How to Cut Your Sales Cycle in Half with Tailored Demos

Odds are you’ve sat in on more than one bad demo.

Sitting through a demo where the presenter drones on about features you didn’t ask for, barely scratching the surface of what actually matters to you.

The dashboards? Irrelevant.

The workflows? Overcomplicated.

And the worst part?

They’re not even listening.

You told them what you needed upfront, and somehow, they’re still giving you the same cookie-cutter pitch they probably gave their last ten prospects.

Now, let’s flip the script.

What if your demos feel the same way to your prospects?

Your team might be diving into features too soon, skipping over discovery too quickly, or treating every buyer like they’re the same.

And if your industry benchmarks say more demos should progress into real opportunities—but yours aren’t—that’s a red flag.

If your demo isn’t connecting and converting, it’s time to rethink your approach, align with your prospect’s actual needs, and tailor every single demo to hit them where it counts.

It’s easier than you think, and it could be the difference between another lost deal and a new loyal customer.

Why Traditional Demos Waste Time

Peter Cohan, author of Great Demo! How to Create and Execute Stunning Software Demonstrations, says that traditional demos are too much like harbor tours where “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?’”

The second problem is the desire to pack as much into the available time as possible. This often comes from overzealous salespeople who believe that showing more features means demonstrating more value.

Prospects only need to see the key capabilities that solve their specific business problems. Everything else falls into what Cohan calls the “buying it back” trap.

By trying to cram as many features and functions into a demo as possible, you risk making your product look overly complicated.

Prospects may walk away thinking, “You showed me all these things I’ll never use, so either take them out or lower the price because I’m only paying for the value I’ll receive.”

To avoid these pitfalls, Peter advises starting every technical proof demo—after conducting proper discovery—with a crisp review of the prospect’s situation. Begin by saying, “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?”

When the prospect confirms, proceed by presenting the key deliverables that matter most to their job title and business needs.

By focusing on what truly matters, you not only engage the prospect but also build trust and reduce the risk of “buying it back.”

The Power of Tailored Demos

Tailored demos flip the script. They focus on what matters to your prospect right now.

As Cohan explains, “The key is to do the last thing first.”

Start with the end result—the dashboards, reports, or deliverables that align with the prospect’s goals.

Practical example: If you’re demoing to a Chief Revenue Officer (CRO), they care about tracking revenue, identifying risks, and managing exceptions.

Show them the dashboards that address these needs upfront.

Don’t bury the good stuff under layers of irrelevant features.

This “slicing and dicing” approach extends to every job title.

A sales manager’s priorities differ from those of a marketing leader, and your demo should reflect that.

Tailored demos resonate because they show prospects you understand their unique challenges.

And when they see that you get it, they’re far more likely to engage.

Step-by-Step Guide to Crafting Tailored Demos

Step 1: Conduct Precise Discovery

You can’t tailor a demo without discovery. It’s like trying to bake a cake without knowing the recipe.

Ask specific questions:

·       What’s their top challenge?

·       What’s the pain driving them to look for a solution?

·       What does success look like for them?

Cohan emphasizes, “Discovery is about understanding the job title, their challenges, and the value they’re looking for.” Build a framework to guide this process and stick to it.

Step 2: Start with the End in Mind

Think of a recipe. What’s the first thing you notice? The picture of the finished dish. That’s what draws you in.

Your demo should work the same way. Start with the “delicious” outcomes your prospect wants—like a dashboard that shows their progress toward quarterly goals. Give them a reason to care before diving into the details.

Step 3: Use the Inverted Pyramid Approach

Newspapers mastered this a long time ago. They put the most important information at the top and let readers decide how deep they want to read.

Apply this to your demos:

·       Show the highlights first.

·       Then, ask if they’d like to explore further.

·       If they say no, great—you’ve saved time. If they say yes, you’ve kept them engaged.

Step 4: Leverage Vision Generation Demos for Early-Stage Prospects

Not every prospect is ready for a deep dive—some are just browsing. For them, Cohan recommends “vision generation demos”—short, high-impact presentations that tease what’s possible without overwhelming them.

Think of it as an appetizer, not the full meal.

Step 5: Train Your Team

Tailored demos aren’t just for your sales engineers. Everyone on your team—from SDRs to marketers—should know how to deliver a compelling vision generation demo.

This spreads the workload and ensures consistency across the board. “When everyone can deliver at least a high-level demo, you free up technical resources for more complex conversations,” Peter notes.

Common Pitfalls to Avoid

Pitfall 1: Overloading the Demo with Features

More isn’t always better. Too many features can backfire. Cohan talks about the dangers of having to buy it back”

It’s similar to the sales advice of “shutting up” after delivering a close. Anything else you ramble on about can change the nature of the negotiation.

Focus on what solves their problem, not on showing off everything your product can do.

Pitfall 2: Skipping Discovery

No discovery, no direction. If you skip this step, you’re flying blind.

Even if a prospect clicks “Book a Demo,” don’t assume you know what they need.

Ask questions. Dig deeper. Tailored demos start with tailored discovery.

Pitfall 3: Generic Storytelling

A “day-in-the-life” demo sounds nice in theory.

In practice, it often drags on and loses relevance. Instead, focus on the “Monday morning” moment.

What’s the first thing your prospect checks when they sit down to work?

Build your story around that.

How Tailored Demos Reduce the Sales Cycle

Tailored demos save time by cutting to the chase.

They eliminate the fluff, focus on the essentials, and show prospects exactly how your product solves their problem.

This isn’t just theory; it works in practice.

Case Study: Cohan shared a story about a pre-sales team member who applied these techniques during a late-night call with a prospect in Singapore.

The result?

A $250,000 deal rescued from the brink.

By tailoring the demo to what the prospect needed, they turned a losing situation into a win.

The logic is simple. When prospects see the value upfront, they’re more likely to move forward. Tailored demos also engage decision-makers by focusing on what they care about most, speeding up the approval process.

It’s Time to Flip the Script on Your Demos

If you’ve been thinking, “We’ve invested so much time into our demo process—why aren’t more of them turning into deals?” then it’s time to bring your demos in line with what today’s buyer wants to see.

Imagine a world where your demos are leaner, sharper, and laser-focused on what prospects care about.

Picture your sales cycle shrinking as decision-makers see value faster.

Think about the confidence your team will feel, knowing they’re equipped to deliver not just a presentation but a persuasive, personalized story.

Your prospects are waiting for you to deliver demos that speak directly to their challenges and aspirations.

Do that well, and you’ll be rewarded with shorter sales cycles and more wins over your competition.

Check out the full episode of the SaaS Backwards Podcast with Peter Cohan.