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Successfully Manage Millennials and Other Generations in the Workplace

Photo by Prostock-studio

This article was based on episode 061 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify, and Stitcher.

The Millennial generation has arrived in the workplace in full force. Some, especially older Millennials of which I’m one, find themselves in positions of authority, leadership, influence and power. Others, especially younger ones, are accepting their first job offers. Regardless of age, the Millennial generation has attracted much attention for their bold behavior, leaving many managers baffled at how to engage and inspire this cohort.

I spoke with Lee Caraher about Millennials and other generations in the workplace. Lee is the CEO of Double Forte PR & Digital Marketing and author of two books: Millennials & Management, based on her experience with failing and then succeeding at retaining Millennials, and The Boomerang Principle: inspire lifetime loyalty from your employees.

Lee shared her take on how to engage Millennials and manage differences within generations to create a healthier workplace for all employees.


According to the Pew Research Center, “Anyone born between 1981 and 1996 (ages 23 to 38 in 2019) is considered a Millennial.”

The Millennial generation grew up with the internet, electronics, and social media. 9/11 was a defining moment. But this within this 15 year span, there are actually three cohorts, each of which has had a unique experience.

  1. The oldest set (those age 31 to 38 in 2019) came into the workforce immediately after 9/11 and unlike their Gen-X counterparts, only know a business world concerned with security.

  2. The middle set (those age 27-31 in 2019) started working between 2008 to 2012 and felt the squeeze of the economic downturn.

  3. The youngest set (those age 22 to 27 in 2019) learned dramatically different from their older counterparts with iPads and other technology in the classroom.


One challenge you may notice when working with Millennials is their distorted expectations around performance and praise. While this is not true of every person of that generation, the academic system in which most Millennials grew up utilized a grading system wholly unlike that of the business sector, creating unrealistic expectations for many Millennials.

Unlike the previous Gen-Xers, Millennials grade point averages increased due to the proliferation of advanced classes worth 5 points (instead of 4). Doing well in school meant a whole new level of success, but that success was often clearly defined by the professor.

New graduates generally are not used to the ambiguity that comes with a new job. They aren’t comfortable with the idea that work may need to be done again because it wasn’t done correctly or wasn’t done well enough. They may feel insecure when their work isn’t praised or taken aback when you provide direct constructive feedback. This can be especially challenging for those who achieved academic excellence as students only the year or two before.

To counteract these tendencies, onboard every new team member with intention and over-communicate your expectation. This approach works well for Millennials as well as an employee of any generation.



When you implement practices and approaches that help Millennials succeed, everybody thrives. Therefore, consider the following approaches to engage employees of any generation, but especially Millennials.

Set The Stage

When you first hire a new team member, be clear about when and how they should offer feedback. Let them know you expect them to have great ideas about how to improve the processes and increase the quality of work, but that you request for them to follow the existing system first. Then, after the first 30 or 40 days, you welcome a conversation about their ideas for enhancement.

Give Lots of Feedback

The first few months on the job will set the tone for that person’s future work. Continue to over-communicate by providing positive and constructive feedback so the person can learn what’s expected and what success looks like.

Be Crystal Clear on Timelines

When you request a document by Friday, do you mean Friday at 9am or close of business? Their time zone or yours? Students are taught to turn in papers by 11:59:59pm, but most businesses don’t follow that practice. Specify exactly what day, date, time and timezone (if you’re geographically disbursed) to avoid unnecessary frustrations and misunderstandings with timelines.

Lead with Purpose

Millennials in particular are inspired by contributing to a larger purpose. Be sure they understand why their role matters as well as the mission or purpose of the team and organization.

Take time at the beginning of any project to define the project: outline its goals, talk about what success looks like, share how this initiative will impact the organization and who else is counting on your team. Provide the context and offer opportunities for your team members to ask questions and share their ideas.

Outline Everybody’s Roles

Millennials are often referred to as the “me generation,” but in Lee’s experience, they’re incredible team players. The fastest way to demoralize a Millennial is to say they let the team down. Leverage their desire to contribute by defining roles so each person understands who is counting on them and why.

Ask For Ideas

While you may be the ultimate decision-maker, engage the group in generating ideas and offering suggestions. When you solicit input and ideas from your team, you are able to gather insights from those closest to the work, build buy-in and get everyone aligned on the same path.

Get It Out In The Open

It can be awkward to report to someone significantly younger than yourself. If you find yourself in this situation, let your manager know it may be a bit uncomfortable at times given the age difference, but you look forward to learning from them, just as you bring your years of experience to the work.

If you notice a younger manager making a rookie mistake, offer to provide feedback. Speak from your experience about what works and why. If possible, offer to help, for example, by being a sounding board in the future.


Millennials are often criticized for their sense of entitlement. Yet Lee offers a different interpretation. Millennials want the same things that everyone wants in the workplace. The difference is that they openly talk about it, and they talk about it really early. They have come to expect things they've heard their parents and the media talk about.

The conflict is likely more about the contrasting experience of older generations which had to fight for or wait for the privileges that Millennials now take for granted.

At the end of the day, there are managers and new employees of every generation who are great and those who are terrible. Sometimes, it has nothing to do with the age.

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This article was based on episode 061 of The Modern Manager podcast. To hear this episode, and many more like it, you can subscribe to The Modern Manager Podcast on iTunes, Google Play, Spotify and Stitcher. Never miss a worksheet, episode or article: subscribe to Mamie’s newsletter.


Instagram: @leecaraher

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