5 Reasons Younger Leaders and Older Leaders Frustrate Each Other At Work


If you’ve tried to lead employees who are under the age of 40, you’ve probably noticed things aren’t as easy as they used to be. (And they were actually never that easy.)

If you’re under 40 and are working for an over-40 boss, you’re probably restraining your eye-rolls as you notice that people just don’t seem to understand you.

Younger leaders tend to love flexibility, the freedom to work remotely when they want,  the ability to call some shots and the ability to develop a side-hustle, all of which seems to either baffle or frustration older leaders.

Many (not all, but many) older leaders would rather see team members have one job (no side-hustle), do their work from the office, be available after hours just in case, and earn a seat at the table before they give much input. And they don’t get the lack of loyalty that they feel a lot of younger adults display.

All of which frustrates younger leaders.

I run into this tension every time I talk to leaders about how the workplace is changing.

Over-40 leaders are smart to study how things are changing so they stay relevant. After all, the gap between how quickly you change and how quickly things change is called irrelevance.

Younger leaders are smart to understand the tension because it will make for far less frustration on their part, and help them advance in the organizations they’re a part of.

I’m an over-fifty leader who’s worked in offices in business and church, in a hybrid environment where some work is remote and some is done in an office, and now run a 100% virtual company that handles my speaking, writing and podcasting. In addition, almost all of my team members these days are pretty much Millennials or Generation Z.

Here are five things I’ve noticed about a changing workplace, and how older and younger leaders can get along better at work.

1. The Idea of an Office Gets More Dated Every Year

Every once in awhile you have this moments when you realize how rapidly culture is changing.

A few years ago I was driving through Dallas and saw some office towers going up, and I thought to myself “I’ll bet one day our kids and grandkids drive by office towers and say ‘Did people actually used to have to go to a building to get their work done? Why?’ (Kind of like the Blockbuster days, when you had to go to a store to get a movie on a disk to watch it, and get hit with late fees if you failed to return it on time.)

One of the reasons offices used to make sense for everyone a generation ago is because the means of production were stored at the office. Your company held the typewriters, meeting spaces, computers, paper, pens, phones, copiers, fax machines and all the things private citizens didn’t usually have. There was a clear line between work life and home life.

Now there’s a very good chance you’re holding almost everything you need to do your job in your hand. Plus your phone, tablet and laptop travel with you everywhere. What about meeting spaces, you ask.  Well, between coffee shops, co-working spaces and restaurants, the need for offices has plummeted.

Older leaders still think about ‘going to work’ because that’s how they cut their teeth.

Younger leaders realize you don’t go to work; the work goes to them because they are the work. As a result, they love to work remotely at least some of the time—from home, from a coffee shop.

Older leaders often see this as lazy. Younger leaders see this as normal.

As Bryan Miles has pointed out about virtual culture on my leadership podcast, remote workers aren’t lazy; lazy workers are lazy.

If you have a lazy worker…deal with it. But often remote work can be far more efficient. There are fewer water cooler conversations, fewer random and useless meetings, fewer interruptions and less distraction.

So does that means offices are gone forever?

No. In a hybrid company that allows some remote work, core hours are a great idea where everyone is in the office, say, on a set day or in a set window to improve team interaction or for meetings. But beyond that, an office isn’t nearly as necessary as it used to be.

2. 8-4 Doesn’t Make Sense Anymore

One of the challenges is that office work took its early cues from manufacturing.

It make total sense if you have a car assembly plant (or a coffee shop, or a retail store) to have workers show up exactly on time for a shift. Because offices at one time owned the means of production (see above) it kind of made sense to the same thing.

But where most of the work is relational, informational and flexible (i.e. almost all white collar office jobs), 8-4 no longer makes sense. After all, unless you’re on the reception desk or doing some kind of work tied to fix hours, you can do most things any time.

Yet far too many older leaders are stuck in a mindset that people have to be in the building at set hours.

As a result, too many people show up at 8 (or 8:05 or 8:15) for no particular reason. It can create a clock-watching culture (is it 4:30 yet? Do I get paid for this lunch???) where your team is in a set place for no discernible rationale.

So here’s the question for leaders: are you paying your team to show up or are you paying your team to produce?

If you’re paying your team to show up, that’s one thing.

But if you pay them to produce, outside of fixed meetings and shared team time, why not let them choose how and when to produce?

Here’s what’s changed: The old economy paid people to show up. The new economy pays people to produce.

As I share in my productivity course,  The High Impact Leader, some of your team’s best productivity might happen when no one’s in the office or working. So why stifle that and make them show up because someone decided that’s when they should work?

3. Most Young Workers Work for Themselves

While they may not articulate it, most Millennials approach life as though they are working for themselves, not for you, whether you hire them as employees or on contract.  (We’ll see about Gen Z. I wonder if this trend will accelerate even more.)

Sure, that might sound strange, but hang on and try to get into their head space for a minute.

First, any younger leader realizes they will likely NOT work for the same organization for 40 years and retire. Not only are the pension plans of the 60s and 70s long gone, but the workforce changes so quickly that most younger leaders expect to have multiple careers throughout their life, not just multiple jobs in different organizations.

Second, thanks to technology, the start-up culture is huge. Many leaders realize they can start things far easier than people could a generation a year ago. You can influence the world through your keyboard, your phone or a microphone. It used to cost millions to launch something. Now you can launch something on a Saturday morning for the price of a phone.

Third, we live (rightly or wrongly) in an era of personal branding. Couples have logos and fonts. And almost everyone wants to express their style through fashion, design, photography or lifestyle

What this means is that most Millennials has subconsciously realized they have to create a life plan that’s independent of any employer or organization.

This isn’t fatal to any organization once you understand it.

What it means though, as a leader, manager or boss, is that you need to come alongside them and help them realize their objectives.

If you see those life objectives as competing with your objectives, you’ll lose them. If they see that you want them to win, they’ll hang around a long time.

Here’s the bottom line with young leaders: If you help Millennials win, you’ll both win. If you merely want them to help you win, you’ll lose.

4. The Side-Hustle and Gig Economy Are Here To Stay

So you hire a young worker only to find out he or she has a design business on the side, or that they’re writing a book or launching a podcast or starting a blog.

What do you do?

Are they being disloyal? Do you rope them in and tell them to give you 100% of their time?

Well, a few things.

First, you don’t own 100% of anyone. Any leader who tries to micro-manage the entire lives of their employees won’t have employees for long. You’re really only managing 25% of any full time employee’s life anyway (40ish hours of 168 hours).

Controlling bosses in the future will have less and less to control all the time.

Second, the side-hustle is here to stay because the gig economy (freelancing) is here to stay.

63% of free-lancers today say they started by choice, not by necessity.

By 2027, the gig economy will be over 50% of the economy.

The majority of Millennials are already freelancers. (Source: Forbes.)

So to think you’re going to have a work force that has one job and stays with you forever really puts you back in 1965.

Brian Houston, founder of Hillsong, has some incredible insights on how to keep young and talented leaders over the long haul. Hillsong has done an exceptional job of keeping great talent and giving them freedom to express themselves in their lives and in their leadership.

His advice? If you want eagles, raise the ceiling.

5. The Cause is More Compelling Than You Are

Older bosses need to realize that most young leaders really do want to work. They just want meaningful work.

You know the stereotype: Millennials want to change the world and believe they can do it.

Again, before you roll your eyes, remember (older leaders), you raised them to have values like these. And some of them are doing it. So cut the cynicism.

What this means though is that your mission is more important than ever.

Leaders who want to preserve the institution, pad the bottom line, or simply grow the organization will always struggle to attract and keep young leaders.

For the church, this should be easy. If you’re truly mission-driven (you want to reach people or impact your community), your ethos has an instant appeal to younger adults. Just keep the mission central.

If you’re in business, profit won’t be nearly the motivator that cause is. If you don’t know what your cause is, figure it out.

Similarly, you might think of yourself as a great leader people want to work with (actually, that’s usually a sign you’re not a great leader), but I promise you Millennials aren’t that impressed with you.

The best way to attract and keep young leaders is to work with them to accomplish a greater purpose.

Leaders, if the mission isn’t bigger than you, you need a new mission.

So…Older Leaders and Younger Leaders: Some Tips

This sounds like a bit of a showdown but I promise you it doesn’t have to be.

For older leaders, the most important shift to make is to manage outcomes, not process. Don’t value leaders for showing up. Value them for what they contribute.

Don’t tell them how to get it done, just hold them accountable for getting it done.

Leaders who manage the what and why and flex on the how will have a bright future.

The old paradigm told people to be at their desks and sit up straight. The new paradigm says ‘value me for what I contribute.”

Leaders who manage outcomes and rally people toward a higher mission will always have a steady supply of young leaders lining up to work with them. I share some additional insights about working with Millennials in this post.

What about younger workers?

Well, first of all, flexibility by your boss is not permission to be lazy. Hustle hard, but produce.

Second, gain influence by being ridiculously great at what you do. If you want to know how to gain influence when you’re not in charge, check out this interview with Clay Scroggins.

Want More?

Do you want to unlock more of your potential in life and leadership without sacrificing time with your family and your health?

Sounds crazy, but it’s not. I know because I’ve lived it. A few years back, I seriously crashed and burned because the demands on my time and life were bigger than the time I had to accomplish them. I promised myself that wouldn’t happen again.

Today, I still have bigger goals than ever before, but I’ve made fundamental changes that have led to a healthier, happier lifestyle without sacrificing my family and vastly increasing my productivity at work. I’ve taken what I’ve learned during this journey and put it into the High Impact Leader course.

You can complete the three-hour course at your own pace. It’s the most comprehensive content I’ve ever created for leaders to help you reclaim HOURS every day so you can become more effective at work and more present at home. When your time, energy, and priorities are all working together for you, it’ll impact everything you do.

  • You become a better leader, because you’re doing what you do best when you’re at your best
  • You become a better spouse, because you’re focused at home
  • You become a better parent, neighbor, and friend, because you actually have time off to relax and engage

These principles will free you to thrive in every area of your life.

You can learn more or get instant access here now.

What Do You See?

What are the frustrations you experience as a younger or older leader?

Scroll down and leave a comment!

5 Reasons Younger Leaders and Older Leaders Frustrate Each Other At Work


  1. […] times I’ve found myself frustrated with my leaders. All frustrations, however, are not created equally. I recognize a few times when my leader frustrated me to help me, and here are three such […]

  2. Eric on May 12, 2018 at 5:26 am

    From an Ecclessiology point of view…:
    Jesus didn’t work remotely….

    There’s something about Incarnation that “working remotely” doesn’t quite get at….

    If the Church is to be a witness to the new Kingdom here on earth, then there’s something different that the Church witnesses to. Part of that is the messiness of community and saying – IRL “I will not block you” – and, “I will persevere in this relationship with you, regardless, even without retreating (which is so easy to do with the ether and a screen as protection).”

  3. Chris Philbeck on May 11, 2018 at 7:13 pm

    “So here’s the question for leaders: are you paying your team to show up or are you paying your team to produce?” The answer is, “Yes,” because these two things don’t have to be mutually exclusive. The same work done at an off-site location can be done in an office. This is especially important when you ask and expect your ministry staff to work together as a team which is a pretty consistent reality in the church I lead. I don’t have any problem allowing my staff the freedom to work remotely at times (I will occasionally choose that option), but there is value in everyone being together in the same place together, working to accomplish the vision and mission of the church. To use your words: working to accomplish a “compelling cause.” I love your blogs, I read all of them and will often retweet some of the things you write (ex: “the gap between how quickly you change and how quickly things change is called irrelevance” I’ve retweeted that from a past blog). I’m sure some of the conclusions in this blog are based on “best case” scenarios with staff members who are responsible, respectful and who understand that everyone is accountable to someone. I can tell you from experience, that doesn’t describe everyone. Thanks for what you do. (59 years old – megachurch pastor – 38 years of service)

  4. Mia on May 2, 2018 at 1:37 pm

    To the first point, I would also add that in a world where it is easy to connect with someone via email or social platform, working remotely adds the opportunity to interact with clientele or potential clientele with real face to face interactions at a coffee shop or other public location. Where as in previous times those interactions would have happened with folks coming into your business during office hours.

  5. Mike Parker on April 30, 2018 at 3:00 pm

    Old guys are usually wise. Very few things are really “new”. Many times we have witnessed several variations of the same idea or ministry through out the years. Communication.

  6. Maureen on April 30, 2018 at 11:29 am

    If everyone is working remotely, what is the point of having office hours and a receptionist?

    • Grace on May 1, 2018 at 1:16 pm

      The reason for having office hours is so the business owner/leader doesn’t get overflooded with phone calls at all times of the day. Especially since most of the world’s population can call/e-mail anyone in the world at any time, it’s helpful to have a specific time-frame to answer business calls and e-mails so that the job doesn’t become a 24/7 job. Even though people can get their work done, basically anywhere and anytime, a lot of us do still prefer to keep our work separate from our personal lives. Hope that helps!

  7. Richard on April 30, 2018 at 10:59 am

    Fantastic (I’m a 50yr old this year, for disclosure purposes). I find myself getting removed from considerations for positions at churches because I had moved to a more ‘remote’ mindset and work ethic; due to my own personal business pursuits and fitting in my busy Dad-life. Beautifully succinct.

    I continue to find your name at the top of my favorite go-to reads on leadership thoughts and blogs.

  8. Jeff Loach on April 30, 2018 at 9:14 am

    Thanks for thinking this through, Carey. I wonder, too, if the “work anywhere, anytime” approach – which in some ways I live out myself – makes it harder to create boundaries in terms of adequate rest and recreation. While it’s true that this approach can promote laziness, it can also promote workaholism if one is not sufficiently disciplined to create boundaries.

    If you “go” to a specific place to work, for a specified period of time, it’s clear that anything outside that time is (at least in theory) your own time. But very often, when we don’t have to be in a particular place for specified hours, it becomes all too easy to be available 24/7 and working for a good portion of that.

    All the more reason, then, that we should develop good personal habits, spiritual disciplines, and healthy boundaries! Blessings.

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