5 Things Millennials Need to Know About Winning at Work



Each generation molds the business world into its own image.  The Mad Men era reflected the values and ideals of the World War 2 generation: regimentation and corporate hierarchy.

Today’s environment reflects the values and ideals of the Boomer generation: mostly individualism that lapses into selfishness.  The Boomers started gaining power in the 1980s, so it’s not surprising that the decade brought us both the personal computer and “Greed is Good.”

The Boomers created a self-centered management culture currently exemplified by insanely long work hours and a general lack of business ethics (the term wasn’t always an oxymoron.)  To survive, Millennials must navigate and ultimately transcend that culture.

I explain how do this (and not just for Millennials) in my new book “Business Without The Bullsh*t.” Here’s some advice, based on the book, specifically for Millennials who must work with, or inside, Boomer-style companies:

1. Make it about them.

Work is not like school, where you get points for knowing facts and taking tests. Work is all about the financial value that you can provide to the company or, more specifically, to its Boomer executives and investors.

Put another way, when you’re trying to impress somebody in the “ME Generation” (aka the Boomers), you’ve got to make it all about THEM and not about YOU.

Therefore, when you’re job searching and interviewing, position everything you’ve done in terms of the value it provided to the whatever organizations that you’ve worked inside.

In a recent edition of the New York Times, the hiring manager at Google provided the following advice for resume-writers: “Frame your strengths as: ‘I accomplished X, relative to Y, by doing Z.'” Like so:


  • Served as chairman of the student business council.
  • Programmed a student enrollment app.


  • Was elected chairman of student business council as the result of writing an entrepreneur’s startup guide based upon the experience of local business owners.
  • Saved the admissions department hundreds of man-hours by creating an app that allowed students to check on their enrollment status on mobile devices.

2. Once hired, make yourself less replaceable.

As a general rule, companies do not care what you want, need, and expect to be paid.  They base salaries and raises on how much it will cost them to replace you.  Your goal once hired, therefore, to make yourself less replaceable. There are three ways to do this:

  1. Become the only person who understands an essential part of the business.
  2. Become a utility player who can and will do just about anything.
  3. Have so many personal connections with co-workers and customers that your departure would reduce revenue.

To make yourself indispensable, do two of the above.  I’d say do all three, but few people can manage do so so (although I’ve known some who did).

It probably should be emphasized that working on the cheap (or, worse, for free) does not make you less replaceable.  It sets a low value on your contribution, thereby making you seem more replaceable.

Hint: The non-compensated internship was a Boomer invention; prior to them, internships were mostly paid positions.

3. Find a good mentor.

To execute the above strategies, it’s helpful to have a mentor. This needn’t necessarily be a Boomer, but they’re certainly natural candidates if you’re in a Boomer-style company. Here are some pointers:

If your employer has an official mentoring program, ignore it. Assigned mentorships are like arranged marriages; the likelihood of chemistry is almost nil.

Finding a good mentor is mostly a matter of asking somebody who’s knowledgeable for advice and noticing who seems to enjoy giving you that advice.

It also helps to understand why people in general, and Boomers in particular, feel a need to mentor.  Mostly it’s because: 1) they want to prove that their experience is worth teaching somebody else and 2) they want someone to watch their backs.

In other words, mentoring is mostly about them. Not you.  (Are you seeing the pattern here?)

Want a crash course in the ups and downs of both mentoring and being mentored? Rent or stream Up in the Air, Donny Brasco,  and The Devil Wears Prada.

4. Understand what your boss really wants.

Don’t start thinking that you’re being paid just to do your job.  That’s never the case.

Bosses expect more than that. They expect you to keep your promises to them, keep them informed but, above all, make them more successful and make them look good.  This has always been the case, of course, but it’s especially true with Boomer bosses.

As a general rule, smart bosses–regardless of their generation–reciprocate and make it their primary job to make their employees more successful.  Dumb bosses don’t, even when it’s in their own interest.

If you find yourself working for a dumb boss, find another job under a boss who understands the concept of reciprocity.  Meanwhile, continue to make your own boss look good because your current job depends on it.

5. Keep your attitude positive and your options open.

As the Boomers finally retire, the business world must evolve and change to match what’s important to the up-and-coming Millennials.

It’s too soon to say exactly what that will look like, except that it will be different from what we’ve got now. It’s up to you, the Millennials, whether that working world will be better than what we’ve got now.

Meanwhile, though, don’t become cynical or discouraged. If you let yourself descend into a downbeat, negative attitude, you’ll be unhappy wherever you work, regardless of whom you’re working for, or with.

By contrast, if you maintain an upbeat, positive attitude, you’ll not only enjoy where you are right now but also be more open to better opportunities when they come around or when you develop them.

If I were to identify the most important element of remaining optimistic, I’d have to say that it’s gratitude. Feeling gratitude does not mean being so grateful for having a job that you’ll tolerate being treated badly.

However, feeling gratitude does mean appreciating what’s positive about your current work situation, including the challenges, which (trust me) will be many.

Want to make work less stressful? Read Business Without the Bullsh*t.