Five Things I Have Learned As A Millennial Working With Baby Boomers

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I am a millennial and I work almost exclusively with baby boomers. My responsibilities require collaboration with many CEOs and CMOs – high-achieving folks who, as you may imagine, are overwhelmingly high-expectation, climbed-the-ladder Baby Boomers with a well-developed sense of workplace professionalism and appropriateness.

Members of Generation Y operate very differently than baby boomers. Basically, the worlds in which both demographics grew up are vastly different. While boomers generally evidence terrific loyalty to their employers, millennials tend to switch jobs frequently. While paycheck size is a significant (and understandable) professional motivator for many boomers, generation Y has different workplace motivations. Perhaps most notable of all, millennials are the first generation of digital natives – and real-time transparency, connectivity, and technical advances have fundamentally altered how generation Y relates to brands, their employers, and even each other. Because of these differences, there is no shortage of articles, memes, and silly videos that touch upon the frustrating differences that occasionally make it difficult for millennials and boomers to get along in the workplace.

While conceding a bit of a struggle at first, I’ve picked up some incredibly valuable lessons as a millennial whose professional success depends upon straddling both the “digital native” (and often perceptually entitled) world of generation Y and the hierarchical (and often perceptually outdated) world of baby boomers.  Here are my five most valuable lessons that I’ve learned as a millennial “change agent” at work in the land of Baby Boomers:


1) The more things change, the more they stay the same

(Baby Boomer lessons are always relevant)

This may sound stupid at first. Of course baby boomers have valuable words of wisdom thanks to years (more than us, to be sure!) of workplace experience – but I mean this on a deeper level. A big part of the disconnect between millennials and baby boomers seems borne of the fact that millennials are generally boomers’ children. Due to age dynamics alone, there seems to exist a perception that either generation – whichever one you are NOT in – is out of touch with reality and/or somehow less informed.

Over client dinners, hard conversations about organizational change, and informal chats with executive leaders, I have learned to deeply understand that lessons relayed from baby boomers about their careers and even personal lives are always (always, always) relevant. In fact, they are gold and generally must be married to any “New Age” ideas in order to achieve success. Maybe this is the millennial in me (we value mentors), but if you listen to the underlying message and focus less on matters of style, you will be hard-pressed not to find a lesson or takeaway that doesn’t apply to your profession today.

An example: I’m not saying that print media is making a comeback anytime soon (a point that is still difficult to communicate during an allocation of resources conversation), but the want to be represented on credible, trusted media outlets (as print has been traditionally perceived due to its diligent review processes) is still a relevant communications objective.  In today’s Digital Age, the market places similar trust in peer review sites such as TripAdvisor and Yelp.  The medium may change, but the strategy remains the same: The market places great value in testimony from trusted resources.

Instead of rolling my eyes (in my head, of course!) and thinking, “Does this person really think that an article in this print-only magazine is going to be a game-changer for the organization?” I now understand the takeaway is that the organization would benefit from a visible, credible endorsement…regardless of the communication channel. And, in turn, part of my responsibility to the organization is to demonstrate the efficacy of other platforms – web, social media, peer reviews, etc. – to achieve the organization’s objectives.


2) A little respect goes a long way

(How you say something can be more important than what you say)

I am guilty of misunderstanding this. In fact, I am so guilty of acting upon some of the more cliché characteristics of my generation that this “lesson” is one that I’m still working to perfect (even having experienced the benefits when I get it right)! My generation often walks right up to the CEO when there’s something that we’d like to communicate – and I observe this happening with millennials in nearly every organization with which I work. This “ambush” reliably seems to stun the CEO who has lived his/her professional life honoring a very specific hierarchy.

Sample size of one here, but I don’t think that we do this at all to be disrespectful. On the contrary, this seems to happen when we are trying to express a concern or truly want to be helpful. Millennials get mocked a bit because on our youth soccer teams, everyone got the MVP trophy. We are all “friends” with bosses and parents on Facebook. We operate in horizontal – not vertical – structures…and we have been raised to believe that our viewpoints matter equally.

Here’s the lesson: It’s not always what you say to the CEO, but how and when you say it that is most important. Our millennial viewpoints don’t always matter to executive leaders. Actually, this is true in life: not everyone’s viewpoints are always the most important viewpoints to anyone other than the person talking. But, if I do have something to say, I find that it has an infinitely better chance of being heard if I abide by the established workplace protocol. Bursting into the CEO’s office and word vomiting generally doesn’t do justice to the passions of our thoughts. As a millennial, it is to my net benefit to respect the way that baby boomers function.  Abiding by a protocol is not compromising the integrity of our ideas – it is a smart tactic to ensure that our ideas gain the maximum traction in the eyes of leadership.  When it comes to the respect that millennials crave, well, you get what you give.


3) Education is important to boomers

(Even if the market is over-saturated with advanced degrees)

I could write a whole blog post about how interesting this is to me, and I write this as someone with some level of academic pedigree. Certainly, an educated millennial seems more likely to be respected by a baby boomer than a millennial with less educational experience. However, I have experienced this preference in several over-the-top, ridiculous circumstances.

Millennials are over-educated. The market is extremely over-saturated with advanced degrees, and MBAs in particular are a dime-a-dozen insofar as this achievement is increasingly common and may not be at all indicative of one’s professional capabilities. That said, I observe many baby boomers holding millennials to very high educational standards. This lesson is more of an understanding than anything else: advanced degrees matter to this generation (which may be why the children of this generation have so dang many of them). It’s difficult: Though those with professional degrees do generally earn more, data suggest that many advanced degrees are not worth their price tag. However, though it is likely that you won’t make your money back, many baby boomers really value this “checkmark.” The rationale behind this perhaps over-valuation is simple: Boomers  find a level of assurance in academic pedigree, and often rely on one’s academic credentials to defend their trust in your work or counsel.  (“They have a Super-Impressive-Sounding advanced degree from Fill-in-the-Blank-Good-School University, so surely they’re qualified!”)

If you have this card, play it…but also realize that this “card” may matter less to future generations – especially if/when “degree inflation” experiences its inevitable correction.


4) Achieving organizational change is MUCH harder than you think

(Watching Boomers adjust is more helpful than watching Gen Y)

Here’s why: Millennials have a reputation for being fast-paced, preferring nontraditional workplace structures, and being connected, entrepreneurial, and nimble. I’m not saying that it’s easy for us to manage change but – let’s be honest – we’ve been in the workplace for relatively little time, so altering our professional foundations may not be quite as big of a deal as someone with decades of experience. Changing a long established, diverse culture is something very different than building a startup of like-minded millennials. When it comes to leadership skill sets, I have learned that a builder builds. A change-maker, however, must rescue everyone from a burning building, let the whole thing burn down, and then rebuild the whole thing. (Yes, I love bad metaphors.)

I’m not saying that a baby boomer CEO of an established organization is innately more…anything…than a millennial CEO of a startup. What I am saying is that the leadership challenges that these positions face are very different…and I fear that my millennial colleagues and I often approach them as if they are the same.

By far and away the most valuable and informative professional (and even personal) learning moments that I have encountered involve observing baby boomers in leadership roles during times of tremendous change. Very many are moving – and they are doing it thoughtfully. For how much I hear my generation gripe about how “slow moving” and “unwilling to adapt to change” older generations may be, I challenge anyone to observe a baby boomer with decades of wisdom leading his or her entire organization into a new era to NOT truly admit, “Okay…Geez, this is rough.” (And then – in that form of admiration that we have reserved only for such leaders as Master Splinter or Mr. Miyagi – “I hope that one day I will be able to do this…”)

Thankfully, every time in my career that I’ve grown frustrated and thought, “Why is this change so hard?!” I’ve had the opportunity to observe a boomer gnawing away at details, serving as a charismatic leader, and just downright making it happen step-by-step and piece-by-piece.


5) We are much more the same than we are different.

It frequently occurs to me – especially when I am frustrated by a seeming hesitance to adapt to new ways of thinking – that we millennials may be faced with these same challenges down the road. Right now they feel so distant and incomprehensible. “The world turns and I know that.” I hope that 30 or 40 years down the road, we still know that – and that we embrace a new generation of leaders. By then, we, too, may be similarly at our wits’ end by the young whippersnappers infiltrating the workforce that we’ve dominated for the last half a century with new methods of communication and different motivations.

Mostly, I’ve learned this: Yield. Do I think we’re a special generation? Kind of, yes. (Really – what kind of millennial would I be if I said otherwise?!) But what I’ve learned most is that boomers are, too. (Yes, those same symbolic leaders of print media and ceremonial hierarchy.)  I don’t intend to preach, to lecture, or to appease. I simply intend to share my own lessons as a member of that first generation of digital natives that has (in this current moment)  shaken up how we do business, how we create change, and how we pursue dreams.

I’m proud to be a member of generation Y (most of the time), but I’m proud and grateful – and even downright lucky – to be able to work so closely with so many inspiring baby boomer leaders that serve as the lighthouses for millennials. My ships (our ships?) would be directionless without them.

…Did I mention that I have a thing for bad metaphors?

Is this a childhood legend or a boomer leading a nonprofit toward organizational change? I cannot tell anymore (but maybe if I get to be Leonardo, then I don't mind).

Is this a childhood legend or a boomer leading a nonprofit toward organizational change? I cannot tell anymore (but maybe if I get to be Leonardo, then I don’t mind the confusion).

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Posted on by Colleen Dilenschneider in Millennials, Sector Evolution, Trends 8 Comments

About the author

Colleen Dilenschneider

MPA. Chief Market Engagement Officer at IMPACTS Research & Development. Nonprofit marketer, Generation Y museum, zoo & aquarium writer/speaker, web engagement geek, data nerd, marathoner, nomad, herbivore

8 Responses to Five Things I Have Learned As A Millennial Working With Baby Boomers

  1. Joann Ballbach

    I’m a Boomer who supervises Millennials. I have to tell you, I genuinely like your generation. I see the idealism of my youth and it gives me a connection with Millennials I never felt with Xers.

    Our most frequent disconnect is a Boomer thing. If I don’t hear from you, I think you’re happy and everything is fine. I appreciate it when Millennials I supervise tell me first of any problem (especially) or idea.

    And that leads into the “follow the chain of command” idea. Going over my head feels like a vote of no confidence, that I couldn’t be trusted to hear or work on concerns. When I feel like I lose face, it doesn’t make me more supportive of your ideas!

    Thank you for explaining the Millennial outlook on these issues. It’s helpful to both generations!

    • colleendilen

      Thanks for the comment, Joann! I’m glad that the chain of command idea feels accurate to you… As I mentioned, I’ve noticed that breaking the chain seems to happen a lot, unfortunately. I’ll blame it on our eagerness (and hope that we grow out of it). 🙂

  2. Jasper Visser

    Thanks for this insightful post Colleen. I’m never quite sure which generation I am, but I can relate to many of the things you’re saying.

    I’m wondering, as you have international experience, do you think there are differences between North America and – for instance – Europe when it comes to these intergenerational working relations? What can we learn from these?

  3. Chris Loynd

    Great insights Colleen. You know what’s on my coffee mug. I have been examining the digital and generational gulf from my side. I agree we can learn from each other. I especially liked your tip #5, but had to look up who the heck Master Splinter was. (Thankfully you had it conveniently linked.)

    Blogging is time consuming, even for fun, but I’ve managed a couple of posts so far:

    • colleendilen

      Thanks so much, Chris. That Dilbert comic still makes me smile every time I use the mug!

      Thank you, also, for sharing your blog. I’ve bookmarked it and look forward to following along!

  4. Brittany Mazzurco

    Great article, Colleen! I work as a member of the administration team of an opera company, and I experience the “rift” between the Millennials and Baby Boomers everyday.

    Our team is roughly 2/3 Boomers, 1/3 Millennials (myself included). Senior members often joke about the office being “the kids versus the adults.”

    I’d be lying if I said I didn’t get frustrated by the generational rift (especially when you begin to debate the differences in musical taste between generations as well).

    However your article made a lot of great points, and it genuinely opened my mind to the experiences of “the adults” within my team. I’ll be sure to pass along!

    Great advice to help prompt a new mindset for 2015 – Thanks!

  5. Ben

    I’m one of 2 employees in my office who are in our 20s. We value certain things about our older coworkers and are annoyed at others. My millenial coworker and I have never carried cash, and my coworkers, even the one Gen Xer (mid 30s) finds this odd. They collect cash for everything – get well cards for people, flowers, even coffee has a collection jar. I don’t like getting an email saying that everyone needs to bring $5 to so and so by 3 today for something coming up, which means I have to go to the bank to actually get $5. This should be a very petty issue, but now I have to go to the bank over my scheduled lunch break. We millenials value flexibility above all and I really want the ability to take my lunch whenever I want it. I feel burdened by all of these scheduled group activities and the formality of it all. At the same time the place feels more like a family with how they go out of their way to put up decorations that reflect the season or holiday and how they always bring in food to work for everyone. Another major difference is small talk. I’ve never heard so many, “Hard at work or hardly workings?” and other phrases that are just odd to me and kind of funny. I guess this goes along with what the post said about how you say things. To them it’s just polite talk and goofing around, and believe me, I joke, but I think I’m a lot more blunt.

  6. Emily

    I can’t say enough how frustrating it is to work with baby boomers. My boss is a baby boomer and has absolutely 0 respect for me. It doesn’t matter how polite, professional or hard working I am she still thinks I’m this stupid little girl playing in a sand box. I am highly educated and have a lot of professional experience for my age (not as much as them of course!). I came into this job with so much passion and willingness to learn and become a better person and day by day she has beaten me down into a shell of human being. I hate my job now and I am just “making it through”. This is not the person I want to be. Soon I will have my advanced degree and I can get the hell out of this hell hole. They have got to turn things around or this business has another thing coming in the next 10 years.


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