June 6, 2024

Building a Benefits Strategy Around Your Multi-Generational Workforce

Before the 2020 pandemic flipped everything on its head, work had remained relatively unchanged over the decades. But after organizations had to adopt remote work, we started seeing other changes in the workplace — a stronger focus on well-being and putting people first. 

But we also saw something entirely new: the workforce became the most generationally diverse in history. Now, up to five generations — Traditionalists, Baby Boomers, Generation X, Millennials, and Generation Z — are working together and organizations must develop strategies to manage their multi-generational workforces.

In this blog, we'll explore traits of each generation and provide tips on how to develop a benefits strategy that resonates with them all.

The multi-generational workforce

As the name implies, a multi-generational workforce is one made up of workers from different generations with different expectations and outlooks. World events, upbringings, and unique lived experiences shape each generation differently, impacting their wants, needs, and values — in and out of the workplace.

Managing a multi-generational workforce presents organizations with a number of opportunities and challenges.

A few of those benefits include:

  • Increased innovation and creativity from diverse ways of thinking 
  • Different approaches to problem-solving based on various perspectives and lived experiences 
  • Higher productivity and efficiency from a more cognitively diverse workplace  
  • Two-way mentorship opportunities between new and experienced employees 
  • Distinct skills from each generation and the ability to transfer knowledge and skills 

But a multi-generational workforce isn't without some obstacles to overcome, like:  

  • How to respect each other's boundaries, particularly around work-life balance across generations 
  • Stereotypes about each generation and how to create a more open and inclusive work environment for everyone 
  • Different communication and collaboration styles and preferences and how to blend them seamlessly 
  • Established preferences on how to work and how to align different styles to be most effective 

Catering to the wants and needs of your employees can be tough with so many variables across generations. 

Baby Boomers and Generation X may value a 401(k) with company matching more than maternity or paternity leave. Or Generation Z and Millennials might crave a robust professional development budget that's less appealing to other generations.  

Such differences emphasize the need for a tailored benefits package that appeals to employees from each generation. We're breaking down each generation, what they value in the workplace, and how to create a benefits package each generation will approve of. 

Understanding your multi-generational workforce

Building a benefits package that addresses all your employees starts with understanding what they have in common and how they differ. First up: Traditionalists. 


Born between 1928 and 1945, many Traditionalists have retired, but a small part remain in the workforce in some industries. Though it’s more likely you won’t have to cater to this generation as part of your benefits strategy, it can still be beneficial to understand who they are and what makes them tick.  

Also known as the Silent Generation, Traditionalists are known for being silent to avoid causing trouble, a symptom of their upbringing amid the Great Depression and World War II.  

As the oldest generation still in the workforce, Traditionalists have a wealth of experience and often mentor younger generations. Like their moniker, Traditionalists hold traditional values at work, like:

  • Loyalty 
  • Helping others 
  • A strong work ethic 
  • Formality and respect 

Traditionalists crave respect, but, unlike their Boomer colleagues, they're also heavily motivated by money. And, as they age, benefits are becoming an even bigger motivator, like long-term care insurance and retirement plans that allow them to catch up. 

Baby Boomers 

Born between 1946 and 1964, Baby Boomers — Boomers for short — are likely to be the oldest generation in your workforce. Before Millennials, Boomers were the largest generation in history, partially due to the exponential increase in birth rates post-World War II. They're also the longest-living generation ever

Despite many Boomers reaching retirement age in 2011, many choose to work longer. Why?   

With salaries that still haven’t caught up to inflation, Boomers have to keep working. And the longer they stay in the workplace, the more time they have to add to their retirement funds while earning a salary. 

It also reduces how long they’ll need to rely on savings and retirement plans when they do eventually leave.  

So, what do Boomers care about at work? While younger generations have pioneered a healthy work-life balance, Boomers pride themselves on their work ethic, proudly touting the "workaholic" label. Some other characteristics commonly associated with Boomers include a highly competitive spirit, a desire for stability, a preference for traditional hierarchies, and the need to be recognized. 

1. Competition drives Boomers 

Driven by their competitive nature, Boomers are exceptionally hard workers with one main goal: to move their careers forward. They want to be the best at what they do — more than other generations — and want people to know about it. Titles with a level of prestige fulfill a Boomer's need to compete and win. 

2. Security is a top priority 

Despite being the generation most likely to have at least one retirement account, only 58.1% of Boomers have one. Coupled with concerns over when social security benefits will run dry, Boomers are anxious about financial security. They're looking for employers who will support their financial goals until they reach retirement age or willingly leave the workforce. 

3. They value the corporate ladder 

When Boomers entered the workforce, the culture was a far cry from today. It was structured and hierarchical — if you did exceptional work and paid your dues, you could climb the corporate ladder. This upbringing underscores some of the more traditional values Boomers hold about the workplace, such as: 

  • Giving authority only to those who have been working for decades 
  • Giving those who have worked their way to the top over the years leadership roles, not younger employees with limited experience 
  • Being loyal to companies 

4. Boomers want rewards, recognition, and benefits 

With financial security a top concern for Boomers, it's not surprising that employee benefits like a 401(k) with company match is a priority. Other benefits, like health insurance, especially as they age, are also appealing. 

But, for Boomers, it's about being recognized and rewarded for the work they do. Benefits are part of that, but they also want leadership and teammates to publicly recognize their efforts. Visibility is big, so tangible rewards and verbal shoutouts that show Boomers that their teams respect them are crucial. 

Generation X  

Likely the second-oldest cohort in your multi-generational workforce is Generation X (Gen X). Born between 1965 and 1980, Gen X is the smallest of the generations, with about 65 million people. They're often considered the middle child or Forgotten Generation because of their position between hard-working Boomers and tech-savvy Millennials. 

Despite being somewhat forgotten in the workplace, this generation is one of the most well-educated, bringing a wealth of skills to the workplace. Gen X is also the first generation where women are more educated than men.

Gen X grew up in a unique time when more women entered the workforce and single-parent homes became more common. Their unique upbringings earned Gen X their nickname — the Latchkey Generation — because they were so often home alone while their parents worked.  

Other characteristics that define Gen X include: 

  • Trailblazers for work-life balance 
  • Fierce independence 
  • A desire for stability, driven by financial stress 

1. Gen X demands work-life balance 

We can thank Gen X for introducing work-life balance. When Gen X saw their parents lose a lot of what they worked so tirelessly for, they began questioning whether it was worth it to work so hard just to deal with financial struggles later on. 

Gen X decided that a healthy balance was preferable to working so hard they'd miss out on life. Employees from this generation won't be working 14-hour days, missing their kid's soccer game, or mixing work with their personal lives.

2. They're strongly independent

Growing up, Gen X children had no choice but to become self-reliant. When they got home from school and their parents were at work, they had to be independent and responsible enough to get their homework done, make snacks, and find ways to entertain themselves.
This independence carried over into the workplace, with Gen X employees preferring to lead themselves over a micro-manager. They're generally less collaborative and subscribe to an "I'll figure it out on my own" mentality.

3. Financial worries drive Gen X 

Unlike any other generation, Gen X has significant financial strains from taking care of their elderly parents and their Millennial or Gen Z kids. And that's not all: Gen X is the only generation where most people don't think they'll be able to retire comfortably. 

While they didn't have to take out as many student loans as Millennials and Gen Z, Gen Xers still average nearly $50,000 in student loan debt — this accounts for 26% of the student loan debt in the United States. 

Needless to say, Gen Xers are worried about their finances. Their primary focus is a salary that can support everyone they're responsible for. Financial security is paramount. 


Millennials are the most populous generation with over 80 million people in the United States alone. They were born between 1981 and 1996, growing up at the turn of the millennium, experiencing the dot-com boom, and the rise of home computers, smartphones, and other technology. While Gen Z often gets credit for being the first generation to never know a time without the internet, most Millennials grew up with technology and are tech-savvy. 

But if there's one thing Millennials are known for, it's job-hopping and being the least engaged generation in the workplace — only 29% are engaged in work. They're also known for being the most educated generation in U.S. history. A few other characteristics include: 

  • Financial concerns driven by previous recessions and world events 
  • A "grass is always greener" mentality 
  • The need for flexibility 
  • Pioneers of a more equitable and inclusive workplace 

1. They're traumatized by the past 

Millennials dealt with the September 11, 2001 attacks, the 2008 recession, and low salaries that didn't account for inflation when they graduated college. While employment recovered from the Great Recession, Millennial wages never did. This had a profound impact on Millennials: 

  • It made them insecure about their finances 
  • They pushed back life events, like marriage and having kids 
  • Many lived with their parents longer 
  • It made salaries and benefits more important than company loyalty 

Millennials want financial security, even if that means going somewhere else. 

2. They're loyal to the salary and benefits

After the Great Recession and sub-par salaries, Millennials became loyal to the dollar. According to Gallup, this job-hopping generation is the most likely to switch jobs, with 60% open to a new opportunity. 

3. Flexibility is essential 

Unlike their Boomer counterparts, Millennials crave a more flexible style of work. Instead of the traditional 9-5, they want a more adaptable schedule that prioritizes a healthy work-life balance. 

4. Values matter  

Along with Gen Z, Millennials have strong opinions about diversity, equity, and inclusion (DE&I) in the workplace. It's not a nice to have — it's a must. They expect organizations to embrace individual differences and judge people based on their contributions.  

Millennials are also one of the more open generations, and they want to work with companies that align with their personal values and practice corporate responsibility. 

Generation Z 

As the newest member of the workforce, Gen Z is the youngest group. They also make up the most diverse generation in the workplace. They were born from 1997 onward and account for nearly 20% of the American population. 

Gen Z is known for a few things, namely being the first digital-native generation and their focus on mental well-being. Gen Z employees share some commonalities with Millennials, but they tend to be even more purpose-driven and entrepreneurial than their millennial counterparts. 

1. Gen Z is about their purpose and values 

Led by climate change activist Greta Thunberg, many Gen Zers are passionate about climate change and sustainable practices. They're activists and proud advocates of social and environmental change. Many were young adults as the Black Lives Matter movement came to a head, deepening their activist roots even more. 

And they expect their employers to be vocal advocates, too. But Gen Zers know when companies are true change agents or simply saying the right things — Gen Z expects tangible action. They want to work for organizations that: 

  • Allow them to do meaningful work 
  • Are socially and environmentally conscious
  • Embrace diversity and inclusion, treating everyone equally
  • Are unafraid to speak up about unjust wars, women's rights, and other social causes 

2. Mental health and well-being is the priority 

Many Gen Zers entered the workforce during the 2020 pandemic. They were in lockdown for part of their college years and had to start their careers fully remote. Gen Z also struggled to cope with spikes in racial injustices and social unrest. Combined, it took a toll on this typically idealist generation. 

  • Gen Z has the least positive outlook on life. 
  • 25% reported feeling more emotionally distressed than Boomers, Gen X, and Millennials. 
  • They report higher rates of mental health problems like anxiety and depression. 

But, unlike previous generations, Gen Z is proactive and open about discussing and seeking help for mental health issues. They'll take advantage of benefits like an employee assistance program (EAP), access to stress-reducing apps like Calm, and mental health days.  

3. Their tech skills are unmatched 

Gen Z kids were practically born with smartphones in their hands, and many can't live without technology — 86% consider it essential to their lives. Gen Z's obsession with tech shows up in the workplace, too, with 70% saying they'd leave their jobs for better technology. 

Gen Z employees want to work with employers that leverage tech for everything from communication and collaboration to automation that makes work more efficient. 

4. Gen Zers are entrepreneurs at heart 

With consistent tech layoffs over the past decade, growing debt, and an uncertain economy, many workers turned to part-time or freelance work and joined what's been coined "the gig economy." Gen Z embraced the gig economy to ease financial insecurity and let their entrepreneurial spirit loose. 

A study by TransUnion found that Gen Zers and Millennials make $2,500 or more per month with gig work, helping minimize their financial stress. Some have replaced full-time work in favor of freelance or contract work, while others supplement their income with side hustles. 

Why generational differences matter 

Aside from being able to better manage your employees based on their varied preferences, exploring how each generation is different — and similar — can help you build a better benefits package for your employees. 

Benefits play a pivotal role in whether a candidate accepts a job offer from your company, but they also contribute to employee satisfaction, which is a contributor to employee retention. Understand what your multi-generational workforce wants from you, by generation and collectively.  

A study from Forbes revealed that, across generations, flexible work options ranked first for preferred benefits. But when you take a deeper look, you see where the generations differ and where you can customize benefits to meet every employee's needs. 

What to consider when developing your multi-generational benefits strategy 

"We're in a new era — organizations now have the most generationally diverse workplaces in history. And while we've seen the benefits of this multi-generational workforce, many organizations are still struggling to adapt their benefits to match their unique and varied needs," says Jane Huston, chief people officer at OneSource Virtual. 

She's right. We reap the benefits our workforces bring — we now need to give them the benefits that matter most to them. But before you start adding or removing benefits, consider a few things.

1. Conduct a benefits analysis

Examine what basic and non-traditional benefits you already offer and if there are any gaps. Do you have any benefits your employees rarely use? Or is there something they've asked for, like mental health resources, that you don't currently provide? 

2. Offer customizable and flexible benefits

Let employees pick and choose the benefits they want with a flexible benefits plan to meet your employees wherever they are in life. Boomers may want more than one or two healthcare plans to choose from while Gen X and Millennials may prefer more retirement options. Flexible benefits get rid of the one-size-fits-all approach to create diverse benefits for your multi-generational workforce.

3. Create your communication plan

Think about how you'll communicate your benefits plan with employees, especially as you make it more customizable. Benefits can be confusing, so transparent communication that educates employees on personalized benefits and their options is crucial. Whether it's an FAQ page or a one-pager explaining benefits, make sure you give employees resources, too. Be sure to include a yearly training when enrollment opens to educate employees on what’s available.

4. Build your benefits plan around employee well-being

For example, if Gen Z employees need help planning for their financial futures, you could provide financial coaching and a streamlined way for them to auto-transfer money from their paychecks straight to a savings account. Or auto-deduct bills so they can better plan, add more shifts when money’s tight, and more. 

Challenges (and tips) to implementing a multi-generational benefits strategy 

Rolling out a multi-generational benefits plan can make a big impact on employees, but it's not without its challenges, like figuring out how to offer flexibility and the right approach to communicating with employees. Don't worry, these tips should help you overcome these obstacles. 

  • Include optional benefits that cater to each generation, like more retirement options or remote work flexibility that employees can opt in or out of. 
  • Communicate with your employees — they should know about their benefits options, when they begin, how they work, and more. 

3 strategies for rolling out your multi-generational benefits plan 

Ready to build and roll out the benefits plan for your multi-generational workforce? Start with your employees, start small, and make occasional adjustments.  

1. Examine your generational workforce

You may already track the demographics that make up your organization, but if generations aren't part of that research, they should be. As we've already seen, each generation is unique, with diverse characteristics, perspectives, and needs.  

Before making any changes to your benefits package, understand these differences — and similarities.  

  • What does the generational composition of your organization look like? If it's overwhelmingly Millennials, this can give you insights into which benefits may resonate most across the board. 
  • Which benefits are people using? Specifically, what generations are using which benefits? 
  • Are there any benefits that very few employees use? 

Once you examine your current offerings, understand the different generations in your workforce, and explore what employees are and aren't taking advantage of, start thinking about your new benefits package. Put together a proposal for leadership with new offerings, what to cut, and the data to explain the rationale.

2. Ask, "What do my employees want and need?"

Like any policy or program that'll impact employees, your multi-generational benefits plan should start with your people. Surveys are one of the best ways to do this because they yield insightful data straight from the people who'll use the benefits — your employees. They'll uncover information like: 

  • What benefits they want and need 
  • Where gaps are in existing benefits offerings 
  • How satisfied employees are with current benefits 
  • Which benefits matter and which don't 
  • Their level of awareness of current benefits 

Use this data to inform your new offerings and how you'll communicate them to employees. 

3. Make data-driven changes

Once everyone in your organization can access new benefits, start gathering more feedback and use it to make the necessary adjustments.  

But don't limit your surveys to just existing employees. What do candidates interviewing with you think of your benefits package? And what about employees who are on their way out? Their inputs could uncover hidden problems or gaps in your benefits offerings.  

You'll also want to track metrics like benefits usage and see if the new program impacts employee satisfaction and retention. By continuously reviewing these metrics, employee feedback, and the demographics of your employees, you can fine-tune your multi-generational benefits plan to be as effective as possible. 

Companies to inspire your multi-generational benefits strategy 

Building a flexible benefits strategy catering to employees from all four generations can be challenging. But these companies are leading the way and are a great place to look if you need help getting started.

AARP takes a unique approach, creating benefits based on their employee's lifecycle. 

  • They look at benefits through the lens of ages to create benefits tailored to different phases of their employees' lives. 
  • AARP treats menopause as a medical condition, so they have benefits to support women going through it, like meditation rooms where they can rest because sleep deprivation is a side effect of menopause. 
  • Employees enjoy caregiver and parental leave as they build families or need to care for their parents. 
  • They offer tuition reimbursement so employees who may be considering going back to school can do so. 

These are just a few of the many benefits AARP leverages to address the needs of its multi-generational workforce.

UPS piloted its on-site childcare benefit in 2022 at a California warehouse after experiencing a spike in sick days due to childcare gaps. The result? Retention increased 27% to a near-perfect 100% retention rate among hourly workers. Many companies have increased childcare benefits, and the results speak for themselves. 

  • 60% of parents at Etsy say this benefit has allowed them to stay in the workplace. 
  • Synchrony reduced unplanned absences by 45% among parent employees by offering 60 days of backup childcare. 
  • 86% of Fast Retailing employees said they're more likely to stay thanks to its $1,000 monthly childcare stipend. 

Ready to start your benefits transformation? 

Once you're ready to deploy your new benefits program, we're here to help. OneSource Virtual (OSV) delivers in-tenant technology and expert services to automate the administrative, transactional tasks of Workday benefits. With over 1,000 customers and 5% customer retention, OSV is the leading exclusive provider of Business-Processes-as-a-Service (BPaaS) solutions for Workday customers. 

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