In tech, we love to demo. On top of that, our culture glamorizes the great sales pitch that leads to a close.

In Wolf of Wallstreet, Leonardo Dicaprio was blessed with knowing that money was his exact customer’s pain – the challenge is, you aren’t.

As a CEO, Founder, VP Sales or any type of of Growth role, or those of us who aren’t selling money, pitching your way to a close is the hard way to sell.

What’s different about selling technology, is our products are new, our prospect pain points aren’t clear and our audiences are segmented.

The more experience we actually have selling our product, the easier it is to make an assumption about our audience. When you start or have your prospect lead you into a demo immediately, you’ve just dropped your chances of making a sale.

Instead you’re setting yourself up for a “maybe” and having your prospect go dark when you follow up.

There’s a law for this: the more irrelevant features you show, the lower the likelihood of a sale.

irrelevant features don't makes sales

Instead of diving straight into your pitch –  figure out the exact problem you’re solving for in the first place. Discover your prospect’s exact pain first and you’ll do a much better job matching up your solution up exactly.

When you jump right into a demo, it’s easy to show irrelevant features that overwhelm your prospect and slow your momentum.

Worse yet, the prospect will start to think that your product is designed for someone else. Even if they find a few features that do meet their needs, why should they overpay for the features they don’t need? Instead they think they should shop around.

When we’re in a sales conversation our job is less to pitch, and more to get our prospect to articulate back to us exactly how they’d use our product.

Try these simple questions before you do the demo:

  • You mentioned you need a new widget system, can you tell me where that’s coming from? (you’re getting them to tell you why…)
  • How long have you been looking for a new widget system? (how long have they been in pain?)
  • What are you using now? (get to know their current process to ID more pain)
  • Why isn’t that working for you? (getting specifics to help you sell)

If you haven’t incorporated questions like this before into your sales conversations – do it. It’s a simple technique that works.

No prospect is ever going to jump into a meeting and divulge this information, you NEED to ask for it. What happens, is you’ll naturally shift the solution conversation from features and benefits to specific and valuable use cases for the prospect.

You’d much rather buy something that appears to be ‘made for you’ right? That’s the idea.

In a growth role, you’ll want to ask these questions anyway for customer development. How can you sell and create more for this customer persona unless you know exactly why they’re buying?

Sometimes a prospect will try to push you into giving a demo early in a conversation – although there are ways to avoid this, if it does happen, here’s a quick fix. Let’s say you’re selling an amazing widget system to a prospect at Coca-Cola:

PROSPECT: “We need a new widget system and are evaluating options. Can you show me a demo?”

YOU: “Happy to do a demo. I want to make sure I show you the right parts of our system so do you mind if I ask you a few questions first so we can make the best use of our time?”


Instead of getting straight into the demo, frame your first questions in a way that shows you’re trying to help them get the most for their time (which you will be) and they’ll appreciate it.

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This guest post is from Juliana Crispo, creator of the leading course on startup sales (free for now) which goes into the psychological hacks used by top sellers. If you’re interested in learning more about her selling framework for startups, here’s a preview: