Confessions Of A Generation Y Infiltrator

by Paul Castain on May 5, 2010



I began my mission in the fall of 2006 high atop my Dale Carnegie vantage point in Hauppauge Long Island. My mission was clear, I was to facilitate a training session for a team at MTV. Being 20  years their senior, I hoped to play that off like an older, balder brother. Who knows, maybe I could be that good.

We started our session and I hit them with everything I had. Our dialogue transitioned to full blown lecture on how one properly communicates in the business world.  I placed my soapbox firmly on the floor, climbed up and told them how wrong it was to rely on email so heavily and how text messages were just inexcusable.

Then it happened, a young woman of about 25, respectfully raised her hand and proposed that maybe the problem was not in their use of these venues, but in my generation’s need to try and change them. My cover was now blown and I kind of felt like the old lady in that commercial who says “I’ve fallen and I can’t get up”

I decided from that point on I would embrace more of a “Seek first to understand” mindset and had by far, one of the most awesome discussions I’ve ever had the privilege of facilitating. School was in session for Uncle Paul.

It’s now almost 4 years later and I’m proud to say that I’ve trained and spoken before hundreds of Generation Y’s and I’ve made them a continual study. Truth be told, my main function with the company I work for now is to make this group of young Jedi’s armed and dangerous.

Here’s what I learned:

1)    Houston We Have A Freakin Problem: And the problem is this need to try and change them instead of working with the landscape we’ve been given. Sure I could insist that they must embrace the old ways, or I could enter their world and teach them how to work smarter within those parameters. I see others getting caught up in this endless criticism of this generation ranging from work ethic to attire and all points in between. Please understand something and know this will sound shallow. There’s no money in that discussion for you!

2)    Respect By Virtue of Age or Experience . . . Think again sista! One thing dramatically different about this generation is that they don’t give automatic respect to those with the title, experience or dare I say their elders;  they give it to those who are the contributors to the organization. The ones who earn it!

3)    Because They Grew Up With Technology . . . they love innovation!  Sales Managers: How can you leverage that? How can you include them in the process? It may also mean that at times they are going to be relying too much on the technology. It may even mean that they have more of a clue than you do with regard to technology and you (yes you) are clinging too much to the days of yesteryear. Sales Reps Selling To Generation Y: How can YOU leverage this with your clients?

4)    The True Jedi’s Will Know How To Lead (and kick the proverbial arse) Across Multi Generations: Ladies and gentlemen, our work force is living longer and they are working longer (quite frankly because they have to). We’re already seeing a huge age range from early 20’s to 60+. In our lifetime, we WILL see that number go dramatically beyond 60. That creates a need. A need for people who have a clue in how to manage across multi generations. And there’s no need to wait for that, because the need already exists now.

5)    When Generation Y’s Sell To The Older Folk: When selling to what experts call the “Oldeus Farteous” understand that you might get called out on your age. Whether that situation stresses you or not, you had better prepare for it. Suggestion: Understand that it’s always difficult to address age so instead, you speak about your experience. If that doesn’t work, feel free to break glass in case of emergency and use this bad boy: “Truth be told Ms Customer, is that a rep could have a kazillion years of experience and still fall short where it counts and that’s delivering results. Maybe because of your perception of my age, that gives me added incentive to prove you wrong and deliver those results for you. Either way, it’s a chance. I suspect it’s the same chance someone took on you when you first started your career”

6)    When The Older Folk Sell To Generation Y: Please forgive me for stating the painfully obvious, but Generation Y’s are rapidly moving into leadership/influencing positions.  Armed with that knowledge, we had better learn how they tick, how they communicate and where they like to spend their online time. We need to start showing up in places like Linkedin, Facebook and Twitter. Why? Because at a minimum, it provides you with a free “listening station” and an incredible opportunity to learn. It helps you get and keep your finger on the pulse and most of all (if you learn how to master this space) it will get you noticed!

7)    Generation Y (and this isn’t a criticism) Expects Their Career To Advance Faster Than We Did. Some look at that as a lack of patience. Once again, there’s no money in that type of critique. I see it as a sense of urgency that as a sales professional, if I can help them attain that quicker, I become more valuable. I guess your million dollar question now becomes “In what ways can I help them look like rock stars so they move to that next level quicker?”

8)    They Are Less Confrontational: There’s a lot that I could say to this point but will take it in a much simpler direction. We’ve all heard the old saying that “People like people like themselves” That’s our cue to embrace our inner “its all good”. Take it down a notch or three.

9)    Lectures and “When I was your age” rants: Don’t go there. I’ve been that guy too many times and it just doesn’t fly.

10) They are socially conscious and “green”. To that end, you need to be prepared to be questioned by this generation on your company’s involvement or position on green initiatives.

My amazing revelation: Once I demonstrated my willingness to embrace and understand their generation, not only was I accepted, they considered me a resource to understand my generation.

And that my friends is where we really begin to progress as an organization . . . that wonderful moment when we seek to understand, celebrate and leverage our differences!

To check out my ridiculously cool Linkedin group click on the rock star    


To get free, lethal sales tips click on the Jedi    


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