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How to Turn Millennial Employees into Budding Entrepreneurs


It is fascinating to me to witness the stark differences in priorities between my youngest and oldest sons. It was strange enough having sixteen years separate them in age. I can recall getting requests like these within five minutes of each other: “Dad, can I borrow the car?” vs. “Daddy, can you change my diaper?” But now that both are well on the path of meeting most of their own needs, I find that gap in ages to be reflective of a very different set of perspectives on what constitutes a life worth living.

With my oldest son, I’d say the priorities are closer to my own—somewhat driven by a tendency to keep score against some preset norms of having a job, a family, a house, etc. My youngest seems driven by a much less tangible vision—something much more qualitative in nature, seemingly aimed at satisfying a set of inner (rather than external) measures. All I know for sure is that it involves living in Brooklyn!

A few years back, I came across an op-ed piece in the NY Times by William Deresiewicz titled “Generation Sell.” In this piece, Deresiewicz takes the reader through his analysis of the millennial generation that seems to be so difficult to understand for many managers today. His central insight is that this is a generation of entrepreneurs.

“Today’s ideal social form is not the commune or the movement or even the individual creator as such; it’s the small business. Every artistic or moral aspiration—music, food, good works, what have you—is expressed in those terms.”

The Millennial Generation Holds Untapped Potential

While millennials may view the small business as the idealized social form of the current times, many of them continue to work in our mainstream organizations. They literally walk among us, having learned how to play the game by developing an ability to fit in rather than drop out and assume the risks of business ownership.

“…it is likely that we have not tapped the entrepreneurial instincts of this generation.”

Given the continued premium we place on compliance, it is likely that we have not tapped the entrepreneurial instincts of this generation. And like it or not, this is why they may eventually leave us. Ask yourself:

  • Do we pay attention to utilization—the effective use of employees’ abilities and skills?
  • Are people being offered the opportunity to use their talents?
  • Are they utilized to their optimum contribution?

This is a big deal to all employees, but especially millennials, as it plays directly into their sense of engagement with both work and workplace.

Engaging Millennial Employees Requires Buy-In

I can recall a time, shortly before I left my position with a Fortune 10 company back in 1979. It was something of an impromptu meeting between a senior line manager (Paul), my manager (Jim), and myself. Paul was very direct. He said to my manager, “Jim, you better find some more worthwhile assignments for this guy,” pointing to me. “Or you are going to lose him. He’s getting bored. You’ve got to give him reason to stick around—and I mean more than money. He’s too creative to be satisfied with the work you’ve got him doing!” As it turned out, Paul was right. Four months later, I turned in my resignation, and I have worked for myself ever since, doing what I find meaning in.

As managers, we might do ourselves an enormous favor by asking not how we can get the millennial employee to be like us, but rather how can we give them reason to stay and invest in our future. One suggestion: give them more of a say in what they are being charged with.

“As managers, we might do ourselves an enormous favor by asking not how we can get the millennial employee to be like us, but rather how can we give them reason to stay and invest in our future.”

The November 14, 2011 issue of the New Yorker featured a Malcolm Gladwell piece on Steve Jobs titled “The Tweaker.” In the article, Gladwell identified Jobs’ genius not so much as that of an inventor but as more of a “tweaker.” By definition:

“The visionary starts with a clean sheet of paper, and re-imagines the world. The tweaker inherits things as they are, and has to push and pull them toward some more nearly perfect solution. That is not a lesser task.”

As managers, we might prefer a team of “tweakers” to a team of inventors since inventors are notorious for lacking commercial instincts and often times are satisfied with proving out rather than perfecting their ideas. Examples abound, including the boon Xerox research has historically been to the technology industry, if not necessarily to itself.

If Deresiewicz is on to something, (and from my knowledge of my own 29-year-old son, I’d say he is), it is incumbent on us to find a way for our millennial employees to contribute by “being in charge” of something they view as important. This has less to do with salary category or titles than it does the idea of having a lot of say in something important to our business—maybe not the final say, but certainly a lot leading up to it.

Turning our millennial employees loose to “tweak” may seem like an invitation to chaos. But it may just be a formula for the engagement and retention of our best and brightest.

What can you do to give your millennial employees more of a say in the business and an invitation to make what is working now even better than it already is?

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