11 Surefire Ways to Impress Your Next Millennial Boss

millennial bossGet ready… the Millennial boss might have a much different approach to management. Here’s how to impress them, every time…

In today’s workforce, Millennials are no considered the young kids on the block. In fact, the early Millennials ‒ those born in the early 80’s ‒ are now (gulp!) can see their 40 year-old birthdays right around the corner.

With age and experience not comes not only kids and a mortgage, but new priorities and career goals. And one of the biggest aspirations of today’s Gen Yers? Leadership roles. Of course, a Millennial might lead quite differently than their Gen X and Boomer predecessors; what has worked to impress an older boss may no longer work for a Gen Y boss. With that in mind, we asked members of the Young Entrepreneur Council (YEC) this question:

What is the best way to get into the good graces of a Millennial boss?

Read along, and then put this high-quality advice ‒ much of which comes from people that are Millennial bosses themselves ‒ to work…


 1. Give Them Your Trust and Respect

Respect is important with any boss, but especially so with a young millennial boss. It’s important that they know they have your respect so you can collaborate efficiently. You don’t want to risk them ignoring your ideas in their quest to prove themselves. Show that you trust them, or work hard to develop that trust. In return, they will trust you as well.

David Ehrenberg, Early Growth Financial Services

2. Look at the Bigger Picture

There is nothing like working with someone who really knows what they are doing beyond just the interview process. They aren’t just concerned with the task they are assigned; they see things through because they are able to view the bigger picture. Want to look good in front of your boss? Show you actually care about the company and its goals beyond the tasks and the role you are assigned.

Sweta Patel, Silicon Valley Startup Marketing

3. Do Good Work

Millennials care about being judged by the quality of their work product rather than their ability to navigate bureaucratic environments. That means Millennial bosses often care more about employees producing great work rather than how they produced that work. Did they work from home? From an island? From a bar? Who cares, as long as the work is good. Get into good graces by doing good work.

Adam Mendler, The Veloz Group

4. Understand Their Communication Preferences

Communicate in a way that your boss doesn’t appreciate. For example, don’t leave your millennial boss a voicemail if they never check it. And don’t leave communication to chance. Find out how your boss likes to communicate then speak their language. Whether it’s by email, text message or by instant messaging, you’ll be able to form a better connection with them by doing it their way.

– John Turner, SeedProd LLC

5. Be Able to Find the Solution Yourself

What I value most in my team members is the ability to figure out solutions. Use Google, or YouTube tutorials, or StackOverflow, or any of the millions of resources out there to self-learn in real-time. Don’t ask me how to do things; I’m probably not an expert and I don’t want to become a bottleneck. If I hired you, it’s because I trust you to take initiative and make good things happen.

Leanne Beesley, Coworker.com

6. Take Initiative

Millennial bosses and managers like employees who are proactive. If you’re in between projects or have extra time, take a moment to determine what challenges your organization faces. Then formulate ideas that can help address the issues at hand. Once you take that initiative to the benefit your company or team members, you are bound to be in the good books with your Millennial boss.

Derek Robinson, Top Notch Dezigns

7. Be Your Authentic Self

Increasingly in today’s workforce, authenticity is more important than any other single attribute. Be honest about what you need and how you can help, be willing to show up and do the work, and be solutions-oriented. Remember, millennials are known to sacrifice pay to be involved in something they’re passionate about. Show that you share that passion, and impress your Millennial boss.

Nicole Smartt Serres, Star Staffing

8. Get to Know Them as People

Millennials, and by extension Millennial bosses, tend to share more about their personal lives online than bosses in the past. While following your boss on social media remains questionable, it’s OK to research them a bit to find common ground. If you have shared interests or hobbies, those topics can make great conversation starters. Your millennial boss will most likely appreciate your interest!

Shu Saito, Godai Soaps

9. Find Out What They Want and Expect from You

Being on the upper end of the millennial generation, I have found the best way that anyone can get into the good graces of a Millennial boss is trying to understand them. In other words, don’t listen to stereotypes; instead, evaluate the person individually. To do that, first find out what they want and what they expect. Then set out to  learn how you most effectively collaborate with them.

Kristin Kimberly Marquet, Creative Development Agency, LLC

10. Consistently Bring Value to the Table

Most people talk about culture fit in regards to getting into good graces with Millennials. I think fewer people talk about the cold hard truth of results. Millennials are adaptable to change; they consistently look for the most effective and convenient option. Just make sure you, and also your work, is the most effective and convenient option for your boss. Then focus on results, not actions.

– James Guldan, Vision Tech Team

11. Don’t Underestimate Divergent Thinking

Be yourself, read the room, and pay attention to culture, no matter who you work for. That’s not to say you shouldn’t show a concerted effort to adopt to new technologies, say, if your boss is particularly tech savvy.  But they hired you for a reason and for who you are now. So don’t forget who you are or underestimate the need for divergent thinking.

Sam Saxton, Paragon Stairs



These answers are provided by Young Entrepreneur Council (YEC), an invite-only organization comprised of the world’s most promising young entrepreneurs. YEC has also launched BusinessCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.



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