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Too Young, Too Old, and Stuck in the Middle: Multiple Generations in the Workplace

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From Baby Boomers to emerging Gen Z entrepreneurs, the cross-generational mix of today’s business environment provides numerous opportunities for valuable partnerships, business growth and rewarding career satisfaction. National Association of Women Business Owners (NAWBO) Chicago and Small Business Advocacy Council (SBAC) came to Catalyst Ranch for a Cross Generational Boot Camp on November 3, 2014, and I had the pleasure of participating with this active group. The partnership between NAWBO and SBAC was a perfect fit as their members share similar demographics and the collaboration set the tone for a day of open dialogue and sharing. Women of all ages, cultures and industries converged in the Polka Room to celebrate our differences and embrace our unique traits.









Rosalyn Wesley of Tristan Reeves kicked off the day, and as a dynamic national speaker, her energy launched the morning with positivity. We were given an introduction to the values of different age groups including Traditionalists, Baby Boomers, Gen X and Gen Y/Millennials. Rosalyn redefined the focus of the day as a discussion that is Poly-Generational:

“Embracing and valuing the MANY generations to the point where we increase our efficiency and effectiveness for simultaneous energy, strength, safety, passion, hope and innovation.”

Put it that way and it sounds like we can’t afford not to create cohesive multi-generational workplaces. And of course we can’t! As younger generations join the work force, their motivations will be different from their more seasoned colleagues and this is because of the time in which their values were established. Growing up, we are exposed to cultural cues that vary in each generation. People exposed to the same cultural cues tend to exhibit similar values and expectations throughout their lives. Values are ingrained responses and expectations we gather from the messages we heard in our formative years. Take a minute to assess how your childhood shaped your values.

Baby Boomers embrace work sacrifice and remain loyal to companies for generations, working long days and weeks to put in their dues. Other characteristics of this group are:

  • Optimistic
  • Team-oriented
  • Workaholic
  • Open minded
  • Prefer face-to-face communication
  • Value their manager’s interest in their personal lives
  • Job status and symbols are important
  • Like pep talks and recognition with wide public profile
  • When delegating, clearly state objectives and expected results

Boot Camp Panel Feedback:

The Traditionalist and Baby Boomer feel face-to-face meetings are of huge importance in business interactions and prefer them to emails.

They understand the younger generation’s propensity towards social media and technology, and that it plays a big role in our daily lives. The panelists in this age group were pushed to use Facebook to stay connected to the children in their personal lives, especially to see photos of grand kids and other little ones. LinkedIn is their preferred social sharing platform for business.

The ideal employer for this age group is flexible, provides autonomy and freedom of expression.  Over the years, Traditionalists and Baby Boomers have built a lifestyle and they want the respect and trust to live that lifestyle. Our Traditionalist and Baby Boomer want to impact the next generation of business leaders as mentors and expect they will learn new things from mentees as well.


Generation X was the first to grow up with technology such as computers in the work place and they tend to value productivity over hours spent in the office. Their characteristics include:

  • Self-reliant
  • Skeptical
  • Approach authority casually
  • Balance in work and family
  • Minimal supervision
  • Easy to recruit, hard to retain
  • Prefer flexible work hours
  • Want regular, honest feedback and mentoring
  • Value autonomy in how to accomplish work and set priorities


 Millennials’ lives are entrenched in technology and they understand how to leverage that technology to increase professional and personal productivity; therefore, they value a balanced life and equality in the company culture. Here are some other common traits:

  • Confident
  • Optimistic
  • Goal setting is a priority
  • Diverse
  • Sociable
  • Search for coworkers with similar work ethic and high ideals
  • High expectations right out of college
  • Prefer electronic communication
  • Want a coach versus a boss
  • Constantly learning and want opportunities to build their skills

Boot Camp Panel Feedback:

While the younger panelists shared that they too value face-to-face meetings, they want to be able to qualify their business connections first using social media. LinkedIn gives them a snapshot of the individual’s professional career, projects, interests and connections all in one place.

The ideal employer of Millennials and Gen Y is socially conscious, philanthropic and entrepreneurial. They want motivation in a form other than money by having autonomy, empowerment and decision-making capabilities.

Millennials want to be recognized for their hard work through a verbal acknowledgment from their employer. After a job well done or a performance review, Millennials want more responsibility as a reward.  It’s not juts about the money!


Why is it important that we all learn to get along and create a happy poly-generational work environment? Forbes contributor Rawn Shah points out the pressure businesses face to be agile in their product development, partnerships and business operations and stay connected to technology-savvy consumers. It’s a tall order. In his article Working With Five Generations In The Workplace, Rawn stresses the importance of a company culture that nurtures knowledge sharing between generations:

“…The experiences, knowledge and cultural familiarity that each generation carries can be best delivered through social learning. It is not simply about mentoring between older people who have more experience in their line of business, but also learning from other peers in other areas and younger folks the how things may work differently in different environments.”


The Boot Camp panel discussion asked five different women from varying generations to speak on their work experiences. Many of the panel fell into the above categories and agreed that they share common traits with their peers of the same age. Each woman also stressed the importance of being empathetic to individual personalities and values. While we fit into buckets, we also have many personal experiences that shape how we interact with coworkers and how we want to communicate.

So what can we do about these differences to avoid conflict? Understand the communication style of each person involved in a situation and manage accordingly. Celebrate the diversity of your team and approach others from a place of empathy. Look at the situation through new eyes instead of being mired in the “way things are” or status quo. Words of advice: Assume Positive Intent! If a Millennial coworker shuts down their computer and leaves the office right at five to meet friends for dinner, don’t make assumptions that they are disengaged. Perhaps they will finish that project at home on their own time as a way to balance their personal commitments and still get the work complete. If a Baby Boomer coworker wants to have a meeting after seven emails about a subject, know that it is not their love of meetings that is driving their decision, it is a value of time and efficiency.

Each panelist left us with one short and sweet phrase; a key takeaway they hope the boot camp attendees remember:

  1. There is no one characteristic for a generation. We are all multi-faceted.
  2. Learn from each other and be open.
  3. Listen, observe, ask and don’t assume.
  4. A diverse team will yield better results because of a variety of strengths. Get further faster through diversity.
  5. Take the time to explain why you are delegating a task.

How are you encouraging a productive poly-generational work environment in your company?