Being a Millennial Supervising a Boomer

by Melanie

It was 2007, right before the recession hit. I was 22 when I got hired to work at a nonprofit as a program coordinator. It was my first big break after college. I had been looking for full-time work, and juggling three jobs for months prior so I was ecstatic to get a job in a field related to my degree, working with passionate and enthusiastic people.

Being my first real career job, I had a huge learning curve. I learned how to manage budgets, write grants, coordinate after-school programs, and most importantly how to supervise employees. I had some management experience while in college, but now at 22 I was managing actual adults, not just students. The majority of my employees were older than me, something that I was well aware of when I started the position. At 22, I was pretty mature and had some decent work experience under my belt. I was at the right place, at the right time, and most importantly in the fresh-out-of-school pay bracket.

As the program coordinator, I managed 7 teachers. In the three years I worked there, I got promoted to manager, then director. As we grew the program, I managed up to 20 staff and volunteers. It was a magnificent challenge, and the proudest part of my work history.

I consider myself a people person, and someone who genuinely likes to engage with others. Building a relationship of mutual respect and trust was really important to me — to run an effective program, I needed people to feel comfortable around me to express their concerns. I set the tone for open communication, with an angle of respect and admiration for their craft. To me, a happy, well-organized staff is the best way to serve your mission.

There was one issue though — one of the teachers was an older boomer who had a clear disdain for me. I was 22, and he was 60. I was technically his boss. I say technically because it was more complicated than that. Although I was hired to manage the program and supervise teachers, the boomer in question had also donated a large sum of money that was essentially paying my salary. Talk about work place politics!

Suffice it to say he had a hard time coming to terms with me as his supervisor.

As a supervisor, I have a pretty relaxed, easy-going attitude. As long as people are doing their jobs, doing it well, and serving the mission, I am fairly hands-off.  There is a time and place for being hands on, and I try to create an environment and work relationship on the front end, to avoid issues later on.

I made my respect very clear to the boomer from day one. He had the wealth of experience (and money) to take the program to the next level, and his commitment was unparalleled. However, we didn’t see eye to eye on several issues and it created a difficult working environment. His vision for the program wasn’t what was best for the organization, which caused friction among us.

I realized there was a huge generation gap between us, and we weren’t speaking the same language. We just couldn’t get on the same page. I think he thought I was a young, dumb, twenty-two year old (I do believe ageism works both ways), and he probably thought I didn’t respect him and his tenure.

As a millennial supervising a boomer, here is what helped me/things I learned:

Creating a Culture of Respect

As a supervisor, the culture and environment starts with you. Creating a culture of respect in the workplace helps facilitate open communication. Once you make it clear you respect the other person, should there be differences, you can always go back to the respect. You are entitled to contrasting opinions, but the respect must be maintained.

Understanding Different Communication Styles

Millennials can often talk in a more casual manner than boomers. Be clear, and careful that your casual style isn’t being misconstrued as unprofessional. In addition, it’s important to understand how others would prefer to be communicated with. In this case, it was not via email or text, it was by phone or in person.

Lots of Changes May Seem Threatening

I was hired for my position during a time of transition for the program. Things were shifting and I got hired on quickly. A lot of changed occurred administratively, and I had a lot of work to build things up. Sometimes rapid change can seem like a threat to your boomer counterparts. I felt like the employee in my case thought I was out to rule the roost and overthrow his vision and all of his hard work. Through continued communication, and discussing our shared vision for the program we were able to overcome some of these fears.

You Will Have to Prove Yourself and Deflect Assumptions

For some silly reason, the boomer thought that I was entitled, privileged, and made a lot of money. While it may have seemed like I just fell into a managerial position, I worked hard all throughout college, and struggled for months post-college, to find my career calling. He also assumed I made a ton of money. I started out making $30k as a coordinator, in Los Angeles. I was essentially getting paid an entry-level salary, for a more advanced job. He didn’t know my struggles and didn’t care to. To overcome assumptions about you and your whole generation, you have to work hard, and be innovative. Keep them on their toes. Come up with new ideas. Challenge their assumptions.

Learn from Their Wisdom

If you are working with boomers, they have been around a while. They have stories to tell, and histories to uncover. Find them and learn from their wisdom. While you learn from their experience, test out new ideas.

Make It About the Mission

I say mission because I have a nonprofit background, but you can replace this with ethos, or the heart of the work. When personalities or egos get in the way, remember why you are there. What do you want to accomplish? Is it for the kids? To make a better world? To increase sales? Whatever the reason, find your common ground and focus on that.

Are you a Millennial who has supervised or worked alongside a Boomer? Or vice verse? What has been your experience?

Melanie
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20 comments

Shoeaholicnomore March 12, 2014 - 2:10 pm

That sounds like a tough position to be in! Glad you found some solutions to the issues presented. Great advice for those who are graduating from college and stepping into a mangerial role.

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deardebt March 12, 2014 - 2:30 pm

Yeah it was, but it was a great learning experience. I got so much out of my first job.

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Alicia March 12, 2014 - 3:03 pm

I’m doing that right now. I’m 28, she’s 52. Honestly, we get along great and because it is a small business it’s a bit more of a comradery relationship than hierarchy. That being said we both know how it plays out if we need to fall into the more traditional roles.

I respect her 20+ years of experience, and she is always willing to give input. She doesn’t try to undermine me “because she is older”. I also don’t try to pull anything like “well, I’m the boss!” Honestly, I thought it would be way more difficult than it has been. As of now we haven’t had any issues.

But I do recognize it can be difficult being the “young whipper-snap” trying to manage another generation.

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deardebt March 14, 2014 - 5:25 am

I love having a camaraderie relationship too. I had that with most of my teachers, but couldn’t successfully achieve it with this guy. I never pulled anything like “I’m the boss” either. Not good form, but you do have to have boundaries sometimes, too.

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Alicia @ Financial Diffraction March 14, 2014 - 10:22 pm

Oh good god, you know what is funny… I meant to type camaraderie relationship, but I typed out that goop that was “comradely”. Thankfully it also makes sense because “we are like comrades” also works.

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deardebt March 14, 2014 - 11:10 pm

Haha no worries. I didn’t even know how to spell the word — spell check told me!

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Morgaine March 12, 2014 - 6:37 pm

I’ve never been in a supervisorial position but I have trained people older than me and you can certainly see how somethings have been engrained over the years and it sometimes can be hard to learn new things or see things from a different perspective. Respect is definitely the key.

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deardebt March 14, 2014 - 5:21 am

I agree, it can be hard to teach a dog new tricks. I feel myself getting that way too as I get older and I have to remind myself to be open and flexible — there is still so much to learn and I never want to be rigid, or think I’m too old to learn something.

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Mo' Money Mo' Houses March 12, 2014 - 11:18 pm

Great post! I’ve always worked with older generations, and so far I’ve never had big issues. I do agree that ageism works both ways, and in my first job I really had to prove myself to be taken seriously. I was 23 at the time but I look really young for my age (still do, I’m 27 and people think I’m fresh out of college) so I needed to show that I could take on big responsibilities and get the job done.

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deardebt March 14, 2014 - 5:18 am

It feels like a lot of pressure to prove yourself when you get your first career job out of college. But you learn so much. Glad you haven’t had any issues.

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Mr Ikonz @ Project Ikonz March 13, 2014 - 12:18 am

I’m not a millennial, but I am quite young in a much older environment.
I think your tips are very valid, it is important to give credit to the experience of someone older and wiser, giving them an opportunity to shine, even if you’re their superviser.

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deardebt March 14, 2014 - 5:43 am

Thank you! The learning can go both ways and is so vibrant when it’s done like that!

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Sarah March 13, 2014 - 1:31 am

Yes, I must say that I had a negative experience working with a millenial. As someone of “boomer” age, I work here and there as a substitute teacher now. I worked in the AM for a young junior high math teacher (a planned half day assignment). She was in the building at a meeting and called to ask if I could work in the PM for her also so that she could leave early for the airport and a weekend trip to Chicago. I agreed. The forecast said heavy snow that afternoon. Her class was unruly. Within five minutes, I had changed my mind and phoned her to say I too wanted to get home because of the snow. She consented, and I went home.

Imagine my surprise when I received a call that she had placed a complaint about me with the district! They called ME because they could not figure out how this could happen. Naturally, I felt it was vindictive and explained it all. Of course, the complaint was removed. They know I am a trustworthy teacher. Entitlement? Immaturity? All I know is that I have worked my entire life and the first complaint I have ever received was from this young woman.

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deardebt March 14, 2014 - 5:14 am

That’s such a shame! It sounds like an awful thing and something that could have been solved with direct communication. I am sorry this happened to you. It’s hard to work your whole life and then have something like this come out of the blue.

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Ryan @ Impersonal Finance March 13, 2014 - 5:09 pm

That’s solid advice Melanie. I manage a handful of people, and while we are mostly in the same age bracket, there are a few older ones. I’ve really learned just treating them with respect, but also still working to prove yourself are two things that go a long way. We might not always see eye to eye, but if they know you have the knowledge to handle the position, the respect should hopefully follow. I definitely do think ageism works both ways, though.

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deardebt March 14, 2014 - 5:09 am

Yes! I think working together, being respectful, and learning from each other is key. Ageism works in both ways, and it’s sad. Our young need mentors, and our elders need to be cared for and respected.

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Aja McClanahan March 14, 2014 - 3:44 pm

I own a database consulting firm and work with a few boomers as sub contractors. Its weird because some are my mom’s age or a little younger. Being in a position of “authority” feels strange. I will say that I don’t have to give much direction b/c many of them are self starters. Honestly I’ve had so much success with using them as consultants because the work ethic and level of professionalism is there. Of course it’s a generalization, but I enjoy the competence and wisdom they tend to bring to the table.

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Stefanie @ The Broke and Beautiful Life March 14, 2014 - 8:05 pm

Ageism definitely works both ways. Lots of assumptions made about millennials can be hard to overcome.

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cot son March 25, 2014 - 10:55 am

I always love a challenge.

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deardebt March 26, 2014 - 3:16 am

It motivates you that is for sure!

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