How Can We Bridge the Workplace Generation Gap?

Millennials have a very different way of working than those of us who have not grown up in a digital age. Maneuvering around these differences can be a challenge in the workplace. Keep reading for some tips that will help you bridge the workplace generation gap—from guest blogger Amy Feind Reeves of JobCoachAmy.

Amy Feind Reeves
4-minute read

Millennials are amazing. Having grown up in a digital world they are able to find and quickly digest huge amounts of information, which make them great researchers. They can separate information from noise, which makes them savvy analysts. And they know how to work hard to meet goals. However, managers of millennials are most often frustrated by what they perceive as a lack of ambition in their 20-something employees. So what’s behind the gap and how do we bridge it?

Here’s the root cause: those of us who did not grow up in a digital world are used to doing things completely differently. When we were kids and played games, they were usually ones we invented ourselves with kids in our neighborhood after school. For the most part, we only played games that came out of boxes when it rained, and rarely took lessons outside of school. When we had problems to solve, we had to find the right resource before we found the right answer - sometimes even before we knew the right question to ask. Not a lot was served up in a roadmap the way, for example, a Google search serves one up for you. When we hit the workplace, we were told what to do and we are off and running. 

When Millennials were growing up, the video games they played were already programmed with all the rules. The free time they had was programmed for them with lessons and clubs, pre-planned by their parents without a lot of time hanging around making up things to do. When they hit the workplace, they expected the same level of planning to be done for them. Often they get told what to do and wait for the next steps to arrive or to be explained. What they are used to are the details being available, rather than the details being what they need to make happen.

So Milennials get to the workplace and they sit in their office and worry: “When is my manager going to explain how to do this project?” 

And their managers sit in their office and occasionally it occurs to them: “Why hasn’t that kid come and asked about the project?”

And there it is, the Millennial Gap. So how do we bridge it?


A little structure goes a long way. If you feel like you don’t have a good idea of how your millennial is progressing, presenting this plan can make a big difference.

“If you’re not quite sure how to approach completing what we discussed, sketch out a quick plan in three columns for me: what tasks you think you need to do, what kind of information or support you’ll need to complete it and how long you think it will take. Then we’ll review it and make sure you are on the right track. I can give you some ideas to help you get what you need.”

Simple and effective, this starts a dialogue between you that (1) doesn’t take a long time, (2) establishes a precedent that says your millennial can come to you with questions as long as they are targeted and informed and (3) reinforces that there is accountability to a timeline.


A couple of things to keep in mind:

  • Your boss has made an investment in you by bringing you on and your success or failure in your role is a direct reflection on her or him.
  • You need to play a role in your own success by speaking up in situations where you don’t understand exactly what is expected of you, or you are not sure exactly how to achieve what is being asked of you. However, you need to do so in a way that makes it easy for people to help you.

1. Formally ask someone for a short period of time to review the situation at hand. Add that you are doing this to make sure that you are spending your time adding the most value to the team and / or the organization. Don’t focus on trying to improve your own individual performance.

2. Prepare in advance by being able to speak about the issue cogently, in a way that quickly brings him or her up to speed on the big picture then follows with specifics, for example: “I’ve been asked to identify the demographics of individuals who purchase our toothpaste at big box stores vs. online. However, I cannot find databases that differentiate between the two purchase sites.  Are there other databases available or can I purchase one?” This is very different than approaching a teammate or boss with “You asked me to do this and I can’t because the data is not available.”

  • In general, mistakes are okay. They happen. Misunderstandings are okay, they happen too. However, sitting on mistakes or misunderstandings and trying to cover them up is most definitely not okay. These can end careers. 

The common thread here is communication. Talking about problems that arise in any relationship, personal or professional is not easy, but it is always easier to do it earlier rather than later. 


Amy Feind Reeves is the Founder and CEO of JobCoachAmy, where she leverages her experience as a hiring manager to help new and seasoned professionals find jobs that make them happy. Her corporate practice focuses on managing millennials. Amy has enjoyed successful careers as a commercial banker, global management consultant, entrepreneur, corporate executive, and non-profit executive. Amy graduated cum laude from Wellesley College and earned an MBA at the Tuck School of Dartmouth College. She is on the Board of Directors of The Philanthropy Connection and teaches financial literacy to middle school students for WE FLY.  

Image courtesy of Shutterstock.