Managing Millennials: How to manage the most entitled generation so far

Manager’s the world over have shaken and scratched their heads over the newest generation to enter the workforce.

The modern workplace has evolved and the importance of emotion over grit, balance over “grinding” and conditions over stability has changed the face of management a great deal.

The biggest challenge amongst it all is the seemingly new problem of managing what could be argued as collectively the most privileged generation the world has seen.

Where do we begin as managers to address this challenge? And, is it even a real problem we face?

It’s mid-week and I’m engrossed in email correspondence to a couple of key partners and clients when my instant messenger rings out with 3 notifications in quick succession. It’s the junior designer who is in their last week of probation. I alt+tab and read the messages.

“I was wondering if u had 5 mins to have a quick chat?”
“If its alright I’ll come down.”

Me being me, I hypocritically fixate on the informality and the fact they’ve missed an apostrophe “it’s”.

“Sure mate, come on down,” I reply.

A knock on my already open door, then some pleasantries are exchanged and I ask them to close the door and take a seat on the less formal couch setting so we can chat.

“So, what’s up?” I enquire.

“Well, I just thought this role would be more creative. I’m doing a lot more challenging admin work and I’m finding direction a little difficult. It isn’t what I imagined.”

“Well, what did you expect. I’m just curious because we talked through the role in a fair bit of detail in the two interviews and so I’m just curious where the expectations are misaligned.” I ask with genuine curiosity.

“I’m just not really sure this is what I want to do, to be honest,” Junior concludes.

“What’s that? Work and be paid?” I reply in my head.

I can see that I’ve already lost this kid. Well, truth is, maybe it wasn’t me. Truth is, I’m already thinking we better usher him out because if I try to debate him staying the future isn’t going to be great for anyone.

“Well it’s important that you follow your heart and find your passion,” I advise. I know that this is the answer they want to hear but is it the right thing to say? You see I’ve been through this a fair few times over the past few years and one thing is consistent.

Although I’m on the cusp of Millennial classification, every person I’ve already experienced this conversation with is on the younger side of the Millennial-scale.

I know that keeping Junior on is going to be more trouble than it’s worth… right? Well maybe not. Let’s discuss the reality.

Is it the generation or the individuals or everyone else?

We are a society of stereotypes and stereotypers. Is it all of the millennial generation or is it just some individuals that we may struggle to manage. We also love a scapegoat to trivialise and classify our problems fairly quickly.

We as humans like to sensationalize just about anything. Why? It makes us feel good to target a common problem and spend our time beating up on it. We also like to be able to sensationalize our views, whether they be positive or negative, in order to sell our ideas and beliefs. The headline to this article is a great example where I am looking to polarize opinion, surely annoying any millennial and getting any of the older generations to jump on the bandwagon of beating up the scapegoat. We as humans, especially in the workplace, love a scapegoat.

Let’s be honest. Ever generation is cast in a similar light by those before them. When we entered the workplace green and unsure we were in the same position as the Millennials are now. The views and criticisms alter slightly between generations but we are not saying things vastly different than those in the generations above us would have said of our generation. And the entitled and victim like views of the struggle Millennials think they face in turn, though different to our own, are as real as anything we deemed a struggle for our generation. It’s simply perspective.

If you’ve ever watched a Simon Sinek talk and particularly his fascinating interview on Millennials in the workplace ( then you’ll get a great explanation from him on why you can’t blame the Millennials. I somewhat agree on some key points he makes and totally disagree on others, but that’s what makes all of this so hard. We all see things differently.

Some of the key takeaways that I took from that discussion were realisations around things I already see between the kids who grew up without the internet and mobile to those that have it.

  • Baby boomers – were raised during post-war depressions and having a job was everything. It didn’t matter if it wasn’t fulfilling or if you were happy. Having a job was enough to keep you happy so be thankful
  • Millennials – your work needs to fulfil you. You need to have a sense of accomplishment and the lucky thing is now we live in a time where if it doesn’t work out you can find something else. I mean you live at home with Mummy and Daddy until you are 30 so you don’t need that job anyway
  • Baby boomers – work hard to be recognised and climb the ladder. Blood, sweat and tears are the only way. And be patient. It takes you 3 weeks to send a letter overseas, you need to arrange a meeting time in advance and wait for your friends to show up (and you won’t know if they’ll show until they do so being punctual matters), you actually had to call in sick and speak to someone not flick them a Whatsapp and you had to wait a week to watch your favourite TV show and the next day when you went to school or work your only topic of conversation around entertainment was what was on TV the night before. Having instant gratification is not what life is about.
  • Millennials – things happen instantaneously. Life is about instant gratification. You can call people from anywhere, text or WhatsApp them exactly what is happening every minute of every day and they can also catch them on your Instagram feed. Options are endless. You can choose your social media apps, your shows, your news articles and waiting 10 seconds for a stream to load is too long already. Now imagine that translated to the workplace. You want to be paid more, do more and make a difference… but you want it instantaneously
  • Baby boomers – be something. It doesn’t matter what as long as it is stable and most importantly when you are something work hard to keep it
  • Millennials – you can do anything you want to. In fact “You can be anything you want to be” is a quote they’ve heard growing up a whole lot. The issue is there’s a part missing. “You can be anything you want to be if you’re prepared to work very hard, be patient to get there and be okay with failing a lot along the way and know that isn’t the sign to give up”
  • Baby boomers – own a house and get a stable income. It’s implicit that is enough and that is a happy life
  • Millennials – live the dream. Travel, own the big house, have a nice car because it’s what your peers project on Insta… and if you don’t have those things as fast as they do are you really happy?

So what’s the answer?

In the end, the above doesn’t help you manage a lot. You can take some away from it but this is my view of what does and doesn’t work with regards to managing Millennials…

Mentorship over delegation. We grew up in the workplace with a lot more delegation. But some of us have been lucky enough to be mentored. The difference is that mentors are patient with you and your mistakes. If you’ve ever been frustrated at not receiving good guidance I guarantee that regardless of the generation this is true. And more so than ever, the youth of today need that mentorship to come from those above and to feel supported. Share your stories of how you got to where you are.

Teach patience and be patient. Keep explaining to people that making a difference takes time. Things do not happen overnight and instantaneously for everyone. It can for some but experience is so important. Spend time learning and persisting with something. If you fail it isn’t a sign that this isn’t right for you, it might be the case or it might be that you need to try again. Being patient is the best way to teach it.

Listen. Listen well and then respond. Truly listen to what the challenges are. Ask questions.

Why do you not find this fulfilling? You want a sports car and this job won’t pay for that? Do you think you know a better way to do this? You think what we do is dumb and you know how to fix it?

Okay, I’ve listened, now it’s your turn to listen out of mutual respect. And this is going to take some time for us to get a common ground of understanding but let’s value the importance of dedicating time to resolve our different views.

Don’t give in and give up too easily. It can be easy to completely nod your head and agree when you manage people. It’s an easy way out of confrontation to let people start steering the ship. Sometimes it’s necessary, sometimes it’s right. But don’t lose sight of why you are the manager. Unless you’ve been completely wrongly put into a position you got there because you showed some leadership, some expertise and some experience. It is your duty to pass on this knowledge to those that you manage especially the young.

Work hard. Work hard yourself to instil the qualities you want to see in your young team or employees. Talk with them and show them you are committed to making them a better worker, a better employee and a better human being. You might just learn the same yourself along the way.

Don’t think you can’t learn from them. Much like listening sometimes taking on board and giving them some room to run may change your world and your work.

And if all the above fails… 

Then be okay to let them go.

Even if the failing may be on your side, if you can’t manage someone and it’s untenable be alright to change the situation by letting them go be it to another manager, team or company.

Whether an unhappy employee is young or old, there comes a point where it’s healthier for all involved to part ways. Sometimes the efforts to force an employee and a manager to work harmoniously is not the solution and everyone should move on. Just take what you’ve learnt from it and build your values, your skillset and your management capabilities.

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