Join Our 5-Day Leading Multigenerational Teams Challenge
Discover how Gen Z, Millennials, Gen X, and Baby Boomers experience work – and how to lead across the gaps
If you manage a team right now, you might be leading people from up to four different generations – Baby Boomers, Gen X, Millennials, and Gen Z – all in the same room (or Zoom call).
Each of these generations came up in different economic conditions, adapted to different technologies, and developed different expectations about how work should actually work. What feels like “common sense” to one generation can feel completely foreign to another.
And that gap creates real friction.
Recent workplace research indicates that a significant majority of HR leaders and managers view the differing communication styles and expectations of multigenerational teams as a major leadership challenge.
And yet most leaders have never been given any real framework for understanding what’s driving these differences – let alone how to work with them.
Every generation brings strengths that other generations lack. When you understand what each group actually needs, you can start working in a way where those differences become an advantage – not a source of silent tension.
That’s what this month is all about.
We’ve created a new 5-Day Leading Multigenerational Teams Challenge to help you understand how each generation shows up at work, what they need from leaders, and how to build a team culture that works for everyone.
The challenge starts Tuesday, March 3rd. Be sure you’re subscribed to participate!
What’s Coming Up
Each day of this challenge focuses on one generation – how they tend to show up as subordinates, colleagues, and managers – so you can start seeing the full picture of what’s really driving the dynamics on your team.
Then on Day 5, we bring it all together with insights and strategies for leading across generational lines and navigating conflict.
By the end, you’ll have a much clearer understanding of why your team members operate the way they do – and what you can actually do about it.
Here’s What to Expect Each Day
Day 1: Gen Z at Work
Gen Z is the newest generation in the workforce. What do they actually want from leaders? How do they collaborate with peers? And for those already stepping into management roles – how are they showing up?
We’ll break down what drives Gen Z as subordinates, colleagues, and managers so you can stop guessing and start leading them well.
Day 2: Millennials at Work
Millennials now make up the largest share of the workforce – and many are in leadership roles themselves. But the way they respond to authority, work alongside peers, and manage their own teams is still shaped by the conditions they came up in.
We’ll look at what Millennials need from the people above, beside, and below them – and where friction tends to show up.
Day 3: Gen X at Work
Gen X tends to fly under the radar in workplace conversations, but they’re often the backbone of the team. Independent, pragmatic, and sometimes skeptical of both the old guard and the new wave.
We’ll explore how Gen X operates across all three workplace positions – and what they need from the people around them.
Day 4: Baby Boomers at Work
Boomers bring decades of institutional knowledge and experience. But in a rapidly shifting workplace culture, their approach to hierarchy, communication, and work ethic can sometimes clash with younger colleagues.
We’ll unpack what drives Boomers as subordinates, colleagues, and managers, and how to honor their contributions without ignoring the gaps.
Day 5: Navigating Multigenerational Conflict
This is where it all comes together. We’ll walk through some of the most common friction points between generations that drive conflict at work – and give you ways to address them.
What Comes After the Challenge
Once we’ve built a solid understanding of each generation, we’re adding another layer: personality.
Generation isn’t the whole story, of course. A Gen Z Analyst and a Gen Z Diplomat are going to experience the workplace differently, even though they grew up in the same era.
So after the challenge, we’ll explore how each personality Role – Analysts, Diplomats, Sentinels, and Explorers – shows up across every generation. You’ll discover:
What tendencies stay consistent across generations for each personality Role
How generational context shifts the way different personalities operate at work
Specific tips for leading each personality type within each generation
This is where the series gets really specific, really practical, and (I think) really fun.
How to Join This Challenge
If you’re a paying subscriber, you’re already in – the challenge will land in your inbox automatically starting Tuesday, March 3rd.
(And expect to see an extra surprise coming on Monday, too!)
Free subscribers will get access to Day 1 and previews of the rest. To unlock the full challenge, you’ll need to upgrade your subscription.
Still a free subscriber? Claim your welcome discount to save 30% on an annual subscription.
Upgrading will give you access to this Leading Multigenerational Teams series plus our complete leadership development archive, which covers topics like:
Leading well as an Introvert
The top 5 leadership challenges each personality type faces
Leading through uncertain times
Managing stress at work
Leading remote (or hybrid) teams
Managing up to your boss
See You Soon
Leading a multigenerational team well doesn’t require you to become an expert on every generation. It just takes understanding what’s driving the differences – and knowing how to work with them instead of around them.
That’s exactly what this challenge is designed to help you do.
Can’t wait to dig into this with you.
P.S. We’ve got something special dropping Monday morning before the challenge kicks off. Stay tuned!