The Generation Game

Understanding the Challenges and Benefits of Today’s Unique Multigenerational Workforce

By Kimberly Olson

Feature2.1Every day, about 10,000 baby boomers retire. As they depart, and as Millennials continue to arrive and step into leadership roles, companies are undergoing an unprecedented shift.

“Over the next ten years, we’ll see the greatest transfer of knowledge in the history of the world,” says Chip Espinoza, director of organizational psychology for the School of Professional Studies at Concordia University Irvine and coauthor of Millennials Who Manage and Managing the Millennials. “This is tacit knowledge that is experiential. It’s not written down. It’s transferred through relationships. If that knowledge walks out the door when baby boomers retire, companies will lose a big competitive advantage.”

Now more than ever, it’s crucial that younger and older employees forge close working relationships. Companies that can help employees do that, experts say, will see benefits beyond ensuring a smoother knowledge transfer.

Research shows that diversity sparks greater insight when it comes to problem solving and innovation—and generational diversity adds yet another layer of richness. “A successful work team should consist of multiple generations, personalities, and talents, all working toward a common goal,” says Rich Milgram, CEO of Beyond, The Career Network. “That diversity enables teams to tackle challenges by leveraging fresh perspectives.”


While experts tout the benefits of multigenerational work teams, there’s been lots of buzz about the cultural clash between the Millennials, Generation X, and the baby boomers—driven by their values, preferences, and work styles.

Companies have always welcomed new generations into the workplace, so why all of the angst around today’s multigenerational workforce?

We’ve entered a unique era, experts say, because the generations have become more distinctive than in previous times. “The more social change that happens, the greater the differences between generations,” Espinoza explains. “If everybody grew up in a tribe on the Amazon, you wouldn’t have much change.”

But in our more dynamic society, social changes have widened the generation gaps. One is upbringing, with the younger generation being more openly communicative. “These children were raised in dialogue,” says Chris DeSantis, principal at and an expert on generational differences in the workplace. “The other generations were raised in a tell mode: ‘You do as I say.’” So older generations are comfortable in the workplace, which is hierarchical, because it mimics how they were raised at home. That hierarchy isn’t quite as familiar for Millennials. Older employees will say, ‘Why are they acting this way?’ But they’re not acting in any way. This is how they behave naturally.”

Also, Millennials are the first generation who haven’t needed an authority figure to access information. “The last place they’ll go for information, many times, is an authority figure,” Espinoza says. “At work, that’s perceived [by older employees] as disrespectful: ‘They think they know more than I do.’ So companies that want to help Millennials transition should focus on the quality of the relationship between managers and Millennials.”


Smart organizations will find ways to help bridge the generation gaps. As Milgram cautions, “When there is doubt or distrust along generational lines, the workforce fails to operate at its greatest potential.”

DeSantis says that every new generation was once considered a problem. “Young boomers were seen as hippies, young Gen Xers were seen as slackers, and Millennials struggle with the mantle of entitled. Every generation self-corrects.”

Meanwhile, it’s important to remember that attitudes and values can cross over generational lines. Both baby boomers and Millennials, for example, value using their work to contribute to society.

When employees better understand one another—and themselves—walls break down, spurring more vibrant, productive working relationships. Differences can even morph into valuable learning opportunities. Gen Xers may feel that younger people overshare, for example, but DeSantis says that Gen Xers often don’t share enough. “If you want people to be more empathetic, you have to develop relationships and share,” he says.

Younger employees, of course, are also tech savvy. “Millennials grew up with tech,” says Chris Szpryngel, acting dean of the Malcolm Baldrige School of Business and an expert on aging in the workplace. “GE started doing a reverse mentoring program where the younger employees mentor older ones on how to use technology.” Such programs have become increasingly common.


Law firm DLA Piper, which has four generations of employees under its roof, takes a thoughtful, holistic approach to helping them work together.

“One thing we focus on is empthy,” says Genhi Givings Bailey, director of diversity and inclusion. “Now that we’re smart about these generational differences and understand how the other party communicates—are they a texter or an emailer, or a come-and-sit-down-in-my-office?—we’re using that to motivate people to be proactive and engage. It’s an awareness of differences and being sensitive.”

The firm has engaged DeSantis to conduct educational sessions with various groups. “One of the things we play with is how Millennials present themselves,” he says. “I teach them how to navigate the system. They have to accommodate some of that system, but I teach them how to play within it.”

“Both the Millennials and the older generations are thinking about their own work styles, and they’re approaching the challenges with more empathy,” Givings Bailey says. “People walk away from these sessions and they’re really energized.”

Leaders at DLA Piper know that they can also benefit from bringing various ages to the decision-making table. Some of the firm’s committees within D&I were partner heavy, for example, so seats are being allocated for employees at other levels. “People are contributing at a high level,” Givings Bailey says. “There’s a lot of energy.”


Meanwhile, at AT&T, Constance “Connie” Missimer, a senior manager of user experience design, gets pumped up about using scientific data to help different generations “get” one another.

“My passion is to understand the neurobiology of the brain as it ages,” says Missimer, who has given a TEDx talk on the subject. “It’s not one of inevitable cognitive decline and black balloon parties. You’re creating 5,000 more neurons every day. As long as everything is working OK, we all have Ferrari brains. But younger people have less terrain to go through, whereas for an older person, it’s a road trip.” She says this can be the source of innocent frustration for younger workers, as their older coworkers may ponder longer.

A University of Toronto study found that people with aging brains are also more easily distracted, but there’s an upside—they’re able to use the distracting information to better solve problems. Their broader focus of attention is actually associated with greater creativity. So employees of different ages—besides bringing varied life experiences to the table—may also bring different thought processes

“I’m a nutcase on the data,” Missimer says. “I like to enlighten people about the cognitive strengths of both older and younger people. When people who are different get together to work, it results in more creative output, which makes for a more profitable company.”

Missimer leads a 50 and Forward employee resource group with about 3,000 members, which sometimes partners with a group for younger workers called Oxygen. “They do infuse a lot of oxygen into the company,” Missimer says. “We team up with them to go out to retirement homes and show people the basics of cell phone use.”

Along the way, solid cross-generational relationships form. “I’m having a ton of fun with someone who is younger than my daughter—she’s probably 24—and there’s no friction,” Missimer says. “We get together and figure [work-related] things out, and then get a latte and chat about other things.”


New York–based public relations firm MWWPR, too, sees age diversity within its ranks as an opportunity.

Like many companies, the firm has a growing number of younger employees—and it’s eager to mine their insights. So last summer, CEO Michael Kempner met with Emily Graham, the firm’s group vice president of corporate communications. “He wanted to figure out how to channel the energy of Millennial employees and heighten engagement,” says Graham. “He said, ‘How do we make their voices heard? Go out there and tell me what you come up with.’”

From that effort arose Verge, a council of representatives of younger employees who brainstorm fresh solutions. Graham’s team asked senior leadership to send the names of their superstars. “They sent us the names of 20 people—from London, Los Angeles, Dallas, New York,” Graham says.

Verge tackles everything from work-life balance, to improvements in the office environment, to cross-team collaboration. They helped launch a program, for example, that allows New York and San Francisco employees to swap office locations for the summer.

Although Verge was primarily created to engage Millennials, Graham—a Millennial herself—says the group is hardly insular. “We don’t want Millennials to be over here and other generations over here,” she says. “We’re anticlique. We want to create collaboration. Verge is helping to put front and center some of the [problems] that can crumble a business, and there are benefits to having so many walks of life and insights. We want to be sharper, smarter. And if you’re not bringing the different generations together, you’re not doing your best work.”

Graham brims with infectious optimism, while also acknowledging the challenges. “I’m a Millennial who manages other Millennials, but my coworkers and colleagues are senior leadership,” she says. “So people come through my door who have a Millennial issue. This is my reality. There’s a perception that Millennials are entitled, annoying, fill-in-the-blank—any stereotype you can think of. And Millennials might think of their managers as stifling, controlling, fill-in-the-blank. You need to get people to speak one another’s language. How do we communicate about the elephants in the room so we can be more collaborative?”

To help employees understand one another, MWWPR is planning an orientation series on managing Millennials—as well as one on being managed by Millennials. “I’m a Millennial, and there are boomers on my team,” Graham says. “They’re my parents’ age. So how do you maintain respect but keep things happening?”

That’s becoming a common scenario. “Multi-Generational Leadership,” a study conducted by Beyond, The Career Network, surveyed 5,771 respondents and found that 83 percent of employees have seen Millennials managing Gen Xers and baby boomers in their office. But 45 percent of baby boomers and Gen Xers surveyed feel that Millennials’ lack of managerial experience could adversely impact a company’s culture. At the same time, over one-third of Millennials say that it’s difficult to manage older workers.

Orientation training programs like those at MWWPR can help build intergenerational trust and teamwork.

Ongoing mentorship and coaching can also sharpen Millennial leadership skills, yet only 47 percent of survey respondents said they work for a company that has a formal mentorship program to support their leadership development.

Meanwhile, team-building exercises can build trust between workers. As Miligram says, “My team has engaged in everything from brainteaser activities to off-site boot camps, where [employees] escape their comfort zones and view colleagues’ abilities through a fresh, new lens.”

Bottom line: Organizations that help older and younger workers connect will reap benefits. “The cool thing about generational diversity is that it’s the most inclusive topic under the diversity umbrella,” says Givings Bailey. “Everyone can see him- or herself within this, so people really engage—and it’s also a lot of fun.” 


Today’s Generations

  • Silent Generation Born: 1925 to 1946
  • Baby Boom Generation Born: 1946 to 1964
  • Generation X Born: 1965 to 1979
  • Millennial Generation Born: 1980 to 1999  (Generation Y)
  • Generation Z Born: 2000 and after

So Your Boss is a Millennial?

You have a new boss—and you were a college sophomore when she was born. You may feel a bit awkward at first, but recognize that this is hardly a unique situation in today’s workplace. Here’s what the experts say.

Be respectful. The situation may be uncomfortable initially, but keep in mind that your younger boss may be struggling as well. He or she may be intimidated by your experience, for example. You’re both in this together, so treat it like any other relationship in the office—professionally.

Take age out of the equation. It can be tempting to say, “My generation feels this way,” but resist the urge.

Be open to new ideas. Avoid saying, “This is the way we’ve always done it.” The world is changing, and your boss’s job is to make sure that your workplace keeps up.

Contribute. Do what you always do—provide useful information and pitch solutions.

Culture Shift

By 2020, Millennials will make up half of the workforce. Younger workers are a diverse bunch, but they tend to have some common beliefs and attitudes that are bound to shape workplace policy and culture.

Money isn’t everything.

A 2011 study of 4,300 college graduates under age 31 by PwC found that Millennials’ top workplace value is work-life balance. Upon joining the workforce, 28 percent said that work-life balance at their company was worse than they expected.

The pleasure is in the journey.

Older generations generally decided on a career in their 20s. Millennials were encouraged to explore their passions, and they take about seven years longer than previous generations to settle into a choice, so their focus is usually on the next year to two.

Diversity matters.

Millennials are the most diverse generation yet, and they want to work at companies with strong diversity policies. At the moment, many are not impressed. Over half of respondents to the PwC study said that while companies talk about diversity, they don’t feel that opportunities are equal for all in the workplace.

Men and women should share the career spotlight.

Millennial men are more comfortable working for a female boss, for example. And a 2014 Mayflower survey found that 72 percent of Millennials would support a move for a wife’s job, compared to 59 percent of boomers and just 37 percent of preboomers.

Kimberly Olson is Diversity Woman’s managing editor.


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