How to Lead Gen YI am extremely fortunate to be able to call Greg Hartle a friend. I met him on Twitter when he began participating in Leadership Chat, sharing genuinely insightful tidbits of wisdom in 140 characters; wisdom that seemed beyond his years.

He read my “Twitter profile” and saw that I was a kidney transplant recipient.  He told me he was as well, the fortunate recipient of a kidney from his mom.  The experience had been life-altering, as it often is, and his wisdom had clearly been earned.

Greg set out on January 1st of this year with a different kind of vision: to show the world that with vision, purpose, fortitude and just $10 and a laptop he could truly change the world through entrepreneurship. He is documenting his journey at

He has a unique and thoroughly inspiring view of Gen Y leadership, and has agreed to Guest Host Leadership Chat this Tuesday evening, October 4th, with Steve Woodruff and me.  I asked Greg to answer some specific questions about leadership – particularly insights into how to lead Gen Y individuals.  This is a topic that many of the CEOs I work with genuinely want to understand!

I was genuinely moved by Greg’s answers and hope you’ll find them enlightening in many ways:

Q1. Lisa: What is the biggest leadership challenge for Gen Y leaders today?

Greg:  First, let me start by saying I don’t consider myself a member of Gen Y. Born in 1978 and growing up and going into business with people much older than me early in my career I definitely feel I’m much more part of Gen X. However, since 2008 I’ve spent considerable time with Gen Y and have even launched several businesses with a few members of that generation. I’ve also stayed with and interviewed many members of Gen Y on my TenLap journey.

To me, the biggest leadership challenge for Gen Y leaders is developing an economic structure that understands the difference between maximizing consumption and maximizing quality of life. And doing so in ways that don’t sacrifice the future for the present.

This is a monumental challenge for two reasons:

1) America’s entire economic engine is built on growth of consumption. What younger generations must first realize, that previous generations overlooked, is growth does not equal prosperity. Only then can we begin to look at an alternative economic engine.

2) America was built on sacrificing the present for the future. Previous to the Baby Boomer generation, American’s made incredibly painful sacrifices. Being an American brings responsibilities as well as opportunities. For decades now we’ve been far too focused on the latter and have shared little time focused on the former.

For America to return to the “shining city upon a hill” we may need an entire generation to sacrifice their entire livelihood for future generations. Does Gen Y (or any living generation) have the will, courage, mindset, or conditioning to do such a thing? I don’t know.

However, one thing I know for certain is America derives its strength from young diverse leaders emerging to consistently find ways of reinventing ourselves. I see no shortage of these leaders and I feel very comfortable knowing America’s future is in their hands.

Q2. Lisa:  What do you believe Gen X and Boomers+ think is the biggest challenge when leading Gen Y individuals? Part 2 of this question – What is your advice to help GenX+ to address this challenge?

Greg:  The biggest challenge when leading Gen Y is the biggest challenge when leading anyone, deeply understanding their worldview. What matters to them and why?

The simple method of the 5 Whys (asking the question “why?” five times in a row to get to the root) can go a long way in deeply understanding what someone values. Only when you understand what someone values, can you begin to lead them.

Further steps would include:

1) Gen X and Boomers+ coming to the table asking, “What can I learn from you, Gen Y?” Followed by, “What would you like to learn from me?”

2) Then use one of the most empowering phrases in the English language, “Let’s”. “Let’s figure this out together.”

The era of top-down leadership is on its last legs. Leadership should be less about what I know that you don’t and more about the formula 1 + 1 = 3. You and me together is far greater and stronger than me telling you what to do.

Q3. Lisa:  What do you think most Gen Y leaders would like other generations to know about them?

This is an easy answer. I hear it consistently. Gen Y leaders do not feel nearly as entitled as previous generations label them. They care. They just want to go about life differently.

Given the connectedness of the world, they tend to move through the egocentric (“me”) – ethnocentric (“us”) – world centric (“all of us”) stages of consciousness faster than ever before. This is why their social graph is much larger and more diverse than previous generations. And why their social graph matters more to them.

Gen Y leaders also want previous generations to know that just because they reject your lifestyle doesn’t mean they reject the principles, values, or history from which it’s foundation begins. In the end, they value similar things. They just want to arrive at the results in a way that serves more people, better.

Q4. Lisa: This blog focuses on Visionary Leadership.  Do you think Gen Y leaders understand the critical importance of having a vision? If so, how are they most likely to have learned this?

Greg:  I think Gen Y leaders understand visionary leadership far better than Gen X or the Boomer generation. They’ve learned this two ways:

1) They’ve personally experienced the extreme highs and extreme lows that come from a short-sited view. The greatest change to behavior will occur based on what you personally experience. They grew up during the rise of the late 90s (one of the greatest eras of America’s prosperity), the sharp fall of the dot-com bust, and 9-11 (In the top 3 of most significant events on American soil).

These events have shaped them unconsciously. And now they’re consciously living as young adults through the mass over-consumption of the mid-2000s followed by the sudden collapse beginning in 2008. The kind of real world lessons that will come from these events will shape Gen Y leaders vision much more so than any schooling, training, or job.

2) Information. Gen Y has grown up with unprecedented access to information. This access has allowed them to shorten their learning curve, make quicker decisions on what’s important to them, find like-minded individuals in far-away places to collaborate with, and develop a deeper and wider vision for imagining a world they want to live in and be a part of creating.

Access to this level of information will be both empowering and powerful for Gen Y leaders.

Q5. Lisa:  On your Ten Dollars and a Laptop Trip, what has been the most impactful leadership lesson?  What has been the most unexpected delight on your journey?

Greg:  The most impactful leadership lesson has not changed since the beginning of TenLap or since the beginning of time: Be An Example Of Possibility.

Countries, cities, communities, businesses, nor families change. I change. And through my example the world around me begins to change. It’s really as simple as that.

Unexpected delight… without question the kindness of strangers near and far. From people I’ve met on the street, in homeless shelters, people who have allowed me into their home, people who have helped me through social networks, and even the guy who while driving by in his Jeep as I was walking down a back road in Vermont reached out and handed me a beer. We didn’t say a word to each other, just shared a facial expression that said, “Yeah man, we’re in this together.”

I have yet to meet a single person unwilling to help. That’s remarkable. And I’m extraordinarly humbled and grateful for each person I’ve met along the journey. And that, of course, includes the kindness and generosity of you, Mr. Woodruff, and the entire #LeadershipChat community.

You didn’t ask this, but if there was one thing I think all leaders should remember it’s that in order for America (it’s businesses, communities, cities, states, and the country as a whole) to thrive each of us must not only give something back, we must pay something forward.  Our nation celebrates the individual, and just as it provides for us, so it expects of us. We must always remember this.


Please share your reactions to Greg’s perspective in the comments, and be sure to join me, Greg and Steve on October 4th at 8:00 pm Eastern Time for our next edition of Leadership Chat on Twitter!  These chats are getting bigger, better and more insightful every week – don’t miss out!


Along with being a life-long entrepreneur, Greg Hartle consults and speaks professionally with businesses, non-profits, and other groups on 21st century capitalism, leadership, and integral life strategies. His latest project, Ten Dollars and a Laptop, explores the realities of building his life from scratch in a major economic downturn.