Generations at Work: Shifting, Sharing, Parenting, and Pressures

March 10, 2023



Generations at Work: Shifting, Sharing, Parenting, and Pressures

Generations at Work: Shifting, Sharing, Parenting, and Pressures

David Stillman is a generational expert, researcher, consultant, and author of three best-selling books on generations. David explains how the major events and prevailing technologies of our early lives shape us and our thinking, producing generational characteristics. He describes the effect of parenting trends on generations’ offspring and how these translate into workplace behaviors. David shares insights on issues causing friction and concern between and among generations including “entitlement”, quiet quitting, side hustles, and mental health.


[02:29] Starting as a journalist, David is asked to study Generation Xers.

[03:40] How generations’ size in the labor market matters as well as inflow and outflow.

[04:40] The ghost of the Traditionalists’ culture still lingers in many workplaces.

[05:20] David believes companies will be haunted by lack of knowledge transfer as Boomers retire.

[06:57] How Boomers disseminate knowledge could be improved and be better received.

[07:19] David sees good healthcare plans as a competitive advantage.

[08:55] Boomers raised Millennials and are more familiar with them—so why the complaints?!

[09:33] 80 million strong, Baby Boomers faced much competition as well as structure, rules, and policies to manage them.

[10:38] Boomers parented their Millennial children to be collaborative—even rule-breakers at home.

[13:20] How technology enhanced Millennials’ group orientation.

[14:50] As a smaller generation, Gen Xers didn’t have to follow policies and procedures, were enabled by technology, and raised independent Gen Z kids.

[16:05] Gen Zs are more competitive and results-focused than Millennials.

[18:42] Employee behavior that many people call “entitled”, David sees as “engaged”.

[22:10] “Quiet quitting” began with Gen Xers and relates to (a lack of) job security.

[23:42] Why would someone go “above and beyond” without any guarantee—just the possibility of burning out?

[24:57] David observes older generations measuring loyalty in tenure rather than engagement and performance which are harder to measure.

[26:59] David discusses the relationship between engagement, performance, and side hustles.

[28:51] How side hustles can support mental health, work-life balance, and skills acquisition.

[31:37] Millennials were smart, changing the tenure paradigm, saying “If I’ve mastered these skills promote me.”

[32:07] Gen Zs are showing interest in pursuing more than one career at one company at the same time.

[33:37] All generations have had work stress, but it could be left at the workplace in the past.

[34:34] New approaches and ideas support mental health at work.

[36:11] Encouraging judgment-free dialogue about mental health.

[38:15] It’s not about who is right or wrong, better or worse—the generations are different.

[38:08] IMMEDIATE ACTION TIP: First, sit down with people from different generations and ask them about a major event that has shaped who they are today. The next step is to ensure there is generational diversity at work especially when targeting any particular generation.


“Everyone's talking about Gen Z right now, and I'd say you need to look at the top of your chart because you're going to have a mass exodus of Baby Boomers and close to half the labor pool to fill those leadership positions.”

“One of the biggest things I think that’s going to haunt organizations is this lack of knowledge transfer.”

“You will not find a generation more collaborative than Millennials.”

“A lot of Baby Boomers did really struggle with the notion of going from competitive rules and procedures to ‘let’s reinvent them’.”

“For every time someone is trying to use the word ‘entitled’, I ask them instead to exchange it with the word ‘engaged’.”

“The side hustle is not only here to stay, but I would say everyone should be embracing it.”

“The first quiet quitters were actually Gen Xers. And anyone sitting in a Gen Z’s or Millennial’s chair would do the exact same thing.”

“Work is no longer a place and time. I do not believe in Monday to Friday, nine to five. We will never have a four-day work week. It's going to be a seven-day work week and a seven-day live week.”