How to Train Yourself to Be More Curious

Good Morning. Today is National Meditation Day. Take five seconds with me. Close your eyes. Breathe in. Let go of the deal that fell through last week. Breathe out. Let go of the prospect who said "take me off your list" last month. Open your eyes. Time to make calls. Now, let's get into today's Follow Up. (:

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The most successful salespeople people in the world are extremely curious.

I’ve noticed this trait in the best sales reps I’ve worked with. But you don’t have to just take my word for it.

Jeff Bezos spent his childhood turning his parents' garage into his personal lab, taking things apart just to figure out how they worked.

Then in his 2018 letter to Amazon shareholders, he dedicated an entire section to what he called "intuition, curiosity, and the power of wandering." He argued that some of Amazon's biggest wins came from people following their curiosity into places a spreadsheet would never take you.

Mark Cuban called curiosity one of the 3 most important soft skills for success.

A study of top reps found that 82% of them scored extremely high on curiosity. They wanted to learn more about their customers, their market, their competitors, and the buying process.

The one thing that keeps showing up across all of the most successful sellers is that they never stopped asking questions about how things work and why.

Telling someone to be more curious is like telling someone to grow a few inches.

“Sure, no problem. I’ll just get a little taller. Thanks for the advice.”

Luckily, your curiosity is something you can improve naturally (unlike height).

Most people assume curiosity is a personality trait. You either have it, or you don't. Research says otherwise.

Dr. Todd Kashdan, one of the leading psychologists studying curiosity, argues that it operates like a muscle. The more you use it, the stronger it gets. A 2021 study found that stimulating curiosity through guided questioning and exposure to new environments enhanced learning and long-term memory retention. Even people who started with low baseline curiosity got measurably more curious over time when they practiced it.

Just like going to the gym, when you train to be more curious, you become a more curious person.

This matters in sales more than you might think. Gong analyzed 1M+ sales calls and found that top performers ask 40% more questions during discovery than average reps. The sweet spot is 11 to 14 questions per call. Fewer than 11 and you're mostly getting surface level info. More than 14 and the buyer feels interrogated.

Curious reps land in that range because their curiosity makes them want to actually understand the problem. They're asking because they're genuinely trying to figure something out.

Here's where it gets practical.

Listen to understand, not to respond. Most reps are already thinking about what they're going to say next while the prospect is still talking. When you actually listen, real follow up questions come from what the prospect just told you, not from the list you had prepped in your head. That's where the best discoveries happen.

Talk to people outside your bubble. Grab lunch with someone in product, marketing, or customer success. Ask them how they got into the role, what problems they're trying to solve, how they view the sales team, etc. Some of the best sales insights come from understanding how the rest of the business thinks.

Be willing to look stupid. Ask the question you think is too basic. When you put yourself in a vulnerable position of trying to learn, people let their guard down and share more. Prospects can tell when you’re actually trying to understand their business versus running through a script. "If I’m being honest, I don't fully understand this yet, can you walk me through it?" opens more doors than a polished pitch.

When something works, ask why. A lot of reps celebrate a closed deal and move on. Curious ones will figure out what actually made it happen. Was it the timing? The champion? The way you framed the value? Figure out why you won so you can repeat it.

Use the "teach it back" test. After a call or a training, ask yourself: could I clearly explain this to my manager or a teammate right now? If the answer is no, you don't understand it well enough yet, and you should probably be asking more questions.

Stay curious, my friends. 🫡

Today’s newsletter was written by Nic Conley