The 37-Year-Olds Are Afraid of the 23-Year-Olds Who Work for Them

As a millennial with a habit of lurking on TikTok, Jessica Fain understood that skinny jeans and side parts were on the steady march toward extinction. But when Ms. Fain, who works as a product manager at a large tech company, heard that some of her favorite emojis might also be confronting retirement — namely that laughing-sobbing face — she decided to seek the counsel of her junior colleagues.

“I heard that using this emoji isn’t cool anymore,” Ms. Fain, 34, said she wrote in a water-cooler-type Slack channel.

“Yeah I only use that emoji at work for professionalism,” she recalled a younger employee replying. “H8 2 break it to 2 u Jess.”

Ms. Fain is old enough to remember when millennials determined what was in vogue: rompers, rose pink, craft beer, Netflix and chill. Now, she gets the foreboding sense from colleagues that her AARP card awaits. Subtly yet undeniably, as generational shifts tend to go, there’s a new crop of employees determining the norms and styles of the workplace. And they have no qualms about questioning not just emoji use but all the antiquated ways of their slightly older managers, from their views on politics in the office to their very obsession with work.

“I feel very sure that I’m uncool,” said Andy Dunn, 42, who co-founded the upscale apparel brand Bonobos, once the uniform for a subset of millennial men. “I’ve come to accept that.”

Andy Dunn relies on his youngest employees to help him keep up with the sensibilities of Gen Z.Credit…Lyndon French for The New York Times

It’s a fault line that crisscrosses industries and issues. At a retail business based in New York, managers were distressed to encounter young employees who wanted paid time off when coping with anxiety or period cramps. At a supplement company, a Gen Z worker questioned why she would be expected to clock in for a standard eight-hour day when she might get through her to-do list by the afternoon. At a biotech venture, entry-level staff members delegated tasks to the founder. And spanning sectors and start-ups, the youngest members of the work force have demanded what they see as a long overdue shift away from corporate neutrality toward a more open expression of values, whether through executives displaying their pronouns on Slack or putting out statements in support of the protests for Black Lives Matter.

“These younger generations are cracking the code and they’re like, ‘Hey guys turns out we don’t have to do it like these old people tell us we have to do it,’” said Colin Guinn, 41, co-founder of the robotics company Hangar Technology. “‘We can actually do whatever we want and be just as successful.’ And us old people are like, ‘What is going on?’”

Twenty-somethings rolling their eyes at the habits of their elders is a trend as old as Xerox, Kodak and classic rock, but many employers said there’s a new boldness in the way Gen Z dictates taste. And some members of Gen Z, defined as the 72 million people born between 1997 and 2012, or simply as anyone too young to remember Sept. 11, are quick to affirm this characterization.

Ziad Ahmed, 22, founder and chief executive of the Gen Z marketing company JUV Consulting, which has lent its expertise to brands like JanSport, recalled speaking at a conference where a Gen Z woman, an entry-level employee, told him she didn’t feel that her employer’s marketing fully reflected her progressive values.

“What is your advice for our company?” the young woman asked.

“Make you a vice president,” Mr. Ahmed told her. “Rather than an intern.”

Gen Z doesn’t hesitate

Starting in the mid-aughts, the movement of millennials from college into the workplace prompted a flurry of advice columns about hiring members of the headstrong generation. “These young people tell you what time their yoga class is,” warned a “60 Minutes” segment in 2007 called “The Millennials Are Coming.”

Over time, those millennials became managers, and workplaces were reshaped in their image. There were #ThankGodIt’sMonday signs affixed to WeWork walls. There was the once-heralded rise of the SheEO.

Millennials point out that for a generation of workers who entered the office during and after the 2008 financial crisis, and felt lucky to land any type of work, it’s unsurprising to see a premium placed on “hustling.” Gen Zers, meanwhile, are starting their careers at a new moment of crisis — in the midst of a pandemic that has upended the hours, places and ways we’re able to work. A fall 2021 survey of Gen Z job candidates from the recruitment software company RippleMatch found that more than two-thirds wanted jobs that will indefinitely stay remote.

The generational frictions are now particularly apparent in companies run by and catering to a largely millennial demographic.

Gabe Kennedy, 30, founder of the herbal supplement brand Plant People, noticed as he recruited Gen Z employees that some had no interest in the rigid work habits that felt natural to his mostly millennial 10-person team. He and his co-founder were accustomed to spending late nights in the office obsessing over customer feedback and sharing Chinese takeout. His youngest employees preferred to set their own hours.

Mr. Kennedy interviewed a Gen Z candidate for a full-time position who asked if she could stop working for the day once she’d accomplished the tasks she’d set out to do. He responded that her role was expected to be a nine-to-five.

“Older generations were much more used to punching the clock,” Mr. Kennedy mused. “It was, ‘I climb the ladder and get my pension and gold watch.’ Then for millennials it was, ‘There’s still an office but I can play Ping-Pong and drink nitro coffee.’ For the next generation it’s, ‘Holy cow I can make a living by posting on social media when I want and how I want.’”

Ali Kriegsman, 30, co-founder of the retail technology business Bulletin, wasn’t sure, in the past, how to respond when her Gen Z employees insisted on taking days off for menstrual cramps or mental health: “Hey I woke up and I’m not in a good place mentally,” went the typical text message. “I’m not going to come in today.” Instinctively Ms. Kriegsman wanted to applaud their efforts to prioritize well being — but she also knew their paid time off could undercut business.

“As an entrepreneur, I want to call out of managing my team sometimes because my period is making me super hormonal,” she said. “But I’m in a position where I have to push through.”

Managers, like Ms. Kriegsman, understand the instinct Gen Zers have to protect their health, to seek some divide between work and life — but some are baffled by the candid way in which those desires are expressed. They’re unaccustomed, in other words, to the defiance of workplace hierarchy.

Lola Priego, 31, chief executive of the lab-testing start-up Base, had to laugh when a Gen Z employee sent a Slack message assigning her a task to complete. Ms. Priego interpreted this as a welcome signal that her 15-person staff doesn’t find her intimidating, but another member of upper-level management was horrified.

Polly Rodriguez, 34, chief executive of the sexual wellness business Unbound, said: “When I was entering the work force I would not have delegated to my boss. Gen Z doesn’t hesitate to do that.”

Polly Rodriguez, the co-founder of Unbound.Credit…Dave Sanders for The New York Times

‘These are political tomatoes’

Has anyone checked in on the kids? They’re talking differently, texting more, wearing the wrong clothes, still texting. Do they ever put down their phones?

Researchers call this the “kids these days” effect — and note it has been happening for millenniums. “It’s a natural thing that people tend to complain about everyone younger than them, going back to the Greek philosophers,” said Cort Rudolph, an organizational psychologist.

Each new generation, christened by marketers and codified by workplace consultants selling tips on how to manage the mysterious youth, can strike the people who came just before them as uniquely self-focused. First came the “me” generation, then the “me, me, me” generation.

Still, many managers feel that ignoring the divide between young and the slightly less young isn’t an option. It shapes hiring. It shapes marketing. And over the last year, it has shaped the way companies respond to a country in tumult.

In June 2020, as Black Lives Matter protests swelled across the country, the Slack channels of corporate America faced their own form of reckoning. For Ms. Rodriguez, it started with a Saturday morning phone call.

Ms. Rodriguez’s co-founder at Unbound, which sells vibrators, called to say that their social media manager, a younger employee, wanted to know what the company planned to do to support the protests. Ms. Rodriguez didn’t usually receive calls on the weekend; she knew that for her employees this signified a state of emergency. But she also wanted time to plan the team’s response. Within days, her company hired a diversity, equity and inclusion firm to offer employee trainings and started a fund-raiser for a group supporting sex workers of color.

Ms. Rodriguez is one of many managers who recalled her Gen Z employees being the first and most vocal in urging companies to demonstrate their support for the protests after George Floyd’s killing. Tero Isokauppila, 37, president of a food business, heard from junior staff asking if his company would post a black square in solidarity with the movement on Instagram. Elaine Purcell, 34, co-founder of the maternity care start-up Oula, got a Slack message from one of her youngest workers after the shootings at Atlanta-area spas in March asking what the team could do in solidarity with Asian Americans.

To many corporate leaders, this invites a welcome correction after decades when businesses were largely silent on racial inequities both within and outside their offices. But some managers are also struggling to balance the demands of their employees for political engagement with their own sense of what’s appropriate for their brands.

“You talk to older people and they’re like, ‘Dude we sell tomato sauce, we don’t sell politics,’” said Mr. Kennedy, co-founder of Plant People, a certified B corporation. “Then you have younger people being like, ‘These are political tomatoes. This is political tomato sauce.’”

Many are aware, too, that a misstep can lead to backlash, or call-outs from staff: “Some young former employees are much more willing to burn bridges,” Ms. Rodriguez said. “To me it’s shortsighted. Is it worth the social clout of getting gratification on social media but then trashing someone who could continue to help you professionally?”

Mr. Dunn, who left Bonobos and is now founding a social media company, hired a Gen Zer to read a draft of a book he’s writing and notify him of any potentially insensitive or inflammatory language. Within a day, she had left 1,100 comments in the document. Mr. Dunn has also begun trying to monitor his gendered language in the office — instead of “guys,” saying “people,” or better yet “y’all.”

“I’m like, ‘Let’s go y’all,’ even though I’m from Illinois,” Mr. Dunn said. “I had a wake-up around Juneteenth when someone was like, ‘Hey are we off?’ I was like, ‘Oh, of course we’re off.’ But I hadn’t thought about that.”

For Mr. Dunn, it was a reminder of how much he relies on his youngest employees. He’s fluent in millennial, but that doesn’t mean he knows all the sensibilities of Gen Z.

He realized that knowledge matters for his bottom line. Entry-level employees might scold him, but they also know what their peers like. “You want to be close to the culture,” Mr. Dunn said.

At many businesses, Gen Z employees are given increasing leeway to drive internal culture, too. Emily Fletcher, 42, who runs Ziva Meditation, noticed that at her company retreat the junior people were the ones who were most comfortable stretching the bounds of what is considered professional conversation.

This became apparent when the staff participated in an exercise she calls the “Suffie Awards”: sitting around a campfire and sharing personal sources of suffering from last year, trying to one-up one another as corny award show music played in the background. It was the Gen Zers, Ms. Fletcher said, getting the most vulnerable by speaking about partners cheating on them or the loneliness of a solo quarantine.

“They celebrate human emotion, instead of having an outdated framework of what corporate should be,” Ms. Fletcher said.

Her company culture has relaxed even more, she added, since the departure of her oldest employee, who was 48. “Now everyone feels safe to be a little more weird.”

As the millennials have made clear through their own workplace ascent, one generation’s weird can quickly become the new normal.

“I think it’s already happening,” said Mr. Ahmed, the Gen Z consultant. “Do I think we already control the power? No. But we’re pushing the envelope.”

And for his part, he confirms that the laughing-sobbing emoji is dead: “It’s an ironic thing, it’s kitschy. I would usually just say LOL.”

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