How to be More Curious in Sales

Good Morning! Yesterday OpenAI dropped Deep Research, a tool that can do hours of web research in minutes. Just tell it what to research and it will scour the entire internet and put all of the info in an easy-to-consume repost. Finally, an AI that can explain what a prospect's company actually does, decode their tech stack, and figure out why they keep saying ‘not right now’ to your calendar invites. Or maybe that’s still wishful thinking. 😁

• How to be curious 🔍️ 

• Hire an AI BDR 🤖 

• Ask what would need to happen ❓️ 

• 7 crucial closing mistakes 👀 

• Sales jobs & a meme 😂

How to Be Better at Being Curious

Being curious is one of the best traits a salesperson can have.

By definition, curiosity is a desire to learn and know more. Which essentially describes the exact action behind being good at discovery and uncovering a prospect's problems.

But simply saying ‘be more curious’ is about as helpful as a sales manager who's never sold anything.

So today, we're breaking down exactly how to be more curious in your sales conversations.

1. Listen to Understand, Not Respond

Here's something we're all guilty of…. While someone's talking, we're already thinking about what we're going to say next. Sound familiar?

This habit is killing your ability to actually understand what prospects are telling you.

When you make the conscious effort to listen to understand (not just respond), the follow-up questions and responses will flow naturally.

Think of it like watching a movie. You don't pause every 30 seconds to plan your reaction to the next scene.

You watch, absorb, and react naturally.

2. Go Beyond Product Fit

It's easy to want to skip straight to how a prospect would use your product.

But the best reps do things differently. They go deeper and try to understand everything about the prospect’s company, situation, and background.

Ask yourself:

• How do they make money?

• What keeps them up at night?

• What would make them heroes at their company?

• How can you help their core business do better?

Understanding their business as a whole (not just their potential fit for your product) unlocks a new level of curiosity.

3. Always Ask Why

At the root of most curiosity is the question of "why".

When a prospect gives you any response, there's always a deeper layer to uncover:

We just started looking for a new solution this month.
Why now specifically?

The last time we bought something like this, it didn't work for us.
Why do you think that was?

Right now just isn’t a good time for us.
Why is that?

Each "why" gets you closer to the real story.

Bonus: Choose an industry and offering you find interesting.

It's a lot easier to be curious about things you find interesting.

• If you're fascinated by AI, sell AI products.

• If you love helping people grow, sell training solutions.

• If rich people are interesting to you, sell luxury goods.

It's a lot easier to be curious when it's something you're interested in.

And it’s a lot easier to sell when you’re curious. 

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