Looking To Be the Best Leader You Can Be…Start by Asking Better Questions
The following is an excerpt from our September 2025 issue of Hey Leader.
Hey Leader, crafted with thought & care by The Perk, is a monthly email series all with the intention to help you lead better. You belong here!
Hey, Hi! —
I have this friend who takes a lot of international group trips with people she doesn’t know…until she meets them for the first time in a new destination.
A big reason for that is that she wants to travel alone without really traveling alone, especially to a country she’s never been to—but she’s also the kind of person who genuinely loves learning about other people.
We were talking about her experiences recently—how some groups are really easy to assimilate into. Things feel light. There’s very little drama, & a lot of excitement about the experience everyone’s about to embark on, together. Then there are some groups where things feel…strange. Distant. A little heavier—like everyone wants to keep to themselves.
“I totally get that some people aren’t as extroverted, & don’t always want to be chatty & talk all the time,” she said to me. “I mean, I’m one of those people, too. But another part of me wonders…when did we stop being curious about other people? When did we stop wanting to know about the lives of others?”
I asked myself that same question on a recent bachelorette party trip, where I was with a group of other women celebrating a bride-to-be. We didn’t know each other super well, so I did what I always do in those situations: start asking questions.
I got answers, which was great. But the strangest part was that no one asked me anything back. It was the last day of the trip before someone asked me if I had kids & what I did for work.
It was a stark reminder that connection requires another c-word: Curiosity. Without it, conversations fall flat, but it’s SO much more than that. People don’t feel seen, heard & valued. And when that happens, it doesn’t matter if it’s an awkward group trip or a team meeting: people withdraw. They don’t voice their ideas or perspectives. And then everyone suffers.
Curiosity is the first letter in our CLEAR Leadership Operating System, & with good reason: it underpins everything else. When you’re curious, you’re not judging. You’re not assuming. You’re not closed off. You’re creating space to learn something you didn’t know before.
As with most truly foundational leadership skills, curiosity gets a bad rep for being too “fluffy.” But in our work with leaders & teams, here’s what we’ve noticed:
Curiosity makes you faster. Leaders often say they don’t have time to ask questions. But without curiosity, you’re making decisions without all the data. As one of our team members put it, curiosity allows you to make decisions quicker, faster & more efficiently—because you’re working with the full picture instead of half the story.
Curiosity makes you braver. At a recent strategy session, we asked leaders to imagine a 15-year-old entrepreneur had just launched a company that outperformed theirs & asked them, “What is 15-year-old doing differently?” The common answer? Fearlessness. Curiosity helps shake loose the fear of failing & opens the door to bold new ideas.
Curiosity makes you more innovative. Instead of bringing a preconceived perspective, curiosity forces us to look from different angles. It’s a direct tie to learning, creativity, & togetherness. It even decreases defensiveness among teams, keeping us humble & open to what’s possible.
Curiosity makes you a Coach. I’m a Certified Coach through Co-Active Training Institute & they say “Curiosity is the quality that starts the coaching process & the energy that keeps it going.” Coaching is all about having questions & developing your team vs. having answers & directing your team. If you want to drive engagement & retention, stop giving your team answers & start asking them powerful questions. Curiosity transforms you from a fixer to a coach, & your team from order takers to intrapreneurs.
Curiosity makes you more human. It builds trust, strengthens relationships, & helps people feel truly seen, heard & valued. When I asked The Perk team why curiosity was so foundational to leadership, the human element was the uniting factor. It’s the skill that makes you a more empathetic, humble, & strategic leader—a real differentiator in a world where too many people pretend to have all the answers.
And here’s the piece I don’t want you to miss: curiosity & judgment can’t coexist.
The moment you find yourself making assumptions about someone—why they’re quiet in a meeting, why they’re pushing back on an idea, why they’re always the first to speak—that’s your signal. You can either close the door with judgment or open it with curiosity.
One shuts people down. The other brings them in.
So if you’re looking for the simplest, most powerful shift you can make as a leader this month? Choose curiosity.
Our #PerkProTip below is full of tips for how to expand your curiosity & many of them are simple shifts that you can make today. And as always, if there’s anything you want to talk through, I’m a message away. (Seriously, message me. I could talk about curiosity forever.)
You’re amazing,
How to Practice Curiosity as a Leader
Curiosity is like a muscle—the more you use it, the stronger it gets! Here are some ways to build it into your daily leadership:
Ask “what” questions instead of yes/no questions. When you’re tempted to ask “Do you like this?”, try: “What excites you about this? What makes you nervous? What’s one question you still have?” Notice how the person you’re talking to opens up & answers shift.
Interrupt your assumptions. If you catch yourself making up a story about someone—why they’re resisting change, or why they’re not as engaged—use that as a trigger to get curious instead. Say, “I’m sensing some hesitation here. What are your thoughts on this?”
Practice curiosity in pairs. One of our favorite workshop activities is having leaders pair up & spend 5 minutes only asking open-ended “what” questions. It feels awkward at first (because most of us are trained to have the answer, not ask the question!), but the impact is huge. People walk away saying: “I felt so seen & heard. I felt like someone truly cared about me.”
Take your curiosity outside the office. We talked about Innovation Safaris in our last newsletter & we’re talking about them again, because they’re a great container to strengthen your curiosity! When you step into an environment totally different from your own—an art museum, a restaurant kitchen, a manufacturing plant—and look at how they solve problems or design experiences, you get SO many ideas about how you might do the same. Grab your team & take them on an Innovation Safari! Or better yet, let The Perk team be your Guide ;-)
Bring it back to the basics. Curiosity isn’t about overcomplicating. It’s about staying open to the possibilities. A simple question like “What’s one thing you need most from me right now?” can change the dynamic of a conversation—and over time, a relationship!
As always, if you try any of these tips, be sure to message us and let us know how it goes! We’re here for you.
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