Working and Leading Across Generations By Deborah Gray-Young

Deborah Gray-Young is a former advertising agency executive who now serves as a trusted advisor to senior executives and SMB CEOs. Known for distilling complexity, challenging assumptions, and clarifying high-stakes situations, she brings candor, strategic insight, and a grounded perspective that helps leaders see possibilities and lead with intention.

We talk a lot about generational differences, especially in the workplace. Sometimes so much so that it becomes a self-fulfilling prophecy. Labels like Boomer, Gen X, Millennial, and Gen Z can help us spot broad trends in values, motivators, and communication styles. But they can also lock us into assumptions and stereotypes that limit real leadership. 

Over two editions, Leadership Axis will unpack the generational puzzle, without getting lost in the labels and stereotypes, so you can focus on leading people, not categories. We’ll unpack motivations, communication styles, and decode generational differences, some of the popular stereotypes associated with each generation, and what can be done to counter those stereotypes. 

There are at least four generations in the workforce, depending on which source you consult. Generational labels can be useful, giving us broad clues about what people value, how they communicate, and what motivates them. But they can also turn into lazy shortcuts that keep us from leading effectively. We hear some clichés far too often:

 “Boomers don’t want to change.”
 “Gen Z doesn’t even read emails.” 

Here’s the thing: Labels can help us understand broad patterns, but they can also get in our way if we treat them as facts. Understanding generational trends is useful until they become an excuse. These aren’t “truths,” just tendencies we talk about. When we lean too hard on them, we risk missing the person and what they have to offer, who might be right in front of us. 

Consider two common traps:

• Stereotyping as shorthand: “He’s a Boomer, so he’ll resist change.”
•  One-size-fits-all messaging: “Let’s TikTok it so Gen Z will pay attention.”

I don’t suppose I need to point out that this pertains to every other type of difference as well, including gender, racial, ethnic, geographic, and religious.

At the end of the day, great leadership meets people where they are and helps them deliver their best work, regardless of their birth year.

Working and Leading Across Generations

By Deborah Gray-Young

Here’s a quick look at what generational “labels” often describe without reducing people to the labels.

Motivators and Communication Preferences by Generation  

Some Things to Think About:

If you work with multiple generations, how often do you catch yourself making assumptions based on generational labels?

• How well do I understand what actually motivates my team?
• What small change can I make this month to improve cross-generational communication?
• Where do I lean on generational shorthand instead of real listening?  
• What can I do to model curiosity and respect across age groups?  

Learn more about Deborah:

Twitter: @coachdgrayyoung

G: @d.grayyoung

LI: Deborah Gray-Young