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Career Advice

Maybe you already know all the Generation Y stereotypes. In case you don’t, let us clue you in on what people are saying about you: You’re entitled. You’re narcissistic. You have a tendency to job hop. You have no work ethic. You need constant affirmations of your over-inflated self-esteem. And you’re afraid to abandon the sanctuary provided by your helicopter parents.

Or consider how the media has proclaimed your supposed inadequacies in headlines like “Generation Y Bother” and “Millennials: The New Office Moron,” or books such as Mark Bauerlein’s The Dumbest Generation: How the Digital Age Stupefies Young Americans and Jeopardizes Our Future.

All that might sound like damning criticism, but don’t take it to heart: Such alarmism is nothing new. Older people have always stereotyped, ridiculed, even tried to marginalize, younger generations. And whether these generalizations are true—or whether you’ve contributed to their proliferation—is irrelevant.

Here’s what matters: You’ve got a bad reputation. As soon as you walk through the door, your gray-haired coworkers will have their antennae up, waiting for you to make the typical millennial missteps. If you play into their low expectations, even a minor mistake may overshadow your abilities and hinder your chances for advancement. If, on the other hand, you know where their sensitivities lie, you’ll be able defy expectations, and perhaps even use those stereotypes about Gen Y to your advantage.


Conventional wisdom holds that Gen Y kids grew up with their parents as their pals. That’s great for parent-child camaraderie, but this kind of buddy-buddy attitude can be problematic in the office, where you may be working with people who are as old as your parents—or even your grandparents. “Generation Y has a reputation for working well only with people they consider ‘friends,’” says Elsie Florido, associate director of career management services at Florida International University.

You might value authenticity and prefer to be people-driven rather than title-driven, but don’t presume all colleagues want to be confidants. “Generation Xers and baby boomers have a home face, a friend face, and a business face,” says Nicole Lipkin, a psychologist, consultant, and coauthor of Y In the Workplace: Managing the “Me First” Generation. “Millennials have to accept those boundaries and work within them.” The takeaway: Not everyone has to be a Facebook friend or drinking buddy.

Similarly, Gen Yers are known for informality, with a casual approach toward personal appearance, information sharing, and communication. Of course, that stereotype has been leveled at every new generation. Yet more than any previous generation, millennials grew up seeing millionaires in flip-flops and T-shirts. Obviously, the culture of every workplace and industry varies, but don’t be too casual about being casual.

For older colleagues, a professional appearance is more than a formality. “If you underdress, they’ll take it as a sign of disrespect,” says Jason Ryan Dorsey, author of Y-Size Your Business: How Gen Y Employees Can Save You Money and Grow Your Business. A good rule: Err on the side of overdressing and choosing conservative clothing. This benefits young employees in ways beyond the obvious, says Dorsey: “The more conservative you dress, the older you’ll look, the more experience people will think you have, the more likely they are to trust you with more responsibility.”

A similar principle applies to communication: always make sure it’s age appropriate. Your accounting firm’s 68-year-old client will probably prefer a phone call to a late-night text. Oh, and FYI: Save the WTFs and OMGs for your friends. “This stuff is showing up in cover letters, interoffice memos, and formal emails, and it’s a real problem,” says Jen Armor, senior manager of university recruiting at Yahoo. You don’t want to look like a fifth grader with his first smart phone.


Your generation enters the professional world with more access to information and more technological savvy than any of its predecessors. For all the snarky stereotypes, millennials are unquestionably creative and innovative. “Stepping into an office, a Gen Y immediately identifies things to be done quicker, different, better,” says Cam Marston, founder of the firm Generational Insights and author of Motivating The “What’s In It For Me?” Workforce.

That’s good. And bad. Management and leadership want to know you can use the systems as they are; they also want you to understand how existing protocols work and why they’re in place. Part of that is practical because every workplace and company has its own culture. “You can’t just go rogue here and write your own code or do your own thing that doesn’t fit the company’s ecosystem,” says Armor.

That doesn’t mean you need to stifle your innovative urges. Want to streamline your firm’s medieval interoffice communications? Got a fresh marketing strategy that makes your company’s current one look like it’s from The Flintstones? Great. Just don’t try to sell it to older colleagues that way. “Think evolution not revolution,” says Seth Mattison of Bridgeworks, a firm that consults with businesses on generational issues. “Ease people into change. Be delicate. Don’t say, ‘This is going to transform everything.’ That may seem threatening or even insulting. Say, ‘What we have in place is great. I think I have a couple of ideas for how to improve it.’”


Millennials have a reputation for being unable to work on their own—and for needing constant guidance. The good news: You can still get the support you need without perpetuating the stereotype.

First, when beginning a project, never approach a supervisor and ask her to tell you what to do. You’ll make her feel like she’s teaching elementary school.

“When you meet, come with substantive ideas,” says Misti Burmeister, author of From Boomers To Bloggers: Success Strategies Across Generations. “Suggest a few different directions; show you have thoughts in your head, and see how your boss responds.” And always be prepared to take notes; with an older colleague, you may want to do this with pen and a notepad instead of an iPhone.

Second, when you need feedback, be careful. Seeking support is essential, but don’t go too far: Avoid dropping into his office every hour for affirmations or neurotic micromanagement. Instead, plan check-in times in advance, says Mattison. “Tomorrow at 2:00, Thursday at 4:00, Monday at noon. That way, you get the support you need, but you’re both on the same page as far as expectations.”

Finally, when you reach an impasse, never say to older colleagues or supervisors, “Can you fix this for me?” Doing so makes your problem their problem. Instead, use phrasing that emphasizes your responsibility and your desire to be independent: “Can you show me how I can correct this?


Probably the most persistent—and damaging—millennial stereotype is the “trophy kid”: deluded by grade inflation, awarded prizes for just showing up, assured she has no weaknesses—only “weaker strengths.” This translates into the workplace perception that Generation Y cannot handle criticism. “Fairly or not, employers say that when millennials mess up and get called on it,” says Florido. “they get defensive or deflect [responsibility] and create problems for other people. Or maybe they just quit.”

The keys are acceptance and perspective. For example, annual reviews are not exercises in self-esteem building. “The people criticizing you are not always going to present it in a flowery way,” says Marston. “Just remember: They’re trying to make you better, and they’re often just as interested in your response as they are in the criticism itself.”

That’s true for day-to-day business, as well. You can’t control what your supervisors say, but you can control how you respond. Processing their criticism and showing you comprehend their feedback is a sign of maturity.

A kneejerk, emotional response is not. “The first thing that comes out of your mouth is usually the wrong thing,” says Lipkin. Likewise, don’t use the occasion to be defensive. Instead, take a deep breath—or take a few minutes to gather yourself. She advises younger workers to run through a checklist: What was I thinking when I made that mistake? What was my goal? What got in my way? How would I do it differently now?

Yes, some bosses are irredeemable jerks. Sometimes personality clashes are toxic enough to justify a job switch. But those are still exceptions, not the rule. A certain amount of disagreement is to be expected. “Don’t be afraid of conflict,” says Lipkin. “When you’re uncomfortable, there’s often a lesson in the tension.”

If you recognize persistent themes, there’s probably some room for improvement in those areas.


True, many businesses are relying less on central authority and more on individual freedom and consensus. That’s great news for millennials, who value equality and teamwork. The key is to realize that by no means has hierarchy been eradicated. Your workplace is likely to have a vertical command-and-control structure. “For older professionals, titles and places in the hierarchy are hard-earned,” says Marston. So ignore the food chain at your own peril.

The primary rule of a hierarchy? Know your place within it. For example, keep to the company’s timetable, not your own. If you work remotely, be mindful that flying solo poses special problems for your supervisors. “Some people work best at 3:00 a.m. on their back porch,” says Armor. “But it’s more difficult for a manager to frame out projects and check in about specific tasks if you’re not at the office, sitting at a desk.”

Make sure you and your boss are on the same schedule. When it’s a choice between your convenience and your manager’s, defer. Second, understand the tendencies of older generations and how they can affect office politics. For instance, the stereotypical baby boomer is intensely competitive and crunched for time, and that can lead to conflict if you approach her in the wrong way. Casually ask to take a project off her hands, and you might appear presumptuous or threatening. Better: “Say, ‘I’m looking for opportunities. Maybe I can take care of some of the lower level stuff and free you up to focus on more important things,’” says Marston.

Also, remember that baby boomers are more wrapped up in their careers than millennials, who tend to place more value on work-life balance. Avoid drawing attention to that generational contrast, which may—fairly or not—call your work ethic into question. A quick tip? Don’t just disappear at the end of the work day, says Marston: “At 5:00, stick your head in your boomer boss’s office and say, ‘I was thinking of leaving—is there anything else I can do?’” Build relationships with older colleagues by honoring their legacy and being curious—about their careers, the company, and the industry.