The Power of a Question: Leading a Generation in Transition

Aug 19
7 min read

David Hyesik Yoon

CEO, 2miles

Author of Cloud: The Birth of a New Tech Ecosystem and ChatGPT Future Jobs 2030

Founder & Organizer of “Job Greegi Camp”, a program designed to foster AI literacy and career exploration for young people

Microsoft Regional Director & MVP (Most Valuable Professional)

Today’s young generation faces an abundance of information, yet many still struggle with uncertainty about where to go and what to choose. What they need is not more advice, but the right questions—and someone who asks them with sincerity.

David Hyesik Yoon, CEO of 2miles and founder of the “Job Greegi Camp,” has helped countless young people find turning points in their lives. He reminds us that true leadership lies not in giving answers, but in guiding others to discover their own first sentence.

The Silence After a Question

Q. What kind of questions can help young people who feel lost find a new beginning?

Anxiety in today’s youth rarely comes from a lack of information. It comes from the uncertainty of not knowing where to go next.

This is why a leader’s role is not to hand out ready-made answers, but to pose the kind of questions that force direction to emerge.

When I meet a young person preparing for a career, I don’t start with advice. I begin with questions:

“Why did you choose this field now?”
“Does this path connect to your strengths, or does it only look stable from the outside?”
“What does stability in a job truly mean for you?”

By the third or fourth question, many fall silent. And that silence reveals the truth: their goals were never fully theirs. They were running along tracks laid down by family expectations, peer influence, and society’s applause—until they lost their own breath.

That is why, in my career camps, I strip it all back to one essential question:

“Why do you want to do this work?”

Helping Them Draw the Map, Not Just the Route

Q. How can we help young people discover their own coordinates?

Many young people struggle because they’ve lived by other people’s standards, only to collapse under the weight of them. In those moments, the role of a leader is to help them avoid being bound by past failures or results.

That’s why I often ask:

“What kind of life do you want to live?”

“Where is your passion truly pointing?”

Before setting career goals, there needs to be a process of articulating the form and direction of one’s life. When this foundation is clear, learning new skills, making career choices, and building relationships all become steadier and more meaningful.

Beyond that, pursuing only personal success narrows the options. But when young people begin to consider how they can help others and what kind of positive impact they can leave behind, that’s often when they discover the work they were truly meant to do.

A leader’s role is not to hand out answers, but to stay close—posing the right questions and offering support as they begin to carve out their own way.

From Barista to AI Team Leader

Q. Can you share a moment when a young person made a decisive turn in their career?

One participant in the career camp was working as a barista. On the very first day, after listening to the mentors’ questions and reflections, he said:

“From now on, I want to test myself in a completely different field.”

Soon after, he left his job and began studying AI through a government-supported program. Six months of intense focus led to his admission into POSTECH’s AI graduate school, followed by an exchange at Carnegie Mellon. Today, he leads a team at a major AI company.

Stories like this remind me that what changes a young person’s path is rarely a grand vision. More often, it is a single, genuine word of encouragement spoken at the right moment.

When Honest Feedback Unlocks Hidden Barriers

Q. Have you seen a case where careful observation and honest feedback sparked someone’s growth?

I once met a young man with strong skills and an admirable attitude. Yet his confidence did not match his true abilities. Through a series of questions, I tried to uncover the reason step by step.

What emerged was unexpected: the real barrier was his pronunciation. Each time he spoke in public, his confidence faltered. He knew it himself, but no one had ever named it directly.

So I chose to tell him with care:

“Your pronunciation is a little unclear. It may take time, but have you considered working on correction?”

After the camp, he immediately sought professional help. A few years later, he not only secured the job he wanted but also built a strong career.

The essence of this story is not dental correction. The breakthrough came when someone dared to say, “This is where you are stuck,” instead of offering empty reassurance.

When the right question reveals the true obstacle, and one clear piece of feedback is spoken at that moment, it can change the direction of an entire life. As leaders, the courage to name what is unseen often becomes the catalyst for real transformation.

From Raw Gift to Real Impact

Q. How do raw strengths become real competencies?

Everyone is born with certain sensitivities—some are attuned to relationships, some to creativity, others to helping people. Yet raw qualities alone rarely earn recognition. Strengths become real competencies only when they are paired with problem-solving, collaboration, and execution.

Take empathy as an example. It can be a gift, but in NGOs or professional settings, it only matters when translated into concrete action and results. That is why, when I work with young people, I examine their upbringing, recurring emotional responses, and the activities that consistently absorb them. One participant, deeply sensitive to color, grew into digital design. Another, though an excellent illustrator, struggled with tools and ultimately chose a different direction. The same talent can lead to entirely different expertise—depending on how it is applied.

The mentor’s role is to surface what is already there, refine it into a strength that society values, and open pathways for it to flourish.

Beyond Tools: Weaving AI Into Your Own Path

Q. How can young people turn emerging technologies like AI into real career strategies?

What matters more than the technology itself is knowing where and why to apply it. Many young people stop at simply learning tools, but true competitiveness emerges when technology is woven into their own experiences and interests.

Some fields—like accounting or marketing—are already being rapidly automated. In these areas, the essential question becomes:

“How can I integrate my strengths with technology in a new way?”

By contrast, in human-centered fields such as caregiving or the arts, the priority is not adopting AI, but sharpening one’s distinctive personal expression.

Career strategy also means looking beyond the red oceans of today to the blue oceans of tomorrow. The problem is that schools often teach skills tailored to current markets, leaving a gap with what the future will actually demand. That is why cultivating the ability to read shifts and generate one’s own insights is critical.

In career camps, I dedicate a full day to megatrend and microtrend analysis. The goal is to help participants put their own possibilities into words. Because in the end, competitiveness doesn’t come from the technology itself—it comes from how uniquely you connect it to your own path.

The Power Only Humans Can Offer

Q. Why does human connection remain essential, even in the age of AI?

Data is everywhere, but it rarely tells us what it means for our own lives. Only when someone says, “This could be your story,” does information transform into real insight.

At the Job Greegi Camp, mentors and I ask young people the kinds of questions AI could never ask:

“Why do you want to pursue this path?”

“What kind of life do you want to live?”

When these questions surface, young people stop speaking through borrowed standards and begin telling their own stories.

But lasting change doesn’t happen in a single encounter. That’s why I created the Vision Circle, a community designed to carry these conversations across generations. Here, mentees grow into mentors, and mentors into grand mentors. Each role gives and receives—mentees gain guidance, mentors expand networks, and grand mentors draw fresh energy from the creativity of the young.

In the end, what young people seek is not the right answer. What they long for is a meaningful connection—someone who can help them read their own lives. And that is a power only humans can offer.

Helping Them Write the First Sentence

Q. What role should leaders play in turning young people’s potential into reality?

Young people carry limitless potential. But the path that potential takes depends on the experiences they live and the people they meet.

That’s why I believe a leader’s role is to help them write their “first sentence.” A single statement of purpose—whether about career or values—can shift the entire direction of a young person’s life.

Rather than trying to teach everything, a leader becomes a companion who sparks expansion. For those without a vision, it means offering direction. For those with clear goals, it means connecting them with the right strategies and tools.

In the end, it is not information that transforms young people—it is human energy. When words are spoken with authenticity and weight by someone who stands beside them, young people find the strength to truly grow.

I, too, once took part in the ‘Job Greegi Camp’ as a LinkedIn career development speaker and mentor. I can still recall the pure passion and bright eyes of the young people I met there, and those moments remain vivid in my memory. Since then, I have continued to stay connected with them on LinkedIn—sometimes receiving encouragement from my mentees, and at other times offering encouragement in return. What I realize most deeply through this journey is that more young people will only be able to discover their true value and path if more of us choose to stand beside them as leaders.