Pitch Less. Ask More. Win More.

We’ve all heard about the elevator pitch—that concise, persuasive spiel meant to capture attention and inspire action in the short time it takes to ride a few floors. It’s a business cliché that endures. However, like many clichés, it deserves closer examination.

The irony is right in the name. Think about the modern elevator experience: you step in, everyone faces the same direction, conversation is rare, and eye contact is often avoided. It’s one of the most socially inert, even sacred, spaces in our daily lives—defined more by silence than speech. So why do we use that setting as the metaphor for our most vital self-introduction?

To truly appreciate how the elevator pitch came to be—and why it needs to evolve—we have to revisit its origins.

The Origin of the Elevator Pitch

The term elevator pitch rose to prominence in Hollywood during the late 20th century. The concept was simple: if you were lucky enough to find yourself in an elevator with a studio executive, you had 30–60 seconds to sell them your movie idea. But here’s what’s often forgotten: most of the people in those elevators weren’t strangers. They were insiders—writers, producers, studio assistants—who already shared a common context. They knew the language, the problems, and the expectations. The pitch worked because the groundwork had already been laid.

That familiarity made the elevator ripe for quick influence. Everyone was part of the same industry, sharing the same pressures, goals, and culture. When someone said, It’s Die Hard on a bus, the meaning wasn’t lost. It resonated immediately. A pitch, in this environment, wasn’t about discovery—it was about fit.

But what happens when you don’t know the other person? What happens when you’re not sure what they need, what they value, or what challenges they’re facing? In that case, pitching without context becomes premature—and tone deaf. You risk making the moment about yourself rather than your listener. And in today’s world, where personalization and empathy win, that’s a serious liability.

So what’s the better approach?

From Elevator Pitch to Elevator Questions

Let’s return to that awkward elevator space. Everyone is silent. Everyone’s facing forward. No one’s asking questions, and no one wants a monologue. It’s not a place where people expect to be sold to—it’s a place where people expect to be left alone. The same is increasingly true in business conversations. Attention is scarce. Skepticism is high. And most people aren’t looking to be pitched—they’re looking to be understood.

This is why we need to rethink the elevator pitch and instead focus on elevator questions.

Questions signal curiosity, not coercion. They show that you’re there to learn, not to lecture. When you start with the right question, you shift from asserting value to uncovering relevance. You invite someone into a conversation instead of demanding their attention.

So, how do you approach that moment with grace? You treat it not as an opportunity to pitch at someone, but to listen—to open the door for something better.

The Structure of a Modern Elevator Conversation

A high-impact conversation—whether in an actual elevator or a chance encounter—should follow three intentional stages:

Ask: The Three Elevator Questions That Matter

Begin not with your value proposition, but with thoughtful inquiry. These aren’t filler questions; they’re probes designed to surface a real challenge or objective. The key is to craft your questions as open-ended, relevant, and human as possible.

Start with this sequence:

What’s the biggest challenge you’re facing right now in your [role or industry]? This creates space for someone to share a pain point, not just their job title.

How are you currently managing or approaching that? This helps you understand if they have a system, are stuck, or are seeking change.

If you could improve that tomorrow, what kind of difference would it make? This puts the potential impact into personal terms—whether that’s time saved, revenue gained, or stress relieved.

These questions shift the dynamic from self-focused to customer-focused. They turn a pitch into a conversation—and a problem into an opportunity.

Personalize: Frame Your Value Based on What You Heard

Only after you’ve heard what matters to someone should you respond with your solution. And when you do, make sure you’re speaking to the specific context they gave you—not a pre-rehearsed script.

Personalization doesn’t mean rattling off your product’s features. It means connecting one relevant benefit to one relevant need. For example:

You mentioned that your team’s biggest challenge is managing client onboarding without losing track of tasks. We built a lightweight platform that helps teams like yours create repeatable onboarding templates—so every client experience feels seamless.

You’re not selling everything. You’re solving one thing. That’s what builds trust and momentum.

Enable: End With a Question That Moves the Conversation Forward

Here’s where most people go wrong. They close with a binary ask:

Are you interested?

Do you want to schedule a demo?

These types of questions invite a reflexive no. Instead, reframe your ask to imply when rather than if. This keeps the door open and guides the conversation toward a logical next step. Here are better options:

When would be a good time to dive into this further?

What’s the best way to follow up on this with you?

Would next week work for a quick walkthrough?

By framing the follow-up as a matter of timing—not decision—you lower pressure, demonstrate respect, and make it easier to say yes.

Is There a Framework for Elevator Pitches?

Many exist, but most overlook the value of listening before speaking. One of the most effective, flexible models is the PAUSE Framework. It honors curiosity and context before delivering value.

PAUSE Framework

P – Problem: Begin by surfacing the core challenge your audience is facing.

A – Ask: Use strategic questions to understand their current state and needs.

U – Understand: Reflect and confirm what you heard before offering a solution.

S – Solution: Share a single, relevant value point tailored to their context.

E – Enable: Invite next steps with a time-based question that facilitates action.

This approach works because it respects attention, prioritizes empathy, and leads to meaningful engagement, not transactional chatter.

Why Questions Are More Valuable Than Pitches

People are bombarded by messages. What they remember isn’t always who talked the most—but who listened the best. When you lead with questions, you demonstrate relevance, build trust, and position yourself as someone worth engaging with, not just someone trying to close a deal.

The modern elevator interaction isn’t about broadcasting your value. It’s about creating a brief moment of insight and alignment. That’s how conversations begin—and how relationships start.

Final Takeaway

The traditional elevator pitch is a relic of a more one-dimensional era. In today’s fragmented, fast-paced world, connection begins with curiosity. Start with thoughtful questions. Listen deeply. Then respond with relevance. And when you do ask for the next step, make it natural, not transactional.

Don’t aim for the yes. Aim for the when.

Because the goal isn’t just to pitch—it’s to continue the conversation.

©2025 DK New Media, LLC, All rights reserved | Disclosure

Originally Published on Martech Zone: Pitch Less. Ask More. Win More.