Bridging the Workplace Generation Gap


What are the generational breakdowns?

generational breakdowns










What does it mean to be a Millennial and Gen Z? How are they different from other generations? 

Millennial and Gen Z  employees value a balanced work and personal life. 

They’re not willing to compromise their personal time for work like previous generations were.

They’re virtually well connected and culturally diverse which brings a vast collection of knowledge and creativity to the table.

Millennials were born during an increased time period of immigration providing them with more exposure to different cultures than previous generations. Gen Z will have the most exposure. 

Millennials and Gen Z are looking at their bosses and managers to be like a mentor to them. They want their job to meet their needs. 

Previous generations see their superiors as strict, ethical and in an authoritative role. They believed that they should meet the needs of the company. 

Promotions and personal growth within a company are more important to Millennials than pay. 

Boomers and Gen X were driven by salaries and moving up the ladder

differences between millennials and baby boomers

What are the common Millennial and Gen Z stereotypes?

They’re obsessed with social media (ie: instagram and facebook), political interests, smartphones, apps, disdain for authority, wanting to work remotely, lazy and bad with money.

What are some of the issues that other Generations have with working with Millennials and Gen Z?


  • Each generation has their own set of stereotypes they unfortunately carry with them. Lazy, old, outdated, stuck in the past, technology obsessed, etc. Before most people are even introduced, these labels are already instilled in their minds from the first look. 
  • Having these first impressions can cause tension and dislike between people which will disrupt your workflow.

Company Culture 

  • Millennial and Gen Z company culture is noticeably different than Boomers and Gen X.  Millennials and Gen Z thrive in cultures where there is purpose, togetherness, open forms of communication through all seniors  and more than just a work driven purpose. Birthday parties, company outings, weekly messages from the owners are all things Millennials expect at work. 
  • Boomers and Gen X may be used to a one time a year Holiday Party, a monthly check in from the higher ups and a more professional, strict culture.   

Personal Goals and Loyalty 

  • Millennials are coming into the workforce with their own ambitions being the highest priority. They’re a generation of employees who are looking to constantly be learning and growing in the company. They expect position changes and recognition more often than their counterparts. If they don’t find personal fulfillment, they’ll move to another company they can find it with.
  • Boomers and Gen X came into the workforce with the company and secured a job first. They do their work as expected and are more in tune with yearly reviews and promotions when the time comes.  These two different motivations and drive factors draw a clear line between the generations. 

Put yourself in a millenial’s shoes that work at big companies. What are some of their struggles? Maybe they’re frustrated with the lack of technology, and not being heard. Unclear as to why they have to go through the chain of command?What is important to them? Culture? Free snacks? Bring your dog to work? IDK – there are a lot of things written about this. Might have to do some research.

Then put yourself in the place of someone who is 60 that just hired 5 new employees between the ages of 20-30. What are their struggles? Seeing that all of these people are entitled? Them wanting to always leave early and work remotely? Wanting 6 weeks of vacation? Them keep talking about mental health? Again, would have to do some research. Don’t be afraid to quote other articles and companies. 

What are some challenges that CEOs have when managing a team of generations? 


  • Millennials and Gen Z rely on multiple forms of communication; text, instant messaging, email and social media. Gen X and Boomers rely on a phone call or email. This mixed with the different terminology and slang can lead to a breakdown in the communication chain. 
    • A great course of action to relieve this would be to bring the teams in for a meeting and work to figure out the best chain of communication for everyone, then teach everyone the proper use of the method together. 

Different work styles

  • Millennials and Gen Z are multi-taskers who can use technology to get their job done in different ways. These work style changes can cause a disruption to the workflow of older team members 
    • Cross training is a useful method to help each generation learn from each other. Giving the Millennial and Gen Z a chance to train the Boomers and Gen X on their methods and practices,  then switching positions. Harvard Business Research showed that each generation can learn something valuable from each other like building networks, to work control methods. 


  • sites that “With such a momentous demographic shift, companies are going to have to (at the very least) revisit their recruiting strategies and fully understand how best to respond to this changing tide.”
    • Previous interviews were structured with the employer screening to see if the candidate is the right fit for the company. Millennials and Gen Z are now trying to see if the company is the right fit for them during an interview. 

What motivates Millennials?

Avocado toast. Just kidding.  

  • Growth and ability to access new experiences  
  • Opportunities to learn and contribute 
  • Committing themselves to work they find meaningful
  • A sense of personal accomplishment
  • Strong core values

According to sites like and Great Place to Work,  the top 5 rated places Millennials have found these motivations like these are:

Ultimate Software

“Our culture is truly lived every day by all leaders and all our executives. They truly care about us and make that known in all the ways possible. I rarely feel stressed at work and even in our busiest times I am happy to be here.” – employee review


“The care that is given to the employees, the flexibility that we have to take care of our personal issues, the fairness and the all the benefits we have, and the endless opportunities for growth to all of us make working at Hilton great.”- employee review


“I really love the passion Salesforce has for fighting injustices and leading the way in being a conscious company that cares about the environment, its workers, human rights, women rights, LGBTQ—it’s wonderful to feel protected.” – employee review


“Workday is invested in growing young talent and helping you find the career path that you love. I’ve moved departments and teams multiple times since I’ve been here and I’ve had a say in what I’m interested in all long the way.” – Employee review


“The firm really works to make decisions about how to do business and treat employees based on our core values and purposes. The firm also is ahead of the learning curve in technology and training new generations of people coming into the workforce.” – employee review

 What is avocado toast anyways?

“While being trendy, Avocado Toast benefits from being versatile, healthy, easy to make, and delicious. In its simplest form, just add avocado slices on top of toasted bread and you’re all set. But there can be an infinite variety of tweaks and variations.” –  

What assessments and personality tests are helpful for managers?

A personality test can give you a look into the inner workings of your staff. Knowing their cognitive, behavioral, and personality strengths and weaknesses can help them grow into productive and highly motivated employees.

Predictive Index 

“At its core, a PI Test is a personality test given by employers to determine a candidate’s potential fit at their company”.  –

Why use it? 

  • It’s a highly accurate test developed by the American Psychological Association
  • It will help you determine the cognitive and behavioral patterns of your staff or future staff and give you a chance to see where they can excel.
  • Learn about your employee’s abstract characteristics such as dominance, extraversion, patience, and formality. 


“The Enneagram test is a way of categorizing the human psyche into 9 different personality types. It’s a typology that is useful for understanding the inner workings and motivations behind human behavior” – Growth Marketing Pro

Why use it?

  • The Enneagram breaks your employees down into 9 different categories to help determine what motivates them. A few examples are: 
  • The Reformer- The Rational, Idealistic Type: Principled, Purposeful, Self-Controlled, and Perfectionistic
  • The Helper- The Caring, Interpersonal Type: Demonstrative, Generous, People-Pleasing, and Possessive
  • The Achiever- The Success-Oriented, Pragmatic Type: Adaptive, Excelling, Driven, and Image-Conscious
  • The Individualist- The Sensitive, Withdrawn Type: Expressive, Dramatic, Self-Absorbed, and Temperamental
  • Knowing your teams key motivating factors will help you bring them to their maximum potential and achieve their goals.

What experiences can bring teams that are ranging from different generations together?

An article recently written for Forbes stressed the importance of an engaging team building activity. It detailed why these activities are more effective than doing something simple like company dinners.

Here are some of our favorite Boston team building activities: 

Trapology Boston – An escape room where your team is forced to work together in order to accomplish a goal.  Trapology covers multiple team-building points without the team even noticing. Productivity improvements,  increased collaboration, encouraged creativity, constant communication, breaking the barrier and getting everyone in a neutral position of power,  and discovering your teams hidden talents can all be accomplished in one hour! They even cater to larger teams over 50+

Paint Night. – Whether members of your team are skilled with the brush, a paint night is a perfect way to get everyone out of the office and together in a relaxed setting. 

Organize a team scavenger hunt-  You can set these up anywhere, your office, an offsite retreat or a local park. There are even companies like Museum Hack that will bring your team to a museum to learn and play! While some scavenger hunts insight competition, they still band together in a strong form of teamwork and communication. 

About Trapology Boston (

We’re a group of local Boston creatives that believe in interactive and immersive experiences that challenge, connect, and entertain. Trapology Boston is Boston-born and bred and we offer escape games for friends, family, and co-workers. Each of our adventures have a suspenseful storyline that will unfold as you and your team explore the room, find clues, and solve a series of connected mind-bending puzzles. Handcrafted locally with creativity, quirkiness and a little insanity. 


Blog post written by By Michael Tremblay and Tina Wood, Trapology Boston (

Blog by Julie Morris: How Busy Professionals Can Reduce Stress 
and Achieve New Goals on a Budget

       Photo via Pixabay by StartupStockPhotos

Busy professionals and business owners often have trouble reducing stress simply because they feel their work is never done, and it can be difficult to delegate to others when you are so passionate about your job and want to be a part of each decision-making process. Financial issues are often at the root of our stresses, leaving us with an uncertainty about the future. However, learning how to cope in healthy ways will allow you to focus on your goals and move forward with them, whether that means opening up a new store or going for a big promotion.

Reducing stress can have significant physical and mental health benefits; according to Corporate Wellness, these effects are measurable. “The physical costs of chronic stress are well known and have direct and measurable effects: high blood pressure, cardiovascular problems, suppressed immune system and disrupted sleep are some of the most common outcomes. But stress also triggers changes in how we think. Stress is a survival reaction which has evolved to keep us safe in the face of physical threats. It’s a short-term solution that gets triggered by the long term challenges in the workplace, and this disconnect between what stress is for and what triggers it at work leads to a number of unhelpful behaviors,” explains writer Damian McCourt.

Keep reading for some great tips on how to reduce stress and keep your finances in shape in order to focus on achieving your goals.

Exercise Daily

Exercise has long been associated with reducing stress and boosting mental health, and getting in a daily workout can help you stay fit and raise self-esteem at the same time. Make sure you have the right equipment and gear for your preferred workout . If you’ll be running or walking often, consider the age of your shoes and whether you need an upgrade (remember, old shoes can cause injury). If you do need to make a purchase, be sure you search for available online deals and discounts at a shoe retailer like Finish Line. That way, your purchase won’t set you back too far.

Buy a New Wardrobe

A new professional wardrobe can help you feel more confident, especially if you’re going to be going out for a promotion or will be networking at a convention. While you may be able to creatively use your existing wardrobe, purchasing a few new pieces may be just what you need to feel more inspired and ready to tackle what lies ahead. Just be sure to shop smart and check out major retailers to reap extra savings. For example, you can find great deals on new clothing by shopping around for a Macy’s discount or an Old Navy clearance special.

Get Organized

Getting organized — both at home and at work — will help reduce stress and boost your mental health at the same time, so remove clutter, keep a magnetic calendar on the fridge so you can keep track of your responsibilities, and consider hiring an assistant to help you stay on top of things. This also applies to your finances — one of the most stressful aspects of many Americans’ lives — so seek the help of a professional who can help you get things in order and keep track of your cash and investments. Check out stores like Office Depot, where you can pick up storage bins and planners, to help keep you organized.

Revamp Your Business Identity

Sometimes, it’s easy to feel as though you’re in a professional rut when you’ve had the same business identity for a long time. Making small changes — such as creating a new logo for your company or ordering new business cards — can make all the difference and can help you find renewed motivation when it comes to your work. Search for online coupons for stores like Vistaprint to help save some money on your business cards.

Overhaul Your Diet

The way we eat and drink can have a profound effect on the way we feel, and when you’re a busy professional who is constantly on the go, it’s all too easy to rely on fast food or easy meals that don’t have much nutritional value, which can leave you feeling sluggish and irritable. Overhauling your diet is a great way to start feeling better right away, and it doesn’t have to break the bank. If you meal prep on the weekend, you can have a week’s worth of lunches ready to go when you walk out the door.

Get Some Good Rest

Our ability to get good sleep is one of the biggest factors in the way we feel; it can affect our mental and physical health and can play into the way we perform at work and school, and a lack of it can leave us feeling unprepared, overwhelmed, and anxious. Creating a good sleep routine will help you get better rest, so look for cost-effective ways to do so (such as swinging by Bed, Bath & Beyond for new bed linens). You might turn off all devices at least an hour before bed, sleep in cool cotton layers, or control the temperature in your bedroom for maximum comfort.

Take Up a Hobby

Picking up a hobby can help you relax and take your mind off work for a bit, which everyone needs now and then. Look for activities that make you feel good in a healthy way, such as playing an instrument, painting, playing a sport, or cooking, and do it as often as you can. Learning to enjoy spending time with yourself can help you focus more efficiently on your goals. What’s great: You can learn a lot by watching YouTube videos for free!

Learning how to reduce stress and anxiety can do more than help you achieve your goals; it can boost your health in multiple ways and keep you on track in all aspects of your life. Look for ways you can get your finances in order, relax as much as possible, and set a schedule that clearly delineates work and leisure time. This can be difficult for those who do a lot of work from home, but it’s important to save some time just for yourself.

This blog was courtesy of life and career coach, Julie Morris. Make sure to visit her website at

GSEA Competition 2018- EO Boston

Let’s think back to when you moved into college. Your comfort items were stowed into boxes. You and your parents may have taken an obligatory trip to IKEA to purchase a small microwave, collapsible laundry hamper, and other space-saving items. Your first year at college introduced you to a new way of life – of student lounges, dorm room hangouts, and a new sense of independence. You may have joined a club or an intramural sport. It’s possible that you may have seen a lot of the inside of a library while cramming for midterms and finals. Perhaps you spent most of the time figuring out the exact amount of minutes it would take for you to roll out of bed and run to class.


Five students, Jacob Becraft, Paul Wiley, Andrew Joshua Nagal, Flavio Somanji, Miracle Olatunji, did all of the above and one thing more.  This one critical element separates them from the average university student.


These five students have something in common with the founders of Facebook, Google, Dell, Dropbox, Kinko’s, Microsoft, Napster, Reddit, Snapchat, and WordPress.


Jacob, Paul, Andrew, Flavio, and Miracle are business owners as well as full time students.

Jacob Becraft – Strand Therapeutics         

Paul Wiley – Wilox Assets

Andrew Joshua Nagal – Bakku Technologies

Flavio Somanji – EcoDemand™

Miracle Olatunji – OpportuniMe


EO Boston, for the last several years, has been part of the Global Student Entrepreneur Awards (GSEA) Competition. GSEA is the premier global competition for students who own and operate a business while attending college or university.  EO GSEA supports student entrepreneurs who require much needed mentorship, recognition and connections to take their businesses to the next level of success. EO Boston members rallied and provided over $300,000 in-kind sponsorship package for the top three winners of our GSEA competition.


GSEA provides student ent the opportunity to accelerate their success, challenge the status quo, connect to an instrumental peer group and make the greatest impact possible in their community.


We congratulate Jacob Becraft – Strand Therapeutics who will be representing Boston in the GSEA National Finals in Denver (January 2019) and hope that he will continue to represent us in the international GSEA Finals in Macau, China (April 2019)! Congratulations to our runners up, Paul Wiley – Wilox Assets and Andrew Joshua Nagal – Bakku Technologies.


Special thanks to our EO Boston Event Sponsors:


Special thanks to the following companies, most whose CEOs are part of the EO Boston Family, who donated to the GSEA Prize Package

  • Cheshire Impact
  • Greek Kitchen Management
  • Trident Growth Partners
  • PropFuel, Inc.
  • SOBOconcepts
  • Sophelle
  • Trapology Boston
  • HireMinds LLC
  • 1-800-GotJunk
  • Boston Human Capital Partners
  • Lexington Wealth Management
  • SimplyDIRECT
  • Growth companies advisor & Business Angel
  • Prism Boston
  • ThinkTech Computers
  • Nicole Chan Studios
  • Window Seat Media
  • On The Avenue Marketing
  • Ayantek
  • Stack Sports
  • Best Delegate
  • Genesis Advisers
  • Trinet


Blog post written by Nicole Chan, Boston EO GSEA Director, and CEO of Nicole Chan Photography


Understanding and Using the Net Promoter Score (NPS) by Dave Will

The Net Promoter Score is one of the most common metrics used in organizations with reported numbers showing that the majority of Fortune 1000 companies use it to measure their customers satisfaction and loyalty.

Whether you’re the CEO of a Fortune 1000, an Entrepreneur with dozens of customers or an Association with thousands of members, the NPS, although not perfect, is a good metric to measure your relationship with your customers periodically.

Here’s all you need to know to understand how it’s measured, and I’m going to keep it super simple.

The customer can answer from 0-10.

  • “Promoters” answer a 9 or 10.
  • “Passives” answer 7 or 8.
  • “Detractors” answer 0 – 6.

The NPS is determined by subtracting the percentage of customers that are Detractors from the percentage of customers that are Promoters. Just ignore the Passives. (They can’t make a darn decision.) The potential score ranges from -100 to +100.

For example, if 80% of your customers answer a 9 or 10, 10% answer a 7 or 8, and 10% answer 0-6, then your NPS = 80-10 = 70.

Here’s a really cool table showing average NPS by industry.

There should be an open ended feedback option to the NPS allowing your organization to record the Voice of the Customer (VOC). That’s another blog post altogether some day.

Of course, there is some criticism of NPS, which is easy to understand. One number can’t possibly tell us how we can improve our customer loyalty.

It’s very difficult to get much information out of one question. But, it’s a simple and easy metric which is good for tracking purposes. By implementing this kind of question quarterly, semi-annually or annually, you can start to get a feel for how your company is trending in the eyes of the customer, as long as you’re capturing more information as well.

This is the “sales” part of this post… THAT’S WHY WE CAPTURE NPS IN PROPFUEL ALONG WITH LOTS OF OTHER QUESTIONS!!!! We strongly encourage organizations to ask their stakeholders questions frequently. Just not too many at once.

If you would like to see how PropFuel can help you capture your Net Promoter Score and other feedback on a regular basis, set up a time to talk to Dave here.

Member Blog: ADHD: An Entrepreneur’s Super Power and Kryptonite

“It was 5 days into my medication, and I thought, ‘Wow, so this is how normal people feel.’” A woman who worked for me shared that reaction; she was diagnosed with ADHD in her early 20s.

Mildly interested, I asked, “Really? So what were some of your symptoms?”  I suspected ADHD was some sort of bullshit diagnosis for parents who didn’t want to reprimand their children. After all, it seemed like an easy cop out to shirk their responsibilities to authorities when their kids were acting out. But my employee went on to describe her perpetual anxiety, an inability to regulate her reactions, and her fierce impatience.

Weird. She was describing me… right down to a sensitivity to fabrics and noise. Lord knows don’t ever try to eat an apple in front of me.

I’m intense. This intensity concurrently has been my superpower and my kryptonite. I struggled in school, and when I say “struggled,” it was more like I annoyed others until they’d physically pummel me into submission. In my freshman year art class, I mouthed off to a senior football player who had an affection for steroids. He decided to “roid rage” on me, and–back–then, teachers and parents didn’t get involved with such things. Or perhaps they simply decided I deserved his wrath. Either way, he smashed a clay sculpture into my head and knocked me to the ground, and it was painful. Ah, yes, you gotta love an old-school parochial education. While this was one of the earlier “stand out moments” from my youth, there were countless other times I was bullied because of my mouthiness.

When ADD first came fashionable, I was in my 20s. Suddenly, every kid was on Ritalin. I just didn’t get it. Yeah, kids are out of control, but isn’t that a prerequisite? They run around like savages grabbing for the conch. Hasn’t anyone read Lord of the Flies? I was in the dark about all of the specifics on ADD because, well, they didn’t hold my attention.

But I knew this: I had struggled with anxiety my entire life. It peaked about five years ago, with a relentless grip. I had started my own business. Suddenly, I needed to focus. And more than focus, I need to manage scenarios that typically would send my anxiety skyrocketing within seconds. Insomnia, which plagued me since my youth, was unbearable. I’d sleep a few hours and then be up all night thinking, thinking, thinking.

I finally sought medical help because the anxiety-lack of sleep combination led me to feel physically sick. My doctor prescribed an anti-anxiety medication, which made life somewhat more serene. Okay, “serene” is stretching it, but I was finally somewhat more comfortable. We adjusted the prescription over the following five years, but I never felt right. I recall my doctor asking me, “Do you ever feel tired during the day?” Nope. I never lacked energy, but my creativity was suffering.

Entrepreneurs always joke about having ADHD, and research shows that those with ADHD always test boundaries and see opportunity when others stop looking. Even I’d joke about it. When my employee shared her story, though, I felt compelled to ask my mother if she thought I might have ADHD. Her response? “Of course! Your father even raised the notion when you were in your 20s!” Huh. Maybe there’s something to this. So I chose to pursue it with a new doctor, who gave me 10 pages of questions about the history of heart disease, diabetes, and all the usual “medical snooping,” which irked me. After all, I was there because of my inability to process information, not because of freaking familial diseases!

When the doctor called me in, she wanted to know what brought me there. I offered a steady stream of consciousness, ending with my employee’s story and wondering if maybe, just maybe, I too had ADHD. She listened patiently because that’s what she’s paid to do, but she started annoyingly looking through my forms about halfway through my verbal vomit, and she appeared especially smug that I listed “poison ivy” as an allergy.

She said there’s no real test for ADHD, but that — based on what I described — it seemed viable. In fact, my medical history showed it could be possible. Really? How did my mom’s breast cancer drive to that conclusion? She held up the clipboard and flipped through the pages. The first page was neat, the second not quite as much, the third was littered with scrawling penmanship. Each page appeared increasingly illegible as I raced to finish the annoying list of questions. She told me that we could certainly try something to help: a stimulant. I was surprised; I didn’t need more energy and had concerns about my inability to sleep. She assured me that if I did indeed have ADHD, I wouldn’t have an issue as mentally and physically I would finally find a balance because the dopamine levels would level off. Cool.

I won’t kid you. I felt like a cat on a hot tin roof for the first few days… but as hyper as I was, I was actually happy. I’ve always struggled with keeping emotions in check (fight or flight, baby!), but I suddenly felt rather normal by day five — just like my employee described. I went through some learning curves over the next several months, mostly adjusting to looking at life through a different lens. I was suddenly feeling a lot — emotions and reactions unencumbered by anti-anxiety medication — but not in a crazy manic way. Today, I feel so good about who I am and what I now know about myself, and that’s why I feel compelled to share this with the world, or the .0000001% of the global population who reads it.

I’m an imperfect middle-aged woman with a late diagnosis of ADHD. I live a better life through outside means because the chemistry set God gave me was shit. It could be worse: I could have a nut allergy. Instead, I just felt nutty for 44 years.

*A great article on what ADHD looks like can be found here 20 Things to Remember If You Love a Person with ADD

“30 For Thirty” – Reward Your Forum & Help Our Chapter Grow

By: Patty Sins (Membership) – The new EO year has just begun and it promises to be unforgettable! With a focus on member engagement and growth, the board is committed to building the chapter and making it stronger than ever. More members means more resources for once-in-a-lifetime events, more networking opportunities, and more fun! The 2017/18 event schedule was designed to Elevate your business, your self, your family and your life.

This year, for the first time, our chapter is launching the EO Boston Forum Referral Program called 30 for Thirty. The goal is to recruit 30 new members to commemorate EO’s 30th anniversary. To make this a win-win for both the chapter and your forum, we’re implementing the following referral incentives, good through June 30, 2018:

  • Recruit 2 new members – Forum receives $400
  • Recruit 3 new members – Forum receives $750
  • Recruit 4 new members – Forum receives $1200
  • Recruit 5 new members – Forum receives $1750
  • Recruit 6 new members – Forum receives – $2400

Please note that this chapter program will complement the EO US East Referral Program which rewards each member $250 for every 3 recruits, $500 for every 6 recruits, $750 for every 9 recruits, and so on. And don’t forget…in the interest of promoting diversity, there is always a focus on recruiting young entrepreneurs (30+) and women. Complete the referral form that is located at and the EO Boston Membership team will take it from there.

This is your opportunity to make a difference so get involved today! Feel free to contact Patty Sins ( or Justin Rolnick (Justin@greekkitchenmanagement .com) with questions.