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To begin with a trite truism: There are two sides to every coin. Which is to say that, for every data point, observation, prediction and proclamation about millennials in the workforce, you can usually find a contradictory point of view. 

So where does that leave the vast legions of millennials who are just launching their careers (or hope to!) and the army of companies that are thinking about employing them (or not!)? Perhaps it begins with a dose of due diligence and a bow to the Dirty Harry challenge of, “Do I feel lucky?”

Just as with colleges and prospective students, corporate matchmaking often boils down to a question of fit and mutual expectations. When there’s alignment — for example, a corporation planning not to invest in a new millennial hire and that hire not planning to stay very long — then the ledger balances, so to speak. But when one side’s expectations are not in concert with the other’s, problems will certainly arise.

Luck notwithstanding, the marshalling of research, experience and savvy — whether by corporate management or millennial aspirant — probably offers each party the best chance for getting what they really want as they address the following five tough questions.

1. For employers: Do I hire just to get what I can out of someone, knowing they’ll soon leave? For millennials: Do I refuse to make a commitment because I know they won’t help me grow?

Bentley University’s PreparedU study revealed widespread discontent among business executives about everything from millennial work ethic to retention. Wharton’s Peter Cappelli chalks it up to generational grousing, but others aren’t so sure.   

Companies like Epsilon, a leading provider of marketing services, believe that investing in millennials will pay off. And they have the programs, stories and data to prove their point. These are buttressed by a recent report from the White House Council of Economic Advisers suggesting that millennials are actually staying with employers longer than Gen-Xers did at a similar age. 

If so, it may be that companies are becoming more accommodating, or that perceptions about economic uncertainty are making millennials more cautious. Or both.

2. For employers: Aren’t millennials as venal as everybody else, caring most about the money? For millennials: Do I go for some decent money, shelve my idealism and desire for work-life balance, and try to find fulfillment outside the job?

Recently, an acquaintance in a high-paying, grind-it-out sort of industry confided: “These kids want the big bucks, but they don’t want to put in the 50 to 60 hours a week it takes to earn them.”

Others may simply pass on the big bucks, as evidenced in those stories about millennials turning down raises and promotions for lifestyle reasons. Even so, it’s no accident that enrollment at schools that offer a petroleum engineering degree, for example, is skyrocketing. And it’s probably not because those millennials have a love affair with fossil fuels and rocks. Yeah, show me the money, Jerry!

But of course it’s more complicated. One reason: It costs a lot for companies to recruit and retain employees. Which is why executives are so concerned about retention. The key for millennials is to understand which companies offer them the best chance to thrive (however they define that).

3. For employers: Do I hire on the basis of soft skills, hard skills, or both hoping to retain my future corporate leaders? For millennials: Do I buy the argument that the liberal arts aren’t dead because employers value them, or do I craft a hyphenated brand for myself?

There’s some indication that corporate execs want to have it both ways. They think that the virtues of the liberal arts are key to long-term success; that said, they’d prefer to hire someone who has “hard skills” and can make an immediate contribution. 

The implications for millennials are profound, not just in terms of what they study but how they package it. Consider these four options:

  1. I am an English major and a lover of poetry.
  2. I am an English major and a digital communications native.
  3. I am a digital communications major.
  4. I am a digital communications major and a lover of poetry. 

Each presents a different picture, a mixture of majors, interests, emphasis and marketability.  Which represents the right picture — for the millennial and for the employer? In today’s market, it is a luxury for some millenials to focus on a single brand definition, even if it’s got some vocational pop. Passion, expertise and broad skills or interests suggest that a hyphenated package or personal brand holds the greatest market potential, at least according to the data. You need to have a story that’s engaging and demonstrates achievement.

4. For employers: Do I try to figure out how to provide entrepreneurial/intrapreneurial opportunities, which seem to be the rage with these kids? For millennials: Do I really go for the cool, start-up entrepreneurial thing and close my eyes to the fact that 90 percent of start-ups don’t survive? 

Definition is important here. There’s actually being an entrepreneur, working in an entrepreneurial or start-up environment (read, really cool), and being entrepreneurial/intrapreneurial within a larger corporate structure (which means making an impact while having the corporate safety net below).

The first is challenging, and can be enormously exciting and ulcerously uncertain — often at the same time. The second also can offer opportunities to innovate and take risks; it can also mean doing scut work because there’s no budget for support (but you get to drink beer and play foosball, if you’re lucky). The third often means you experience a number of opportunities within the corporation and, after finding one you like, you get a chance to make an impact. To a degree, all may appeal to the roughly 70 percent of millennials who, according to Deloitte, see themselves working independently at some point in their lives. And for a more insightful description of intrapreneurs, read David Williams in Forbes.

There’s some indication that corporations are responding. Millennial Branding founder Dan Schwabel, writing in Entrepreneur magazine, cites an American Express study finding that 58 percent of managers are very or extremely willing to support employees who “want to chase business opportunities.”  

5. For employers: Can I define my firm’s social impact in ways that go beyond the occasional volunteer day or matching gift program so that millennials will be impressed? For millennials: How much do I really care about social impact? It doesn’t have to be a choice between Wall Street or Occupy Wall Street, but what really matters?

There is no denying millennial interest in making a positive impact on society through the companies that employ them. And, more and more, there’s a recognition that mission is central to the people/planet/profits mantra that is largely embraced by the millennial generation.

But a question for millennials and corporations is how best to define social impact and how to measure its importance in the workforce. Begin with the fundamental corporate mission. Is a mutual fund, which helps retirees survive and parents pay for college tuitions, any more worthwhile than an insurance company, which prevents people from having their lives destroyed by catastrophic loss, or an advertising agency, which helps satisfy consumer needs while making entertainment and information freely available?

Perhaps the question is open to debate but it would seem incumbent upon millennial and employer alike to really focus on that discussion.

Then there are the proxy indicators: chances to volunteer, to support good causes, to pursue green practices, to access matching gifts, etc. All are important in their way. All can contribute to making the society a better place. Perhaps the trifecta would be a nonprofit organization that pursues green-energy practices and provides volunteer opportunities for its employees (who are well compensated, of course). 

In the end, for this question and the others, it comes down to understanding what both the millennial and the corporation value — for themselves and in each other. In that regard, there may not be a right or wrong, a good or bad, although each party ignores societal and marketplace trends at their peril. Rather, at any given point in time, what may matter most is alignment, just like in a good marriage.    

Sometimes that’s easier said than done. Which is why a little bit of luck could come in handy.

Vic Schlitzer is Director of Brand & Content Marketing at Bentley University