How Companies Can Do Leadership Development for Millennials

Tim Royan
April 2, 2020
How Companies Can Do Leadership Development for Millennials

I’m pretty sure you’ve seen all the articles churned out over the past few years about how millennials are ruining everything, right?

In case you haven’t, here’s a quick rundown of some of the things millennials have been accused of ruining, destroying or killing: the 9 to 5 workday, golf, marriage (and, of course, divorce), the housing market, vacation days, the mall, dinner dates, napkins and, yes, obviously mayonnaise.

Yeah, our generation has become infamous for effectively destroying everything society once held sacred... like golf.

I guess that explains why social media recently erupted in an intergenerational Sharks vs. Jets gangland war — albeit with less choreography — over the dismissive social media phrase “ok boomer.”

Boomers weren’t about to take that from those dang lazy, entitled millennials and their avocado toast. And a particularly savage internet war broke out — a confusing one, admittedly, since all the combatants seemed to be Gen X and Gen Z...

Anyway, I bring this all up because — on behalf of all millennials — I’ve come to make peace and apologize. We’re genuinely sorry we so cruelly murdered mayonnaise.

And, despite our transgressions against condiments and starter homes, it would be a mistake to dismiss us — especially when it comes to leadership development in your company.

We’re the largest section of the workforce and every day more of us are stepping into leadership roles. So, it’s more important than ever before that companies get better at engaging, retaining and equipping millennial talent.

But, since our cohort is so hell-bent on doing everything from communication to breakfast sandwiches differently, you might have to adjust your approach a little if you want to invest in leadership development for millennials.

Luckily, there are some surefire ways you can.

How should companies do leadership development for millennials? When it comes to millennials, your company should be investing in leadership development that:

  1. Is both human-centered AND individual-focused
  2. Deepens connection to your company and its mission
  3. Is practical and applicable to real-world jobs at your company
  4. Provides active coaching and mentoring
  5. Harnesses the power of the peer group

Let’s dive into what actually differentiates millennials and figure out what it means for leadership development.

What do millennials want out of their careers?

Millennials overwhelmingly say the most important thing they want from their employers is an opportunity to learn, grow and develop.

But most millennials feel this is severely lacking at their jobs.

To be fair, retention and engagement are lacking across the board — over half of any given company’s employees say they’re currently looking for another job — but it’s even more pronounced with millennials.

And companies really are trying to develop their high-potential employees, even the ones trying to ruin the watercooler with their cold-brew srirachas. Alright… that’s not a thing, but you get my point.

The problem is that even most executives admit leadership development programs targeting these high-potential millennials are failing.

So what can we do?

Leadership development shouldn’t reduce millennials to a number

I get it, your company, like most, wants to do learning and development at scale.

But here’s the problem with that approach: Nobody wants to be reduced to a number — and especially not millennials.

We want to feel known, appreciated and like our employers are actually invested in our individual success, not just part of a wholesale, one-size-fits-all approach.

So, if you want to actually develop leaders and not just pay lip service to a warm and fuzzy initiative, you need to focus on the growth of the person as a whole. Don’t just try to install some new productivity software on some generic work machine.

Even if this wasn’t a concern for millennials, it’s a good idea. An employee — and future leader — in your organization who is not just killing it at work, but also killing it in life is more valuable in the long run, anyway.

When you hear your millennial employees — without a trace of that sarcasm and irony we’re known for — gush over your leadership development as their favorite employee benefit, you’ll know you’re winning.

Leadership development should align with your company’s values

Maybe this has you wondering: What if I invest in my employee and it backfires?

Or maybe you think it’s a silly question. But, the truth is, so many companies out there actually do try to invest in their employees’ overall success — like covering tuition or access to online video libraries — and...

It blows up in their face when their employee builds more meaningful relationships outside of the organization and goes somewhere else.

So, what’s going wrong?

Yes, you need to invest in an employee’s overall growth as a person, but you need to do it in a way that aligns the employee’s personal values and the values of your organization.

Helping them access generic classroom materials that have nothing to do with your company’s mission, values or vision doesn’t do this at all.

The good news is, your company culture is an expression of your company’s “why” lived out by its employees.  So if you work on your culture (and nail it), it’s a given that aligning your values with your employees’ should be pretty easy.

Are you developing leaders for jobs in your company?

This one seems like it should be obvious, but I see companies struggling with this all the time.

Is your leadership development practical? Is it geared towards real jobs that actually exist in your company?

Millennials will tune out if you’re foisting development programs that are based on vague, abstract theories about leadership we can’t apply to where we actually work.

And despite the stereotype, we don’t actually want participation trophies — we want to win in our careers.

If your approach to leadership development isn’t creating a clear picture of how your employees can become effective leaders in your company, you're basically saying you don’t care whether they do.

You’ll end up wasting your employees’ time as well as your own but, more importantly, you'll be wasting your investment. Why put money, time and resources into anything if you don’t care about the return?

So make sure you connect your leadership development to structures and systems within your organization that will give you an actual return on your investment.

Are your leaders being actively coached and mentored?

This is huge — if you want to retain your high-potential millennial, you should make sure they are.

Millennials need guidance and help navigating their careers from someone who has gone through the process themselves. Preferably someone who can speak their language and actually make a real connection with them.

And no, not through memes or — to be honest, I’m running out of millennial stereotypes — is Vine still a thing?

Anyway, it's important to share experiential wisdom and convey heartfelt interest and genuine belief in their success.

This is the key to engagement and retention. Millennials who say they intend to stay more than 5 years with their company are twice as likely to have a mentor than their flighty counterparts.

So before lamenting that millennials lack loyalty and dismiss them as the job-hopping generation, maybe you should ask: What’s driving them away?

After all, it’s hard to develop leadership in employees who’ve fled your company.

Are you harnessing the power of the peer group?

I’m not talking about peer-pressure — us millennials grew up on wacky D.A.R.E commercials involving fried eggs that taught us to just say “no” to that.

I’m talking about getting your high-potential millennials interacting with their like-minded peers to mutually support each other’s successful growth within the organization.

There’s a trend right now amongst effective CEOs and entrepreneurs to create “mastermind groups.” And while that may sound like an impromptu guild of villainous mad scientists tired of James Bond foiling their plans, it’s really a venue in which top leaders can learn from one another.

Basically, by getting together with other successful leaders they tap into the collective energy, experience and expertise of their peers in order to accelerate their own leadership growth.

For companies wanting to try a similar strategy with its high-potential employees, this has a name less amenable to a shadowy criminal enterprise: collective leadership development.

And for it to work, you need to bring together growth-oriented individuals and leverage great content, structure, systems and the momentum and accountability the group format provides. If you do, you’ll inspire and grow some really effective leaders.

But it’s more than a book club — which is good because I am sure there is a journalist sitting down to write how millennials are ruining them, too.

It really is a peer group, a community in which to build camaraderie, share goals, develop friendships and, most importantly, take action together to create the kind of momentum it’s hard to achieve when going alone.

These groups electrify the soul of a company. They help build the kind of culture where you talk to any and every employee and immediately know what the organization stands for.

And that’s exactly the kind of organization in which millennial leaders thrive.


Really, despite the bad press, millennials aren’t that different. We want to grow in our careers and become effective and successful leaders just like any other group.

So, if you want to win at leadership development with the millennials, just remember:

  1. Make it about the whole person and tailored it to their individual needs
  2. Make sure you deepen your employee’s connection and commitment to your company and its mission
  3. Make sure it’s practical and applicable to their real-world jobs
  4. Provide mentors who can connect with them in a meaningful way and help them grow as leaders
  5. Harness the power of the peer group and unleash your millennial employees

If you want more content about leadership development or culture, be sure to subscribe to Crafting Culture on Apple Podcasts, Spotify, or follow along on our website (before millennials ruin the internet, too).