Millennials Working For Boomers: Here’s The Inside Scoop

October 10, 2016

millennials working for Boomers

As a millennial entering the workforce, you might worry about how to get your boss to understand you—to give you a real chance. There are all those stereotypes you have to overcome. It’s easy for millennials working for Boomers to feel overwhelmed or intimidated… or overcompensate to prove their worth.

What if there’s an easier approach?

What if instead of trying to get your “older generation” boss to understand you, you could get inside your boss’ head? As a Boomer who has worked with a lot of Boomer owners, leaders and executives, here’s what we want from you… plus a few insider secrets.

Make me look good
When you do the basics, like show up on time, dress appropriately, and are eager to learn, you make your Boomer boss glad she hired you. Going beyond the basics is even better. When you see a co-worker struggling and you step in to help, you show initiative. When you finish your assignment and have some spare time, you make your boss look good when you ask if there is anything else you can do.

Insider secret: Be careful about making your boss look bad in front of others. For example, when you share a complaint in a company meeting and catch him off guard, you make him look bad—especially if he has a big ego. Instead, share first in private and let him know in advance that you will be addressing it in the meeting. He will see you as a partner looking out for his best interest.

Make it easy to change my mind
Your boss is human. Because you are young, she may have bought into all the hype about millennials instead of looking at you as a real person wanting to learn. You have to make it easy for her to change her mind about you. There is a right way to do this, and a wrong way. The wrong way is complaining about being judged, or life not being fair. Or trying to show you are superior in technology or some other skill.

The right way: Show up as a partner and respect your boss first, if for no other reason than because she is older and has a superior title. It’s not fair to you that she believes the negative stereotypes of millennials working for Boomers. However, she had the same mountain to climb at your age, so respect her seniority even if you are more skilled/knowledgeable in some areas.

Insider secret: Your boss is eager to learn from you, but you need to show that you are a collaborator, not a competitor. The key is to build trust by focusing on the relationship and your position in it.

Engagement is a big deal to bosses. Don’t wait for your boss to figure out “engagement initiatives” to get you interested or involved in your job. Take initiative and show that you are willing to learn, experience, and be engaged on your own. Anticipate areas where you can make small decisions that offer value. For example, when a customer asks a question, don’t act shy or intimidated. Instead, be determined to find the answer quickly. Rather than saying, “I don’t know,” say, “Let me get that answer for you. I’m here to help.” If you feel uncertain about areas of your job, ask for additional training.

Insider secret: Your boss may have never had leadership training, and might not be the best role model. In a perfect world, your boss would make sure you get the right training, but if he or she hasn’t had management development, it won’t happen without your cooperation. Make it a game to manage up, and your boss won’t even know it.

There might be a “generation gap” when it comes to millennials working for Boomers, but there are so many things both cohorts can learn from each other—making the relationship mutually beneficial.

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About The Author

Marlene Chism is an executive educator, consultant, and author of Stop Workplace Drama (Wiley, 2011) and No-Drama Leadership (Bibliomotion, 2015). She works with executives and high-performing leaders who want to transform culture in the workplace. She can be reached at


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