We’re Raising a Generation Afraid to Get It Wrong and Then Asking Them to Lead
I teach more than 250 college students a semester.
And lately, I’ve been experiencing something that’s both frustrating and fascinating.
I ask a question. Not a trick question. Not something with one perfect answer. Just a question designed to make students think, challenge an assumption, share an opinion, or connect what they’re learning to the real world.
And sometimes?
Silence.
I wait. I encourage. I push a little.
Still, silence.
If you’re managing a team and wondering why people aren’t speaking up, taking initiative, or solving problems independently, you might recognize this silence.
I’ve spent more than 30 years leading businesses, coaching executives, and developing teams. Now, as a college professor, I’m discovering that getting students to think independently, speak up, and take risks can be harder than teaching them the material.
I don’t want students memorizing information, repeating it on an exam, and forgetting it the next day.
I want them to think, communicate, connect, and act.
Because that’s what the workplace needs.
But here’s what concerns me: We may be developing talented young people who are more comfortable knowing what to do than figuring out what to do.
And that’s a problem for all of us.
The Problem Isn’t Intelligence. It’s the Fear of Being Wrong.
I love working with Gen Z.
They’re capable, thoughtful, technologically sophisticated, and full of potential.
But many have spent years in environments where success meant following instructions, meeting expectations, and getting the right answer.
Then they enter the workplace.
Suddenly, we’re asking them to solve unfamiliar problems, make decisions with incomplete information, challenge assumptions, and take initiative without being told exactly what to do.
And we wonder why some hesitate.
I see it in my classroom. A few students are courageous enough to tell me they don’t like the ambiguity or pressure to participate. I respect that honesty.
But what about everyone else?
How much of the silence, reluctance to participate, or resistance to exchanging ideas comes from fear?
Fear of embarrassment. Fear of judgment. Fear of disappointing someone. Fear of being wrong.
Not every quiet student is afraid. Some are processing, some aren’t prepared, and some may need a different invitation to contribute.
But I believe fear is one of the biggest obstacles between human potential and human performance.
And it’s not just a Gen Z problem.
What Our Research at Marlee Tells Us
At Marlee, our research into generational differences at work revealed some fascinating findings.
Compared with earlier generations, Gen Z demonstrated:
- 120% higher emphasis on being detail-oriented.
- 100% higher desire for best practices and doing things the right way.
- 73% lower emphasis on having multiple options and different ways of doing things.
These are relative differences in measured work motivations, not proof that Gen Z is more fearful or that every young person behaves the same way.
But think about what they suggest.
We have emerging talent that often values clarity, structure, detail, and proven methods.
Those can be tremendous strengths.
But what happens when there are no instructions?
When the manager doesn’t know the answer?
When a client changes direction?
When AI gives you five plausible solutions, and someone has to decide which one makes sense?
Detail orientation helps you execute. Critical thinking helps you decide what deserves execution.
We need both.
Our job as leaders isn’t to eliminate the desire for clarity. It’s to help people become comfortable thinking and acting when clarity doesn’t yet exist.
A Mel Robbins Conversation That Got Me Thinking
Recently, I listened to a terrific episode of The Mel Robbins Podcast featuring Professor Marina Cooley from Emory University’s Goizueta Business School.
Huge credit to Mel for bringing practical, empowering conversations to the world, and to Professor Cooley for helping students learn how to stand out, communicate their value, and navigate what she calls the attention economy.
Professor Cooley teaches a course called Amplify.
I love that word because it captures something I’ve spent my career trying to teach: You have to show up. Speak up. Understand what you bring. And be willing to share it.
One theme of their conversation is knowing what you want and being willing to ask for it.
Sounds simple, right?
But how many people spend their lives waiting for permission, recognition, certainty, or confidence before taking action?
Their conversation challenged me to rethink how I teach these skills. Not as another lecture, but as an experience.
I’m Changing How I Teach
My Business Professional Development students don’t just need career information. They need practice becoming professionals.
That means asking meaningful questions, presenting ideas, listening, building relationships, and making decisions when the answer isn’t obvious.
I’m increasingly structuring classes around three exercises: one at the beginning, one in the middle, and one at the end.
More participation. More practice. More feedback.
Less sitting and listening.
Instead of explaining networking, I have students interview one another using deeper questions. Instead of lecturing about presentation skills, I ask them to stand up and communicate their value. Instead of providing every step of an assignment, I ask them to identify the problem, evaluate alternatives, make a recommendation, and explain their thinking.
And yes, that creates discomfort.
But productive discomfort, combined with encouragement and support, is how we grow.
I don’t want students to feel unsafe. I want them to discover they’re capable of doing difficult things, making mistakes, and getting better.
That’s a distinction every leader needs to understand.
I’m Not for Everyone. And I’m Learning From That, Too.
My wife once bought me a shirt that said, “I’m not for everyone.”
She knows me pretty well.
I’m direct, passionate, energetic, and sometimes impatient. I challenge people because I believe in what they’re capable of.
But I’ve also learned something important.
Sometimes my delivery doesn’t land the way I intend.
And that’s on me to understand.
I want students to speak up, take risks, and think independently. But I also have to ask whether I’m creating an environment where they feel comfortable doing those things.
Am I listening as much as I’m pushing?
Am I challenging them in a way that builds confidence—or sometimes making participation feel riskier?
Those aren’t always comfortable questions for someone who’s spent a lifetime coaching others. But they’re necessary.
I refuse to lower my expectations. However, I’m absolutely willing to change how I help people reach them.
I care deeply about my students and the people I coach. I’ve lived many of the challenges I’m asking them to face. And if my approach isn’t helping, I want to know.
I’ll listen. I’ll reflect. I’ll adjust.
Because that’s exactly what I’m asking them to do.
The goal isn’t to get people to think like me. It’s to help them develop the courage and judgment to think for themselves.
AI Makes This More Important, Not Less
AI makes it easier than ever to produce something that looks like an answer.
An essay. A presentation. A strategy. A recommendation.
But producing an answer isn’t the same as understanding the problem.
Curiosity. Critical thinking. Judgment. Communication. Connection.
I want my students using AI. They have to, with the way the world is going. But I also want them to question it, challenge it, evaluate it, and understand why an answer makes sense.
AI should amplify our thinking, not replace our responsibility to think.
Leaders, Stop Giving Every Answer. Start Building Thinkers.
I see the same challenges in organizations.
Why won’t employees take more initiative? Why don’t people speak up? Why do managers have to provide so much direction?
I believe the solution begins with changing how we coach and lead.
- Ask before you tell. Instead of immediately providing the solution, ask: “How would you approach this?”
- Reward thinking, not just correctness. Recognize thoughtful reasoning, curiosity, and intelligent risks—even when the outcome isn’t perfect.
- Create clarity without eliminating autonomy. Explain the objective, boundaries, and what success looks like. Then let people figure out how to get there.
- Make participation safer—and expected. Invite different perspectives. Give people time to think. Don’t punish imperfect ideas. But don’t let silence become the default.
- Turn action into learning. Encourage experiments. Get feedback. Reflect. Adjust. Repeat.
And teach people to ask better questions.
“What am I missing?”
“What’s the real problem we’re trying to solve?”
“What would you do differently?”
Great questions create understanding. Understanding creates connection. And connection opens opportunities.
The real measure of leadership isn’t how many answers you provide. It’s how many capable thinkers you develop.
Fear Doesn’t Disappear Before Action
For years, I’ve taught a simple principle:
Beat Fear → Choose Action → Build Confidence → Create Impact.
It’s at the heart of my work as a speaker, professor, and coach.
Action creates clarity. Clarity builds confidence. Confidence strengthens connection. And connection creates impact.
Not perfectly. Not overnight. And not without setbacks.
But every time we act, reflect, learn, and try again, we get stronger.
It’s bigger than Gen Z, too.
It’s the executive afraid to challenge the CEO. The employee afraid to ask for a promotion. The parent who solves every problem for their child. The manager who won’t delegate because someone might make a mistake. The student who has something valuable to say but won’t raise a hand.
Different generations. Different situations. The same human challenge.
And an opportunity to choose differently.
I don’t pretend to have this all figured out. Teaching hundreds of students is challenging me in ways I didn’t anticipate. Some days, I walk out of class frustrated. But I also walk out convinced this work matters more than ever.
Because the future won’t belong simply to those who know the most.
It will increasingly reward those who can learn, question, adapt, connect, and act.
We don’t need another generation of people waiting for the right answer. We need people brave enough to help create better answers.
Tomorrow, I’ll walk into another classroom and ask another question that doesn’t have one perfect answer.
I hope more hands go up.
But I’ll keep asking, listening, challenging, and adjusting.
The goal isn’t to teach students to give me the right answer. It’s to help them develop the courage to find their own.
And that starts with how we teach, coach, parent, and lead.
How I Can Help
I see this challenge every day—in college classrooms, executive coaching conversations, and organizations trying to develop the next generation of talent.
And I believe we can do better.
Through keynotes, performance and executive coaching, and leadership development, I help leaders and teams replace fear and hesitation with critical thinking, confident communication, meaningful connection, and action.
If your people are waiting for answers instead of creating them, let’s change that.
Let’s build thinkers. Let’s build confidence. Let’s create impact.
Dan Negroni
Keynote Speaker | Performance & Executive Coach | Generational Expert | University Professor
With appreciation to Mel Robbins and Professor Marina Cooley for inspiring this conversation. Listen to their episode, How to Stop Being Overlooked & Start Getting What You Want here: https://www.melrobbins.com/episode/episode-443/
Research referenced: Marlee’s Gen Z at Work Study: https://rc.marlee.com/blog/gen-z-stereotypes.
