I’ve been working with Ryan Hanley for just over a year now. He’s not my first manager, but he’s certainly one of the best. Does that mean nothing ever goes wrong? Of course not. But it does mean I have zero desire to work somewhere else.

That’s a big deal in a professional environment where Millennials jump from job to job every 2 – 3 years. I’ve seen a number of my friends on the job merry-go-round in the last few years. And it’s no fun. But it’s even less fun for their employers. It takes a long time and a lot of resources to train someone into a position; not just in terms of the daily tasks their role requires, but in terms of their part in the office’s culture. So how do you keep the younger generation motivated to hustle for you and your business (aside from the standard insurance message of ‘Flexibility and As-Much-Commission-As-You’re-Willing-To-Work-For’)?

What I’m about to tell you is Ryan Hanley’s secret Millennial Manager sauce. I’m not promising all of these things will work for you or for the employees you manage. Remember that everyone is different, even if they fit into a demographic age group. But I will say that the amount of work we accomplish on a weekly basis blows me away considering the size of our team (p.s. we’re all Millennials) – and I attribute a lot of that to Ryan’s managerial techniques.

Ask Why

Every time I suggest something, Ryan asks why. At first, I was like “oh hey, this is cool.” Then I was like, “ok, this is getting annoying.” Then finally I realized his game. 😉

Of course, any time you ask someone why interestedly (instead of immediately dismissing their idea by telling them why you think it might not be a good one), they feel respected.  They feel like their idea was good enough to cause pause.

Millennials have a desire to be recognized and respected for their ideas. They are always looking for an opportunity to prove themselves…and a good idea is a dang good one.  But it’s easy to be consumed with the recognition you get for voicing the idea rather than whether the idea itself was actually, truly a good one.

Ryan’s “Why” strategy equalizes every idea. It forces us to think through any idea we suggest. It opens up discussion, different perspectives, and challenges. The pressure to be recognized suddenly collapses in the face of collaboration on the best idea. We don’t need to prove that we’re good enough; we need to work together to find that one idea that’s good enough.

p.s. in case you don’t believe me – I searched the word “Why” in my Slack conversations with Ryan. Here’s the 1st of 16 pages of results:

(Yes, that is Ron Swanson. Yes, we all chose Parks & Rec profile photos. Just try and guess who I am.)

Make Failing Positive

Like I said before, up and coming generations are always trying to prove themselves. And failing is the opposite of that.

But it’s also both normal and necessary, which is why I’ve had previous bosses tell me that it’s ok to fail. In my mind, that neutralizes failing. It’s recognition that it happens and that it’s a part of life. But it still feels ‘bad.’

Ryan takes it a step further. He’s told me that he actually wants me to fail. Failing is a sign of execution, it’s a sign that you’ve tried and experimented. It’s a part of success. This redefines failing as something positive. It’s now a learning process, not a terrible end in and of itself.

Direct, Don’t Navigate

I’ve done some work for Navigators. It’s suffocating. We all know those people who have to be involved in and question every single step of a project. All you can do is try to hold back the urge to shout “I know what I’m doing! Just trust me for once!” You didn’t come here to be a glorified paper-pusher, after all.

Directors are more hands-off. They create goals, but they give you the flexibility and freedom to determine how you reach them. They inspire you to take ownership. Ryan hires people he trusts and he trusts that they’ll do good work. Instead of mapping out every step we take, he point us in the right direction and watches us run.

Sometimes this means we don’t do exactly what he might have envisioned. He’s ok with that.

(The cool part is that because he shows us this trust, we often ask him for guidance during steps where we feel uncomfortable.)

Talk About The Future Often

Anyone who says Millennials don’t want to work hard hasn’t spoken to enough of them. We will work our butts off. But it’s easy for us to get lost in the daily grind, the hustle, and neglect to think about why we’re grinding every day in the first place! We sometimes miss that perspective (that you have). When we remember where we’re headed, how our goals move the business forward and move us forward, it’s energizing.

Ryan drops these little reminders about the future of the business and our team’s future almost every time we have a team meeting. He keeps our eyes up and our drive focused. He’s also very open with us about the business’ future plans and what steps are being taken to reach those goals. This helps us see how each department’s accomplishments are collaboratively moving us forward as a company.

Use Hashtags

Ok, he literally made up the below hashtag all by himself.

And my grandma responded:

I love my grandma to death AND she is one of the coolest people I’ve ever met, but (and this is one of the only times I’ll say this): don’t be like my grandma.

Ryan is incredibly intentional about getting on our level and learning our language. He talks in emojis, hashtags, and gifs. He doesn’t give us the dismissive “oh you young kids and your weird words;” he wants to be a part of it. He takes a stand on whether gif is pronounced “gif” or “jif;” he joins in on the fun. That helps us all bond and gel so it’s not all business all the time.

(Seriously, you should see our Slack conversations.)

The Last Ingredient

The last ingredient (that I’ve figured out at least) will seem pretty obvious, but is often lost in these types of “let’s stereotype all Millennials one way” pieces.

Remember that motivation isn’t one-size-fits-all. Yes, there are generational trends (and “human” tendencies), but we’re all unique. What takes me from ‘0 to 100’ may not work or may need to be tweaked for someone else. The other day I was chatting with Ryan and he dropped this on me:

“When you say ‘dude, dude, dude dude!!!!’ I know you’re about to hit me with something big. When you go ‘yeahhhhhhhhh,’ I know you’re about to hit me with something bad.”

Both are totally on point and the weird part is I didn’t even realize I was doing them until he said something. But that’s what makes Ryan such a solid manager; he cares about understanding each of his peeps individually.

Long story, short – if you’re wondering how to inspire the Millennial workforce in your agency, (speaking from experience) Ryan is a solid guy to follow.

Thanks for reading, as always, friends!


P.s. Just for the record, he had no idea I was writing this.

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