Understanding Generations in the Workplace

While turkey, stuffing, and pumpkin pie are some must-haves around Thanksgiving, other essential ingredients are connection, humor, and meaningful moments! With multiple generations gathered around one table (or Zoom screen), Thanksgiving is a great opportunity to appreciate the unique perspectives we each bring. Every generation has a unique approach and being mindful about personal preferences can help make everyone’s holidays more enjoyable.

Before gathering around the table, let’s consider how we can connect with the multiple generations! 

Connecting with Multiple Generations

• Baby Boomers (1946–1964): Boomers often cherish long-standing Thanksgiving traditions, help prepare meals, and value reflective moments of gratitude. Questions like, “What’s your favorite Thanksgiving memory?” or “How has Thanksgiving changed over the years?” can create meaningful conversations.
• Generation X (1965–1980): Often balancing work, family, and hosting duties, Gen Xers appreciate efficiency and creativity during the holidays. If they’re hosting, ask how you can assist. Bringing a side dish or helping with cleanup goes a long way.
• Millennials (1981–1996): Millennials love to make Thanksgiving their own, often hosting “Friendsgiving” celebrations in addition to traditional family gatherings. Millennials value collaboration, so involve them in planning the meals or activities! For example, let them curate a Thanksgiving playlist or suggest a unique side dish. 
• Generation Z (1997–2012): Tech-savvy and trend-driven, Gen Z loves documenting the holiday for social media. They appreciate transparency and humor. Share funny or imperfect Thanksgiving moments to make the gathering feel real and relatable.
• Generation Alpha (2013–present): The youngest generation brings pure joy to Thanksgiving with their unfiltered excitement and curious questions about family traditions. Keep them entertained with crafts, like making gratitude turkeys or decorating cookies. Maybe even share fun facts like, “Did you know cranberries can bounce?!”

Activities & Games for Thanksgiving Fun

“According to the National Institute for Play (NIFPlay), “play is as critical to the development of a human being as sleep and nutrition.” It strengthens the connection in our brains that controls our ability to regulate emotions and solve problems. One study found that engaging in play for just twenty minutes a day could improve mood, quality of sleep, and reduce stress.” Whether you’re celebrating with family, friends, or colleagues, incorporating games and activities can turn any gathering into a space of connection and collaboration.

Thanksgiving with Colleagues

1. Gratitude Wall: Set up a “Gratitude Wall” in the office or use a digital tool like Padlet for remote teams. Each team member writes what they’re thankful for on sticky notes (physical or virtual). Add a twist by encouraging generational reflections, like “What’s one technology you’re thankful for?” or “What tradition makes you feel grateful?” Get inspiration from these 19 Fun Gratitude Wall Ideas for the Office from teambuilding.com! 
2. Generational Trivia: Divide employees into teams with representatives from different generations. Trivia questions should cover various topics, such as “What was the best-selling toy in 1985?” or “Who was the top artist on Spotify in 2023?” Check out jeopardylabs.com for a fun virtual experience with categories ranging from Traditionalists to Generation Z! 
3. Pie Swap: “We’ve all heard of cookie swaps, but have you heard of pie swaps? If you’re in-person, each team member can bring a pie (homemade or store-bought) to share with the team. If your team enjoys some friendly competition, have everyone vote for their favorite pie and award a prize to the winning baker.”

Thanksgiving with Friends & Family

4. Thanksgiving Time Capsule: Create a time capsule with contributions from family members and/or friends—write letters to future selves, including photos, or small items representing the year. Set a future date to open the capsule, such as five or ten Thanksgivings from now, to reflect on how things have evolved.
5. Generational Charades: Prepare prompts based on cultural moments from different eras, like “Doing the Moonwalk,” “Explaining AOL,” or “Recreating a TikTok dance.” Teams must act out the prompts while others guess. Consider playing Mind the Gap — “the ultimate generational trivia game that includes pop culture questions from Boomer, Gen X, Millennial, and Gen Z generations, as well as hilarious challenges that will get you out of your seat to recreate nostalgia from everyone’s glory days.“

Humor: The Universal Connector

When all else fails, Thanksgiving is a perfect time to laugh together. Shared laughter fosters a sense of belonging and community. It’s a powerful reminder that despite our differences, we’re all human. Playing lighthearted games, sharing funny holiday memories, or watching a classic comedy goes a long way. “For people who are laughing together, shared laughter signals that they see the world in the same way, and it momentarily boosts their sense of connection,” says social psychologist Sara Algoe, co-author of the study with Laura Kurtz. Let’s zap the Thanksgiving gap this year with gratitude, humor, and connection—and create a holiday everyone will be thankful for!

In a world filled with diverse viewpoints, cultures, and beliefs, we often find ourselves divided… not just by our preferences and opinions but also by the years we were born. Baby Boomers, Gen Xers, Millennials, Gen Zers, and now Gen Alpha all navigate the world with unique lenses, shaped by distinct events, technologies, and societal shifts.

A term I use to describe these distinct events and shifts is “generational signposts.” These signposts can be profound, creating additional barriers and misunderstandings. As we celebrate World Kindness Day (international observance on November 13th), it’s worth considering: Can kindness be the bridge that helps us “zap the generational gap”?

This question lies at the heart of my message as a generational speaker and enthusiast! I’ve spent over two decades connecting with organizations and associations, helping them tackle generational challenges, myths, and misunderstandings head-on. Every generation carries its own set of assumptions and judgments, often rooted in stereotypes. We might think, “Millennials are entitled,” or “Boomers don’t know how to use technology.” These beliefs create barriers before we even get to know each other! But kindness challenges these assumptions. Kindness means we’re willing to look beyond the surface and consider each individual. It’s a commitment to seeing people for who they truly are, rather than reducing them to any stereotypes.

How Kindness Breaks Down Barriers

According to the Mayo Clinic, a “simple, free, positive and healthy” act of kindness can:

• Increase the giver’s self-esteem, empathy, and compassion
• Improve mood
• Decrease blood pressure and cortisol (a stress hormone)
• Increase connectivity to others, enhancing relationships and reducing loneliness
• Release endorphins and boost serotonin and dopamine, lighting up your brain’s pleasure centers and leading to a feeling of satisfaction and well-being. 

Consider implementing one of these DEI activities this November: 

“Random Acts of Kindness” Cross-Generational Challenge

• Invite employees from different generations to participate in a “random acts of kindness” challenge over a week. Encourage them to participate in small, thoughtful acts for someone from a different generation. Examples include sending a personalized note, sharing a helpful article or resource, or even offering to mentor or learn from someone of a different age group. The Random Acts of Kindness Foundation has FREE Kindness in the Workplace resources, like the one below.

Kindness Brainstorm for Community Impact

• Organize an intergenerational brainstorming session to generate ideas on how the team or organization could give back to the local community. Teams should be mixed generationally and asked to work together on a kindness-themed project, such as a volunteer day or fundraising campaign. “Many studies have shown that volunteer programs boost productivity, increase employee engagement, and improve hiring and retention. For example, a study I conducted in 2013 showed that the more people volunteered (even if it was on their own time instead of on company time), the better they performed on work tasks.” – Harvard Business Review

Multicultural Holiday Potluck & Recipe Swap

• “Multicultural potlucks provide a space for building community and connection while celebrating workplace diversity and inclusion.  No matter what the cuisine, each unique dish carries with it a story, a history, and a heritage, and offers an opportunity to cross borders and share new experiences.” Host a holiday potluck and encourage employees to bring dishes that represent their cultural or generational backgrounds. To add a kindness element, pair people up to share why their dish is meaningful, encouraging cross-generational connections. For ideas, check out these 23 Diverse Potluck Ideas for the Office by CultureAlly! 

World Kindness Day – Key to Multigenerational Connection & Collaboration

World Kindness Day reminds us that kindness is a universal language and a powerful tool for fostering genuine multigenerational collaboration. We often think of kindness as something “soft”—a warm smile, a friendly gesture, or an encouraging word. Kindness is powerful. Kindness is a fundamental part of the human condition which bridges the divides of race, religion, politics, gender, and location. It can disarm, to open minds, and to build trust. When applied across generations, it becomes a catalyst for connection and growth. 

DEI Activities can certainly foster a sense of belonging…

Spooky season is near its end and we’re heading into the busy holiday season… Before we get wrapped up in all the busyness, Generational Enthusiast Meagan Johnson wants to recommend some fun! Fun and DEI (Diversity, Equity, & Inclusion) activities foster a sense of belonging, which helps improve employee engagement.

Research by Deloitte has shown that organizations with a strong sense of inclusion experience up to 2.3 times higher employee engagement than their counterparts lacking DEI initiatives. Playful activities in the workplace have also been shown to significantly reduce stress levels. According to the American Psychological Association, promoting fun in the workplace, such as team-building exercises and casual social activities, helps reduce stress and improves mental health! 

Source: Diversity and Inclusion in the Workplace: Benefits and Challenges by Kellie Wong

Spooky Fun DEI Activities 

1. Campfire Chronicles Encourage a “campfire” storytelling session (virtual or in-person) where employees from each generation share their own “ghost stories” from the workplace – moments that were frightening, challenging, or eye-opening. These could range from silly tech fails to career-defining moments. It’s a powerful way to bond and it’s also how our ancestors passed down knowledge, traditions, and values!”Campfire leverages our natural storytelling techniques by giving players a format and a space in which to share work stories–of trial and error, failure and success, competition, diplomacy, and teamwork,” write Gray, Brown, and Macanufo. Especially in multigenerational teams, storytelling allows employees to see each other’s humanity, laugh together, and gain insights into one another’s unique journeys.
2. Costume Swap: Walking in Someone Else’s Shoes Encourage employees to dress in costumes inspired by the fashion and pop culture of another generation. Pop culture nostalgia can create shared laughter and unexpected points of connection across age groups. Popular costumes this year draw inspiration from recent movie releases and nostalgic reboots. According to Google, the top trending costume this year is Shrunken Head Bob from Beetlejuice Beetlejuice, a recently released sequel to the 1988 classic. By combining modern and throwback costumes, employees can enjoy the opportunity to see the influences that have shaped each generation’s culture and humor! 
3. Guess the Ghoul 👻 This is a fun spin on Meagan’s “Guess the baby photo” keynote activity! Have employees submit photos of past Halloween costumes from childhood or teenage years. Assign each photo a number then post the photos on a bulletin board or gather everyone around for a slideshow presentation. Give employees a blank card to “guess the ghoul” in each photo, by writing down the name. Award prizes for the most correct guesses, and the “Sneakiest Ghoul” that avoided the most correct guesses. Childhood costumes and full-body costumes tend to work best for this activity, as these disguises make it harder to guess. This game helps coworkers get nostalgic and learn more about each other’s personalities while reliving memories of Halloween past.
4. Spooky Playlist Collaboration “The studies on the power of music stretch far and wide, from improved job performance, reduced stress, heightened creativity and focus to increased productivity, improved employee morale, and job satisfaction.” In Meagan Johnson’s keynote, she shares a client who has implemented the power of music by having different employees choose the music every hour. Similarly, host a spooky playlist showdown where each generation contributes songs from their era to create an eclectic Halloween soundtrack. From haunting hits of the 60s to modern, spooky synth beats, this activity allows generations to appreciate each other’s musical tastes while creating a shared festive vibe.
5. Generations’ Graveyard: Busting Myths and Misconceptions Set up a “graveyard” of common generational stereotypes and misconceptions. Have each generation write down myths they’ve encountered about their own or other generations on faux tombstones or signs. Then, host a Halloween social hour where everyone can “lay these myths to rest” by discussing and debunking them. This activity allows everyone to update their biases and welcome a fresh perspective on generational differences.

Embrace the Spirit of Halloween Year-Round

Halloween’s festivities remind us of the value of embracing different ideas and personalities, even those we might not fully understand at first. Just as we celebrate unique costumes and personalities during spooky seasons, we can celebrate the diversity of generations year-round by nurturing curiosity and mutual respect. These DEI activities are a playful start to Zapping the Generational Gap. After all, the real treat is the chance to connect, learn, and collaborate with colleagues of all ages—no tricks necessary. Happy Halloween everyone! 🎃

P.S. Did you know? One-quarter of all the candy sold annually in the U.S. is purchased for Halloween! 🍬