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Younger Boss? 5 Tips for Surviving and Thriving!

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Younger Boss? 5 Tips for Surviving and Thriving!
We’ve all thought about it at some point in our careers, the situation that many workers fear: a younger boss! Have you experienced it yet? Here’s a reality check from the world of work: guess what’s much more common after 50, older boss or younger boss?

According to Pew Research, as of 2015 Millennials became the largest single generation in the workforce, surpassing Gen X after already having blown by the Baby Boomers in 2013. Coupled with the fact that Americans are staying in the workforce longer than ever, it’s easy to see how many over-50 workers might be reporting to someone born after them.

But fear not! If you manage it correctly, you and your “youthful” manager can develop a mutually beneficial relationship that could boost your career. Really!

Here are five “younger boss” strategies-for-success:

Accept it

I know what you’re thinking, easier said than done right? After all, the reality of having a younger boss feels unnatural. It goes against our preprogrammed association: rank with seniority! The opposite can make us uncomfortable. But like much else, times are changing.

Today we live and work in a new reality. With five generations currently in the workforce, younger bosses are becoming commonplace. So, let’s get comfortable with the idea. You won’t be alone. According to a recent survey, 87% of workers 55 and older are comfortable having a younger boss.

Start off on the right foot

In any boss/subordinate relationship, it’s important to establish a positive rapport from the get-go as it’s all too easy to fall into a self-reinforcing cycle of negativity. This breeds mutual resentment and decreased productivity. Since this is MORE likely with a younger supervisor, make sure you start off (or reset) your professional relationship on the right foot.

Give your boss the benefit of the doubt. Assume they are the right person for the job and that they can handle the responsibility. Recognize that you both probably have age-related insecurities. Remember – the best way to work through issues is to communicate clearly. Talk to each other. Don’t let things fester.

Master your reactions

Have you at some point in your career sat and listened to a supervisor talk about a new policy, project, or assignment, and started subconsciously shaking your head? Don’t worry, we all have (though it’s not something to be proud of). In any professional environment mastering your emotions and outward reactions is important, but your reactions towards your younger boss are even more critical!

You might catch yourself thinking, “this person doesn’t know what they’re doing” or “this project doesn’t make any sense”, but those thoughts shouldn’t be writ large on your face. Be patient, don’t overreact, watch your body language, watch your words, and be outwardly positive. Don’t resist change for no reason, and don’t be obstinate. Ask yourself if your reaction would be any different if your boss was older. And whatever you do, don’t go over their head to speak with a higher-up that’s “a little older”. This is terrible practice in almost all professional instances but it is especially toxic when your immediate boss is younger than you. If you have concerns, find some time to speak with them directly and move forward positively.

Avoid age-based roles and stereotypes

Which description sounds better: “Mary is smart, super reliable, and has an unmatched depth of experience” or “John is a good employee, he’s like our office Dad and is a great person to go to for life advice”? While the second description isn’t all that bad, if you’re a career-focused professional then you’re probably striving for something like the first. Avoid thinking of yourself as an “older employee” or your supervisor as the “younger boss”, and don’t play into these roles with your behavior.

Avoid age-centric comments and topics unless they’re part of a positively framed discussion. Your “war stories” from years of experience are valuable, but frame advice so it doesn’t invalidate how your younger boss or coworkers are doing things. Never start a sentence with “in my day”! Don’t age yourself, or go the other way and try to fit in with the younger crowd. Be yourself, be authentic, and be professional.

Maximize the benefits

While working for a younger boss can be tougher to manage, it can also result in outsize career benefits – for both of you. Compared to a normal manager/subordinate relationship, you’re far more likely to have less similar, and more complementary, skills and experiences. For you, two main areas that these benefits typically occur in are tech-focused skills and networking.

As a general rule, younger people are more comfortable with technology. It takes effort to keep up to date. You may not be the Salesforce or GoToMeeting guru, but take the time to become competent with the tools of your job – and – show a willingness to learn. This is where your younger boss (or coworkers) can help. Learn from them and leverage their skills to enhance your own.

You can also leverage their networks. You may have a larger network (you’ve “been around” longer), but with time it’ll shrink (retirements, obsolescence, illnesses). Your younger boss’s network, though, will be a vibrant resource for you to tap into down the road! Now, that’s a win!

Editor’s Notes: Justin Ridgely is the Founder of Reboot Careers (, a platform built specifically for experienced job seekers. Justin and the team at Reboot Careers believe that while the many new career-focused technology products can be helpful, these tools have been almost solely built for young job seekers. In contrast, Reboot Careers‘ goal is to help us over-50 professionals surmount the many challenges of today’s job market by providing critical career-focused services, tools, and support.

Reboot Careers has launched with a focus on job matching, review, and tracking, but there are big plans for additional features and platform expansion. The company is committed to building out its platform to connect job seekers, career changers, career returners, and semi-retired workers with companies that will hire and value them. If you work at a company that eschews ageism and wants to hire experienced, knowledgeable over-50 professionals, please reach out directly. We are also proud to share that Reboot Careers, headquartered in New York City, is a veteran-owned business.

Justin Ridgely founded Reboot Careers in 2017 after watching his mother struggle to transition to a job she was passionate about and realizing that she was far from the only over-50 job seeker experiencing this problem.  As he says, “Many people over 50 want to make some sort of career change but have trouble figuring out what they want, how to translate what they want into real job openings, and how to succeed in an application process they are out of practice with. And that’s before taking into account ageism and employment practices that fundamentally favor the young. Reboot Careers’ mission is to help over-50 job seekers overcome these challenges and achieve their career goals.”

Prior to founding Reboot Careers, Justin worked in finance both at a startup and as an investment banker focused on mergers and acquisitions.  Earlier in his career, he served as an Army Infantry Officer with the 101st Airborne including a combat tour in Afghanistan.  He holds a BA from Emory and an MBA from the University of Virginia – Darden.

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