How Curiosity Can Transform Your Company and Your Leadership

Most founders assume the biggest advantages you can have in business are things like capital, timing, or raw intelligence. But there’s another factor that determines who actually pulls ahead, and it’s one we often overlook: Curiosity.

In the decades I’ve spent building my own companies and coaching others, I’ve watched as some people accelerate faster than everyone around them. It’s rarely because they start out more skilled. It’s because they choose to stay curious. Not casually so, but in a way that draws them deeper into the mechanics of their work and the systems they touch. They're the ones who pull ahead and make the biggest impact on the organization by asking questions long after others have settled for the first acceptable answer.

The truth is, people who embrace curiosity develop at a different pace. And I’m not talking about the sporadic kind of curiosity that sends you bouncing from one shiny thing to the next. I’m talking about curiosity that’s grounded, disciplined, and tied to a genuine desire to understand how things really work.

So let’s talk about why we should treat curiosity as a discipline to both practice and nurture as our company scales — and I'll share six simple steps to help you and your team get started. 

What Curiosity with Purpose Looks Like

One of the clearest patterns I’ve seen inside growing companies is this: Those who practice curiosity with intention outperform those who don’t. Not because they’re trying to impress anyone, but because they truly want to understand the real nature of their work. They take the time to learn what their Seat is actually responsible for, how it connects to the roles around them, and how their decisions move through the rest of the organization.

It’s not endless brainstorming through every possibility without getting anything done. It’s a disciplined effort to understand the system they’re a part of. They study the upstream inputs and downstream consequences. They pay attention to the flow, the interactions, and the timing. And because they understand more, the quality of their contribution rises. It’s not about working harder, it’s about working smarter.

When someone approaches their work this way, their growth accelerates naturally and you can count on them to not only ask better questions but make better decisions. And over time, they become the people you instinctively lean on because they don’t just complete tasks, they see how their contributions fit into the broader vision.

You’ll know you have the right people on your team when they don’t need to be pushed to learn because they’re already seeking out answers on their own. When they don’t wait for someone to tell them what to do because they take the initiative to understand the full context of their role and its impact. What sets them apart is the focus behind their curiosity — it’s aimed at understanding, not distraction.

This is the version of curiosity that becomes a true advantage for both the individual and the organization. It sharpens understanding, strengthens trust, and elevates the work of everyone around them.

The Compounding Effects of Curiosity

Disciplined curiosity doesn’t create instant breakthroughs. It builds slowly. Over time, people who engage this way start connecting ideas, recognizing patterns, and making decisions with a level of clarity that stands out.

It’s the same dynamic Shane Parrish described so clearly: “Think of it like studying: the genuinely curious person will remember and connect ideas in ways that the person just trying to pass will never. Being all in doesn't just beat partially in; it crushes it.” And when someone brings that level of engagement to their work, the pieces start coming together quickly, each new insight sharpening the bigger picture.

This is also why hiring curious people matters so much. When someone shows up with a genuine drive to understand, not just execute, their growth compounds quickly. They’re the ones who elevate conversations, strengthen decisions, and make the entire system smarter simply by engaging with it more deeply. You’ll feel their presence inside the organization because they increase the rate of learning for everyone around them.

As their understanding deepens, they move from reacting to shaping. Meanwhile, those who only learn what they need for the moment rarely experience the same acceleration. Their growth stays linear. Their decisions stay narrow. And the gap between those two groups widens with time — one gains momentum, the other trails behind.

For those of us who want to build productive, humane, and resilient organizations, that momentum matters.

When you're only halfway interested in something, you'll lose to someone obsessed. It won't even be close.

Shane Parrish

Farnam Street

6 Steps to Practice Disciplined Curiosity

If you want curiosity to become a true advantage inside your company, you can’t leave it to chance. You have to build it into the way you and your team work every week. The good news is that it doesn’t involve adding a huge new initiative. You just have to be intentional about how you already think, ask, and decide.

Here are six simple steps to help you turn curiosity into a disciplined practice for you and your team:

1. Start by naming what you’re trying to understand: Before you start asking questions, get clear on the topic. Are you trying to understand a process that isn’t producing the outcomes you want, a customer trend you don’t quite get, or a pattern in your numbers? Give your curiosity a specific target. “I want to understand why X keeps happening” is much more powerful than “I should probably dig into things more.”
2. Ask one more question than you normally would: In your next meeting or conversation, don’t stop at the first answer that sounds reasonable. Ask the follow-up: “What’s underneath that?” or “What’s driving this?” or “What might we be assuming here?” That extra question is where disciplined curiosity starts to take you further than you would have gone otherwise.
3. Connect the dots across roles: Pick one important workflow and trace it from start to finish. Talk with at least two people in different roles who touch it. Ask each of them how they experience it, where it helps, and where it makes things harder. You’re training yourself and your team to see the whole system, not just the piece each person owns.
4. Build a habit around learning, not just doing: Choose one recurring meeting each week where you reserve 5–10 minutes for “what we’re learning.” Not updates, not status, but one insight from the work itself. Over time, this builds a culture where reflection is the standard.
5. Document what you’re discovering: Curiosity becomes much more powerful when you capture what you’re seeing and share it with others. Add notes to a Slack channel, update a process description, or jot a quick summary in your meeting notes: “Here’s what we learned about this issue and what we’re trying next.” You’re creating a record that your future self and your team can draw from.
6. Notice who’s leaning in: As you practice curiosity yourself, pay attention to the people who naturally engage. Who brings thoughtful questions? Who takes the time to understand beyond their own role? Those are your high-curiosity teammates. Invest in them. Give them more context, more responsibility, and more room to grow.

As you and your team walk through these steps, upgrading your BOS to a platform like Ninety makes it far easier to capture your insights and turn them into shared understanding. It gives you a place to collect what you’re learning so your curiosity can compound over time. And when that becomes part of how your team works every week, you’ll start to see just how quickly a curious organization can evolve.

The Discipline That Shapes Great Companies

If there’s one thing I’ve learned watching companies grow, it’s that curious organizations don’t happen by accident. They’re shaped by founders who model the behavior first. When you stay curious, you give everyone around you permission to do the same. And that mindset not only helps you understand what’s happening today, it prepares you and your team to navigate whatever comes next.

As a founder, your commitment to this practice matters. Your team watches how you ask questions. They notice where you invest your attention. They learn from the way you seek to understand before making decisions. That’s how a culture forms — through consistent example.

Choose to practice curiosity with intention, and you’ll become the leader people rely on for clarity. You’ll become the person who sees what others overlook. And you’ll build an organization that grows not just bigger, but smarter and more resilient.