Leadership by 16Personalities

Leadership by 16Personalities

Baby Boomers at Work

Day 4 of the 5-Day Leading Multigenerational Teams Challenge

Carly from 16Personalities's avatar
Carly from 16Personalities
Mar 06, 2026
∙ Paid
Cartoon of a woman dragging an older man away from his office desk by his legs while he clings to the desk, as coworkers watch, with a caption joking that some boomers don’t want to retire but their spouses want them to.
Original artwork from cartoonist Jerry King

Welcome to Day 4 of the Challenge

Born between 1946 and 1964, the youngest Baby Boomers are in their early sixties and the oldest are pushing eighty – yet many of them are still in the workforce.

Some are staying by choice.

Others are working longer out of financial necessity.

And many are taking on part-time or advisory roles after stepping back from full-time positions.

A lot of the norms, structures, and professional expectations that many workplaces still run on reflect Boomer assumptions about what good work looks like. So understanding what shaped this generation isn’t just useful for leaders who manage Boomers, it’s also useful for understanding the systems we’re navigating at large.

Before we dive in, here’s a reminder of where we are in the 5-Day Leading Multigenerational Teams Challenge:

  • Day 1: Gen Z at Work

  • Day 2: Millennials at Work

  • Day 3: Gen X at Work

  • Day 4: Baby Boomers at Work (You Are Here)

  • Day 5: Navigating Multigenerational Conflict

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The Conditions That Shaped Baby Boomers

To understand how Boomers tend to show up at work, it helps to look at three formative forces.

1. Hard work as a navigation strategy

Many Boomers came of age during postwar economic expansion, when sustained effort and institutional loyalty were positioned as reliable paths to stability – and for many, that deal held. But the picture is more complicated than “Boomers had it easy.” They also navigated the stagflation and turbulence of the 1970s during early career years. What many absorbed wasn’t pure security – it was the belief that hard work and organizational commitment were the tools for navigating uncertainty, not avoiding it. That logic made sense in context. It also calcified, over time, into norms around presence and hours that later generations would come to experience as rigid or performative.

2. A generation that adopted technology – repeatedly

Boomers’ relationship with technology is frequently mischaracterized as one of resistance. In reality, many have navigated more significant technological transitions than any other generation: pre-computer offices, mainframes, personal computers, email, the internet, mobile technology, and now AI. Each shift required deliberate relearning. That doesn’t always produce intuitive fluency – but it often produces something else: a pragmatic skepticism toward novelty for its own sake, because they’ve seen enough technology cycles to know that not every new platform delivers on its promises.

3. Building from within the institutions they once questioned

The popular framing of Boomers as institutionalists who resist change misses that many of them were the generation that challenged institutions in their youth – civil rights, feminism, anti-war activism. What changed over time was method, not values: many moved from challenging institutions to working within and eventually leading them. The professional norms they internalized along the way – formality, hierarchy, long hours as a signal of commitment – were simply the prevailing norms when their expectations were forming. Norms feel like common sense when you grow up in them, which is exactly what makes them invisible until they create friction with someone who didn’t.

What this adds up to: None of these forces apply to every Boomer. But together, they help explain some common tendencies – a respect for established structure, a tendency to equate sustained effort with professional commitment, a preference for experience-based authority, and a more formal orientation toward professional communication.

Next, let’s look at how these formative conditions tend to play out in the three roles people occupy at work – as subordinates, colleagues, and managers.

Baby Boomers as Subordinates

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