Managing Generational Differences at Work, A Millennial's Perspective

Photo by  from  Pexels

Photo by from Pexels

Being in the corporate world as a consult for a number of years I, like all Millennials in a similar position, was exposed to the generational disconnect and value mismatch between the Baby Boomer executives, Gen-X managers, and my peers in the Millennial generation. The amount of frustration I felt every time upper management mentioned the “entitlement of my generation” and the lack of weight my opinion held in their eyes caused a lot of disdain, that was until I took a step back and wondered why. I thought about who these people were, and what my relationships were like with others in those generations outside of the workplace, and realized things about each of them that put me on their side, and in turn, them on mine. So if you are struggling with older managers, read on and try to use some of the tactics I learned after a lot of trial and error.

Baby Boomers

Baby boomers are a tough breed, they worked hard for what they have because they weren’t given much (if anything) to start their lives. They are also, for the most part, our parents. They are the ones that demanded we all get a trophy, not be left out, and receive every advantage possible. The Baby Boomers are the reason many of us Millennials are the way we are, entitlement and all. This also means that we are seen as their kids, always in need of help, lazy, and in some cases, being directly compared to their children, which can cause a great deal of animosity.

If you find yourself working for a tougher-than-usual Baby Boomer, chances are they have an internal thought similar to “I’ve already helped out my children to a dizzying and expensive extent, so helping out or giving attention to another entitled little shit is not something I want to go through again.” Their kids got away with everything, and they refuse to let that happen in their work life, so they are hard on you, they are short, and tend to be less than helpful. The key to getting in with the Baby Boomers is to show that you can, and will, work hard for them. Effort, and sometimes even just the intention of effort is paramount here. What you’re doing doesn’t even have to be completely right, as long as you show them you are working hard and long to benefit them, they’ll start to lighten up and give you some leeway.

The other easy way to earn the respect of Baby Boomers is looking the part. They grew up having to wear suits and getting dressed up nicely for work for the last 30 years, and then we came in and said: “I’m not doing that.” What little shits we really are. Even while many Baby Boomers have embraced the new business casual office life, the effort the younger generation puts in (or doesn’t put in) to look good at work doesn’t go unnoticed. The way you dress shows how much you care and can trigger a “well they at least put in the effort to look nice and presentable for me today, their head must be in the right place.” In short, show the Baby Boomers you are working hard, stay in the office longer, and look nice when you meet with them; these are the old pillars office culture used to be built on and that’s what they understand and value. Do this and gain favor at the top.


Gen-Xers typically fall into two buckets, the big brother or sister to their Millennial coworkers, or scared egomaniacs that hate us. Gen-Xers are smaller in number and because of this, are the only generation in the workplace that has never and will never be the dominant demographic within the corporate ecosystem. This means their time at the top will likely be short lived. Baby Boomers dominated the workforce before them, occupying positions from lower management all the way to executives for the past 20 years, and now the Millennials are coming up behind them quickly, many of us getting placed in higher positions to help the current Baby Boomer executives manage and understand the largest segment of their workforce. This has forced Gen-X to either ride the wave and buddy up to the incoming generation to make sure they don’t get passed over and left behind, or resent everything and try to claw their way higher.

To become the favorite sibling of those who are riding the wave, I find that sharing music and listening to copious amounts of Third Eye Blind and Eagle Eye Cherry are great ways to connect. Beyond that, doing good, efficient work is key. They don’t care about the long hours as much as the Baby Boomers do, they just want good, effective, efficient work to be done so you can all go get a beer and hang out before bed.

On the flip side, the resenting Gen-Xer needs a bit more finessing. Remember, you are coming after them with blazing speed in their eyes. The big idea to push when working with a begrudging X manager is that you want your team to rise together. Your goal is to push them higher, and in turn, hope you’ll be good enough for them to bring you with them. These people are ego monsters and their egos must be fed with the destruction of yours. You don’t have to believe it or permanently hitch your cart to these scared Xers, but as long as you’re working with them, that's what they need to believe your intention is. You’ll know they trust you when they stop tutoring you about work-related issues after 7pm and start asking questions about your personal life. So share your music, especially from the 90s, do efficient work, and when necessary, feed their ego.

What tips and tricks have you used in managing your managers of other generations? Let us know in a comment below!