Does Generation Matter in Workplace Change?

This week’s webinar sparked one of the most lively and insight-rich conversations
we’ve had all year. What began as a simple question—“Does generation
matter?”—quickly evolved into a thoughtful exploration of conditioning, expectations, feedback culture, and the messy beauty of multigenerational workplaces.

What Practitioners Are Seeing on the Ground

The chat lit up early with an observation many resonated with: Gen Y and Gen Z are far more willing to speak up. Some saw it as refreshing; others noted that
confidence can quickly flip into disillusionment when change is handled poorly.
Several participants raised an important nuance—are younger generations truly
“more positive,” or simply more vocal about what’s not working?

At the same time, attendees pointed out the flip side:

• Baby Boomers and Gen X often give feedback directly, preferring one-to-one
  channels.
  Many older workers carry conditioning that asking for help is “selfish” or a
  “weakness.”
  That conditioning can create friction when Ys and Zs ask clearly and
  confidently for what they need.

One of the standout moments was Sue D’s reflection: “Is it really neediness, or are
they simply better at asking for what they need?” . It was a question that caused many to pause… (shout out to Jillian Reilly, author of 10 Permissions!)

Common Threads Across Generations

Despite lively debate about differences, the chat strongly agreed on one universal
truth: all generations crave connection, clarity, and the feeling of being heard.

Whether you grew up being told to “just get on with it” (hello, Gen X) or taught that
speaking up is expected (hello, Gen Z), the underlying human needs remain the
same.

Participants also raised:

• The tension between positivity and scrutiny—too much optimism can mask
  real issues.
• The overemphasis on training as a silver bullet for change.
• The role of life stage, financial security, cultural background, and
  tenure—often more influential than generational labels alone.

Bias, Labels, and the Risk of Weaponising “Generations”

A recurring caution was the risk of turning generational labels into shortcuts or
stereotypes—what one attendee called the “lazy shorthand” for more complex
dynamics like aspiration, conditioning, or confidence.

Some attendees had witnessed generational framing being used as a form of quiet
discrimination (“She’s just a Millennial,” “He’s old-school”). Others asked for
strategies to challenge derogatory language when they hear it.

The most grounding reminder came late in the session:

Our job is to unpack the person in front of us, not design for the label.

A Final Insight: Generational Differences Are a Doorway, Not a Destination

While opinions varied, participants agreed the generational lens can be helpful—if
used as a doorway to deeper inquiry, not as a box to sort people into.
Some suggested surfacing conversations about “growing up stories” as a way to
build empathy and context across age groups. Others noted the opportunity to
support older workers navigating longer careers, cognitive and physical changes,
and caregiving responsibilities.

The Collective Verdict

Generations matter…
but not in the way we think.

What matters more is:

• Conditioning: what each cohort was taught about work, voice, and worth.
• Context: culture, tenure, security, identity, upbringing.
• Capability: how well leaders create clarity, safety, and collaboration for
  everyone.

And above all:
Designing change for real humans, not generational caricatures.

A big thanks to Teamgage for sharing their research and the fabulous attendees who shared so generously!

Watch the replay below