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Engaging Every Generation: Leaders' Tips for a Diverse Workforce

What’s the biggest hurdle to effectively managing and engaging a multigenerational workforce? 

And how can leaders overcome it? 

These are crucial questions for organizations seeking to thrive in today’s diverse work environment. 

To find answers, we went straight to the source, asking HR and business leaders from various industries to share their perspectives. 

Each expert offers a unique challenge they’ve encountered, paired with a practical solution they’ve found effective. 

This HR Spotlight post compiles their insights, providing a valuable resource for anyone navigating the complexities of a multigenerational team.

Read on!

Yosef Adde
Owner, Buy Houses Torrance

Yosef Adde

One of the significant difficulties in handling a multigenerational workforce is the difference in communication style preferences.

For instance, younger workers are more inclined towards instant messaging, via Slack for example, while their older colleagues may be more interested in interacting through phone calls or prefer longer emails.

This is a problem since it may foster misunderstandings and disruption in working together.

Putting diverse communication into practice is one practical solution to this challenge.

Get team members to reveal their preferred modes of communication and use technology that fills such gaps, such as hybrid meetings where participants can attend both physically and virtually.

Also, creating an environment where team members elaborate on “why” they do things in a certain way can be helpful in building the understanding and respect among the team members.

Casey Cunningham
Founder & CEO, XINNIX

Casey Cunningham

One distinct challenge associated with managing and engaging a multigenerational workforce is how they prefer to communicate within their day-to-day responsibilities.

One simple and easy way to address this challenge is by bringing the respective generations together to agree on preferences and ultimately the final solution.

By allowing the multiple generations to contribute to the conversation, the culture is being shaped and embraced as one that cares and listens to their employees.

Marco Manazzone
CEO, Zzone Homes

Marco Manazzone

One challenge associated with managing and engaging a multigenerational workforce is the differences in preferred communication styles and interpretation of tone between generations.

For example, older employees may prefer face-to-face meetings or phone calls, while younger employees might favor instant messaging or email.

One way to address this challenge is to establish clear communication guidelines that accommodate various preferences while promoting inclusivity.

This could involve training sessions to raise awareness about generational differences in communication styles and encouraging team members to express their preferences openly.

Kirsten Bombdiggity
Fractional CXO, Bombdiggity

Kirsten Bombdiggity

The most fascinating challenge in today’s workplace is how each generation fundamentally defines what it means to be ‘professional.’

I’m seeing younger team members who view authenticity as non-negotiable – they bring their whole beautiful selves to work, build deep friendships with colleagues, and approach client relationships as genuine partnerships.

Meanwhile, our seasoned professionals are masters at the art of meaningful boundaries, viewing professionalism through the lens of structured relationships and intentional work-life separation.

I suggest implementing ‘Value-First Communication Guidelines’ – a flexible framework that celebrates these different styles instead of fighting them.

For example, team members who value clear boundaries can establish dedicated focus time and structured meeting protocols, while those who thrive on organic connection can maintain open-door policies and collaborative spaces.

When we stop forcing everyone into one ‘right’ way of being professional, and instead create systems that honor multiple approaches, we build stronger, more innovative workplaces.

Stephen Greet
CEO & Co-founder, BeamJobs

Stephen Greet

I’d be delighted to share insights on managing and engaging a multigenerational workforce, including strategies we’ve seen create alignment and foster innovation.

My experience helping job seekers communicate their value across diverse teams has provided me with a unique perspective on bridging generational divides in the workplace.

One of the toughest challenges I’ve observed in managing a multigenerational workforce is breaking through assumptions.

For instance, there’s often an unspoken divide: older employees may assume younger colleagues lack experience, while younger team members might view their older counterparts as resistant to change.

This dynamic doesn’t just create tension—it stalls collaboration and innovation.

I think addressing this begins with fostering cross-generational mentorship.

Pair a tech-savvy Gen Z employee with a seasoned Baby Boomer, for example. This isn’t about assigning teacher and student roles but rather creating a platform for mutual learning.

In one instance, I’ve seen such mentorships improve workflows dramatically—where the younger employee streamlined tech processes, and the experienced colleague shared invaluable industry knowledge.

When employees begin to see each other as collaborators, not competitors, the assumptions fade.

This builds trust, unlocks fresh ideas, and aligns everyone with the company’s bigger vision.

Alexander Anastasin
CEO & Co-Founder, Yung Sidekick

Alexander Anastasin

Different generations bring varying expectations about work-life balance, job stability, and career growth.

Older generations may prioritize loyalty and long-term employment, while younger workers often seek flexibility, quick advancement, and alignment with personal values.

HR teams should implement customizable benefits and development programs.

Offering flexible working hours or remote options caters to younger employees, while robust retirement plans and mentorship opportunities appeal to older staff.

Organizations can harmonize expectations and boost engagement across the board by creating a workplace culture that values individual needs.

Adam Hamilton
CEO, REI Hub

Adam Hamilton

I think one of the biggest challenges with managing and engaging a multigenerational workforce is actually that the different generations often don’t naturally engage with each other as much.

Especially when it comes to more than one difference in a generation, people tend to stick closer to the people they are closer to in age because of relatability.

When you are managing a workforce and trying to engage everyone, a key aspect of that is getting them to work together and engage with each other well so that the team as a whole strengthens.

So, things like team bonding can make a big difference.

Darrin Murriner
CEO & Co-founder, Cloverleaf

Darrin Murriner

One of the most pressing challenges in managing a multigenerational workforce is addressing the subtle but significant communication barriers that can emerge between team members from different age groups.

These gaps often stem from distinct expectations around how ideas should be shared, how feedback is received, and what it means to collaborate effectively.

Without the right tools, these differences can lead to frustration or misalignment.

At Cloverleaf, we focus on equipping teams to better understand and connect with one another.

Digital coaching provides friendly, actionable nudges that help team members recognize communication hazards—whether it’s about being more direct, listening more carefully, or making space for others to contribute.

When people feel heard and understood, it creates a foundation for genuine collaboration and deeper trust, regardless of age or experience.

Alison Stevens
Senior Director – HR Services, Paychex

Alison Stevens

As the workforce continues to evolve with the rise of Millennials and Gen Z, workplaces are increasingly adopting flexible schedules and leveraging emerging technologies to enhance productivity and job satisfaction.

However, for other generations, these rapid changes can feel challenging and complex as they navigate a landscape that is noticeably different from the one they built their careers in.

Despite these challenges, Baby Boomers bring invaluable skills and experience. Their deep industry knowledge and years of expertise offer perspectives that younger generations may not yet possess.

This wealth of insight is a critical asset for any organization seeking to balance innovation with seasoned wisdom.

HR teams play a pivotal role in bridging generational gaps within the workplace.

By tailoring onboarding processes to address generational strengths and challenges, pairing employees from different age groups, and providing upskilling and educational opportunities, HR professionals can foster collaboration and ensure that all generations contribute to a dynamic, well-rounded team.

Skills-based hiring and training further enable organizations to capitalize on each generation’s unique abilities, creating a truly inclusive and high-performing workforce.

Kelley Rexroad
Founder, Krex Consulting

Kelley Rexroad

The biggest issue is assuming communication.

This includes understanding cliques used, urban slang words used, abbreviations used, and lack of specificity.

It also includes  the method of communication. Some people hate text, others prefer the telephone, and some want video calls.

Using a non-desired communication tool sets up the exchange  for a less-than-good result.

People assume and use what they like, not necessarily what the audience of the communication likes. 

The way to combat this is to ask questions.     

What is your preferred way to receive information?  

How often do you wish for information?  

What do you mean by “it will be hard”  to get done by then?   

Questions show that we are listening to the other person and not listening to reply.

Questions bring listening, which brings understanding. This is how respect and value are exchanged, and the “extra ”is the quality and speed of work.

The HR Spotlight team thanks these industry leaders for offering their expertise and experience and sharing these insights.

Do you wish to contribute to the next HR Spotlight article? Or is there an insight or idea you’d like to share with readers across the globe?

Write to us at connect@HRSpotlight.com, and our team will help you share your insights.

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