The Art of Questioning: Leadership Beyond the Status Quo

Just like designers, leaders question everything.

Leaders don’t accept the status quo. They don’t default to “this is how we’ve always done it.” Instead, they ask: Why? What if? How can this be better?

Where a manager maintains, a leader disrupts. Not for the sake of disruption, but to create movement. To shake loose what no longer serves. To make space for growth.

At the heart of modern leadership is a designer’s mindset – one that values curiosity over control, questions over answers, and progress over comfort.

Because the truth is: you can’t level up a team without challenging what holds them down.

But how do you do that?

By asking the right questions:

• Why do we do this the way we do?

• What are we really trying to achieve?

• What’s holding us back?

• What happens if we take this one step further?

Simple questions. But when asked with intention and listened to with presence, they shift culture.

Leading Through Curiosity

Great leaders don’t just tell teams what to do. They invite teams to challenge how things are done. They create the safety to question assumptions and the clarity to pursue better outcomes. But most of all, they inspire a culture of questioning.

A space where everyone feels encouraged to challenge, to improve, to think deeper. A place where better questions lead to better ideas.

As Warren Berger writes in A More Beautiful Question, questioning is not just a skill – it’s a way of thinking. He argues that questioning drives innovation, problem-solving, and personal growth, yet it’s often overlooked or even discouraged in traditional education and corporate settings. Berger challenges leaders and teams to develop a “questioning mindset” that treats curiosity as a competitive advantage.

And that’s exactly what modern leadership demands:

Less knowing, more discovering.

Less directing, more exploring.

You don’t need to be a designer to lead like one. You just need to stay curious. Because when leaders ask better questions – and encourage others to do the same – that’s when transformation begins.