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How to Lead Someone Older Than You

I found myself talking about “generational diversity in the workplace” twice during podcasts recently. In response, I’ve had young leaders send a specific question: “How do you lead someone from an older generation who is, well…different from you?” It’s a good question.

Generational diversity in the workplace can be just as challenging as ethnic, economic or gender diversity. But I know great leaders who find a way to bring out the best in every person on their team, regardless of their age—even when that person is older than you.

Leading a Seasoned Veteran

This was one of my earliest tests as a young leader, less than a year out of college. I attempted to both lead and motivate team members, some of which were old enough to be my parents. I felt awkward and out of place; in fact, I even wondered why they were listening to me.

Whenever an older person is being led by a younger person, it can be tricky and perplexing. Gen Xers and Baby Boomers can wonder why they’re following someone with so little experience, age, background, etc. Especially when attempting to transform a culture, there can even be differences in what the culture should look and feel like. Let me offer a few insights I learned as I faced this challenge over the years:

1. Always display humility. Whatever you say, approach the conversation with grace and humility. Admit you’re still learning and even want to learn from them as a more experienced colleague. By acknowledging this, you take the words out of their mouth and leave them believing you may be wiser than your years.

2. Always seek to add value to them. When I first worked for John C. Maxwell, I was in my twenties and knew I needed to do things that would be valuable to him (i.e. saving him time on a project; offering some research on a project). When I did this, he was more apt to listen to a person 14 years younger than he is.

3. Invite them into a conversation with a question. Instead of leaders imposing their own thoughts (even if they are brilliant) why not invite them into a conversation about organizational problems by asking leading questions, ones in which you know you’ll find common ground? In fact, ask a lot of questions that will get them moving in the same mental direction. In a sense, you gain favor with them by asking them to add value.

4. Be sure to speak their “love language.” By this I mean, if they value “keep it short” or “keep it real” be sure and signal you know those are things they value. When you lean into their style and preferences, they will be more apt to lean into you and your likes too.

5. Remember—this is an art more than a science. Human relationships are tricky and rarely completely predictable. My favorite Habitudes® (images) on this subject are:

  • Chess Not Checkers—the pieces don’t all look alike in chess. Be sure to know the strength and personality of each team member.
  • Bridge Not a Wall—be sure to work hard to build a bridge to the people how are unlike you; sadly, it is easiest to build walls to those people.
  • Velvet Covered Brick—leaders need to show velvet (grace and support) as well as brick (strength and convictions) to their team. You must be responsive and demanding.

Emotional Safety and Security Is a Must

I will never forget when John Maxwell placed me in charge of a team and gave us an important objective to accomplish. Everyone on the team (except for one) was older than I was, with much more experience. I was intimidated and I think it showed. Within a matter of months, Darin, one of the team members, asked to be removed from the assignment. I was crushed, but I could understand why he left. I was just 24 years old.

My response?

I asked him if he’d meet with me to talk about it. He agreed, but came with a defensive attitude, ready for combat. Instead of begging him to stay on the team, I apologized, then empathized, saying I completely understood why he’d made his decision. Then, however, I won him over by saying, “Darin, my problem is: I don’t know what I’m doing. I’m new here and trying to learn as fast as I can, so I don’t slow us down. I sure could use some help, if you’d be up to it.”

He got tears in his eyes. I think he was completely disarmed by my honesty. Darin stayed on the team and together, we made some big progress as a multi-generational team with a very big goal. I wouldn’t have traded it for the world.

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