Your Leading Multigenerational Teams Challenge Recap
Missed a day or two (or five)? Catch up here.
Last week, we explored how each generation tends to show up at work – as subordinates, colleagues, and managers – and what leaders can do when those differences create friction.
Whether you followed along daily or you’re just discovering this challenge now, here’s a quick overview of what we covered so you can jump to the section that’s most useful to you.
If you haven’t already done so, be sure to download your copy of the Generational Workplace Tendencies Guide – a practical, at-a-glance reference for understanding how different generations tend to show up at work.
Day 1: Gen Z at Work
Best for: Leaders managing their newest employees, anyone navigating the gap between Gen Z’s expectations and older organizational norms, or managers trying to build trust with early-career employees.
You’ll learn:
What economic, technological, and cultural conditions shaped Gen Z’s expectations about work
How Gen Z tends to show up as subordinates, colleagues, and early managers
What the most common Gen Z friction points actually signal – and how to respond without defaulting to frustration
Day 2: Millennials at Work
Best for: Leaders managing or working alongside the generation now shaping organizational culture, anyone trying to make sense of the generation now occupying every level of the organizational hierarchy, or Millennial managers who want to see their own tendencies more clearly.
You’ll learn:
How high expectations followed by economic disruption shaped Millennial workplace instincts
How Millennials show up as subordinates, colleagues, and managers
Why Millennials are often caught between older organizational norms above them and newer Gen Z expectations below them
Day 3: Gen X at Work
Best for: Leaders managing Gen X, anyone who wants to understand the conditions that shaped this generation, or Gen X managers and employees who want to see their own tendencies more clearly.
You’ll learn:
Why self-reliance and institutional skepticism were rational responses to Gen X’s formative conditions
How Gen X tends to show up as subordinates, colleagues, and managers
Why Gen X employees’ engagement is easy to underestimate – and what leaders miss when they do
Day 4: Baby Boomers at Work
Best for: Leaders managing or working alongside the generation that built many of the systems everyone else is navigating, anyone who wants to understand Baby Boomers better, or leaders new to managing older employees.
You’ll learn:
How postwar prosperity, repeated technological transitions, and institutional norms shaped Boomer workplace expectations
How Boomers show up as subordinates, colleagues, and managers
Why understanding what shaped Boomers matters for understanding the workplace itself – not just the people in it
Day 5: Navigating Multigenerational Conflict at Work
Best for: Any leader who has felt the quiet cost of generational tension on their team, managers navigating AI adoption disagreements, or anyone who wants practical tools for working across generational lines.
You’ll learn:
Why generational conflict is more costly than most leaders realize
How to navigate three specific friction points: AI adoption, differing definitions of hard work, and memory bias
Why every generation tends to believe the one behind them has it easier – and what to do about it
What’s Next
You’ve now worked through all four generations and the most common friction points that show up between them.
Next up: We’re adding another layer to this picture: personality! We’ll be exploring how each personality Role – Analysts, Diplomats, Sentinels, and Explorers – shows up at work across every generation. Stay tuned for the Analyst article releasing next week.
Know a leader navigating a multigenerational team? Share this challenge with them. This article is free and open for anyone to read.




