belief. You made claims without proof. You told a story without the setup. You sold the sizzle before you showed the steak.
And when that happens, their brain starts looking for holes in your arguments. That’s when the bad “how” creeps in.
How to Overcome Buyer Skepticism by Eliciting the Good "How"
How do you earn that good, curious, “tell me more” kind of “how”?
I could spend an entire presentation workshop showing you how to build a pitch deck that creates interest and intrigue... one that leads to lots of good hows. But in the interest of time, here are four recommendations:
- Start with the prospect's problem. Paint it vividly. Use a confirmation sequence to demonstrate that you understand their issues and have the perfect solution. More importantly, after you finish the sequence, STOP and ensure they agree.
- Use visual language. Walk them through a story. Use metaphors. Make it tangible. Remember, people prefer stories to stats. Create memories they'll recall days later when they're deciding what to do and who to hire.
- Give them the “why” before the “how.” Prospects aren't buying tactics. They're buying outcomes. Anchor your pitch in what it will do for them, then explain how.
- Drop strategic breadcrumbs throughout the pitch. Forget the seven-slide case study full of stats and graphs. Instead, pepper your pitch with compelling insights drawn from research or prior work you've done to show you have a strategically supported plan, but not so much that you start to sound like a blowhard.
Build intrigue. Leave room for inquiry. They'll do the rest.
Tips to Avoid the Bad "How"
As I shared with the crowd at BABA, the words you use matter, but how you deliver them might be even more important if you want to create trust and credibility with a prospect or client and avoid stimulating buyer skepticism.
Here are a few tips to steer clear of the kind of “how” that signals doubt.
- Rehearse clarity, not just delivery. If your pitch isn’t crystal clear to someone outside your agency, revise it until it is. When I wrote The Invisible Sale, I had to hire a technical editor—someone in sales but unfamiliar with social selling—to read every chapter before submitting it to the publisher. When people tell me how easy the book is to understand, I quietly say a little prayer of thanks to my technical editor.
- Bulletproof your transitions. Often, the bad “how” comes between two good ideas that aren’t well connected. Bridge every section. Make sure each idea flows into the next. Then do the same for the presenters. Handoffs should seamlessly flow from one to the other like the baton from one 4x100 relay runner to the next.
- Anchor ideas in evidence. Tell a strategic story supported by case studies, metrics, research, and comparisons. Anything that grounds your claims in something real. If their first thought after hearing the idea isn't "of course, that makes perfect sense," you did it wrong. Go back and rethink the setup of the pitch.
Remember, you're selling belief. After you finish the deck, ask yourself an honest question: would I believe this?
Going from 'How' to 'How Soon Can You Start'
Next time you build a pitch deck, don’t just aim to inform—aim to resonate. Your words should do more than explain. They should move.
Trust. Excitement. Anticipation. Confidence. Belief. That’s the real goal.
Don't be afraid to explain the "how," then leverage it to start hearing "yes" more often.
And if you need help with that, let us help you learn to build the perfect pitch deck.
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. Till next time.
This post was originally published on Painless Prospecting, the weekly sales and marketing blog created by the fine folks at Converse Digital. If you want to learn how to create, engage in, and convert conversations into new clients and customers, give them a call.
