Linda M Perry On How To Navigate The Generational Differences That Are Disrupting Workplaces

An Interview With Cynthia Corsetti

Start with WHY. The first thing I do when I work with companies is to start with WHY. In my case, WHY Is a tool I use to understand the core motivations, strengths and challenges of a team. By understanding some of the subconscious drivers of individuals, you can begin to have better conversations and the ability to cross generational differences. When we recognize that at our core, we are all somewhat similarly motivated — we can approach problem solving from a different perspective. We can solve problems from what is really important rather than what is different for all of us.

Today’s workplaces are a melting pot of Baby Boomers, Gen Xers, Millennials, and Gen Zers. Each generation brings its unique perspective, work ethics, communication styles, and values. While this diversity can foster innovation and creativity, it can also lead to misunderstandings, conflicts, and productivity challenges. How can businesses effectively bridge these generational gaps to create harmonious and thriving work environments? As part of this series, we had the pleasure of interviewing Linda M. Perry.

Linda M. Perry is a master mindset coach, business strategist, speaker, and recovering attorney, who works with individuals, business owners, and their teams to become more self-driven and move toward 7-figure success. So many people get stuck on a plateau and don’t know how to move forward; Linda uses a mindset-first approach to support individuals and teams to tap into their core motivations and strengths and free them from their blocks so they can soar past 7 figures.

Thank you so much for joining us in this interview series. Before we dive into our discussion about succession, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

After spending 17 years as a federal criminal defense attorney, I became fascinated by the ways our brain and specifically our beliefs end up sabotaging our goals and dreams. I left the law to study shadow work under Debbie Ford and became certified as a mindset coach to help others move beyond their blocks and achieve more. As an entrepreneur myself, I saw how much business owners block success and began creating strategies to effectively help them (and their teams) scale, improve communication and build stronger leadership from within. The result is that business owners are better equipped to reach their goals, hire the “right” people to support their mission and ultimately make more money!

What do you think makes your company stand out? Can you share a story?

What makes my company stand out is that I combine mindset and practical strategy to help business owners first become clear visionary leaders, then work with their team to help them identify core motivations and strengths that improve effectiveness and productivity. I had one business owner call what I do “practical woo” because I focus on internal beliefs, while creating specific targets and goals to be completed each week. In many ways, I am a cross between a coach and consultant, trusting my clients to know what is truly best for them, but providing strategic pathways for them to take action.

I also can truly pinpoint each individual’s strengths and core motivations using a WHY assessment tool that allows for business owners to change the way they communicate with their team, hire employees and convey leadership. For example, I worked with a team where the visionary had a WHY of Trust, which meant that she had an unspoken expectation from each member to follow-up with their word and stay loyal to the mission. By sharing that with her and her team, she could convey expectations more clearly, embody the message into her culture and mission and also recognize when she might be taking things too personally. Her team also understood how important it was to be clear with their communication and step up — that didn’t mean perfection, but simply sharing more actively about their precise actions.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

1) Clarity. Having clarity of vision is incredibly important as it provides direction for the leadership, growth and the team. Too many business owners focus on goals instead of really focusing on what the big picture looks like for the company and it’s employees. I often tell business owners that a lack of clarity is like getting into a car and telling your GPS to go somewhere fun! You might end up somewhere amazing like Disney World, but more often than not you’ll end up in the middle of a corn field in Iowa with a lot of unhappy passengers!

2) Confidence: Confidence is not something you can fake — real internal confidence can be seen in leadership. For example, I was working with a small business and their team when I noticed side glances back and forth between the junior team members whenever the owner of the company spoke. When I addressed the issue from both sides, I learned that the junior team often dismissed the business owner because she equivocated in her statements. They felt comfortable rolling their eyes and even passing slack messages back and forth regarding the boss and her demeanor. What resulted was a culture that lagged in productivity, enthusiasm and professionalism. I then began to work with the business owner and discovered she was a people pleaser — we focused on her owning her self-worth and setting a different tone so her employees could follow suit and actually work on the tasks that would free her for growth. Little by little, they began to take her more seriously and even volunteered to take on bigger tasks.

3) Curiosity: Without curiosity a leader is apt to jump to conclusions and finger-pointing. Instead of blaming, demanding or assuming, curiosity allows a business owner to learn from their mistakes and take bigger leaps toward success. Curiosity means not assuming the worst in a team member who misses a deadline or seems to be uninterested, you can ask questions like, “what got in the way?” Or, “How can we learn from what happened here?” Or, “What support could be helpful here?” The truth is that curiosity opens up opportunities for growth where assumptions break down teams.

In your experience, what are the most distinct characteristics, values, and work preferences of each generation currently present in the workplace?

This is one of the firs periods in time where we have four separate generations present in the workplace, each with their own distinct characteristics and beliefs! Here’s how it breaks down.

Boomer: While many boomers are retiring, they still are present in the workplace and are responsible for setting the tone and culture of a workplace. Boomers value hard work and believe that everyone needs to learn the way they did — the hard way. There is a belief that suffering is part of education and if they went through something, so do younger generations. They were not raised with emotional awareness and do not value it in the workplace. They think hard work is key and absolute dedication to the job! It can lead to clashes with younger generations and they are often disregarded as “old fashioned” and “out of touch”.

Gen X: Generation X also values hard work and pragmatism, but they have greater emotional awareness and willingness to learn. Gen X was raised during a time when they were “lucky” to have a job and to “simply suck it up”. Overgiving and pleasing people became a survival strategy so they experienced a lot of overwhelm and burnout. Gen X is the first generation willing to try things out differently, but often are torn between the way things “should” be and how they are.

Millennials: Millennials are the first tech savvy generation and so they value efficiency and freedom! They are the first generation that didn’t expect to be in the same job their entire career and value work-life balance. They like collaboration but struggle to receive feedback as they are part of the generation where praise became the common parenting norm. They struggle with leadership because to them it may come across as harsh and they sometimes appear to lack the confidence of previous generations.

Gen Z: Gen Z is the youngest generation and they probably have the highest emotional IQ of any other generation currently in the workplace. They have grown up during turbulent times, so they struggle to know exactly how to show up in the workplace. Bullying and aggression have been a common narrative for many, so communication skills are challenged — even though they are the most tech savvy generation yet. They value work-life balance and prefer to pursue their passions than simply getting a job. They do not expect to stay in one job, but value culture and do work hard.

Can you describe a specific instance where generational differences caused a significant challenge in the workplace? How was it addressed, and what lessons were learned?

One of the most common challenges where generational differences cause a significant challenge is with communication. While the current generation has been given more tools to communicate, they have the hardest time communicating — especially around the status of projects, assignments and tasks. One instance that comes to mind is an agency that was preparing for an event and the team member had been given the task to have the marketing material prepared and ready by the Friday before the event.

Despite the clarity of the assignment, the team member went on vacation the week prior to the event and provided no updates or information regarding the marketing material. Worse yet, they failed to check email and were otherwise not in communication with the office the entire week. The manager who assigned the project was in a panic until Friday when the team member finally checked in and allayed everyone’s fears.

What seemed like common sense to the manager — updating the team before the team member left on their vacation — was something that escaped the team member’s thought process. They assumed everyone would know it would be done. But in the end hours were wasted and a lot of productivity was lost.

To remedy this problem, and any future problems like this, we focused on two things: internal processes and mentorship. One of the biggest problems is that the current generation hasn’t had the opportunity to work inside an office or receive mentorship like previous generations. What might seem obvious to some regarding what, how and when communications should be delivered, is not obvious when you have no experience. When that happens, having very clear systems along with incredibly clear instructions on how communications should be delivered regarding status and deadlines is a must! It’s a simple fix, but one overlooked by so many companies.

Technology adoption varies greatly between generations. How do you recommend companies bridge the tech-savviness gap without alienating any generational group?

This is not as big a problem as it might appear. I think most generations value having the latest technology. The one place where there is a struggle is with AI. Older generations struggle with using AI as a tool, but the way to truly bridge the gap is to have regular training and tutorials available to older generations. This also means making training a part of the company culture, rather than it being another thing they have to do along with client work and management.

How can organizations create cross-generational mentorship programs that allow older and younger employees to learn from each other?

Cross-generational mentorship programs are the key to company growth! Mentorship is absolutely essential especially in hybrid or remote working environments. One of the biggest problems in the current workplace is that younger generations have not received the same kind of mentorship they normally receive because of COVID and the changing landscape of the workplace. Rather than simply focusing on cross-generational mentorship programs, it’s important to consider aligning mentors and mentees along their core motivations. One of the things I teach companies is to look for mentors whose WHY aligns with teaching and sharing valuable information with others. Some individuals are actually not meant to be mentors! Then the key is to partner them with compatible WHYs. That doesn’t mean the mentor and mentee shall have the same core motivation, it simply means they will understand each other and be able to facilitate learning faster. This can be done both 1:1 and in a group setting. They key is that they get exposed to everyday circumstances that may seem commonplace — but are necessary for learning communication, leadership, and even kindness.

From face-to-face conversations to instant messaging, each generation has its communication preference. How can businesses foster effective communication that caters to these diverse preferences?

There has to be a mix of communication in a workplace. Having each generation default to their own preferences doesn’t allow for growth or for expansion. There are some ground rules that may cut across the board, however. For example, Generation Z loves to text — but often that is not good for preserving records or clarity! There are myriad tools in the marketplace from Circle to Slack to Zoom that can enhance electronic communication, but it is important that there is something that can be learned from each different generation and preference. In person communication, for example, may be best for mentorship and the nuances that might be missed in learning and communication via electronic methods!

How should training and development programs be tailored to cater to the unique learning styles and expectations of different generations?

Regardless of generational differences, training and development programs need to cater to different learning styles and even neurodivergence. We live in a great time where we understand more and more that people learn differently — and being able to provide different learning opportunities to team members has become easier and less expensive. As someone who has worked for years in helping business owners with their digital training and online learning programs, it’s essential that training and development cater to auditory, visual and kinesthetic learners. There also must be opportunities for those who struggle with learning challenges to access information in more than one way! When I work with companies, I ensure that there are myriad different ways to access the same material. For example, many love video learning — but for me to be able to read text is vital to my comprehension and allows for greater speed and consumption of information. Providing avenues for choice not only supports inclusiveness, but also gives each participant an equal opportunity to advance as other workers.

In what ways can leaders ensure they’re being inclusive and not harboring unconscious biases towards one generation over another?

This is hard because we all carry unconscious biases — they are, after all, unconscious! But, it is possible to become aware of your own biases and beliefs by simply listening to your own language! Whenever I work with leaders, I am always listening for absolute statements, and also the phrases “should” “have to” “must”. Those typically indicate to me there is a bias or belief at play, especially when talking about a certain group of people.

While it may be true that Gen Z struggles with challenges around communication, assuming that each individual comes to you ill prepared in this area is a mistake. As I shared earlier, the best thing a leader can do is remain curious. Look at your own thought processes and actions to learn what is hiding within and when working with team members, look at the individual for their strengths and challenges and then adapt!

As we look towards the future and the eventual integration of newer generations into the workforce, what strategies should businesses implement now to be prepared for even more diverse generational dynamics?

It can be hard to guess how diverse generational dynamics will impact the workplace, but I believe that companies must consider a few key strategies that will make adjusting to new generations easier. First, it’s important to do the hard work of visioning. Each company must understand where it is going so that it can draw in a new generation that can get behind and support each new initiative. Second, having clear structures and procedures is vital. There is too much assumption that people will simply “know” how things are done and businesses don’t invest in the structures to make bringing in new generations easier. Lastly, they have to remain curious and open to new ways of thinking, being and doing things. Work-life balance is a prime example. Gen-Z is no longer satisfied with simply working non-stop to afford a home and tangible things — in fact, they don’t believe that much of that is actually accessible to them as it was in previous generations. They rather would work for a company that values them and their life as an individual rather than be seen as expendable. The ability to remain flexible to the drives, motivations and beliefs of a generation will bring together more cohesion and even growth! I know I have personally learned a lot from younger generations about redefining success in a way that feels more balanced and healthy.

What are your “Five Things Leaders Need to Know About How to Navigate the Generational Differences that are Disrupting Workplaces”?

1 . Start with WHY. The first thing I do when I work with companies is to start with WHY. In my case, WHY Is a tool I use to understand the core motivations, strengths and challenges of a team. By understanding some of the subconscious drivers of individuals, you can begin to have better conversations and the ability to cross generational differences. When we recognize that at our core, we are all somewhat similarly motivated — we can approach problem solving from a different perspective. We can solve problems from what is really important rather than what is different for all of us.

2 . Seek First to Understand. Generational differences inevitably lead to a lot of finger pointing and judgment. But here’s the thing, judgment is merely resistance and something we do to validate ourselves or feel better. Sure, we can point fingers and say our generation would never do that, but that only feels good for a few minutes and then you return to the same problem. Seek first to understand means that you ask better questions and try to understand the individual perspective rather than assume you know better! When I first started working with Gen Z team members, I learned they would often defer to casual dress, conversations and preferred texting as a primary method of communication. I found myself getting frustrated with they way they showed up and often the lax attention they had toward deadlines! I could hear myself complaining and thinking how “I would never act this way at their age.” But, I then realized how unhelpful that is to really getting what I wanted! So, instead, I started to ask questions as to why they did things a certain way. What I learned is that communication for this generation is particularly hard because each comment or word could come back at them, be used against them. Many had experienced bullying in some form, so delivering bad news (or undesirable news) became a huge trigger. Learning that allowed me to create a structure for how and when to communicate issues and deadlines (and not over text!). Both their ability to share improved, as did my ability to clearly set better expectations for what i wanted and needed.

3 . Not Everything Is A Threat. There is an automatic assumption when things are not done the way a previous generation did things that it threatens the status quo! The truth is each generation has had tools available to them previous generations have not. The current generation is better equipped to understand the emotional drivers that cause them to get stuck! That’s incredible — especially if we can learn to communicate with them and ask them better questions. It also allows us to see their strengths more clearly and put them in a role that can support us (leaders) in moving forward and doing less of the things that slow us down. I am constantly teaching leaders to look at the changes as opportunities — perhaps some new way of looking at things will allow for improved delegation sothe business owner can focus on the things that will actually move the company forward rather than simply being overwhelmed all the time.

4 . You Must Lead by Example. This is more important than ever. In the past, you could learn as much from a bad mentor as a good one, but because the current generation hasn’t been as exposed to live mentorship, it’s increasingly important that leaders lead through action rather than just through words. The current generation is still looking for role models when it comes to behavior, leadership, communication, support and who they want to be. Many of them feel lost and need to see what it means to move through challenges instead of simply hide from them. You can’t teach this through words, but instead must really use every misstep as an opportunity to learn lessons, grow, show what it means to overcome adversity and still be kind. What I have seen with the strongest leaders is that their younger team members tend to soak up this kind of knowledge and apply it readily to the way they want to show up!

5 . Educate Yourself: It’s not enough to know your craft. Educate yourself on different mindsets, leadership styles, strengths and communication skills. Look, I know that leaders currently have a lot on their plates, but by getting educated on how to lead, foster growth from within and improve communication, you 10x your ability to scale and move forward. You can’t rely on your middle management to run the key areas of your business — you have to provide inspiration and direction. The only way to do that is become more educated on the things that matter to younger generations. This isn’t solely about having a job and earning enough money to buy a house, your team members want to feel fulfilled and do meaningful work. You can’t foster that kind of culture if you don’t educate yourself first on what matters!

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

It was 2006 and I was just contemplating leaving the law. I was driving down Lake Shore Drive in Chicago on my way to work when I was listening to the CD version of 7 Habits of Hghly Effective people by Stehen R. Covey when he read a powerful quote that changed the way I look at what’s possible in life. He read a quote from holocaust survivor and psychologist Viktor Frankl that says:

“Between stimulus and response there is a space. In that space lies our power to choose our response. In our response lies our growth and freedom.”

The quote struck me because up until that point I had been living a life based on what others thought was right for me. Instead of giving my power away to external circumstances, what others wanted for me and my limiting beliefs, I had the agency to choose my outcomes. Like so many, I had felt helpless to the cards I was dealt, but after hearing this quote, I realized it was up to me to create my success. After this point, I was able to take charge of my life — leaving my career in law, starting my own business and even moving abroad to live in Lisbon!

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

Like so many leaders, doubt can creep in. Am I on the right track, am I doing what I need to meet my own financial goals and terms of success. Before doing mindset work, those kinds of thoughts would drive me to work harder, say yes to opportunities that didn’t fit or feel stressed out at all times. Now, I simply look at those doubts as information and I double down on my vision and goals.

I go back to what it is that I want and my plan to get there and I remind myself to stay the course. The reality is that most businesses fail because they don’t stay the course or keep focused on where they are going. When you stay clear, you can make better choices — even as your doubts wake you up or cause you to worry!

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Honestly, the movement is the one I’ve worked on over the last years — and that is to put mindset first! We all try to find our voice, our self-worth and success outside of ourselves in the things we do. But truly, it is all about who you’re being that predicts the outcome of your daily life and your success. We live in a world that values so much what you’re doing, how you’re doing it and what others think. But, when you can truly free yourself from your limiting beliefs and put your mindset above strategy, life and success take on new meaning. I would bring mindset (not mindfulness) strategies to children in school so they can begin to understand that the beliefs they hold are not really their own! It would change confidence overnight!

How can our readers further follow you online?

Your readers can find me at lindamperry.com. I am also active on LinkedIn at lindamperry and on Instagram at linda.m.perry.

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!