Webinar: Communicating Across Four Workplace Generations

Baby Boomers, Gen X, Millennials, and Gen Z all communicate differently and sometimes don’t understand each other. Feedback is misinterpreted, people are quick to judge, and we’re stuck with labels like “boomer” and “snowflake.”

What does it take to break free and connect with each other in the workplace on a human level? How can we listen, empathize, and truly engage with each other? The answer is by talking about it!

This entertaining discussion with four panelists, one from each age group, can help bridge the gap between generational communication expectations and blind spots. We will start with a real-time anonymous survey to uncover misconceptions, hear about the four communication styles, and discuss with our panelists how they prefer to communicate and receive feedback… and have fun in the process.

This workshop is intended to be interactive, including an opportunity to network and welcomes active participation from attendees. Please register in advance and bring your generational communication challenges to share and discuss.

Moderator & Guest Speaker:

Dan Kaplan

Founder of Confident Communicators, LLC, Dan Kaplan is driven by the belief that anything is possible if we can just learn to talk to each other.  

As a mountain-climbing expedition leader, Dan has guided many teams through difficult conversations and high-altitude danger.  

Combined with his nearly 30 years of communications leadership experience across the public, non-profit, and private sectors, Dan helps leaders and teams communicate to their audiences and each other.



This recording was presented live March 21, 2024.

Slide Deck



Session Transcript:

Jeff Plakans (00:02):

Okay. Welcome, everybody. Thank you for joining us today for our webinar and panel discussion about communicating across the four generations that are now in the workplace. This is a huge topic for us. We at Commonwealth have every generation in our workplace. We did not choose to have them all on our panel today. We chose a very random set of individuals to represent every generation to join us. We’re going to be led and moderated today by Dan Kaplan, who will introduce himself in a minute. Thank you, Dan, for joining us today. The idea today is that this is going to be a quick, fun one-hour discussion about this communication topic across the generations.


The idea is we want everyone who’s on the call, not just the participants in the panel, but everybody, if you can, to go ahead and put your camera on. We want to hear from you and we want to hear what you have to say about the things that we’re talking about and the things that the panel is talking about. The livelier the discussion we have, the better off everybody’s going to become. Again, we thank you for joining us and for giving us your lunch hour. Without further ado, allow me to introduce Dan Kaplan from Confident Communicators. Dan?

Dan Kaplan (01:30):

Thanks, Jeff and thanks, everybody, for having me. I’m a communications trainer and a coach, and this is a topic that comes up a lot. As Jeff said, we want this to be fun and interactive, so if you have your cameras off, I’m going to please ask you to turn them on so that we can read your body language. This is about communication. I, as a presenter, want to see how my message is landing with you. I want to be able to read your expressions, so please turn on your camera. Please participate with us, and what I’m going to ask everyone to do is just remain muted unless you have a question. Then either raise your hand or hit us up in the chat. We do want this to be interactive, but we’re planning on having about 30 people here, so we’re going to try to keep it a little bit controlled. All right, so we’re going to start with just a few statistics about the generations in the workplace.


We’re going to dispel a few myths. We’re going to bring up a few myths and dispel a few myths, and then we’re going to turn to our panel conversation where my hope is that you get to ask each of the generations a lot of questions about how they perceive communication, how they prefer to be communicated with in particular giving and receiving feedback, which as we know can be a difficult topic across the generations. So thanks, everybody, for turning on your cameras. All right, so I have a question for you all, and we’re going to use this interactive Slido tool to everybody. I just want to know what generation you’re in, who’s on the call? So you can use your phone and hit the QR code or if you’re on a computer, go to slido.com and hit use the code Common. I’m going to answer myself. I’m a Gen Xer, latchkey kid. “Come home when the lights are on.” “Figure it out yourself.” A lot of those qualities as a kid really translate to how I communicate at work.

Kathy Doyle (03:45):

What does that pink line mean?

Dan Kaplan (03:48):

That means I have to turn off the drawing tool.

Kathy Doyle (03:52):


Jeff Plakans (03:54):

Of course, we know we misspelled millennial.

Kathy Doyle (03:57):


Dan Kaplan (03:59):

That’s my fault. Okay, looks like we got a lot of Gen Xers, a couple millennials, boomers, good. It’s good to know who we’re talking to. All right. I already did the agenda. We can skip that. Here’s a couple statistics for you all. Boomers, generally defined as born between 1946 and ’64. We’ve got our Gen X, ages 39 to 54, generally born between ’65 and ’80. Millennials, age 23 to 38, and Gen Z, the newest generation in the workforce up to 22 years old. Anybody want to take a guess at which age group is now the largest part of the workforce? Anybody want to take a guess? Put it in the chat.

Workshop Attendee (05:03):

Guessing millennials.

Dan Kaplan (05:04):

Yeah, you got it right. 2016, millennials became the largest generation in the workforce. About 39% now of the workforce according to Capterra, Gen X is 35% and boomers, 19. Okay, another question for you. What are some of the labels and the stereotypes commonly held about Gen Z? What are some of the things you might think or might hear in the workplace about Gen Z? Let’s get it all out on the table so we can start really seeing if these assumptions are true. All right. Now, as people are putting in these stereotypes and labels and assumptions about Gen Z, if you are a Gen Z, I’m going to ask you to respond to some of this in the chat. Give us your perspective. Don’t just say, “Yes, I agree.” “No, I disagree,” but why do you think some of these stereotypes exist? We’re going to talk about this later in our discussion, but right now, we’re just getting the issues out on the table. Gig-focused; lazy; wants a lot of positive reinforcement; entitlement; dreamers; not self-motivated. Boy, we got a lot to say about Gen Z, don’t we? Transactional.


All right. Well, there’s actually been a lot of research about this… don’t like to use telephones. There’s actually been a lot of research around this, and here’s one myth about Gen Z that’s simply not true, that they’re lazy and they don’t care to work. 49% of Gen Zs actually do view their work as more important than exercise, music, hobbies, etc. It’s really has a lot to do with the researchers telling us, it really has a lot to do with the fact that they came of working age and they saw their parents at home during the pandemic and they didn’t like what they saw. They did not see a work-life balance, saw a lot of stressed-out parents. Let’s do the same thing for our millennials. Pages 28 to 43. What are some of the labels and stereotypes about millennials? Also entitled, can’t take negative feedback, disillusioned, lot of generalizations going on here, but that’s what I asked for.


Need a lot of positive reinforcement; want to be promoted after a week; motivated but confused. Okay, lazy and entitled; think they have all the answers; stressed out. Yep, these are some of the common assumptions that I’m hoping we can get through and get past today. Want to be president on the second week. All right, thank you everybody. Oh, two more people. I’m going to go back, let you answer. I’m an inclusive guy. If you were putting in your answer and I cut you off, please go ahead and put it back in. Want the balance but can’t get what they want, still have it; not realistic, whiny. Okay. All right. So according to Connecting Generations by Claire Raines, it’s not that they don’t want to work, it’s that they don’t believe in the value of work for its own sake. A lot of millennials tell us if you believe this to be true, but really are motivated by cause, and feel strongly that their work should be making a difference. If they don’t feel that or they don’t have that, then it may lead to some of these generalizations that we just saw.


All right, how about Gen Xers? Pages 44 to 59. What are some of the generalization stereotypes and labels we often hear about Gen Xers? Very driven. We rock. Now keep in mind there are a lot of Gen Xers on this call, so the data may be skewed. Too tough, innovative; work too much; resilience. It’s a lot of positive things here. What are some of the negative stereotypes? Give too much; too high expectations; both ways uphill. I remember that Bill Cosby skit. Too direct. Oh, okay. Good. Hardworking, this is great. Thanks, everybody. Two more people. Okay. Blunt. All right. Common myth is that the hours you put in is a reflection of how hard you work. This may be a holdover from pre-COVID days where when you were in the office that was a signal or a sign of how hard you worked. But there’s an argument to be made by a lot of the younger generations today that there’s other ways for me to work smart.


If I take two hours in the afternoon to go to the gym and can be more effective because of that, then isn’t that okay? Because my productivity is going up even though I’m not sitting at my desk for 8, 9 hours a day. All right, last group, boomers. Boomers, 60 to 78, What are some of the stereotypes and labels we apply to the boomers? Inflexible; dictatorial; out of touch; concrete; not great communicators; not tech-friendly; retire already. I got bad news for the person who said to let the Gen Xers ascend. I think we’re going to get overtaken by the younger generations. Hardest working. In fact, I just read a report this morning that said that Gen Z people are being promoted 1.2 or 20% faster than previous generations. Work hard, not smart; resistant to change; struggling with retirement decisions; dependable. Okay, great. Thanks, everybody. All right, one more consuming everything.


Here’s a common myth that boomers aren’t embracing technology. We saw that in the Slido, but Pfizer did a study. 56% of C-suite execs are working with AI. 25% of a younger group, 18 to 29 year olds will actively avoid participating in a meeting if they thought the tech tools might cause disruption. Actually, before we started, there was a little discussion we had about if people left meetings if you knew that it was being recorded. We noticed that a lot of younger generations are more likely to do that. Okay, so why do I bring all of this into your consciousness? Why do I raise these labels and these stereotypes? Really, because the purpose of today is I want everybody to be thinking not about generations and how to manage them differently, but about individuals, about individual people.


When we talk about communicating, particularly when we talk about giving and receiving feedback, I’m here to say that it’s much more important to understand the individual person that you’re talking to and how they like to be communicated with, how they prefer to receive feedback than it is to be thinking in these generalities. When we put people in a box, when we label people, it limits life. We form a mental model of them, and it’s very difficult to break out of that mental model. So I’m going to ask people to think more about the human being in front of them than any generalization label or stereotype. Why? Because there’s a serious problem we have in our culture right now with communication. Did you know that the average worker wastes seven hours a week on poor communication and teamwork?


That’s a lot of time. It’s two months a year of time that could be going to production, relationship building, et cetera. All right, so we’re going to move to our panel discussion now. The way that we’re going to do this, I’m going to ask everybody to introduce themselves. We have four people representing each of the four generations, and I’ll be asking a lot of questions, but my hope is that you ask a lot of questions as well. So please use the raise your hand tool or the chat. I’m monitoring both, and we’ll hopefully have a lively conversation just about how individuals prefer to be communicated with, how the generations might affect the way that they communicate. Let’s try to get past some of these myths so that we can improve the way that we communicate the workplace. All right? Sound good?

Kathy Doyle (15:50):


Dan Kaplan (15:50):

All right, let’s start with Kathy. Kathy, you’re here to represent our baby boomer generation. Would you mind introducing yourself?

Kathy Doyle (16:00):

Sure. I’m Kathy Doyle. My company is FireFlower Alternative Energy. We help companies who own commercial real estate profitably invest in renewable energy, and I also have a real estate company as well.

Dan Kaplan (16:16):

Thanks, Kathy. Okay, next we’ve got Tom, Tom representing our Gen X group.

Tom Elkins (16:21):

Yeah, so Tom Elkins. I’m with Trilogy Financial. I’m the director of our retirement planning division, and yeah, the Gen Xer.

Dan Kaplan (16:31):

Great, and Liam. Liam is here to represent our millennials.

Liam Griffin (16:36):

Hi, everyone. Yeah, my name is Liam Griffin. I work with Jeff over at Commonwealth Payroll, and I’m a implementation project manager.

Dan Kaplan (16:45):

Great. Great to have you. All right, Cassidy. Cassidy is our Gen X rep.

Cassidy Susi (16:51):

Hi, everyone. I’m Cassidy. I recently worked at Deloitte, but now I work at Wellstar Advisors, and I’m becoming a financial advisor.

Dan Kaplan (17:02):

Great, thanks. All right.

Jeff Plakans (17:04):

Cassidy is our Gen Z representative, Dan, you misspoke on that.

Dan Kaplan (17:08):

Did I say Gen X? Okay, thanks, Gen Z. All right, I’m going to start with Liam, if you don’t mind, Liam. We saw a lot of negative things that people had to say about the millennials, and one of them I thought was interesting about how they want everything now. They want fast advancement. Tell us a little bit about your perspective of that, how you and your generation see that stereotype about you?

Liam Griffin (17:43):

Personally, looking at myself and my friend group and the people I know in my age band, that’s not one I really with, or sorry, it is one I disagree with. No one is expecting to walk into a company and advance quickly. Everyone wants to have a level of success and respect and knowledge in the role that they’re in. But no one I know is expecting to walk in the door of that, especially when if it’s a new company, maybe in a new role or a new industry.


Everyone I know is that that’s something that needs to get built. The accessibility piece you mentioned is, I think that’s more access to information than access to a need to climb up the ladder of an organization. We want to know what’s going on. We want to have access and transparency to why decisions are getting made, and usually, that kind of discussion happens at a higher level. So I think maybe that gets misperceived as, “Oh, I should be on the management team. I can roll into the C-suite coming in the door here,” but I think we just want to know what’s going on.

Dan Kaplan (19:03):

That’s key. Thanks for sharing that perspective. So Kathy, I’m going to go to you because you’re representing our boomer generation. Boomers don’t necessarily think that way, do they? Right? “I understand that they’re gatekeepers to information, and some things I’m not privy to because of my level in the organization.” Is that how boomers think? Is there a disconnect between the way that boomers think about access to information and what Liam just shared?

Kathy Doyle (19:36):

I guess it’s hard to say, am I in the mode of representing all boomers, or I’ll tell you what I typically do in terms of communication is I’m very direct. I try to tell people, “The intention I want here is X,” and I don’t want to go into details with them about how to do it. I just want it to be done on time. Years ago I took a coaching class called Strategic Coach and there were four rules, they called them referability rules that I live by, and they are, show up on time. Do what you say you’re going to do. Finish what you start. Say please and thank you. Those are very basic rules that I don’t care who you are, a five-year-old or a 70-year-old, I feel like if you do that, we’re going to get along great. If not, then probably not.

Dan Kaplan (20:31):

Interesting. Good. So Cassidy, I want to go to you as our Gen Z rep. What’s your thoughts on some of those stereotypes that were said about Gen Z, lazy, misdirected, want everything now?

Cassidy Susi (20:53):

Yeah, I guess it’s hard because, in some ways, I can see how those are correct, and others I think that they’re just a misperception. So when it comes to being lazy, I think sometimes we’re just highly efficient. Others may see that as cutting corners, but I think we just grew up in a time that efficiencies are just always advancing and we’re always looking as to how to do things faster and obviously with less effort. So that can be seen as lazy, for sure.

Dan Kaplan (21:25):

Yeah. I’m interested, do you have an example and maybe give an example of how that might’ve been misinterpreted?

Cassidy Susi (21:32):

Sure. I think a great example might just be us wanting to work from home or us wanting to do things virtually more often than be in person. I think a lot of us got pulled out of our college experience to do it online and have just gotten so used to the learning environment being from the comfort of our own home. So then the additional hour commute to work and hour commute back and all of that doesn’t seem as beneficial for us. We’re not used to not getting paid for it either-

Dan Kaplan (22:01):


Cassidy Susi (22:02):

… so it’s a two-way street.

Dan Kaplan (22:08):

Steve in the chat said, “Gen Z is highly entrepreneurial. Agree. It’s the social media effect.” Highly entrepreneurial. Tom, as our Gen X rep, do you see Gen Z is highly entrepreneurial?

Tom Elkins (22:25):

It’s interesting, I do. This actually relates to the question you were just asking a moment ago, too, highly entrepreneurial, to the point, super efficient. I think what rubs Gen Xers in my group, and potentially baby boomers, the wrong way is that I think that we do see it as cutting corners. “Yeah, you’re being efficient and you got to X, Y and Z, but you don’t know L, M and N. What if that comes up next time, and we lose a client because you didn’t know that?” And it just rubs us the wrong way. So I do agree there’s a lot of entrepreneurism, but I think time will tell if the “perception” that our generation, the Gen Xers, if we get in the way potentially of that because we’re not allowing them to blossom in that entrepreneurial way because we think they’re going to fail.

Dan Kaplan (23:35):

Fascinating. Good. So let’s bring this to communication now that we’ve talked a little bit about our perceptions of these stereotypes. I’m still talking to you, Tom, if you have a Gen Z person who you think might be cutting corners, yes, in their mind, efficient, what’s your approach to give feedback to somebody like Cassidy about that issue that you just said and the reasons why it’s important to learn all the steps. What works for you?

Tom Elkins (24:12):

Well, yeah, so I guess for me-

Dan Kaplan (24:14):

What hasn’t worked for you?

Tom Elkins (24:15):

Well, yeah, what hasn’t worked is me behind the scenes giving instruction and then letting them go do it, and that could be my instruction was bad. What has worked is, in terms of what I do, I’m in front of a lot of clients every day, having them on appointments and giving them more and more and more to do on the appointment so I can see it and then immediately afterwards giving feedback on what worked and what didn’t work. I find that, for me, at least that’s working with my young folks.

Dan Kaplan (24:55):

So more immediate feedback, not waiting for the annual review or the monthly sit down, but giving it more in the moment?

Tom Elkins (25:04):

Yeah, in the moment and letting them have more opportunity to be the star of the show a little bit in front of you. So it’s like, “Okay, I took the training wheels off, but I’m standing here in case you fall over.” That’s working for me.

Dan Kaplan (25:17):

Providing that support, good. So Liam, I’m going to flip that issue of constant feedback to you as our millennial rep. Just read an article in The Wall Street Journal about how the annual review is going away, get ready for a fire hose of feedback. The profile talked about a lot of companies that are now providing in-the-moment feedback to people in meetings. They rate meetings and performance during the meeting. Is that kind of feedback more effective for you and your generation where it’s constant and not a big deal like in an annual review situation?

Liam Griffin (26:05):

I know I would definitely prefer it like that. The annual reviews are great and they serve a purpose. I think in my mind they serve more as a time signature for when an annual raise is going to come more than anything really constructive. I would much prefer the constant course corrections, whether it’s good or bad. If I’m doing something improperly, if I’m skipping L, M and N, like Tom was mentioning, I would rather know right away. If I’m doing something really well, I would rather know right away so I can continue to reinforce that. I think it goes back to what I said a minute ago, too. I would rather have more information than less. It’s easier for me to get better and course correct that way than have quarterly meetings of, “Oh, I like what you did here, but you should have done X, Y, Z,” and build off that.

Dan Kaplan (27:08):

So a common myth is that millennials are super sensitive. If I’m your boss, how can I deliver that course correction feedback in a way that you’ll hear and won’t appear to me to be oversensitive? What works for you?

Liam Griffin (27:29):

Just talk to me like a person. I always get confused on the oversensitive bit. I don’t really have a good definition for what that means and what that looks like. No one wants to be talked to rudely, and I don’t think that’s what we’re trying to talk about with oversensitive as well. I don’t have a great example of myself feeling sensitive in a conversation like that. If you talk to me like a person and say, “Hey, I like what you’re doing with A, B, C, I think X needs to be adjusted a little bit,” that’s fine. I definitely don’t want anyone kicking my door in and saying, “What the hell happened here? I can’t believe you let this slide through, blah blah, blah, blah, blah.” But I don’t think anyone wants to be talking to that.

Dan Kaplan (28:22):

We’re all human, right?

Liam Griffin (28:26):


Dan Kaplan (28:28):

In the chat, Kathy said, “We had a rule in our office that became a company culture of sorts. If someone had an idea, the only way that anyone was able to comment was to start with, ‘I like that idea because…’ ‘My concern is…'” so showing that care for the person. I don’t know if anybody’s read Radical Candor by Kim Scott, but she says that feedback should do two things: it should challenge directly, but it should show that you care personally. If you’re doing both of those things, then the feedback will have a much better chance of landing. But while we’re on this topic of sensitivity, Cassidy, if you don’t mind, I want to turn to you and ask you that same question as a younger person because we have a lot of Gen Xers here on the call. What do you do to give feedback to your boss about how you like to receive feedback? Is that common for you and your generation?

Cassidy Susi (29:29):

I do think that we have the confidence a lot of times to speak to our boss about what we need. Something that I’ve been dealing with lately at the new job. I think what I often express that I need is definitely a lot of structure ’cause we’re just so used to all this overwhelm of information. We’re constantly just being bombarded with different things to look at, and we’re expected to be these sponges of information in our job and learn everything so quickly. So I think definitely giving feedback to us that’s very direct and is very clear and not being as concerned about saying it in a way that isn’t going to hurt our feelings, I would at least appreciate. If members of my generation don’t appreciate that, that’s going to be something they need to learn, I guess.

Dan Kaplan (30:26):

Is it easy for you personally to give that kind of constructive criticism to your boss? Kathy, if you haven’t guessed yet? I’m going with that same question to you next and let’s hear it in reverse, but let’s start with Cassidy.

Cassidy (30:43):

I find it a little scary, obviously. I think I personally and maybe people in my generation would agree, we don’t feel always well-equipped to be doing our job ’cause we didn’t do a lot of things in person and we didn’t get a lot of learning in person. So I think that imposter syndrome definitely kicks in as we’re starting these careers. So then trying to state what we feel is right or wrong about how the information’s being delivered or how we’re being trained and whatever else, it feels like we don’t necessarily have the right to correct or the right to suggest anything to people above us.

Dan Kaplan (31:21):


Cassidy Susi (31:22):

So I think just respecting the courage that somebody has to bring that up is important, ’cause it’s not easy.

Dan Kaplan (31:29):

Words of wisdom. Thank you. All right, Kathy, I want to go to you and then after this we’ll open it up for more questions, ask everybody to unmute. But let’s look at that issue from the reverse. So we have a younger employee who is cautious, maybe intimidated to say something to their boss, how they want the boss to change their behavior maybe or be aware of the impact that the boss is having on them. What are your thoughts about, first of all, that generational difference? What works for you, for your younger employee to be able to come to you and make you feel safe enough for them to tell it like it is and speak their truth?

Kathy Doyle (32:21):

So I would say one of the first things in my interview process I ask, “How do you like to get information, and how do you like to give information?” It’s a helpful thing for me to know. Before I sit down with somebody, I try to review the personality profile testing that I’ve done so I can remind myself of, “Okay, what is this person’s mindset for that?” I understand I’m intimidating to people, but I’m always shocked by the fact that people are afraid to sit down and talk to me because I’m like, “Me? Little old me?”

Dan Kaplan (32:58):


Kathy Doyle (32:58):

But they are. I tell it like it is. So if you did a good job, you’ll know, but if you didn’t do a good job, you’ll know that too. I try to say it in as nice a way as possible, but I don’t pussy foot around either. I’m just like, “Hey, this didn’t work out. Here are the five things I think you should do differently next time. Do you have any questions?” I should be more flowery about it.

Dan Kaplan (33:30):

So get to know the person as an individual, if you have a personality assessment, rely on that. The other thing I heard was ask them. Ask them how they like to receive feedback, what works for them, build that relationship. Sounds like a good takeaway. All right. Well, I’d love to open that question up to the whole audience. Does anybody have anything they would like to share about what works for them or what doesn’t work when giving or receiving feedback across the generations?

Jeff Plakans (34:06):

Dan, I have a question to the panel, and this is something many of us in our early management training learned a technique to sandwich two positives around a negative, which I never felt worked very well and always thought it was pretty transparent in a negative, manipulative way. But I’d love to hear-

Dan Kaplan (34:31):

[inaudible 00:34:32] my training?

Jeff Plakans (34:32):

… from everybody their thoughts and experiences around that and how that hits differently.

Tom Elkins (34:39):

Jeff, it’s so funny you bring that up, because you know the Oreo cookie, right? I think it’s always driven me crazy, “Mike, look, if I did something wrong, just tell me. You don’t have to sugarcoat it ’cause you’re wasting my time,” and I could take it. But it’s funny because when I don’t use the Oreo cookie, I find that with some people, and I know I’m a very Type A direct person, I made an employee 10 years ago cry ’cause I didn’t do the Oreo cookie and I was just direct. I was like, “Wow, that meeting did not go well. We’re going to need to talk about that.” I didn’t even say anything more than that, and 10 minutes later, I find out they were crying, and I’m like, “Wait, what?” So I think there is a place for it, for sure, but it doesn’t work for me when I’m receiving it, that’s for sure.

Liam Griffin (35:30):

Well, to jump in, I think part of the reason why it sounds artificial when you hear it is because the rest of the conversation after the cookie segment is only the negative. It goes, “Oh, you did this well. This was tough, this worked, but you still did all this wrong, so blah blah, blah, blah, blah.” Whether the Oreo cookie in itself is good or bad, I don’t know. I don’t really buy into it. I agree with what you’re saying, Tom, but I think the effect of we’re throwing in two good things, but we need to talk about the bad thing is what makes it sound artificial.

Dan Kaplan (36:12):

Max, you raised your hand. Do you have something to add?

Max (Workshop Attendee) (36:20):

I’m happy to talk about as a millennial my relationship with my Gen Z employee or what it was like leaving a consulting firm because I failed to mediate between Gen Z raising issues and a very risk-averse set of partners not wanting to respond to it. But for me, I think attachment styles are a more predictive and useful way of discriminating how and who to give feedback to in what way more so than generational divide, for whatever that’s worth.

Dan Kaplan (36:50):

Good. Thanks.

Kathy Doyle (36:53):

I’m going to chime in on Liam’s comments too and say one of the things Tony Robbins years and years ago taught me was the way you say things and the words you use are really important. I remember him giving us an example, “Your girlfriend is pretty, but…” versus, “Your girlfriend is pretty, and…” In most situations you can change the but to an and have the same meaning and not set people up for that. “Oh, god, what’s coming now?”

Dan Kaplan (37:26):


Kathy Doyle (37:28):

I’ve trained myself to use and as many places as I can, and it does make a difference, that one word, particularly when delivering news about performance, it really makes a difference how it’s heard.

Dan Kaplan (37:44):

Yeah. Good. I want to share something from one of my trainings to piggyback on what you said, and this is also from Radical Candor. I’m going to tell a very quick story from the book. So Kim Scott used to work for Sheryl Sandberg at Facebook, and Sheryl Sandberg asked Kim Scott to present to the executives. After the meeting, in the hallway, Sheryl Sandberg says to Kim’s Scott, “Kim, you know you have a bright future with this company, but are you aware that you say, ‘um,’ and, ‘ah,’ a lot when you speak?” Kim gives her one of these, “Oh, that’s nothing.” Sandberg squares her up and says, “I can see from that little shoo fly gesture that I’m going to have to be very direct with you. When you say, ‘um,’ and, ‘ah,’ a lot, you sound stupid. I have a communications presentations coach, would you like me to put you in touch with her?”


Kim Scott said in the hallway two-minute conversation, that was some of the most impactful feedback she had ever received in her life. The story goes to show this idea of both challenging directly and caring personally, we call the Oreo, in our trainings, we call it the shit sandwich because people can see it coming a mile away. If you’re interested in a resource that can help you learn how to give really good feedback to anybody, it’s radical candor. She uses this formula, first, signal something’s coming. Nobody likes to have a ton of bricks dropped on them. Then give the why, explain the reason, the impact of their behavior on the people around them, on the project. But that’s non-judgmental language, it’s just the facts. Then you very clearly ask them to start or stop doing something and then you finish by offering support. So that’s a formula that anybody can use to improve the way they give feedback. All right, any other questions from the audience?

Workshop Attendee (39:38):

I have one.

Dan Kaplan (39:39):


Speaker 9 (39:40):

So this was actually proposed by a student and I thought it was fascinating, so let me preface this. This is for the panel and it’s not intended to be political in nature at all. What for your generation do you believe as far as the American dream? We used to hear it a lot, where are people following?

Cassidy Susi (40:10):

I going to go first. I think my version of that is that if you work your butt off, you can have a house and you can have a steady income. You don’t have to feel like you’re financially struggling, and you can look for the regular things in life. But obviously, nowadays, I find a lot of people my age seeing each other fall short of that dream just because I think we’re getting married later, which we’re just doing things later. So what we expect with this age isn’t happening even though we’re working hard. Also, no one could buy a house now too, because they’re so expensive. So that’s what I figured the American dream was, I guess.

Liam Griffin (41:00):

I agree with Cassidy on that. I think we all have a similar idea of maybe what the American dream means. I know at least for me is that it’s starting to feel further and further out of reach just with everything costing more. Then it’s harder to find jobs, it’s tougher to get promotions, everything’s priced way out of whatever we can reach at this point in our lives. So I think that pushes a lot of the milestone dates back that would help build what that American dream is. Whether it’s getting married and having kids or being with a partner and going on vacations or whatever, I think, yeah, it feels more out of reach.

Tom Elkins (41:46):

I’ll actually comment on that as a Gen Xer, but my comment’s not about Gen X. I’m very skeptical about a lot of things. My background is in science, and I did research originally probably 20 years ago on where that phrase came from and it was from Colonial America. It was actually a marketing slogan that was basically telling people go West to buy land. It turned into after World War II, “Buy houses.” I personally think, and this is again, not a Gen X view, but it’s just pure marketing and the dream really should just be whatever floats your boat and not necessarily this you have to be a homeowner or anything ’cause homeownership isn’t for everybody. It is harder, I think, for millennials and Gen Z to buy houses, ’cause especially in the Boston area, things have spiraled out of control, but that shouldn’t define who we are. I don’t know. That’s a personal statement.

Kathy Doyle (42:55):

I don’t know, I-

Dan Kaplan (42:56):

It was very Gen X statement. Sorry to interrupt. Is it?

Kathy Doyle (43:02):

Yes, you’re all good. I grew up in the projects on welfare and so to me, the American dream is financial security and financial freedom to do anything I want. I don’t care if I own a house or whatever, I just care that if I want to go on a safari in Africa, I can do that. If I want to start a nonprofit, I can do that. If I want to work and have my own company and dial it up and dial it down as my personal life affords me the opportunity to do that, that’s what I want. That’s freedom to me, and freedom to me, is the American dream.

Dan Kaplan (43:46):

Beautiful. All right. Thank you, Kate, for that awesome question. No conversation about communicating across the generations will be complete unless we talked about technology. We got the Slack generation. We got this idea that younger people just won’t pick up the phone. We’ve got email where everything gets misinterpreted and it’s a really difficult medium to be subtle in, or should I say an easy medium where things are misinterpreted? So I’m going to start with a general question to the four panelists about your preferred channel, your preferred technology, preferred methodology. But as you share that information, also give us listeners here on the call some recommendations and some tips so that we can get through to you in that channel of your preference. Cassidy, would you mind starting us off?

Cassidy Susi (44:57):

Yeah, I think the most preferred method for a lot of people my age is texting. It’s the easiest thing for me, but I do think the best thing that ever happened to me was getting a work phone ’cause we enjoy texting. I don’t think we like to get on email. It seems a little formal for us when it comes to just something short you need to explain. But when you use texting too often, then it can seep into your personal life as well if you’re trying to communicate work information. So definitely benefit from having a work phone, and then other than that, just pinging me or something. Email, it’s not efficient in my eyes. There’s too many of them and it’s not quick, I guess.

Dan Kaplan (45:44):

So do you use the phone part of the phone?

Cassidy Susi (45:48):

I personally love a phone call, but I’m also a social person so I’ll chat all day. But I know a lot of my friends rather not have to answer in real time or show up and be on camera and stuff or FaceTime, they’d rather just have someone text them.

Dan Kaplan (46:07):

As I was preparing for this, I read a statistic about 46% of people under, I forget the age group, but in the younger group have anxiety when their boss calls them. Is that true?

Cassidy Susi (46:23):

Yeah, I totally agree with that. I feel like I have a lot of friends who have anxiety just ordering a pizza. It’s really gotten that bad. So I don’t claim every part of my generation, but I do think stuff like that is a lot more common among us for sure, ’cause it is just gotten a little ridiculous. We just have so many crushes that it’s just like we’ve taken tests with Quizlet and everything, too. We don’t have to really answer on the spot for anything anymore.

Dan Kaplan (46:49):

Oh, that’s interesting. So give us some advice on if we need to have a phone call with you, how we can… Do we text you in advance and say, “Hey, I want to talk at 2:00?” How do we do that?

Cassidy Susi (46:58):

I think that’s a great way to do it. Just send a text, say, “Hey, we’d love to chat with you about this at 2:00 if you’re free,” or, “I’m about to give you a call. Are you’re free?” Anything like that would work. If it’s just something quick that you could say in a text, maybe just text somebody. But yeah, those would be the most efficient ways in my eyes.

Dan Kaplan (47:24):

Yeah, we used to say, “This meeting-

Cassidy Susi (47:27):

I’m seeing in the chat everyone’s daughter is 22. I’m 22, 23 this Friday.

Dan Kaplan (47:33):

Yay! We used to say, “This meeting could have been an email.” Are you saying, “This phone call could have been a chat?”

Cassidy Susi (47:41):

No. See, stuff like this is what I think people my age appreciate. We don’t really get to chat outside of work with people older than us and gets to see their perspective beyond what they want us to just do. I think and know people in that way rather than just a source of work allows us to see you guys as more than just, “Oh, when this person talks to me, it’s going to put another task on my plate.” So this stuff’s important.

Dan Kaplan (48:07):

That is so important. Thank you for reminding us of that. Bob, you raised your hand. Do you have a comment or question?

Bob (Workshop Attendee) (48:16):

Yeah, I just got a comment that, I’m project manager and I also try to lead the organization about how to communicate. I would say in our case, there’s no one tool. There’s no one tool. It really has to do with the level of communication you need to make, the urgency, maybe the project where you might want to have some continuity. So as a slack, have a Slack conversation with something urgent, or I just need to do this. I would agree, email is the least favorite. Email is something like, “I have to do this particular attachment. Something needs to be there,” that’s not good to Slack, so you want it there.


Have some memorialization or a project manager tool where you want to have that conversation there and all the notes there. You don’t want to get siloed in some Slack conversation. Of course, in fact, to Cassidy, have the conversation sometimes. Sometimes you get on the Slack, just do the huddle. Don’t have the back and forth, say, “Hey, do you have five minutes? Let’s just huddle for two minutes, and we’ll hash this out rather than typing back and forth.” So my point is just there’s no one way. I think it’s multiple ways, but then just working with everyone to understand what ways work best and just work from those constructs.

Dan Kaplan (49:22):

So this is great. Help us think through this. Okay? So what I hear you saying is that the channel should depend on several factors. What are those factors? What are the things that we should be thinking about before we choose our channel?

Bob (Workshop Attendee) (49:41):

So urgency, and even with the context of urgency, we talk about slack as we even give rules, like maybe sometimes Slack is you even put in there, “For information.” So the person knows this is just something to tell you something or, “Needs action.” So you’re basically saying, “I need something. I need something responded.” Then when the context of that, we might even say, “I need this now. I need this by the end of the day. I need it by tomorrow,” to also give that level sometimes ’cause people will see Slack, they’re like, “Oh, I got to answer this right now.” They could say, “This requires action, I need an answer from the client by tomorrow.” You just tell people to set those expectations. That’s the important thing because Slack and that like, “Oh, my God, Slack came in, drop everything.” Then you respond, it’s like, “Well, I didn’t need an answer up until the end of the week.” It’s like, “Oh.” [inaudible 00:50:26]

Dan Kaplan (50:26):

Okay, so we’ve got urgency of the message. That was a good tip, by the way, to give your deadlines. Urgency-

Bob (Workshop Attendee) (50:33):

Expectations, right?

Dan Kaplan (50:35):

Expectations of the other person, so consider your audience, right?

Bob (Workshop Attendee) (50:38):


Dan Kaplan (50:39):

Consider who they are as an individual, how they like to communicate. Anything else?

Bob (Workshop Attendee) (50:44):

Make sure you’re communicating to the right people. So if you are going to put it in a big channel where you want people to see it. Don’t just say, “Hey, everyone, can somebody answer this question?” ‘Cause then no one answers.” Right?

Dan Kaplan (50:57):


Bob (Workshop Attendee) (50:57):

It makes you say, “Hey, I’ve got a question from the client. By the way, Travis, do you know the answer?” Because he might be the best person, but I also want this to be here so that a wider audience might know that something’s going on that’s important so it doesn’t get silent in that Travis and me conversation. It might be something that a wider audience should be aware of. So again, trying to pick the right audience but keep the noise level down.

Dan Kaplan (51:18):

That’s great. So just to summarize what I heard in choosing a channel is to consider the information that needs to be communicated, the urgency and the context.

Bob (Workshop Attendee) (51:32):


Dan Kaplan (51:32):

I think, Kathy, did you have your hand up? Did I see that?

Kathy Doyle (51:37):

Well, I have a couple of things to say about communication preferences, ’cause I’m on a few boards too. Boards are a little bit different in that people are coming from different organizations. It’s easier to be in one organization, say, “These are our organizational rules for communication.” But when you’re on a board, one group likes Slack, the other group likes texting, the third wants an email, and the fourth wants a newsletter. All that is going on. It is really hard.


I will say from my own experience, and I’ve heard everybody say email is the least favorable. Let me tell you, when you’re 10 years or more into your position and you need to go find that thing you had, you’re not going to find it on Slack and you’re not going to find it in your text string. It’s gone. In email, you can do a search and you can call it up. I don’t think email is the ideal, but the main reason I like emails for my business communication is because if I ever need to go back and find that thing, even if it’s 20 years ago, there it is in my search. It’s way easier than all the other ways to find things in all those other tools from my experience so far.

Dan Kaplan (52:55):

Thank you. How about the phone? What are your thoughts on just pick up the phone? Is that still true for you?

Kathy Doyle (53:01):

Yeah. Remember the days you just used to call somebody without five texts back and forth? “Can I call you at this time?” Or, “Can I make an appointment to call you?” No, that’s not a thing anymore, but I really miss those days.

Dan Kaplan (53:13):


Kathy Doyle (53:15):

Just was easier to reach out, and I made a lot more progress when I could make more phone calls in a day.

Dan Kaplan (53:23):

In addition to what Bob said about the efficiency of it, it’s the human connection. You can hear somebody’s tone of voice. You can get their inflection, even better, Zoom, just a quick Zoom call. So I always ask people to have their cameras on because we are establishing a human connection. I get to read your body language, I can look you in the eye like I’m doing right now. I can establish that connection. I’m building that relationship, building that bond. I get the efficiency of texting and Slack and all that, but something serious is lost in that mode of communication. I really do believe it’s incumbent upon all of us to always remember the humanity and to find ways to reestablish that, ’cause that’s what’s missing to me in the workplace is people taking that effort themselves to go first and understand each other as humans. But I digress. Liam, how about you talk to us about your preferred channels, and give us a couple tips for how we can communicate with you better on those channels.

Liam Griffin (54:37):

Man, I don’t know how to top what Bob said. He took the words out of my mouth. I know for me personally, email’s at the bottom. If we need to have a conversation or go over something, email has its place and it’s good for not that in my mind. If we’re going to talk, if we have something to go over, give me a call, shoot me a Slack message. It doesn’t really matter to me. I’m happy whichever way, let’s just talk about it. But I would be happy leaving emails behind if we could. I understand the memorialization aspect of it, but I-

Dan Kaplan (55:24):

What are the worst channels for me to give you feedback on? I’m not talking about a factual correction, I’m talking about asking you to change your behavior, start or stop doing something.

Liam Griffin (55:36):

Yeah, and the worst channel for that, I would say email. In my mind, email is too formal and that kind of conversation I feel should be a little more personal. I would prefer that face-to-face or on the phone or on Zoom call like this. But even if it’s a Slack message, there’s that level of formality that’s in an email that’s missing. So I would rather you shoot me a Slack message saying, “Hey, I was looking over what you did for this. Can we try not to do that again in the future?” Or whatever would need to be said. I would rather see that as a Slack message than an email, preferably phone call or face-to-face, but…

Dan Kaplan (56:24):

Okay. Good. Thanks. All right, Tom, take us home. We got two minutes left. Share with us your preferred channel and give us a couple tips.

Tom Elkins (56:38):

So my preferred channel is either phone or email. My firm has Slack. I don’t have it. I don’t text. I don’t have Facebook. My daughter tells me I’m in the Stone Age, but there’s a reason for that. I do get between three and 500 emails a day, and all of them for the most part, have an action to them. So I have to be very smart with what I’m doing. So I scan my email box in the morning, what needs to be done. I call somebody on my team and I say, “Here’s the 40 emails you’re going to address today,” and I want to get it all done. It’s the phone call for me to make it happen. I hate email, but that’s my form of communication. Because of my industry, I’m not allowed to do all the other things, so I think it’s the phone. Really, honestly, it’s picking up the phone, it’s having a conversation and you avoid the back and forth. Just 60-second phone call could get rid of 10 minutes worth of thinking about in an email or a text or anything else.

Dan Kaplan (57:47):

Great, thank you. Can we get a round of applause for our panelists today who really shared some good information and some good tips? Really thank you all for your time. Jeff, I think we might need to have another webinar on communication overload? 500 emails a day? We need some prioritization.

Tom Elkins (58:10):


Dan Kaplan (58:10):

Anyway, I’m Dan Kaplan, I’m the communications trainer, and I thank you for being here. I thank you for listening. Jeff, I’m going to let you take us home.

Jeff Plakans (58:19):

Well, thanks, everybody. Thank you to our panel for giving us not only your time but your insights. We really appreciate it. I was just going to add on that the thing that I feel like is missing with email and text and even Slack is tone. Tone has everything to do with it. Obviously, then, the efficiency of communication, which I think is really what unifies all of us is we want to be efficient in how we communicate. So thank you for helping us, Dan, get to that. Again, to everyone on the panel and all the attendees today who’ve added value and come off mute to be able to share your perspectives on that, it’s been very, very helpful, so thank you for that.


Again, at Commonwealth, one of the things we’re trying to help all of you and all of our clients do is be more effective employers, and there’s a lot of different ways to do that. So a session like this is hopefully, going to allow you to do that and allow all of the attendees to take something away and, again, become a better employer and become the best employer and that’s the employee. That’s what we’re all about. So thank you, everybody, for attending today, for joining us. Of course, look for more sessions like this one and maybe Dan will be back talking about information overload. Tom, I feel you with your three to 500 emails a day. It’s painful to me, so thanks, everybody. Thanks for your time, and have a great rest of your day.

Cassidy Susi (59:55):

Thank you.


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