We’ve all been there: sitting through a demo that feels like a marathon tour of irrelevant features.

It’s annoying.

The dashboards? Not what you asked for.

The workflows? Confusing.

And worst of all, the presenter isn’t even listening.

You told them your needs, yet they’re delivering the same cookie-cutter spiel they likely gave to their last ten prospects.

Now, here’s a tough question: could your demos be making prospects feel the same way?

If your team is diving into features too soon, skipping discovery, or treating every buyer like they’re identical, it’s no surprise if your demos are failing to convert.

Misaligned demos waste time and lose deals.

But there’s good news: with a few key adjustments, you can transform your demos into a laser-focused, value-driven experience that moves prospects closer to signing on the dotted line.

Let’s break it down.

Why Traditional Demos Fall Flat

Peter Cohan, author of Great Demo! How to Create and Execute Stunning Software Demonstrations, describes the classic demo as a “harbor tour” in a recent interview on the SaaS Backwards Podcast.

“You put the prospect on the boat, they can’t get off, and you drive them around the harbor for an hour or two, continually asking them, ‘So, have you seen anything you like so far?’”

This approach often stems from an eagerness to show off as many features as possible.

While it might seem like a good idea, Cohan warns against this, explaining, “By trying to cram features into a demo, you risk making your product look overly complicated. Prospects may think, ‘You’re showing me things I’ll never use, so either take them out or lower the price because I’m only paying for the value I’ll get.’”

Instead, Cohan recommends a tailored approach: start every demo by reviewing the prospect’s specific needs.

Open with, “If I recall correctly, when we met last week, you told me this, this, and this. Before we go on, is that all correct? Has anything changed?”

Once the prospect confirms, dive straight into showing them the key capabilities that solve their unique business problems.

The Power of Tailored Demos

Tailored demos turn the typical script on its head. Instead of overwhelming prospects with features, they focus on what matters most—right now.

“The key is to do the last thing first,” says Cohan. Begin with the end result: dashboards, reports, or deliverables aligned with the prospect’s goals.

For example, a Chief Revenue Officer (CRO) cares about revenue tracking, risk identification, and managing exceptions.

Start by showing dashboards that address these priorities. Don’t bury the good stuff under irrelevant details.

This “slicing and dicing” strategy ensures that each prospect sees a demo uniquely tailored to their needs.

A sales manager’s demo should look different from a marketing leader’s.

This level of customization not only engages prospects but also demonstrates that you genuinely understand their challenges.

Steps to Craft Tailored Demos

1. Conduct Precise Discovery

You can’t tailor a demo without discovery. Ask specific, insightful questions:

• What’s their top challenge?
• What pain point drove them to seek a solution?
• What does success look like to them?

“Discovery is about understanding the job title, their challenges, and the value they’re looking for,” Cohan emphasizes.

Build a discovery framework and use it consistently.

2. Start with the End in Mind

Think of your demo like a recipe: the photo of the finished dish is what grabs attention first.

Similarly, lead with the outcomes your prospect wants, such as dashboards showing progress toward goals. Show them why they should care before diving into the how.

3. Apply the Inverted Pyramid

Borrow a strategy from journalism: put the most important information first.

Highlight the key features upfront, then let the prospect decide if they’d like to explore further.

This keeps them engaged and ensures no time is wasted.

4. Use Vision Generation for Early-Stage Prospects

Not every prospect is ready for a deep dive.

For those still exploring options, present a “vision generation demo”—a short, high-impact preview of what’s possible without overwhelming them.

5. Train your Team

Tailored demos aren’t just for sales engineers.

Everyone on your team—from SDRs to marketers—should be capable of delivering a high-level demo.

This ensures consistency and frees up technical resources for more complex conversations.

“When everyone can deliver at least a high-level demo, you free up technical resources for more complex conversations,” Cohan notes.

Avoiding Common Demo Pitfalls

Pitfall 1: Overloading the Demo with Features

More isn’t always better.

Overloading a demo risks overwhelming prospects and devaluing your product. Focus on what solves their problem and resist the urge to show off every feature.

Pitfall 2: Skipping Discovery

Without proper discovery, your demo has no direction.

Never assume you know what a prospect needs—ask questions and dig deep to uncover their priorities.

Pitfall 3: Generic Storytelling

Generic “day-in-the-life” demos often lose relevance. Instead, focus on the “Monday morning” moment: what your prospect checks first when they start their workweek.

Build your story around that.

Why Tailored Demos Work

Tailored demos save time by cutting through the noise and showing prospects exactly how your product solves their problem.

This approach doesn’t just work in theory; it delivers results.

Cohan recalls a late-night call with a high-profile prospect in Singapore.

They had expressed interest in the product but had become increasingly disengaged as the sales process progressed.

By the time of the late-night call (due to time zone differences), it was clear the deal was in trouble.

The primary challenge?

The earlier demos had missed the mark. They were too generic, failing to address the specific pain points and priorities of the prospect.

Instead of feeling that the product was a perfect fit for their needs, the prospect felt overwhelmed and unconvinced.

Realizing that the deal was slipping away, the pre-sales team decided to make a last-ditch effort.

Instead of delivering another cookie-cutter demo packed with features, they pivoted to a fully tailored approach.

This time, they leveraged the insights gained during discovery, even though it was clear earlier interactions hadn’t fully utilized this information.

The team began the demo with a clear recap of the prospect’s challenges, using Cohan’s recommended phrasing: “If I recall correctly, when we spoke last week, you mentioned these were your top priorities: [specific goals or pain points]. Is that still accurate, or has anything changed?”

Once the prospect confirmed, the team immediately showcased the specific capabilities of the product that addressed those exact challenges.

They skipped all the extraneous features and workflows, instead zeroing in on the deliverables that mattered most to the prospect’s business outcomes.

This hyper-focused demo re-engaged the prospect.

By showing that they truly understood the prospect’s needs—and could deliver meaningful solutions—the sales team rebuilt trust and reignited interest.

They demonstrated value in a way that felt personal and relevant, instead of overwhelming or impersonal.

The result?

A deal that had seemed lost was not only salvaged but closed at $250,000.

Ready to Transform Your Demos?

If your demos aren’t driving deals, it’s time to rethink your approach.

Tailored demos are sharper, leaner, and more impactful.

They resonate with decision-makers, shorten sales cycles, and win more business.

Deliver demos that speak directly to your prospects’ challenges and aspirations, and you’ll stand out from the competition.

Not Getting Enough Demos? That’s a Different Problem.

If you’re not even getting enough demos on the calendar, the issue runs deeper than just tailoring them—it’s your messaging.

Vague, hard-to-understand messaging that fails to inspire action is the silent killer of your demo pipeline.

Prospects aren’t booking demos because your messaging isn’t compelling them to take that first step.

That’s where our Marketing and Messaging Review comes in.

We’ll help you uncover exactly why your messaging isn’t driving demos—and, more importantly, how to fix it.

Our comprehensive review dives deep into how your current content is performing, whether it’s your website, content, or ads.

We pinpoint gaps, vague language, and missed opportunities that may be causing potential prospects to scroll right past you or bounce off your site.

With actionable insights and clear recommendations, we’ll show you how to craft messaging that speaks directly to your target audience’s pain points, sparks curiosity, and gets them thinking, “This is exactly what we need!”

Here’s what you’ll gain from our Marketing and Messaging Review:

• Clarity and Focus: Messaging that’s simple, impactful, and easy to understand—so prospects immediately see your value.
• Increased Engagement: Strategies to make your content resonate with your ideal customers, driving them to take the next step.
• More Demos: Messaging that compels action, filling your pipeline with high-quality prospects who want to see what you have to offer.

Here’s the truth: Your demo problem starts with your messaging.

If prospects don’t understand how you can solve their problems, they’ll never make it to the demo stage. Fix your messaging, and you’ll start seeing a ripple effect through your entire sales process.

Ready to stop leaving opportunities on the table?

Let’s make your messaging work as hard as you do.

Learn more about our Marketing and Messaging Review here.