Managing the 20-Somethings

I had the privilege of attending the 2018 National SHRM Conference in Chicago a few weeks ago. The highlight reel included Adam Grant, Sheryl Sandberg, Wrigley Field, and Second City – but I must confess my real “a-ha” moment came from attending Brad Karsh’s session, “Dude, What’s My Job?” – managing 20-somethings.

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We started Juno 8 years ago and had very little management experience and no real management training – my most recent position was that of an individual contributor in a very small office. Juno’s first employee came in the form of a recent college graduate, who happened to be the daughter of a close personal friend and someone I’ve known since she was a kid. For all these reasons – it was an interesting dynamic to manage to say the least. From there, we kept growing – every time we had a new hire, I was managing a bigger team than I ever had before. Today, we have 18 people across two cities, and the majority of our employees are still in their 20’s or very newly in their 30’s – hence my interest in attending Karsh’s session.

In the early days of Juno, we agreed that we’d manage our employees as we wanted to be managed in previous companies and as we manage ourselves. Our mantra was our lives were not more important than our employees’ lives, our kids are not more important than our employees’ kids, and the flexibility we enjoy should be enjoyed by them, as well. As long as the work is getting done – who cares? Flexibility and trust – that was the goal. Need a work from home day? Take it and we’ll trust that you are working from home – not running a million errands and calling it a work from home day. Need a day off to reconnect with your kids? Take it – we’ll trust that you understand business continues and will be responsive as necessary – just as we would do. With that in mind, we implemented two policies – unlimited PTO and the ability to work from home one day a week. Both of these perks were things we also enjoyed and wanted to grant our team.


In the beginning, it seemed to be successful enough (or no one told me otherwise) – we were a small tight crew and all hands were always on deck. As we grew; however, and added different personalities and different generations, we found there seemed to be a disconnect around said policies. Also, I’m not an effective communicator – and I know this to be true, as anyone close to me has been offering this feedback (unsolicited) for the better part of 40 years.

As an example of my poor communication I present an actual scenario – snow would be in the forecast and the employees would start chattering about what to do in a variety of situations – if the snow starts at x time, should we still come in? If the snow is cleaned up by y time, should we still try to come in? My reply was always, “Use your best judgment.” Which is what I would have loved someone to tell me and what I’d do in that situation. If it was stressful and dangerous, I’d work from home. If not, I’d go in. What I discovered; however, was that everyone hated that answer, as it was unclear and they feared there was a way to be wrong. To be clear, I actually meant use your best judgment…we are all set-up to work from home – laptops, cell phones, messaging services, etc. But admittedly, I can be moody – and not direct, so perhaps that exacerbated the feelings of uneasiness from our employees.


This is one example, but there has been a myriad of others over the years (that’s how bad I am). Of course, we’ve had employees come and go who would take advantage of our good and trusting nature. It’s always transparent when it’s happening, not to mention so frustrating – but then again, we set a policy in hopes that every employee would mimic the way the owners behaved. Two women in their 40’s who own the company - #whytho?

I have struggled with this for years – and in particular, how to manage the 20-somethings in the office who seem to need tons of direction and specific feedback (generalization). And this is why Karsh’s session was so illuminating! Karsh first gave us a history lesson – which helped provide context for how different generations have been exposed to different world events and technology, huge contributing factors to behavior in the workplace. Through this lesson, I began to recognize some of my big issues and struggles with managing the Millennial generation. I’m Generation X, who largely grew up as latch-key kids whilst women entered careers and began to realize they could be professionals, too. And so, we were alone a lot, figuring it out for ourselves – we had two working parents and not as much structure or a home with traditional roles – as the previous generation had. Conversely, Millennials have had every step of their lives carefully crafted for them. They actually had little downtime, as they got carted from one activity to the next – leaving them with no need to be creative or troubleshoot things like, “Mom has to work late – what are we going to eat?” Karsh even joked that on some schedules you’d see, “Unstructured playtime from 1pm – 2pm.” Whereas our parents kicked us out of the house in the morning and told us to be home by dinnertime.

And so, we manage our employees the way WE would want to be managed, but it’s not the way THEY want (need) to be managed, thus creating a huge disconnect and a lot of frustration. And, it’s our fault – not theirs. I have an office full of 20-somethings, not one of them is lazy – this is not the lazy generation, as some people believe. They are also not entitled – but they do not thrive in the same environments we do, therefore it’s our duty to create an environment where they will thrive and grow.

How do we do that? There's never a magic bullet, but this could be a start: a bit more structure, a bit more feedback, a little more checking in, more positive affirmation...without going overboard (on the structure part). They still want to enjoy flexibility - but in the form of policies. You get one work from home day a week - instead of "flex schedule", figure out what that means. You get 20 PTO days a year, not "unlimited" but you'll feel guilty when you take them. 

I've also found leaders need to be flexible in their management style - I adamantly wanted to treat everyone the same - but I've found that no two employees are the same. You can be fair AND flexible. In short - get to know your people. 

Mikal Harden