Conversations with Generation iY Students

This summer, we celebrate the fourth anniversary of the book Generation iY—Our Last Chance to Save Their Future. Amazingly, it continues to sell better now than when it was first published! It’s all about the young Millennials, and it seems adults everywhere are seeking how to better connect with young people, engage them, and help them become ready adults. After hundreds of events and focus groups on the topic—I have a thought.

We’ve talked ABOUT these kids for years now. I think it’s time to talk TO them.


One of the questions I often get from parents, teachers, coaches, employers and youth workers across the country is:

“How do I talk about these challenges we face? How do we discuss the negative impact of technology? How do we broach the subject of soft skills and emotional intelligence? How do we encourage empathy in kids through meaningful conversation?”

Practicing ICU

I think it’s time for a crash course in conversations with the digital generation. Just as hospitals have Intensive Care Units (ICUs), l believe we must walk through our own “ICU” concerning young people. It’s simply an acronym for the stages of conversation we must have if we’re going to understand them, help them mature, and develop their life skills along the way. It’s going to require us to Inquire, Connect and Understand:

Inquire About Them

When conversing with students, I always try to begin with questions, not statements. It’s not that I’m interrogating them, but I want to communicate that I don’t assume I understand them; I’m not stereotyping them or lumping them in with all the other kids from their generation and I really want to get acquainted. So I bring questions with me to every gathering of students I teach or mentor.

  • To a middle school student, I may ask: What’s the toughest part about being thirteen years old? What’s one change you wish you could make in your life?
  • To a high school student, I may ask: What do you wish adults understood about your generation? What’s a personal dream you wish became a reality?
  • To a college student, I may ask: What’s the scariest thing to you about life after graduation? What do you wish you knew about your career?

Connect with Them

Once you hear their fears, joys, concerns and passions, it’s easier to connect their heart with a principle they must understand. I believe students learn on a “need to know” basis. Now that you’ve found a pain-point, why not have a conversation about an appropriate Habitude? (Habitudes® are images that form leadership habits and attitudes.) Each image represents a timeless principle for life and leadership. There are over eighty of them to date, in six books, and—because pictures are worth a thousand words—they foster mentoring discussions about life principles.

Understand Them

Once you’ve experienced a discussion that connects a life-principle with their need or pain-point, you now enjoy a better understanding of what makes them tick and how you can best prepare them for their future. It’s uncanny how young people will actually listen to adults… if they think we actually understand them. I don’t believe students have an innate need to get their own way, but I do believe they have an innate need to be understood. Actually, that’s true of all ages. Once we feel loved and understood, we’re willing to go on a journey of change and growth. We feel safe.

Tomorrow, I’ll share one big question I asked students recently. Their answers were telling.


Join tonight’s Twitter Chat as we discuss today’s students at 5pm ET.
Use #iYChat to join & ask questions.

New Free Chapter to Generation iY

Conversations with Generation iY Students