How to Cultivate Curiosity as a Leadership Skill

#leadership #humanintelligence #curiosity #intentionalleadership #bossatthehelm #minibutmighty Jun 29, 2026

For years I cut parchment paper circles by hand. I traced my round baking pans, snipped along the line, and still ended up with a lopsided oval every time. Then one day I watched someone on social media roll a sheet into a triangle, set the point in the center of the pan, cut once, and unfold a perfect circle.

I had been doing it the hard way the entire time. Not because I lacked the skill. Because I never paused to ask if there was a better way.

That is what we do to curiosity at work. We get busy, we move fast, and we stop questioning how we operate. Curiosity is a Human Intelligence skill, one of the capabilities no algorithm can replicate. The good news is you can practice and improve it. Here is how.

Ask Better Questions

A poor question only seeks to confirm what you already believe. A good one helps you explore. Warren Berger suggests treating questions like tools you use to learn, innovate, and evolve, and asking “what if” and “how” far more often. When you lead others, drop the advice disguised as a question. Instead of “Have you tried this?” ask “What approaches have you considered?” The first answers for them. The second helps them think for themselves.

Challenge What You Believe

Sometimes we get too comfortable in how we think and operate. Challenging an assumption does not mean attacking it. It means pausing to ask, “Why do we do this, and why do we do it this way?” At a team level, ask, “What do we believe, and why do we believe it?” Maybe the belief still holds. Maybe it is an old one you no longer need. I asked this about the software used across my global teams and found not only duplication of software and costs, but real opportunity to collaborate and remove regional silos.

Make Room for Wonder and Play

Curiosity needs fuel. Hobbies, creativity, and downtime give your brain the space to ask new questions. A brain that is always on cannot create. If you have let a hobby slide, make time for it again. Take a beginner's mindset to something you already know well and watch how many new paths open up. Pay attention to what you're paying attention to...you look at the forest floor and see plain green and brown until you look closely and see the textures and life packed into it. That noticing follows you back to work.(Check out Karen Walrond for more on beginner's mindset.)

Curiosity is one of the skills machines will never master. You can. Pair it with your Humanity Skills and you become the kind of Unmachined℠ leader no algorithm replaces.

Learn more in our four-part series on curiosity:

 📍Part one – Curiosity Is a Leadership Skill. Are You Killing It on Your Team: talks about curiosity as a human intelligence skill and why it's important in life and in leadership.

📍Part two – Stop Being So Certain. The Best Leaders Ask Questions: we explore civil debate and the importance of curiosity in exploring multiple POVs.

📍Part three – How to Stay Curious and Think for Yourself in the Age of AI: dives into the demise of curiosity in the rise of AI

📍Part four – How to Cultivate Curiosity as a Leadership Skill: details how to cultivate and strengthen curiosity as a skill

Subscribe. We publish new Mini but Mighty℠ Leadership Lessons every Friday on YouTube.  

 If you lead an organization and want your managers practicing Human Intelligence skills like curiosity at scale, our workshops and cohort programs are built for exactly that. Reach out at bossatthehelm.com/contact.

 Lead yourself. Then lead others. Be a Boss.

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