Why the Best 21st Century Leaders Are Question Askers

The view through a rain-streaked windshield from a car pulled over on a highway shoulder, phone in hand

Sometimes your best leadership insight arrives while you're parked on the side of a highway in a hurricane.

In September 2024, I was driving south from New England to Florida while the remnants of a hurricane were moving north.

At some point in West Virginia, the wind and rain became persuasive enough that I pulled over. My husband and father had both already strongly suggested this would be a good idea.

Conveniently, I also had a scheduled interview with business writer Rebecca Knight.

The question I wasn't ready for

We spent about an hour talking about how leadership has changed. Then Rebecca asked one final question:

"What is the biggest aspect of leadership that has changed in the last 40 years?"

My answer surprised even me:

"The best leaders of the twentieth century were question answerers, setting the vision and strategy from above. But the best leaders in the twenty-first century are question askers."

I had never said it quite that way before. But three ideas I'd been thinking about suddenly clicked together.

Three ideas that clicked

First, the world now moves too fast for any leader to have all the answers. Whatever you know today may be outdated tomorrow. The more valuable skill is knowing what to ask, whom to ask, and how to make one's way to a good answer quickly.

Second, talented people don't simply want instructions. They want to contribute, think, challenge, and help steer the ship. Good questions draw out their best thinking instead of shutting it down — and leave them excited about having made an impact.

Third, 1,000 brains beat one. Even when that one belongs to a very smart CEO.

What happened next

After I answered, Rebecca went quiet for a few seconds. I could hear typing.

A month later, I discovered that thought had become the opening idea in her Harvard Business Review article, "6 Essential Leadership Skills and How to Develop Them."

The experience reinforced the idea for me.

Leadership increasingly isn't about walking into the room with the answer.

It's about walking into the room with the questions that help everyone else find it.
Kirstin Lynde

Kirstin Lynde

Founder & Principal, Catalyze Associates

Kirstin Lynde is the founder and principal at Catalyze Associates, a firm dedicated to intensive, immersive, and metrics-based leadership development and coaching programs. She has led leadership programs as an executive at Randstad USA, Forrester Research, Digitas, and Ropes and Gray.