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    


  • Paul – As an official member of the “Oldeus Farteous” species, I hear you! Your point #4, I think, is especially important. We all need to learn to understand, merge and leverage the perspectives of all the generations in the workplace. For example, I’m in my 50s and have sold a few engagements helping 40-something sales managers coach 20-something reps in selling to 30-something decision makers. Fascinating discussions! – Todd

  • @ Todd Youngblood: First and foremost, thank you for your comment. Your point is so valid Todd. I think starting from the perspective of knowing that we ALL have to navigate this and then finding ways to help everyone thrive is just smart business to say the least.

    And thank you for the nice mention in your awesome blog today my friend. Very nice of you!

    Thanks again for stopping by to contribute Todd!

    Paul Castain

  • Richie DeMarco

    Paul as always a very interesting and informative post!

  • As usual, Uncle Paul, great post! There are allot of people out there that should read this! In fact, I think I’ll “tweet” it their way! Thanks for always kicking it up a notch!

  • Thank you Uncle Paul. I am not even 40 and I feel old sometimes. I am literally in the middle now, I am not too old yet but I am not with the young anymore. I am extremely thankful for my close relationships with my teenage nieces and nephews (they help me to be somewhat up to date). I would be completely lost with out them.

    This definitely worth sharing.


  • Matthew F.

    I subscribed to your sales tip emails and have truly enjoyed each and every topic. I myself am a member of “Generation Y,” but blend the old and new style sales approach. I also see that you mentioned you were a member of Dale Carnegie. The company I work for, Emo Trans, Inc., has offered to send me to do this training. Where are you located?

  • Some one must have listened to you Paul:

  • Pam

    You are my favorite blogger! I try to make you viral………

  • larry

    umm, this is the same for all “generations” and has always been and always will be. it is the “responsibility” of the youth to “rebel” by doing things different than their elders and it seems the domain of the elders to complain about the youth and say they will ruin the world. nothing new here at all, been happening for 10,000 plus years. was this way in the the 1960’s or the 1920’s (examples that older folks might recall). but if you do what you do with passion, with true conviction, not trying to change people but to inform them of why you feel the way you do then people of all ages will respond and some will still not like/get it, which is fine and you should not change your message thinking that will make them get it.

  • I see folks from all walks of life over the counter of our quick print and enjoy speaking with every generation. I love to engage the older folks to talk about the old days and try to get the younger folks to open up and let me in if just for a minute or two. It’s all good. One thing I find interesting though is there are a lot of Ph. D’s in this town who seem to be embarrassed by that fact , I never miss an opportunity to address a Ph. D as Doctor and if they protest I remind them of how hard they worked for that honor. Dan

  • Great post!

    With Gen Y’s so willing to be completely transparent over the internet, I am curious to see how much this can help or hurt them as they enter the work force. It really hasn’t happened until now that you have an entire generation where the internet is their resume.

  • Bob Van Winter

    Paul, even my barber has the courtesy to lower the mirror while displaying the back of my head so the glare off my dome is not quite so evident but you hit me right between the eyes with my age! Thank you! Very valuable points, I am beginning to get “texts” from my customers. Time to embrace gen Y. Excellent advice.

  • @ Richie (my fellow New Yawka) Thanks!

    @ Nikki: Now that you stopped by, I have this need to admit that some of my Generation Y knowledge may have come from observing their behavior on Beale St. But then again, they were able to observe my behavior too 🙂

    @ Jos: And that’s only the beginning. Thanks for sharing that link.

    @ Pam: You are too kind. I want to take a trip over to Jersey in the next few weeks. We need to get off this virtual stuff and meet for coffee or something!

    @ Larry: How true! And isn’t this what makes it interesting?

    @ “Herb” A completely off topic response. Dude I miss my early days as a pressman in a quick copy shop for exactly the reasons that you referenced. The different types of people, each with a unique story. It was kind of like Cheers but with the smell of ink and a boss who only paid me $14k a year.

    @ Hef: You get a gold star for that one! How true!

    @ Bob Van Winter: Yep. I remember when I started getting texts. I took it like someone said “Your Momma” Might have even had my gun pointed sideways at them too. Now, its just another day in the life.

    And thank you all for taking time out of your busy day to weigh in and contribute such wonderful content.

    All the best!

    Paul Castain

  • Melissa

    ABSOLUTELY INSIGHTFUL. you are and always have been amazing!! i miss you!

  • @ Melissa: OMG! Long time no see my friend and I just saw your Dad a few weeks ago!

    Thank you so much for the kind words and lets catch up one day soon!


  • Paul,

    I like it. As a “cusper” those born closer to the end of X than the peak of Y, I find a lot of value in what you are saying. @BillSledzik did a post about Millennials that took off, he in turn linked to my original professional blog because of the dialogue he and I were creating in his comment section and as a result I have started my own Millennial Focus Blog.

    I love a lot of what you have to say in your post. I have in large part been predicting a HUGE culture clash coming based on the fact that a lot of people from older generations are not willing to make the compromises you did to connect. I always point to the fact that SILO mentality is a decidedly Boomer generation work place effect, which infuriates the more collaborative types in X and the entire Gen Y populations. However some Silos are strong and those who worked hard to build them will not give them up so easily.

    Another blogger commented to me that the older Generations are feeding their guilty conscience of workplace reticence by perpetuating the whole “failure to launch” … as in, I don’t want to give up my job so my child can have one, so I will just let my child stay at home LONGER… I thought it was an interesting point to consider. Anyways, I digress as that is not the point of your blog…

    Keep preaching and teaching people from all generations to work towards the middle… I love your photo to lead of the blog… very appropriate!


  • Paul, this is the only time in history where you have 4 generations working at the same time. Traditional, Boomers, X’er (or latch Key) and the Y generation.

    All 4 have to live togather but they all will be managed different.

    Traditional wants to be heared and wants to give advice, where Boomers want to be a TEAM. X doesn’t know what a team would look like but give them an assignment and back off as they will do it at the last minute, but it will get done.

    The Y’s want to know what is in it for them RIGHT NOW, they want instant gratification. They win points on the games they have played since birth, they have won tropheys while playing soccer while they lost all their games, and the have NO BOX what so ever because if they have a Box they wouldn’t know how to play inside of it.

    Y’s you can show traditional items to, but they want to know how to convert it to technology.

    The iPad is one of those items, and even though it has not made an impact YET on the business end of the industry, it will.

    In the traditional information of print, a Y will want to know all in information they can get on the item via of the internet, they want to get all the comments from their social media groups.

    But the funny thing about a Y’er is before they purchase a meaninful item they want to touch printed material as then and only then does it bring a true emotion to the purchase of this meaningful item.

  • Hi Paul,

    I always enjoy reading your blogs, they’re fun and full of valuable content. I’m a firm believer in “seek first to understant” and it’s all too important to “know your audience”. Whether it be a co-worker, a client or a prospect. Our ability to build, cultivate and grow professional relationships are dependent upon how well we can relate to and understand our peers! The tides are changing and with technology being the most significant driver of business, the change is timely and sorely needed!


  • Todd Spare


    A very timely post for me….I am doing more and more presentation work and to some extent have been “fighting the intrusion of the connected world”……This has helped me understand that I need to be understanding……Thanks

  • Pingback: Outside Perception: Who We Are Defined by Who They Are « TheGenYblogger's Blog()

  • Paul

    There’s a lot to be said for knowing your audience, no matter what generation. Cultural influences run deep and have a vast impact on our ability to connect. It occurs to me that your notes on Gen Y refer to a segment of middle class American culture born after 1980. Meanwhile, hundreds of other cultural sets exist within this generation in other countries and even in our own land! Can we know them all?

    With this in mind, the value of seeking to understand becomes even more powerful. It is the table stakes to conversation with any cultural group – not so much that you DO understand, but the attitude of sincerely caring to understand. Some things we will never understand, or be able to relate to, but if we will open ourselves up to listening we will be far and away ahead of the crowd no matter what the genre – even among their peers.

    What I take away from your post is that you started out presenting and quickly found much greater value in interacting. May we all find ways to engage our audiences and thus reap the rewards of truly connected conversations.

    Don F Perkins

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