Christin Myrick Shepherd

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Bridging the Gap Between Boomers and Millennials


Alex is a curly haired, dark eyed Millennial with a contagious smile. Alex works hard, shows up on time, is reliable, and an overall exemplary employee. She is also losing her passion. Alex has simple, technologically savvy ideas that could revolutionize her organization, but time and again she gets push back from her Baby Boomer bosses. The back and forth is exhausting for everyone and Alex engages less and less with her work, ideas, and company.

Does Alex’s story sound familiar? Maybe someone like Alex works for you. Maybe you are Alex. Either way, you know the gap between Millennials and Boomers that I’m talking about. The gap we need to bridge because if we keep doing what we’re doing, we’re going to keep getting what we’re getting: a disengaged, dispassionate younger workforce and an older workforce that feels devalued.

This dilemma won’t resolve on its own accord anytime soon. As of 2015, the workforce was roughly split into thirds between:

  • Baby Boomers (born 1946-1964),
  • Generation X (born 1965-1980), and
  • Millennials (born 1981-1997). 


In the years to come, many Boomers don’t anticipate leaving the workforce at all.  Research by AARP found that almost half of employees between ages 45 to 70 see themselves working until the age of 70 or older. There could be a number of contributing factors to this phenomenon including wanting to contribute to society, but loss of life savings in the economic crash (or no retirement savings at all) is most likely chief among them.

This means that the Boomers at the top levels of management will continue to stay there while Gen Xers and Millennials are unable to move up the chain of command. Like Alex, most Millennials are currently (and will continue to be) unable to enact significant change in their organization and they become more and more disengaged with their work. The average American worker stays at their job for an average of 4.4 years (Bureau of Labor Statistics), but Millennials are expected to stay three years or less. Alex made it just under five.

This job hopping can be beneficial for employers (eclectic knowledge base and utilizing other fields of technology, for example), but can be disastrous for transferring institutional knowledge. The question many employers are asking is: how do we get people to stay? How do we engage them? And, how do we create connection and collaboration between the generations?

Luckily, Google (which has repeatedly been named the number one place to work) has already answered these questions for us. Google performed a study called Project Aristotle that analyzed what made the perfect team. What made people happy? Why did they stick around? Project Aristotle uncovered that a team was efficient and effective not because of the right personality mix, geographic closeness, hours worked, or friendship among team members. It wasn’t even because of good management, although, heaven knows that plays a role. The most important factor for a happy and sustainable team is psychological safety. Psychological safety means that every person (from the highest to lowest ranking) felt that: a) that there was adequate opportunity to speak their opinion and (maybe more importantly), b) that they were genuinely listened to, feeling that their peer group heard them and assimilated their needs into the whole.

In a multi-generational work environment, it is psychological safety that will cultivate change in a manner that is enlivening to Baby Boomers and Millennials alike. It will bridge the gap, but both ends of this generational bridge will have to do their part. 


4 Ways Boomers Can Create Psychological Safety

1)   Transfer Wisdom and Knowledge: For the first time in history, the generation entering the work force will have more advanced technology skills than those leaving it. Millennials can build a website, link personal photos, and share the whole thing on social media before you can say “What’s SnapChat?” Millennials have skills. What they don’t have is direction. As a Baby Boomer with decades of experience, you can help them find their way.

Seventy-five percent of Millennials want a mentor. They are starving for someone to teach, challenge, and help them grow. Someone to help them not only understand how to do the job, but also why they do it. Millennials crave greater impact and social change. Helping them discover their own ‘why’ will result in higher levels of engagement.  

Write a list of the most significant lessons you learned throughout your career and mentor your younger counter parts on their finer points. For example, if you learned that real connection is vital to client relationships, teach your mentee how to build those relationships and tell them why it’s so important. Convey how this piece of the puzzle is so important to what you do. Infuse every ‘what’ with a deeper ‘why’.

2)   Trust Them to Get the Job Done in Their Own Way:  Some people think the Millennials are lazy and full of themselves but, according to a study by Michigan State University, recent high school graduates are no more egocentric or individualistic compared to other generations. Millennials aren’t lazy, they just do things different. In engineering, for example, we create detailed and complex design drawings. What used to take a draft-person two or three days, now, thanks to advances in technology, can be compiled and rendered in 3D in a matter of hours. Just because a Millennial does something different doesn’t mean they’re doing it wrong. Will it look exactly like how you would do it? No. Will your Millennial underlings learn from the process? Absolutely. You might be surprised how humble they are and how creative they can be when you give them a little room to spread their wings.

3)   Let Them Fail: Millennials work hard when they have a ‘why’ they believe in. Whether that why is supporting your work load, building viable habitat, or cultivating people skills. They want to be challenged. Millennials aren’t really old enough to have failed spectacularly and, therefore, don’t completely know their limitations. Sure, they’ve gotten bad grades, been grounded, didn’t make try outs for the Basketball team, or wrecked a car. But that spectacular, free-fall, I-gave-my-whole-heart-to-this-and-I-will-be-devastated-if-it-doesn’t-work kind of failure? Not so much. Give them responsibility. They can’t care about something that isn’t theirs. Let them try. Let them fail or succeed, but let it be theirs. Be there for them all along the way (see number one and two again). They’ll learn a ton in the process.

4)   Let Go: This will, perhaps, be the most challenging request, but I cannot stress it enough. Google’s Project Aristotle was born from another study called Project Oxygen which analyzed what made the best manager. It turns out, the most effective managers allow the person closest to the problem to solve the problem. So, let others solve the problem. When you embark on a task or project, ask yourself if someone else could do it and then let them. Like water droplets filling a pool, it will take time. Be patient. Be kind.

Let go a little bit and trust. You will not lose your job or become irrelevant. You will create a self-sufficient and self-motivating team that relies on your wisdom, expertise, and guidance. If that isn’t an excellent legacy to leave, I don’t know what is!


Four Ways Millennials Can Create Psychological Safety

1)   Stay Awake: There’s a beautiful poem by Rumi that says, “The breezes at dawn have secrets to tell you, do not go back to sleep. You must ask for what you really want. Do not go back to sleep.” The world needs your generation, the secrets that you gather from the breezes at dawn. It needs your vitality and ideas, your passion for social and environmental awareness, your global perspective, and your innovation. In order to stay awake, you must ask for what you really want. Get crystal clear on what your heart desires: for yourself, but also for the world we live in and then ask for it.  You will get turned down. People will think you are crazy. People will tell you it can’t be done, it’s never been done, and never will be done. Ask anyway. Listen to the wisdom of your heart and do not go back to sleep.

2)   Boil The Frog: It is important to know that just because you ask for what you want, doesn’t mean it will be given to you right away. You have to give people time to adjust to change, especially Baby Boomers. It’s like boiling a frog. You don’t boil water and toss the frog right in because it would jump right out again. To boil a frog, you place it comfortably in lukewarm water and slowly turn up the heat (I apologize, my mother is from the south and I grew up with these kinds of slightly disturbing metaphors). For you and your brilliant, multi-channeled, instantaneous Millennial mind, the change needed is simple. It’s so easy, it’s right there! Remember, however, that your idea of a small change (however efficient, money saving, or socially beneficial it may be) is going to look insurmountable for most of your Boomer higher-ups.

Take small steps and convey your message in terms of benefits to everyone. If you want to work from home, explain how your efficiency is improved and benefits the team. Then prove it. If you want to implement some new software, see if you can do a test trial and then prove that your technology works. People need to see the change with their own eyes and they need time to adjust. Don’t invalidate any person or process already in place, just present an alternative. Give it a test run. Continue to check in and drop it into conversations. Let people get used to the idea. Change happens slowly, but it does happen. Boil the frog.

3)   Volunteer and Learn:  Volunteer for anything that sounds even remotely interesting. The intern in my engineering department is a 23 year old, shaggy haired, Biology major. One day, he sauntered into my office and said, “I just had a realization,” he said, “I have to tell people what I want to do.” He went on to explain that in college and high school, he was given syllabi and assignments; he was told what to do to learn. In the working world, he had work and tasks to accomplish, but no one told him how to grow. This was such a simple idea and I couldn’t believe that I hadn’t thought of it when he first started!

You have to actively tell people what interests you and volunteer for it. This will help you discover what you enjoy, what skills you want to master, as well as help you discover where your natural talent lays. It will also, mercifully, help prevent burn out while at the same time conveying to your employer that you are capable and care, thus contributing to the ‘prove it’ portion of number two above.

4)   Listen Deeper: At almost every major human transition (birth, graduation, marriage, death) there is a ceremony: a community gathering of some kind that marks the transition as noteworthy and significant. This is true of every major transition in western culture except aging and retirement. In these cases, we devalue and diminish it.

There was a time when human beings were tribal. Our social structure had a place for all generations, but especially for elders. There was a time when we sat around fires, shared stories, and had a means of transitioning folks from one stage of life to the next. We have lost sight of that communal experience and what it means for us as human beings. We are losing a bit of our collective Soul.

We need something more akin to a rite of passage; a congregation of genuine gratitude that supports rather than squashes transition by listening deeply to the Baby Boomers as if they were elders conveying wisdom. You might think your Boomer counterparts have no wisdom, that they are outdated, and irrelevant. Some of them probably are. Some of them have been Rumi’s version of asleep for so long, they cannot remember what it was like to be awake. Listen anyway. Pretend we sit around an ancient fire and the words spoken are sacred because you can listen to what’s beneath them. Be patient. Be kind. Hold compassion and honor your role as steward of sacred transition.


Bridging the gap between Boomers and Millennials is, ultimately, about connection. It’s not a business problem, it’s a human problem. It’s about showing up authentically and trusting the powerful and ancient instincts that have been with us since the dawn of mankind. The meaningful impacts of psychological safety require participation from everyone in order to be realized. Like a bridge being constructed from both sides, Boomers and Millennials alike have to do their part until the gap is closed and we meet in that sweet middle ground of human connection where anything is possible.



What about you? What are some of your tips for a multi-generational work environment? What has worked and what hasn't? Leave your thoughts in the comments below.


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