After finishing graduate school this past summer, I was fortunate to stumble upon a great job with a commercial furniture manufacturer. After packing up my apartment and moving three hours away I found myself smack dab in the middle of the real world, in a position typically reserved for someone a generation or two my senior. Like all of us, I was chomping at the bit to show my skills, prove myself to the organization and most of all flex my “Gen Y” muscles.  As it turns out, my company is 92 years old, headquartered in a tiny rural town, and still full of 60+ year old senior management (and even older board members!) My attitude, confidence, and affinity for anything digital must remind my co-workers of their children or grandchildren, who are likely “spoiled, inexperienced, poor communicators, and spend too much time on that damn Facebook.”

After eight months on the job, I’ve learned a lot about what it takes to win over your older superiors, and I continue to work at it every day. Talented Gen Y’s should be desired by today’s employers, not shunned or feared because of generational differences.  I believe my experiences will help you shine your Gen Y light in a dark sea of aging Boomer bosses and let you debunk many of their misconceptions about us…


After landing your job, the first obvious hurdle you must overcome in the eyes of management is your lack of experience.  Because most of us actually do lack experience, we must remember to maintain an air of professionalism in everything we do.

  • Dress a little nicer than you have to
  • Keep your hair cut and face shaved (if applicable, of course).
  • Always show up on time
  • Keep your smartphone in your pocket during those long meetings, even if you are only checking work email.

These are the little things that our generation luckily doesn’t get too hung up on, and as a result I was a bit naive about their importance to our older peers. Ten years from now these things may not matter, but for now I’ve discovered that if you want to win over the old pros, you have to act like an old pro. Emphasis on old.

(One moment while I remove my tie and put on my hat at this airport bar.)


The next preconceived notion about us, which all too often holds true, is that we are bad communicators. How can this be? We invented Facebook.  And twitter.  And texting.  Exactly. While our digital communication skills are virtually flawless, many of us struggle with interpersonal, face to face communication. Our increase in digital communication has taken its toll by decreasing our amount of face to face and telephone communication.  While this is one of Gen Y’s worst attributes, the big winners will be those of us who can master both digital and interpersonal communication.

  • Speak up in those big meetings to become comfortable speaking in front of groups.
  • Talk to random people in the airport, or engage conversation with random co-workers.
  • Get in the habit of calling people rather than text or email, when appropriate.

All of these things will help build confidence and keep you from having a reputation of being unapproachable.

(Excuse me while I send a few texts, check my Twitter and email my mother.)


Finally, something everyone knows we do well!  Technology is the one area where the younger generation will always dominate, and I’m not looking forward to the next generation taking that crown from us.  But for now, your technology expertise can help you stand out and win over your boss. That is, if you approach it the right way.  First you must ask yourself “what do employers our parents’ age fear about technology?” They fear people knowing too much about their personal lives via Facebook, they fear not understanding all the ”weird slang we use in text messages” (Do you all text in slang? Neither do I.) They fear the unknown world that is Twitter, and most of all they fear the time their employees “waste” on all the above. Your job is to show your superiors how your tech knowledge can help the company.

  • Offer to set up and manage the company’s social networking accounts.
  • Respond quickly to every email via your smartphone.
  • Keep your Facebook clean! Become the go-to guy (or girl) for all of your departments tech needs.
  • Finally, one that has worked for me: befriend the I.T. guy. No matter what your role, he likely knows more about technology than you would ever care to. People trust him.  Management trusts him. If he respects you and your technological savvy, he trusts you and you’re in.

Now you can use your status as a digital native to gain the trust of your office full of digital immigrants. (I’m still searching for an email I deleted…wait we use Outlook instead of Gmail? It’s actually gone forever? Oops…)


Finally, try to have some patience. Like many of us, when I took this job I was wondering how long it would be before I moved on to another job.  If not a new job I was at least hoping for a raise or change of title.  I had only been there a week! We all know Gen Y’s change jobs a lot.  We are loyal to people but not organizations, we saw how the latter worked out for our parents.   Our parents told us all we were awesome, and most of us believe it (Am I wrong?) It is ingrained in our minds to be the best, and we can’t wait to get there.  But when it comes to your first job:

  • Just slow down
  • Learn all you can
  • At least act like you’re paying your dues.

Your Gen Y advantages will get you where you want to be much quicker than you think.  Outside the office, however, we should all be marketing ourselves, branding ourselves, and networking our way to the next opportunity. Just be sure your company knows you’re happy to be there and in for the long haul. Besides, long haul can mean different things to different people, right?

We Gen Y’s are taking the workplace by storm, but we are still working for older bosses with the 9-5 mentality who thinks hash tags are only for drug dealers. Each of us has the skills to be successful in any job we choose, but it all depends on our plan of attack.  If you can mix the right amount of Gen Y talent with a little bit of Baby Boomer charm and professionalism, you have the advantage and you can go far.  I know I’m not there yet, but I’m getting closer every day. What about you?

(After a long day of work here in Denver, my plane is boarding.  With any luck I’ll be in Lexington having a drink with my college buddies before the night is over.  I’ll put the tie back on tomorrow.)