Greg Singleton is well known for his ability to get the best out of the person across from him. He is the founder of CSB Coaching, and he has transformed his experiences into a powerful coaching framework designed to help others empower themselves to live fulfilling lives.

How many times have you heard an older generation misunderstand the younger generations, and vice versa? So many of us get stuck in our own way of life, never leaving room for new perspectives or understanding. We all think we know how things should be done.

But what happens when you take the time to truly get to know the generations you interact with daily? What could you learn if you put aside your preconceived notions? How much more could you accomplish by blending your understanding with those who think differently from you?
There are endless questions to ask and a wealth of insights to uncover. I’ve had the privilege of working with and learning firsthand from Katherine Jeffery, PhD, about how we can improve communication across generations by understanding the research behind our differences. After completing her master class (link below), you’ll find that it changes how you choose to communicate with different generations—not just in the workplace but in life as well.
Let’s be honest, we could all use a refresher course on approaching conversations with an open mind rather than pounding the table and insisting we’re right.
I hope this helps!
Understanding yourself first
No matter which generation you were raised in, whether Traditionalist, Boomer, Gen X, Millennial, or Gen Z, there are common threads woven into our way of thinking throughout our upbringing. Even if you feel you cannot relate to those older or younger than you, pieces of you exist within them all. We just need to set aside our egos to find the connections hiding in plain sight.
All of us were raised by the generation that came before us. Our decisions are shaped by the lessons passed down from those who lived life through a different lens. How we communicate, solve problems, work, and think, along with many other facets, are instilled in us during childhood and influence who we are today.
Here is the cool part. When you realize that who you are is a reflection of who they were, you begin to integrate rather than separate.
Take a moment after reading this to reflect on the impact of those who raised you. Consider the good they passed on, the mistakes they made, their unique expression of love, the resilience they taught you, the strength they instilled in you, and ultimately, how all of it shaped the way you live today. There will be good and bad. That is the beauty of self-awareness. We measure the highs against the lows, the lessons against the struggles. And here is the key. You get to choose what you carry forward, implement in your life, and pass down to the next generation.
This realization carries an incredible weight. You mean everything to the generation that follows. Filter out what no longer serves you, embrace the lessons that provide clarity, and always leave room to learn from the world that is unfolding before you.
Understanding yourself means you respect where you came from, know what you stand for now, and have the clarity to evolve as time goes on.
Boomers
An amazing generation that led with the “We live to work” motto. They sacrificed an immense amount of time working in a career, many of them staying in the same one their entire lives, so they could provide for their families. Throughout their lives, they tried to put themselves and their families in a position to succeed in the future.
“They leave behind a legacy of mentorship and dedication.” – Katherine Jeffery, PhD
Gen Xers
A generation often referred to as “Latchkey Kids,” where self-sufficiency, appreciation, and adaptability were integral to their lives. With both parents working, they sometimes had to assume a small portion of parenting responsibilities until one or both parents returned home from work. Relationships mean a great deal to them.
Millennials
A generation that loves to work smarter, not harder. They integrate flexibility between work and personal life. Technology is part of their everyday lives because they grew up with the internet. Collaboration means a great deal to them.
Gen Zers
A generation that has prioritized life/work balance, not work/life balance. Technology is an extension of who they are because they grew up with a phone in their hands and access to any answer at their fingertips. They are inclusive and have a strong sense of living life beyond just work.
Understanding the gaps in communication
Each generation has experienced life through vastly different circumstances. I believe technology is one of the biggest factors in bridging the gap in how we communicate with each other. Boomers did not grow up with technology, Gen X lived without it and then had to pivot to adopt it, Millennials were raised in a tech-immersed world, and Gen Z has technology ingrained in their daily lives as an extension of themselves.
We all rely on technology today (you are using it right now to read this), so why would we not take the time to understand how each generation uses, or does not use, it to improve communication?
Boomers prefer face-to-face meetings because that’s how things got done when they were growing up.
Gen X is comfortable with face-to-face meetings, emails, and, depending on the topic, texts.
Millennials would much rather text and use email sparingly.
Gen Z prefers texts (with the right emojis) or direct messages (DMs).
Once you understand how each generation prefers to communicate, you start to see the gaps that cause miscommunication between age groups. Bridging these gaps requires effort from both younger and older generations. It is a two-way street. The key is to recognize the differences and find a way to meet in the middle.
Do not stand on a soapbox demanding that one generation cater to another. Just because something was done a certain way in the past does not mean it cannot evolve. And just because we do things differently today does not mean we cannot learn from those who came before us.
We all have egos, both personal and generational. Set aside both so you can create space to listen, learn, and grow in both directions, not just from the top down.
How to communicate better between generations
We all learn differently, have unique preferences, grow at our own pace, and see the world through different lenses. But one thing matters above all: our ability to teach and pass along the knowledge we have gained throughout our journey. This is the essence of humanity. Information was never meant to be hoarded; it serves no purpose when kept in a space where others cannot access it to grow.
How you choose to present information to someone willing to receive it is entirely up to you. If your ego matters more than the message, if your goal is simply to be right, you will deliver information in a way that suits you without considering how the other person processes it. When that happens, communication breaks down, and gaps form.
However, if you prioritize the message itself and the opportunity to share it, you will find a way to deliver it in the most useful and impactful way for the person receiving it.
Here is a challenge for each generation:
Boomers – Send a quick video or direct message to your grandkids.
Gen X – Collaborate more with millennials and Gen Z.
Millennials – Reply to that email once in a while.
Gen Z – Meet face-to-face from time to time.
A little effort in communication goes a long way. Knowledge grows when it is shared, not when it is guarded.
How to learn more
When you sit down to take the master class by Katherine Jeffery, PhD (found here), you will gain a deeper understanding of how much we all need to listen to each other. I have been working with her to expand her consulting business and share this valuable information with as many people as possible.
If you are interested in educating yourself or your workforce on how to improve communication across generations, please reach out to her or me. We would love to help!
As always, celebrate others, do not alienate others!
Read more from Greg Singleton
Greg Singleton, Perspective and Mindset Coach
Greg Singleton is a certified NAMI (National Alliance on Mental Illness) peer-to-peer leader, and his coaching guides people with the correct perspective and mindset to overcome imposter syndrome, build confidence, and embrace a healthier mindset. He has dedicated the last 10 years to helping others overcome their fear and embrace their inner confidence to become who they strive to be. He is the CEO of CSB Coaching. His mission: Celebrate others, don't Alienate others.