Season 5 • Episode 6

For the first time in history, five generations are working simultaneously in the workplace. As a result, tensions arise as work trends shift in ways older generations have never seen, and fear-based differences create gaps among employees that may seem impossible to close. In this episode, we sit down with certified coach and trained speaker Lindsay Boccardo to discuss the four factors of employee engagement, and how humanizing your workforce and learning to manage emotional labor through self-awareness and regulation are the first steps to bridging the generational gap. In addition, we discuss the value of mentorship in preventing the retirement brain drain and how authenticity may be the key to attracting younger generations.


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About DE Talk

For DirectEmployers, it’s all about valuable connections and meaningful conversations. This monthly podcast features honest and open dialogue between powerhouse industry experts on a variety of HR topics ranging from OFCCP compliance advice to emerging recruitment marketing trends, diversity and inclusion initiatives, and insightful solutions that help infuse new life into your HR strategies.

Hosted by Candee Chambers, Executive Director of DirectEmployers Association.

Guest Host

Headshot of Mikey Meagher

​Mikey Meagher

Manager, Diversity, Equity, & Inclusion Strategies

Mikey Meagher is the Manager of Diversity, Equity and Inclusion Strategies at DirectEmployers Association and is focused on fostering relationships with veteran and diversity organizations to promote workforce inclusivity. Mikey began her career recruiting within the IT industry, which made her transition to DirectEmployers partnership team a natural progression as relationship-building and strong communication are core components of both. Within her current role, Mikey works to facilitate conversations between Members and existing partners and provide outreach resources to both parties, as well as identify, develop, and promote new local and national level partnerships. Mikey holds a Bachelor of Science Degree in Criminology from University of Florida, a Master’s Degree in Organizational Leadership from Jacksonville University, and is a certified Windmills Trainer and Diversity, Equity & Inclusion professional.

Episode Guest

Lindsay Boccardo

Lindsay Boccardo

Career Strategist & Corporate Trainer

Lindsay Boccardo is a nationally-recognized millennial expert, working with young talent and the organizations that employ them. She has been providing education and training to organizations through one-to-one programs, group coaching and seminars for more than a decade. She is also the creator of the “Seven Steps to Rock Your Twenties” & “Unleash My Career” programs for high achieving millennials. Lindsay holds a degree in psychology and public communication from Syracuse University, and a coaching certification from the International Coach Federation.

Episode Transcript

Candee Chambers (00:02):

Get ready. The DE Talk podcast starts now, insightful conversations and dialogue, helping you put the human factor back in HR.

Mikey Meagher (00:14):

For the first time in history, there are five generations in the workplace, traditionalists or the silent generation, baby boomers, gen X, millennials, and gen Z. And boy, do each differ. Each new generation joining the workforce brings its own set of qualities, traits, and values. For example, when searching for employment, baby boomers sought job security, gen X sought work-life balance and professional progress.


And now we see millennials and gen Z seek everything from a company’s ethics to a decent work-life balance. What kind of challenges does this present for today’s employers? How do generational workforce differences affect our ability to manage people effectively?


Well, today we are excited to have Lindsay Boccardo or Boccardi get this party started to join us on the DE Talk podcast to discuss all things generational differences and the work we can do to harness each generation’s strengths and capture multiple levels of experience, skills, expertise to be able to build more efficient and cohesive teams. Let’s dive in and welcome Lindsay. Thanks for joining us today.

Lindsay Boccardo (01:28):

Thanks for having me, Mikey. I’m excited to be here.

Mikey Meagher (01:30):

Yeah, me too. We just recently discovered that we grew up in Syracuse or upstate New York, rather.

Lindsay Boccardo (01:37):


Mikey Meagher (01:38):

You went to Syracuse University. I decided to go South to Florida and stay there. Not loving the winters.

Lindsay Boccardo (01:47):

Understood. We would walk through, the joke on campus was they’ll never cancel a class or classes for snow, and we would walk through what felt like hallways of snow. Snow that was four feet, five feet plowed high.

Mikey Meagher (02:00):

Oh, yeah.

Lindsay Boccardo (02:00):

Just to get to class. So you know it’s no joke. People think I’m exaggerating. I’m really not, am I?

Mikey Meagher (02:06):

No. They’re so prepared with the salt and I guess it is the salt city for a reason, but they’re ready to go and lay that down and get you to class.

Lindsay Boccardo (02:16):

That’s right.

Mikey Meagher (02:17):

Snow days are not as plentiful as people might think.

Lindsay Boccardo (02:21):

Yeah, exactly.

Mikey Meagher (02:22):

But I know some of the staff has had, our staff at DE anyways has had the opportunity to hear you speak at a TrueU event. I’ve heard nothing but great things. I’m loving our conversation already and even the intro to all of this. But for those who aren’t familiar with you yet, just share some background. Who is Lindsay?

Lindsay Boccardo (02:45):

Yeah. So I’m a certified coach and trained speaker. So most of my time you’ll find me on stages talking about generations at work, talking about change management, how we need to think differently for the future of work. And so that’s where most people encounter me and we spend some time together at a conference or sometimes even at trainings at some of the companies I love across the country.


That’s where most of my time is invested and spent because I see this huge shift happening and everybody’s feeling it, but you’re seeing in our society that the way that things are changing with technology, with the way that we relate to each other, with what we think work actually is and what it isn’t, how we make money, how we measure success, all of this is changing so quickly that older generations who had certain rules that they played by, those rules are getting obliterated. And it’s really upsetting.


It’s really upsetting if you did things a certain way for decades and now these young bucks are coming in saying, “Oh, I’m not working. I’m not working 40 hours a week. Oh, I’m not working five days a week. Oh, I’m not coming to the office.” What a mind breaker that is for those in leadership positions or those who have been working for a few decades. So my job is to help us all kind of understand where we’re headed and how to see the bright side of that and to see the hope in that and not to feel like doom and gloom, this is bad, bad things are happening.


And so about a decade ago I went back to school for coaching and got my certification through the ICF, the International Coach Federation so that I wouldn’t just be spitting facts at people. But coaching is really the study of the process of helping humans change, evolve and grow. And so that’s the work I love to do. Either one-on-one groups online. I do some of that virtually. Helping us all look to the future and deciding that it’s going to be big and bright based on how we behave today. That’s what I love to do.

Mikey Meagher (04:36):

That is awesome and very involved. And you bring up a good point in the doom and gloom and because it does very much feel like that. And sometimes I feel like also being a millennial, as part of my generation, you’re balancing the before and after these generations. So it’s kind of an interesting place to also be in.


And you find that we’re really operating, from what I see, under the same, not necessarily wants, but it’s fears. So we’re working to protect, maybe it’s millennials and gen Z to protect more work from home. Whereas in the past, the fear was, “If I’m not in the office 12 hours a day, I don’t want to lose my job because I need to provide for my family.”


So it all was, it seems like it’s fear-based more than trying to work for the wants and the things we do love about our lives and not working to protect these fears that we all have, if that makes sense. It just kind of feels like that there’s this shift. And I see that more with the millennials because I am one, but you just see that a lot in the workplace and balancing the generations.

Lindsay Boccardo (05:57):

Yeah. Well, it’s hard to have fear around what work is becoming if you’re brand new to the marketplace. But the reason there’s fear and angst and anger and frustration is these older generations are like, “Wait, wait, wait, wait, wait, wait. There’s rules that we play by. You can’t just come in and play monopoly and flip the board and turn it into a checkers board. What are you doing?” And that’s the piece that older generations have the fear of change around.


The reason they have that is because they had to do it a certain way and there were very prescribed rules and most people didn’t have multiple income streams. Now half of millennials have an income stream where they make eight to 10 grand a year. And it’s even more so for gen Zs, with creators. And so when you change the rules on somebody halfway through the game, it’s much more irritating than if you and I are just setting up the board for the first time. And so that’s part of what you’re seeing. It’s human nature.

Mikey Meagher (06:51):

Yes. Yes, it definitely is. And I love that you have the passion to go out and facilitate these conversations and be like, “Stop it. Stop with the fear. Stop with the doom and gloom. This can all work and be cohesive.” So love that.

Lindsay Boccardo (07:08):

Yeah. Well, and that’s really the first step. It’s actually, this always surprises people, but I don’t have to tell people to stop because they already know that something is amiss. What they actually need is somebody to say, “I get it. It makes perfect sense that you’re feeling this way because of how you were raised, because of the rules that you had to play by. And it feels really unfair that now that you are at the top of the pyramid, we’re changing all the rules around. Of course, that doesn’t feel fair.”


And so the other piece that I love about coaching is it’s helped me understand human nature. I’ll make more impact by being precise and gentle and compassionate. I can make much more of an impact by understanding people’s perspectives, especially boomers and gen Xers than I can coming in big and telling people, “This is the way it is. It’s reality. Get used to it.”


So it’s kind of this interesting dance that I do of making sure that everybody in the room feels seen, heard and understood. Even as a keynote speaker where I’m not having one-to-one conversations, I really try to embed any presentation I do with a huge dose of compassion and understanding because that’s how people become pliable. They feel like, “Oh, you get me. You understand why I feel this way. Makes sense.”

Mikey Meagher (08:24):

Yeah. I mean, and you definitely exude that. I mean, just from the start of this conversation, but before we went into recording. It’s nice when somebody takes the time to want to understand who they’re talking with.

Lindsay Boccardo (08:36):


Mikey Meagher (08:37):

And to be able to have is just, it’s so important and crucial. And leading into that, I understand you were in a band.

Lindsay Boccardo (08:46):


Mikey Meagher (08:47):

So how has that led you to what you do today, if any involvement?

Lindsay Boccardo (08:53):

Well, I love music. I always have it playing somewhere in the background in my car, in my AirPods somewhere. And when I was a little kid, I tried every instrument. Right? So piano, I was so bad at piano. My teacher would always look at her wristwatch and I knew she wanted me to get out of there because I was never practicing. I just sucked. And I went through all these instruments and I finally landed on the drums. And it is a totally, being a drummer is kind of a different way of thinking than guitar player, vocalist, piano. It’s just a different wavelength.


It’s you think in patterns, you think about leading the band rhythmically. It’s just different. And I loved it. And I had a phenomenal teacher that taught me how to play to real songs. And so by the time I graduated from Syracuse, I knew this is my one chance in life. I’m in my twenties, this is my chance to tour and be in a band and do the thing, do the American dream for me. It was my American dream. And that’s exactly what I did.


And through long rehearsal days, through painful injuries, drumming injuries, through traveling in a car across the United States and back more than once, I’ve spent a lot of time in vans. I saw that as much as I love music, what I love more was connecting with the people before and after shows. And so after years of touring and lots of cups of Wendy’s Chili, please don’t send me Wendy’s Chili. I decided to take my love of pattern, which I understand in music and shift it and say, “I know there’s patterns in people.


It’s not just music that has a pattern, that has a verse, chorus, bridge.” Humans are patterned beings. Our psychology is patterned. My undergrad was in psychology. And so I went back to school for coaching and I saw so much that happened in my band that went wrong. I started to understand, “Oh, I see why that didn’t work. Oh, I see why.” Even in my dynamics in my band, I started to understand why humans get along, why they butt heads, why they can’t be creative together anymore, why they part ways.


I started to really understand these patterns in humans, and that’s my passion. That’s my passion now is to help other people unlock the patterns that are happening inside of them and the patterns that they see in other people. And to become the type of person that creates positive, connecting, loving patterns at work, that’s every single person’s responsibility, and it’s the future of work.


It’s how we’ll recruit. People don’t, you’ve mentioned this, but gen Zs don’t just come for a paycheck, they come for a vibe. They come to have an experience. They come to be connected and belong inside of a company. So there’s a lot more work to be an emotionally intelligent human than there was 20 years ago. And that’s what I love to help people learn.

Mikey Meagher (11:38):

Yeah. And just there’s so much more access and information surrounding people too. So that also plays into it. And that’s next level thinking that you’re able to see that patterns aren’t only in music and what you were doing in your band, but to transfer that into the human experience is, I mean, I’m applauding right now.


You can’t see me, but I love that. That is truly thinking out there and it’s just amazing. And that’s also led you to, I mean, you’re extremely busy. You also have a blog series, band virtual trainings and your own podcast. So what’s that all about? Walk us through how you got through all of that and to where you’re starting.

Lindsay Boccardo (12:34):

I have a dual degree in psychology and public communications. And so when I was in college, y’all, we were recording on tapes. Oh my gosh, I’m aging myself, but I’m proud of my age. I’m 39. We were still recording on tapes. We had the cell phones with actual buttons. Okay? And being in media in the early two thousands, I went to school from 2002 to 2006 at Newhouse, which is a media school at Syracuse, everyone was buzzing with what the next thing was going to be.


Spotify wasn’t out yet, but we knew newspapers were dying. All media was shifting. I was doing radio internships as a DJ, which I still love. But I started to see this is going to change too because nobody’s listening to a radio on their iPod at the gym. They’re listening to sound files, what is happening? And I started to understand that we’re in this kind of volatile time in terms of how we get messages to other people.


So it looks like I’m really busy and I do keep a very full schedule, but what I’m really doing behind the scenes is testing how my people, my community wants to receive information. So sometimes it’s like maybe they do want to receive a podcast, they just want the audio so they can walk their dog and learn something about generations or learn something from another leader.


That’s great. Some of the people in my world say, “Lindsay, we just need a 30-minute training a month. Please don’t do these huge summits or big three-day retreats where we forget half of what we learned. Just give us a 30-minute soft skill that we can practice with our team.” And so that’s what I’ve been doing. That’s what is, it’s… we call it the band because the idea is that you got to practice behind the scenes before you get up on stage. And that’s what we do in those trainings. So…

Mikey Meagher (14:21):

Love that.

Lindsay Boccardo (14:24):

Yeah. So we find these little pockets and I basically see if the people I love to be around, my community, if it’s serving them or not. So when I get feedback like, “Hey, Linds, your podcast is not really serving me.” I mean, they don’t say that to me, but I can see it in the data. Then I pause and it’s all about getting out there and trying these different mediums and not being afraid to kind of what would look like failure on paper, not being afraid to test things out publicly. That’s really what it is.

Mikey Meagher (14:52):

Wow. Again, I mean, your level of thinking, I want to talk to you all day long. I want to getting so many ideas by you and I want to be a part of this behind the scenes training as well.

Lindsay Boccardo (15:04):

Yeah, I love it. You’re welcome to join.

Mikey Meagher (15:06):

Awesome. I think I’m going to. And so to bring it back into the generations, talking about the four factors of employee engagement, how do these vary in importance between these generations? And just kind of walk employers through how they can navigate this. Because I know I’ve heard of issues coming up as well, and again, we don’t want to look at them as issues, but let’s have some resolve. So how do you help walk employers or anybody through that scenario?

Lindsay Boccardo (15:43):

Yeah. Let’s talk about, here’s the four factors. If you are a note taker, this is a great little note to make, but I’m going to walk through these for you and you’ll see they’ll make sense intuitively in a moment. The first factor that matters right now for employees is purpose in work. It means, what am I doing here? What are we doing together and how are we changing the world? So purpose in work.


If you are a local bank and you’re trying to figure out how do we recruit the next generation, well, we’re going to have to show this next generation how their employment here will not only grow them personally, but change the world around us too. And I see when companies are thinking this way, let’s not just have a single bottom line of growing and making more money, but actually having purpose in our work, purpose in this world.


And so that’s the first one, purpose in work. The second one is influential relationships. This is no mystery, but we like to be around people we like. Everyone’s got certain types of people they enjoy to be around and having friends at work is a key retention factor. Even in Gallup research with the Q12, we know this is true. And so having relationships at work, we are social beings more than we are productive beings.


When you think about the priorities of the brain, our social relationships, our emotional connection is more of a priority than sending emails and being productive. And so influential relationships is the second big factor of employee engagement. Do we create those here? Do people come here and feel plugged in and connected? The third one is personal development. We have this concept of professional development, which is kind of like professional etiquette, how to write emails, how to not look like an idiot in a sales meeting.


There’s those professional skills where you don’t want to look foolish, but the other side is personal development. When I work here, do I grow more as a human? Do people give me ongoing feedback? Do I get input for my own self-awareness? Do I know where I’m growing to beyond just climbing a ladder? Do I know who I’m trying to become and do I have support there? Personal development is key. And the fourth factor is whole life understanding.


You mentioned this earlier, this idea, Mikey, of a work-life balance, you got to work for security. What is it? Well, whole life understanding is something that we have been talking about since 2015, but COVID brought this into view, brought this into focus, this idea that every single person that’s on your team has other life priorities that should and do matter more than being productive for your sake.


Things like family health, personal health, mental health, their safety and security at home. And if you’re the type of employer that can see somebody as a whole human who happens to give their time and attention to build your bottom line, you’re sitting correctly. If you feel like, “I own these people nine to five. I don’t care what’s going on in their world, they need to show up a hundred percent every day,” you’re going to have a major problem.


And the next generation can sniff this out if you actually see them as whole people or almost objects and cogs in the wheel, if you will. So these four factors, purpose and work, influential relationships, personal development and whole life understanding, these are the four that create more connection and retention at work or when they’re missing, people get a little listless, they get a little visionless, they head somewhere else where the grass is greener.


The funny thing is whenever I share this, I got to tell you, every generation comes up to me after and said, “These four factors sound awesome.” So this isn’t like, these aren’t kind of factors that only hit gen Zs. It’s that this may be the first time in history where humans get to push back a bit and say, “No, these are the four things I need to want to be here. And I vote for the best company culture with my own time and energy with where I decide to work.”


And so you can imagine it’s not that all of a sudden these gen Zs want to have purpose and whole life understanding. It’s well, humans are starting to understand how to humanize the working experience. And everyone that reads these says, “These are great.” No one’s like, “Ew, personal development. Let me shrink in my personal influence.” That, no one says that are great. These are rules for human flourishing.

Mikey Meagher (20:26):

Wow, personal development over, it’s kind of one of those things over professional development you think, okay, but they both go hand in hand because at some point you’re growing. And when you’re growing, yes, that is going to help you professionally.

Lindsay Boccardo (20:42):

That’s right.

Mikey Meagher (20:43):

But moving yourself up or like you were saying before, climbing the ladder in all of this, just because you’re bettering yourself professionally can mean that you’re worsening yourself personally. So it’s not as if A, then B. It’s you kind of need to have that personal growth before anything else can happen.

Lindsay Boccardo (21:06):

That’s exactly it. And I would say the foundation of all that is self-awareness. And let’s, can we do an example together?

Mikey Meagher (21:14):


Lindsay Boccardo (21:15):

Let’s do an example. Say most people are in therapy. I have a fantastic therapist. I think it’s one of the best things we can do for ourselves. We’re in therapy for self-reflection, self-awareness, self-compassion and emotional regulation. Those are some of the reasons we might go to therapy. You have an acute scenario happening in your life, you lose a parent, you go through a divorce, you go through something traumatic, or you just had a rough childhood and you never realized it.


And now you’re seeing how difficult adulthood is to adapt to for different reasons. People go for all different reasons. But take emotional regulation for example. I’ve had people, leaders tell me, “It’s not my job to help my employees learn how to emotionally regulate.” Okay, I understand that that is something that happens in therapy through a process. Cognitive behavioral therapy is a great place to learn this.


And what happens when you have an employee who doesn’t know how to regulate their emotions? They create triangulation, they create drama. They cause a lot of friction in the system. In most research, there are so many papers about this that it’s worse to have a negative Nancy. It’s worse to have a bad vibe in the room than it is to have an incompetent person in the room because this person that doesn’t emotionally regulate tears the team apart with their drama.


And so is it your job to become a licensed mental health therapist and train people how to do this? No. But if you don’t, if you don’t find a solution for that and support your people in what you might consider personal growth, it’s still going to impact the team. And so it reminds me a lot of this emotional learning, social learning, learning how to connect, say what your needs are, understand boundaries, all of these types of people skills.


We are just now seeing at the young childhood level how important it is to embed that in people as they grow. And so certainly for millennials, we didn’t talk about this. Gen Xers didn’t, boomers didn’t. When we come together at work, if we don’t have these self-awareness skills, we’re going to wreak havoc on our teams. And this is where we get a little confused about the difference between personal, professional development because it’s exactly what you said, Mikey, they really go hand in hand. But the foundation is growing personally so that you can bring professional skills to what you’re doing.

Mikey Meagher (23:39):

Yes. And I think being able to embed that into the company culture, and I would say definitely maybe boomers and even gen X here and there, but that was something that was told not to talk about, not to bring to the workforce. And so it was just now it’s like, “What? Now I’m being told we do need to do this.” It’s culture. And it’s not anybody’s fault in the sense of the way that they’re viewing it, but it’s what’s been drilled into the past and trying to really dig out of that.

Lindsay Boccardo (24:26):

Yeah. And if we were to look at the definition of professionalism, maybe when our parents were growing up, professionalism was, “Leave your emotions at home. You’re here to do a job. You’re paid to produce. Get the job done.”

Mikey Meagher (24:41):


Lindsay Boccardo (24:41):

The confusion is that people now think professionalism is bring it to work. Everybody’s going to help take care of you. We’re going to hold hands. We’re going to have a little snuggle session on beanbag chairs. And if we get to work, if your heart feels right, we’ll do work. That’s not professionalism.


I would say now the definition of professionalism is know what’s going on inside of you, be able to acknowledge it and regulate and take care of yourself so that when you come to work, you are not dependent on your coworkers to regulate you on your behalf. That’s the emotional labor that we bring to work. And we all have horrible moments.


We all have traumatic things that happen in our life. On the day-to-day scale, most of our problems, our emotional challenges are self-made and have nothing to do with our coworkers. And that’s if we can understand the difference between, “Okay, this is a problem that I need to resolve. I’ve got antifreeze dripping out of my car today, can I manage that and do I need to bring my team in on that or is that something I can regulate around, get a plan with and just make happen and not ask my whole team to help support me in that?”


That’s what we’re trying to learn. That’s what we’re trying to find the balance of, that professionalism would be you get to be a whole human, you have emotions, they come with you. And when consciously do we tap into our team to help us regulate and problem solve those things. And when do we say, “I got me. I’ve got me. I’m okay. Let’s keep moving forward with this project right now.”

Mikey Meagher (26:14):

Would you say that that, between regulating emotionally and professionalism, is that I guess one of the more common conflicts you see arise in these generational differences? Or what are some of the common things that you are seeing?

Lindsay Boccardo (26:32):

Well, anybody under 25 is on a different developmental stage, is in a different stage of life than those who are older. Your frontal lobe, your executive functioning is still coming together in your brain matter until you’re about 25. So the main thing that I see are young employees who get a flat tire and feel completely dysregulated because they’ve never dealt with this. They’ve never had to deal with it outside of mom and dad helping them.


And they don’t have full executive functioning yet to manage their emotions around it. And then somebody who’s got three decades on them, it’s like, “Kid, what’s wrong with you? Just pull over, call AAA. It’s not a big deal. We still have a day’s worth of work to do. You’re not getting the day off because you got a flat tire.” And so it’s understanding the tension between generations is usually developmental when it comes to managing stress.

Mikey Meagher (27:25):

Yeah. That’s actually a really good example because I think we’ve all been there before and we also are going to reach a point where we forget that we’ve been there before.

Lindsay Boccardo (27:34):

That’s exactly it.

Mikey Meagher (27:36):

And so just trying to, it’s like practicing. So just trying to keep that in the back of your mind and be aware.

Lindsay Boccardo (27:46):


Mikey Meagher (27:46):

Awareness you were talking about, and remembering that those moments did happen to you, they’re going to continue to happen to you. But when you get to a point where maybe it’s not as common because you know how to deal with multiple situations at once, but to-

Lindsay Boccardo (28:01):

You got it.

Mikey Meagher (28:03):

… to look at that 24, 25-year-old and be like, “Oh gosh, I know exactly how you feel right now. And that is stressful.”

Lindsay Boccardo (28:11):


Mikey Meagher (28:11):

“Let’s walk you through this.”

Lindsay Boccardo (28:13):

Yeah, of course it isn’t stressful to you now, you’re 50.

Mikey Meagher (28:15):


Lindsay Boccardo (28:16):

You’ve grown since then, but the first time… We all had the first time we used, we went to use our health insurance card and we pulled out our car insurance and the doctor’s like, “That’s for Chevy.” We’ve all had these moments of adulting. Everybody had the first moment that they made a meal without their mom helping them.


Everybody’s had these moments where you go off to college or you get your first apartment and that first night you’re like, “It’s really quiet. What have I done? I’m in this, whoa, my life is changing.” And to have compassion for our younger selves and to remember how scary those moments were gives us more compassion for those who are in that stage of life.

Mikey Meagher (28:55):

Yes. Yeah. And that kind of leads us into when each generation, as we talk about, has its unique experiences and knowledge, but when you leave the workforce knowledges feels like it could be lost forever and it’s part of the danger of that as well.


And so as boomers are now reaching retirement age, what are some ways that they’re able to transfer their invaluable knowledge and what they have put into the workforce already to not also be lost? Because I think everybody has something special that they bring into this whole conversation and that’s why we’re here having it because we have so many generations right now in the workforce.

Lindsay Boccardo (29:47):

Yeah. Well first, I’m always pushing against this idea of ageism, that the older you get in American United States culture, we say the older you get, the less valuable you become, the less relevant you become. Every other people group reveres elders as those who have gone before them who have more lived experience.


And it’s because technology has kind of created these micro generations that we tend and the senior living kind of way that we think about grown adults who are retired, that we put them in a retirement home, we put them away from all the young kids. We know that’s actually not good for the human psyche, not good for the younger folks and certainly not good for those who are in isolation. And so thinking through, if you are in that boomer stage, acknowledge that, “I probably have my own ageism.” I’ve had women come up to me so many times and say, “No one cares to hear from an old lady.”


They’ll say that to me. And I’m like, “I do. You’re the exact person I want to talk to because I’ve never had this experience. I never had this. You have more perspective.” And so for each of us remembering that ageism hits us differently, when I was a young buck, when I went to coaching school, I was 27. I was the youngest person there by a decade, and I had the same type of ageism thoughts.


“Nobody wants to hear from me, I’m 27. What do I have to offer?” And so recognize that there’s a part of you that’s believing this narrative that’s not true and not helpful for us. And so for boomers, I would hold onto, I have something valuable to offer. I’m still learning. There’s technology that’s coming out that I want to understand, I want to be able to engage with. So think about how can I be a mentor to somebody younger than me?


But not just a mentor, how can I also stay curious about the future? So one thing that I get to do, I’m lucky enough to have two amazing kids, and one of them is in college and so I hang out with college students and I ask them a ton of questions. They’re 20 years younger than me and I’m still like, “Tell me, how would you define a good boss? Tell me what you think. Tell me what you think about when you review your teachers, what do you think about reviewing them on?”


I’m getting curious about how their brain is perceiving reality and what they’re looking for in life. And so I would say if you’re a boomer, any generation, think about, “Who can I mentor and at the same time learn from and be open and curious to?” Mentorship is not supposed to be a power dynamic. If it is, you’re thinking of something other than mentorship.


Mentorship can be two equally valuable humans coming together to learn from one another. And that’s what I would encourage everybody, if you’re going to retire and you’re going to stop working full time, it’s very important to keep your cognition fresh, to keep your brain continuing to grow and evolve. And mentorship is a great way to do that.

Mikey Meagher (32:45):

Yeah. And a lot of companies also are trying to start different mentorship programs or different things like that. And something interesting as we’re just sitting here talking about that is get ahold of those employees who are getting ready to retire and see if they want to be a part of a, still have involvement with the company after they retire and maybe once a month they’re helping mentor another employee at that company or giving different advice or be like, “Yeah, when I was there…” Talking to senior leadership still and working out something that the mentorship doesn’t have to just stay within people who are midway through their careers and are going to be there longer. I think there’s so much to be learned still from that point on as well.

Lindsay Boccardo (33:44):

I think anytime you can create some type of legacy series or something that you can bring to honor those who invested a lot of time in an organization or company, to find a way to interview them, bring them back in, have them available to younger generations. It’s really the organization’s job to set up a culture that says, “There’s a lot of people that have gone before you that are a wealth of knowledge, understanding wisdom that can shave off years of trouble for you.” So we create a system and an ecosystem where they are in our world even after they retire. I think that’s brilliant.

Mikey Meagher (34:23):

Yes. I love that. And it’s like you get, how many times in high school or whatever have you sat there and you’ve had a guest speaker come in that went to that high school years before, but because they’re doing certain things or whatever it is with their lives, the school’s bringing them back? And that gets lost somewhere as we get into the workforce and out of an education, I guess, way of life and moving into that next chapter. But that really is lost on, sure, you have guest speakers come in, but not necessarily related to that company or somebody who’s been there before them.

Lindsay Boccardo (35:09):

Yeah. I think that’s one of the best ways that we borrow courage from each other is we say, “Okay, here’s somebody who’s already done it.” I’ve got friends who have done such cool stuff. I’ve got several friends who’ve been on Shark Tank, got people who’ve been national women soccer players. It’s like you’re the folks that the younger generations need to hear from to borrow courage from to see, “Oh, if they did, I can do it.” We learn best through modeling.


There’s a lot of research around this because of mirror neurons, because of being social creatures that. And one of the best ways to learn is to be around people who are doing what you long to do. And that can be actual real interactions. It can be reading their biographies. There’s a lot of ways to do that, but you’re exactly right. That’s why we bring people back in to remind everybody of where we’ve come from and to borrow courage.

Mikey Meagher (36:01):

Yeah. So we all know, especially with millennials and gen Z, that culture is, that is what’s attracting them to a company, whether they’re staying or leaving. I guess, and this may be a broader question, but how can employers attract, keep that going? Right? And keep attracting the next generation, at least coming in and building out that culture? Because ultimately that is what is going to happen at some point where that needs to just be fact. But I think it’s really hard to build that because we’re at an in-between.

Lindsay Boccardo (36:48):

I mean, I think it comes down to leaders having a clear vision of what they are building to the exclusion of other things. I think to believe that you have an environment that’s really for everybody everywhere all the time, no, you don’t. You don’t. No one does. And so to get crystal clear about who you are, the behaviors that you all engage in as an organization, the behaviors that you do not engage in. Not getting so stuck up on, “Let’s make sure we paint the values on the wall of the office so everybody sees them in paint every day.” That doesn’t change anything.


And so to think about how do we embed certain behaviors in our organization that tell people, “You are safe, you belong here,” but also get crystal clear on who you’re looking for. I see in the recruiting world, we try to recruit everybody like, “Oh, we got a hundred applicants,” but only two of them are actually good fits. I’d rather have you narrow your job post and get so specific and hyper-focused on the one type of person you’re looking for that you only get four applications and they’re all dynamite.


And I’ve done that work before with coffee shops and different groups where they’re saying, “We’re getting a lot of applicants, but not a lot of them once we start talking to them is a good fit.” That tells me that you’re not clear enough on who you’re looking for. They’re out there. You’re just not clear on the avatar of the person that you’re looking for. And so I even saw, I was talking to one CEO that I really admire.


They had just built out, can you imagine building out a whole new standalone office? Gorgeous. It had to be millions of dollars right before the pandemic. So you’re like, “Oh my gosh, you just put all this money down on a building right before the pandemic.” And so they decided based not just on the fact that they had this new building, that wasn’t the factor. It was, “We work better in person.”


Because of the type of work they do, it’s very collaborative, you have to be very creative thinking, problem solving. And so the CEO said, “Everyone’s back. We are doing just full-time in office. If that’s not a good fit for you, we understand, but we are staying the course. Post-COVID, we’re staying the course and everybody’s coming back here to work full-time.” And just the fact that they were that crystal clear about it. They weren’t like, “Oh, we’re going to try hybrid. We’re going to try this.” It’s like, “Nope, this is what it’s going to be.


If that doesn’t work for you, we understand.” That’s actually a clearer boundary for people to say yes or no to. And so I think that’s where we get caught in almost corporate people pleasing, “How do we kind of make this work for everybody?” You don’t need everybody to work for you. You need 30 people to work for you, or you need a thousand people to work for you. You don’t need everybody. So getting really defined on who you are so that people can see and understand that, that’s the key. Even with gen Zs and millennials, it’s getting very clear on who you are and what you stand for.

Mikey Meagher (39:44):

Yeah, that’s a really good point. Whether the message is so clear and it’s a direction that you’re like, “Well, that’s not for me, and I want to be hybrid or I want to be remote.” So if that’s not the case anymore, then yeah, you’re going to go look for somebody that is going to be true of, and that you can work for that way. But it may not always be what we want to hear, but at least we know, and-

Lindsay Boccardo (40:08):

That’s exactly right.

Mikey Meagher (40:09):


Lindsay Boccardo (40:10):

Now we know and we’re saving time.

Mikey Meagher (40:12):

Yes, exactly. I love that. I never even looked at it that way. Anything else before we close out and go into our kind of rapid fire questions? With some fun questions, anyways. Even though all this has been fantastic information, anything you want to add for employers to be mindful of? Again, kind of a more broad general thing, but anything you always like to close out with?

Lindsay Boccardo (40:41):

Yeah. Actually, I would say each of us has this opportunity right now in human history to make a very potent decision. Will I be the leader I didn’t have?

Mikey Meagher (40:58):


Lindsay Boccardo (40:59):

That’s the decision that every one of us will have to make. And that means you’ll have to bridge the big gap between what you feel is fair. We have a bias towards this idea that as we grow up and we spend more time and we have more authority, that we should get to be more rigid and everyone should have to flex around us. And I’m telling you, the rules of work have flip-flopped. That is no longer true. So the core of the core question is, will you be the leader that you never had? Will you learn those skills?


Will you learn self-regulation, self-awareness? Are you open to therapeutic interventions in your life? Are you open to self-compassion? If you are willing to be the leader you never had, gen Zs will smell it from a mile away. Authenticity is the number one Googled word you can think about everyone is looking for. How do you become through and through? How do you become so authentic that people can feel it buzzing off of you? And this is how you do it, these conscious decisions.


I’m becoming a leader I never had. I was driven with fear. I was driven with judgment. I lost one of my jobs when I was coming up in my twenties because I came out and the HR person said, “You can’t be gay here.” And I was like, “We’re going to have a problem.” I’ve had to lose friendships, relationships, communities, to be true to myself. And that’s what people feel when they’re around me, is that I have a moral edge to me.


I am going to be the leader I never had. I am going to create space for other people. I will pay the price for whatever it costs me to be the type of person that’s safe for others, anyone, other people. Not just a place where I thrive, but where everybody does. And so we all have to make this decision, will I be the leader I never had? It’s unfair, it’s unjust and yet we get to decide.


And if you decide to be the leader you never had, you’ll have people knocking on your door all day wanting to work with you. And if you decide to stay the course and hold onto your, “I’m holding onto this ship that’s going down, there’s a way things should be done, and I should be at the top.” And if you want to hold onto that, be my guest. It is going to be a rough ride and your ship is already sinking. And that’s the gut of the gut question that we all have to answer for ourselves.

Mikey Meagher (43:19):

I just wrote that down because I love that. And I feel like that needs to be a title of a book that you write.

Lindsay Boccardo (43:28):

Well, thank you. Let’s put that in my notes. Hold on.

Mikey Meagher (43:31):


Lindsay Boccardo (43:32):

In my notes. Yeah. We talk about this idea a lot, and I think it’s a call to bravery.

Mikey Meagher (43:39):


Lindsay Boccardo (43:40):

It’s a call to take on the battle between how you were raised and who you will become for others.

Mikey Meagher (43:49):

Yeah. Wow. Very good point. And I’m going to read that book someday whether-

Lindsay Boccardo (43:56):

I love it.

Mikey Meagher (43:57):

… whether you’re in the middle of writing one or not, you need to be.

Lindsay Boccardo (44:00):

Thank you, Mikey.

Mikey Meagher (44:03):

Well, thank you so much for being here today and talking with us. And to close out, I know we started our rapid questions that weren’t quite there in the beginning, so we won’t get to hear those, but I want to hear from you now. And I’m going to start with what is your favorite holiday?

Lindsay Boccardo (44:26):

Christmas all day. Great memories. I got married right around Christmas, so there’s a lot of love and warmth and rest in celebration tied to the Christmas season.

Mikey Meagher (44:41):

Yeah. Oh, fun. Best career advice you’ve ever received?

Lindsay Boccardo (44:44):

Go to therapy. You can only grow as much as you’re willing to look at yourself, the good, the bad, the ugly, the uncomfortable. And as a public speaker, that’s one thing that I encourage everyone to do is make sure you know how to take care of yourself. It’s not to find out how you’re messed up.


It’s to say, figure out how to take care of yourself so fully, so well, that you can genuinely pour into other people without expectation. And we all need this. It’s one of the things that I think our culture sucks at, listening to each other, making space for each other. So we’ve, for the chosen few that decide to learn how to listen and make space for other people, they’re gems. And most of us need a therapist to play that role, at least for a season.

Mikey Meagher (45:29):

Yes, and I myself can advocate and attest to that as well. It’s been one of the best things.

Lindsay Boccardo (45:36):


Mikey Meagher (45:39):

All right. Next one is finish the phrase. The way to my heart is…

Lindsay Boccardo (45:45):


Mikey Meagher (45:47):

Same. Yes.

Lindsay Boccardo (45:48):

I mean, you-

Mikey Meagher (45:49):

All day long.

Lindsay Boccardo (45:50):

… you’re doing a puppy fundraiser, take my money. You need me to hold your puppy, I’m there. What do you need? Puppy TikTok, this is my life. Puppies.

Mikey Meagher (46:03):

I know. My Instagram feed is pretty much of pink and puppies. Literally it’s like, “You might like this.” I’m like, “Yes, I do.”

Lindsay Boccardo (46:14):

You nailed it.

Mikey Meagher (46:15):

Good job, AI. All right. Favorite book or podcast?

Lindsay Boccardo (46:21):

Oh my goodness. Well, I got to say I am a huge fan of Mel Robbins as a communicator, as somebody who understands how to package information for people for self-growth, I would highly recommend the Mel Robbins podcast. They’re fantastic wealth of knowledge. And on the entertainment side, I love My Favorite Murder. So, it’s weird, true crime. It’s a trend. And there might be some things that-

Mikey Meagher (46:51):

I love it, too.

Lindsay Boccardo (46:51):

… you learn about me because I like true crime. But yeah, a little bit of both. But mostly Mel Robbins. Fantastic. Grab her books, listen to her podcast. She’s got a lot of good stuff going for all of us to learn from.

Mikey Meagher (47:04):

Right. Yeah. My favorite book so far is the one that has to be written yet, which is Will You Be The Leader You Never Had?

Lindsay Boccardo (47:12):

Mikey. It’s coming. I just started it today. We got the title. I love that. That’s so thoughtful. It’s so kind to say.

Mikey Meagher (47:21):

I’ll expect a little dedication section in there.

Lindsay Boccardo (47:25):

You got it. To my Syracuse Orange.

Mikey Meagher (47:29):


Lindsay Boccardo (47:30):

Who you are, Mikey. This all started on this podcast.

Mikey Meagher (47:33):

Yes. Love it.

Lindsay Boccardo (47:34):

I love it.

Mikey Meagher (47:37):

Well, that’s it for now. Again, thank you so much for being here. I hope we get to collaborate more actually in the future and do different things and get you back in at some point with DirectEmployers too, to come in.

Lindsay Boccardo (47:52):

I’d love that. However I can be helpful, I’m happy to do it. And I love getting this time with y’all. Thank you for taking the time to ask me such thoughtful questions and plan this interview, and I can’t wait to see how it comes out.

Mikey Meagher (48:06):

Yes, me too. Have a great rest of the week.

Candee Chambers (48:09):

Thank you for tuning in for another episode of the DE Talk Podcast. Stay connected with DirectEmployers on Facebook, Twitter and LinkedIn and subscribe to our emails by visiting to receive notifications of new episodes each month.

Candee Chambers
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