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Quotable Podcast Episode #61: “Get Your Cross-Generational Selling Right” with Warren Shiver and David Szen

Hosts: Kevin Micalizzi, Tiffani Bova
Everyone talks about millennials in the workplace, but did you realize there are three generations working shoulder to shoulder — and that each may have a different motivator, requiring a different approach? Join Warren Shiver and David Szen, Managing Partner and Principal Consultant, respectively, from the Symmetrics Group and authors of The Multigenerational Sales Team. Listen in as they share insights on how baby boomers, Gen Xers, and millennials work together. You’ll learn the best ways to sell into a dynamic situation that spans generations.

Broadly speaking, Gen X as a group has adopted social-selling technology tools like LinkedIn, website research, and so on, more than any other.”

Warren Shiver | Founder and Managing Partner, Symmetrics Group

Episode Transcript

Kevin Micalizzi: Communicating across generations can be challenging. Join us as we speak with Warren Shiver and David Szen, both of the Symmetrics Group and the authors of The Multigenerational Sales Team. Warren and David share their advice and research on how to effectively collaborate and sell across generations.

Warren, David, I am so excited to have you guys on the podcast with us today. For our listeners who aren’t familiar with you, would you share a little bit about yourselves? Warren, why don’t you start?

Warren Shiver: Yeah. Absolutely, Kevin. It’s great to be with you and your listeners today as well. I’m Warren Shiver. I’m based out of Atlanta, Georgia, and yeah, I’m passionate about all things sales. And specifically business-to-business sales. So I lead an organization called Symmetrics Group.

And we really focus on working with, again, mainly business-to-business sales teams around sales strategy and structure and then helping them improve their performance and execution with customers in the areas of sales process, selling skills, and also some sales leadership and coaching-type work.

David Szen: Yeah. I’m David Szen. Pleasure to be with you, and thanks for having us today. I’ve got a little over 25 years of collective experience, and I, too, share a mutual passion for sales, sales leadership, and also delivery in workshops.

My background comes from leading some of my own teams over the years. I’ve had a couple of executive roles in my life, but I’ve spent an awful lot of time carrying a bag and also selling directly to high-profile customers in a few different industries. Today I spend a lot of time with sales professionals and sales leaders as we design content for Symmetrics and for clients.

And then I also deliver a lot of our workshops and work very closely with a lot of our clients and sales professionals both in classroom and out in the field in front of customers. So I’ve pretty much spent all of my time, as well, in and around the world of professional selling and leading high-performance teams.

Micalizzi: I love it. So, I’m Kevin Micalizzi. I am the Executive Producer of the Quotable podcast, and I am joined today by my co-host Tiffani Bova. Welcome, Tiffani.

Tiffani Bova: Thanks, Kevin, for having me.

Micalizzi: When Tiffani and I came across The Multigenerational Sales Team, the book you guys authored, we were both super excited to get you on the podcast.

Because I think there have been so many conversations — and there’s a focus, I’ve seen, on parts of what you talk about in the book. But definitely not the kind of comprehensive coverage. Would you explain what you’ve seen — especially around what generations are in the workforce?

Because I know a lot of the conversation tends to be around, “Oh, how do you work with millennials?” But would you level-set for us?

Szen: So when you think about the question you just asked, there’s an easy way to answer it in terms of how many generations are in the workforce today.

I think it’s important to look back a little bit and always ask yourself, “Is this the first time this has ever happened?” And the answer to the question is, “No, it’s not.’ But this is a much different situation that we’re in today.

So statistically speaking, we have three distinct generations in the workforce. Today we have baby boomers, which, at one point, were the largest part of the workforce, but actually are the most rapidly declining part of the workforce as we sit today. We have generation X, which is wedged in-between the millennials and the baby boomers.

And we have a huge percentage of our workforce today — and in fact, by 2025, the statistic is 75% of the workforce is going to be millennials. Which means they’re going to be the generation that’s 37 or younger that’s dominating the workforce by 2025.

So you’re seeing an enormous sea change in the population of people that we have together in the workforce. So the initial question of why does it matter today and how is it different is, when you just think about what it does specifically to the world of sales, it causes some friction that must be paid attention to.

So just try to think about it this way: If you’ve got a 31-year-old sales professional with five years of post-college experience calling on a 58-year-old decision maker, you’ve got some things going on in-between peoples’ ears. And if you’ve got a 55-year-old sales professional sitting across the table from a 34-year-old decision maker, you’ve also got some things going on in-between peoples’ ears.

So when you look at a lot of the generational research that’s been done, a lot of it is all done from the perspective of, how can we all just get along better? Which is important to think about. But when you consider professional sales and coaching, there’s a little bit more going on there.

There’s the between-the-ears dialogue, that unfortunately causes decision makers and sales professionals to have a little bit of pause before they choose to do business with each other — just because they’re so different.

We take a different approach on it, which is, “We’re all here together. We’d better figure out how to figure this out as it relates to professional sales and coaching.” So those are the three distinct generations.

So, think right out of college up to 37 to find the millennials, 38 to 50 to find generation X, and 50 and older is the baby boomers.

Micalizzi: So I find it fascinating — a lot of what I read and a lot of what I see focuses on the different generations within the sales team. So how do you manage them, how do you work with them? But it makes total sense that you’d focus not only on that kind of self-oriented perspective — and how does our team work together — but on the buyers themselves. Were you seeing other folks talking about this or researching it?

Szen: We really didn’t. And that was kind of our wedge. There’s some fantastic material out there about generational differences, and we’ve put a headline on that in our work, because there’s some great stuff that’s out there.

But we did not see a lot that focused on the buyer and focused on the transaction between the seller and the buyer from generational differences. I say this jokingly, but I actually kind of mean it. So if you think about a 31-year-old sales professional with a 58-year-old decision maker, that decision maker is sitting there going, “I have socks as old as you.”

Micalizzi: [laughs] That’s true.

Szen: And that’s really what’s going on in-between their ears. And what’s happening is, that decision maker has to make a decision about that sales professional, and, unfortunately, they’re filtering some of that decision through, “My god, you look awfully young to be doing this.” Or, “ . . . to be calling on me as a decision maker.”

So, no, we didn’t see a lot out there that was focused on the transaction between buyer and seller or between seller and coach. And that was kind of what inspired our work.

Bova: I find it interesting, because I, like David, have carried a bag, run some sales forces over my career. Now I help them. And I never hear the conversation of, I hear we have sort of “traditional sellers,” quote unquote, guys or girls that have been doing this for a long time, so they’re in the habit way of selling. So we have difficulty breaking those habits.

And whether it’s generational. Probably that’s some part of it. But I definitely hear the, “I can’t break the habit,” and they’re not coming in and saying, “We just don’t have a diverse enough mix of sellers themselves between age and men and women or whatever it might be.”

So do you hear people actually calling that out, or when you come in and start talking about it, do they go, “You know, we never thought about it that way”?

Shiver: No, I think that’s exactly right, Tiffani. We see them calling that out in a couple of ways. One way — I’m sure the listeners are familiar with some of the tools out there that profile buyers or even team members around personality or preferences, like a DISC tool or HBDI or — you know, there’s hundreds of those four-quadrant personality tools.

And in one sense, I think we would counsel that you can’t overthink this. When we think about being flexible around generations, this is just another tool in the toolbox, per se.

But also structurally, to your point, as David was talking about, one of the other motivations for writing the book is, we did have another of clients, to your point, that have more homogenous, traditional sales forces. And now they’re also calling the reverse scenario to David’s.

You’ve got a 51-year-old seller, especially in markets like technology or advertising, selling to 20-something, 30-something, you know, younger, more millennial-tendency buyers as well.

So certainly the impact and the effect of generational differences can obviously cut both ways.

Bova: Yeah. And do you worry a little bit about — I mean, I definitely think from a marketing perspective, I hear a lot of marketers make these big-swath segmentations of the generations, right? Baby boomers, generation X, etcetera. Do you think that that’s too categorically specific, or do you find gray zones between those?

Shiver: Yep. That’s a good one. And I think we try to advise early and often in the book, you know, and our research proved this — you can’t make too much of it, and you certainly can’t trust all of our gross generalizations and perceptions.

So one of the key concepts that we wanted to outline in the book to that point is really taking, quote, “a slice.” So, thinking about things that we have from a perception (stereotype) around generations.

But, really, like you would do in any good sales conversation in terms of profiling your buyer — what motivates her, what are her decision criteria, etcetera. This is just one more lens, but it’s really one small piece of the overall pie of what’s going to make you successful, either as an individual or team, in a specific sales scenario.

Or, to your point, looking at your overall sales team structure, your strategy for go-to-market. Again, this is one consideration, but it’s certainly one of many.

Szen: Add to that — it’s interesting you asked the question about gray zones or gray areas with that. I led a workshop, recently, and we were teaching the concepts, and we had a number of people in the room as far as a mix of generations. And when we got to that discussion about being careful, Warren had mentioned taking a slice of a generation.

An example I’ll give you is, if you take a 35- or 36-year-old millennial that’s in a relatively responsible role in any company — and maybe even has some people directly reporting to them — that’s a millennial that’s got life moving. They’re probably married, have a couple kids running around, maybe a mortgage hanging around as well.

If you compare that millennial to a 27-year-old that just came out of grad school and is still spending all their time on Snapchat taking pictures and can’t get their mind out of Facebook, those two millennials are nothing alike.

They’re in the same generation — and in fact, the older millennial who’s making a name for themselves in the workplace is a little offended when you compare the two of them. So we kind of recognize that — that’s very consistent, too, with baby boomers.

It’s really hard to compare a 52-year-old baby boomer who’s probably got a good 15 years of career left to somebody who’s 63, and every day wakes up and goes, “How much longer do I want to do this for?” Especially in sales. They’re completely different producers within organizations.

Bova: And for me, I think it had a lot to do with — I sort of grew up with the rolodex. I’m right on the cusp. So I’m gray anyway. I’m right at the age when you change between one or the other, so, can I pick which segment I’m in? Does that work that way?


Bova: But where I adopted technology fairly early — so for me, it’s kind of always been, especially with salespeople, it’s more been about their willingness to use technology than which generation they were in.

Some of them are born with it in their hand — obviously now with the millennials. And now I like to call sort of “Generation Ground Zero,” where they know nothing but. Would that be a fair way to [categorize them] — adoption of technology? Another way — especially in sellers — of [determining] where they would fit?

Shiver: Yeah. Absolutely, Tiffani, and to your point: One of the myths we sought to dispel or confirm in some of our research was — to your point — the use of technology and so-called social selling techniques — is that something that’s exclusively used by technologically savvy millennials, or how did the other generations typically stack up?

And surprisingly, what we’ve found is, broadly speaking, Gen X as a group has mostly adopted social selling technology tools like LinkedIn, website research, etcetera, more than any others.

So I think, increasingly, millennials with convert their innate growing up with iPhones, with technology, etcetera — they’ll convert that into using it in a professional sense. But I think, to your point, some of the things that we take for granted as a generalization around millennials may not necessarily prove true.

Or it doesn’t prove true at the expense of — David and my case, and probably yours as well — in terms of our fluency with technology as it’s used in selling today.

Micalizzi: You also see differences in perception of whether there is generational friction between the three different generations that we’re talking about here. Millennials perceive the friction between the generations differently than Gen Xx or baby boomers. What did you find in your research?

Szen: Couple things I’ll call headlines to, as far as what we found in the research was, the friction is perceived between all three. When you look at what we found in doing the surveys and the interviews that we did, everyone acknowledged — I mean, the overarching number was, over 70% of the people that we participated in our research acknowledged generational differences or friction as part of the selling process.

So universally, everyone says it’s there. How they communicate about it — it really was interesting when you look at how these generations tend to interact with each other. So your baby boomers tend to be a little bit more politically correct and formal.

So while they may perceive the differences to be there, they’re going to take a much more soft approach and a politically correct approach to how they deal with it. The Gen Xers tend to speak their minds and be a little bit more upfront about differences.

I like to say that they’re not very good at inner thoughts, so they’ll just let it out in terms of those differences being there. It’s the open debate style discussions. And the millennials, they recognize it as well, but they also are tending to take a little bit more of a formal or a respectful tone about the generational differences.

With the occasional exceptions of people that just behave a little bit differently. But their tone tends to be a little bit more formal, friendly, and respectful. So we saw it come out that way. Everyone recognized it, but the tone they take when they’re dealing with the friction is different.

Micalizzi: Now, when you look at the sales process, though, I had seen in the book, you found pretty consistently — whether we’re talking individual sellers, managers, executives — that communication style or method was the area that had the greatest impact on the sales process.

Szen: Correct. Communication style or method being — whether it’s face-to-face, telephone, or email, or however it is they’re communicating with a client — was the place where we saw the most significant place where people spoke up about differences.

Bova: So, Warren, David, either one of you. I’m interested to hear when you’re in front doing — sales teams doing these workshops, and you kind of step through — or even at the management layer, what have you found as the receptiveness — because sometimes you’re talking to a sales manager who’s sort of grown up, and he’s on his third, or fourth, fifth career move. He might be 15 years left in his sales career, if you will. And you’ve got, maybe, others that he’s managing [who] are much younger. And have you seen resistance to this thinking? And how have you overcome those things?

Shiver: Yeah. I think, across all generations we’ve seen so far to the topic, there can be a healthy dose of skepticism coming in. So I think, specific to your persona, the sales manager that has 20, 25 years under his or her belt — certainly I think they’re anchoring on their experiences — which, they have significant experiences.

But what we will do, typically, to overcome that is a couple of things. One — again, we did some primary research to support this. So we’ll typically hit them with some of the facts that we’ve seen from both the research — other peoples’ research, as David highlighted at the outset.

And then also our own experiences working with other clients. So that’s just kind of one piece. And then the second piece is, as David was just outlining, around communication preferences. We’ll typically work through some exercises with these managers and their teams to really try to bring it to life.

So it’s as simple as talking about expectations for tone, for communication frequency, for feedback — things in those areas. And I won’t say we overcome objections on thinking about this as a softer skill to develop all the time.

But it is interesting to think about and see some of the perceptions change from, say, a morning to an afternoon in this type of session. And then finally, as part of a couple of the stories that we tell in the book — we typically have people come with their own stories in terms of things that they’ve experienced, in terms of working with their teams or working with customers.

Where generational influences come into play. And so we’re able to pull those out as well and then talk about those around the structure. Again, we’re not looking for wholesale changes, but really a three-step approach around just being aware that these exist for all of us.

Thinking about how do you pick up the clues? And then how do you adjust as appropriate? So, yeah, it’s truly interesting to see the preconceived notions and experiences that people bring when we’re engaging with them in this topic.

Bova: Yeah, [I’ve seen] that some of it might have been uncomfortable, too.

Shiver: Absolutely, right? Because, obviously — in your experience as well — it’s one thing to talk about account planning or sales process or business planning or forecasting. Which typically has some defined standards.

As you get into the softer side of selling and skills and behaviors and influence — of which this is certainly a piece — yeah, you get a lot of opinions. You get a lot of experiences that people have, both good and bad. It certainly makes for a robust discussion, whether it’s a speaking event or a workshop or where we’ve integrated some of this content into areas where we’re rolling out maybe a sales leadership and coaching program.

Micalizzi: So you talked a little bit about what you’ve called generational flexibility. I’d like to shift a little bit and talk a little bit more about how generational differences are affecting the sales process and what people can be doing to neutralize the effects of that.

Szen: Things to think about when it comes to generational flexibility: So, first and foremost, we talk about it in three steps. First step is, educate yourself and get as much information as you can. Which, hopefully, via a podcast like this helps people get some of that information.

The second one is, observe behavior. But I’ll put an important star next to observe behavior. An important star is — observe behavior over time, not just one time. Not just one time.

Because you need to see to what extent people embody the generational nuances that they’re a part of or not. And then the third one is, adjust as needed. Sometimes that adjustment could be major, sometimes that adjustment could be minor. That’s the way we talk about generational flexibility.

So the advice we would give about to what extent you should adjust again depends upon how much that person is part of that generation and some of the characteristics that come with it. I’ve got about a 55-year-old sales leader I was working with last year, and he is coaching largely a millennial sales force that’s coming into professional selling roles in the technology space.

And the reason that they’re primarily employing millennials is, it’s just what they’ve been hiring. Their [comp] leans more towards bringing millennials in to get started in the roles. It’s just what they attract. So what he’s struggling with the most is — his definition of “get out and prospect” is much different than the millennial’s definition of “get out and prospect.”

And what he’s finding is, they’re spending a lot more time trying to generate interest and generate voice either on LinkedIn or in other ways that are a little bit safer on the internet to get to do some of their prospecting.

And his pedigree — or the way he grew up — was at some point, pick up the phone and call some people and ask for face-to-face appointments. And let’s go ahead and start burning some numbers up and see how many people we can actually get in front of.

So they have a different meaning in their head when it comes to how to get in front of more customers and prospects. What he was battling as a battle of meaning. Meaning, the way he sees prospects and gets out in front of customers and the way the millennials did were just different.

Neither one was wrong, but unfortunately, in the period of time that he was in, he had to give them a better way to get it done, just because they’re not going to do things the way he did them when he first started in sales.

So sometimes it’s just a conflict of understanding and meaning. So the advice we’d give is, be careful before you adjust too quickly for generational differences. Because they might not be as severe as you think.

And then make sure that you’re respectful of those as you coach — and also as you work directly with customers and prospects.

Bova: So do you think that there’s an opportunity — unfortunately — for bias during those observations between those generations? So if you have a baby boomer observing a millennial — I’m oversimplifying and going back to those same categories.

But I would think there may be an opportunity, unfortunately, for some bias in some of this observation and coaching.

Szen: There is. And you, in fact, could get it dead wrong. And that’s why we talk about, in step two, observe behavior. Because you could make some assumptions about the person and their approach based on generational differences that are dangerous assumptions.

Because you could get it completely wrong. I’ve seen it happen myself, where you make an assumption about what somebody’s approach is gonna be, or the way they’re gonna communicate, and they surprise you. So that’s why we talk about observe behavior over time, not just one time.

It keeps you much safer from insulting people. Which in sales, we all know, usually doesn’t win you any new business.

Micalizzi: Now I know you talk about creating a client profile that you then do verify by observing that behavior. What do you normally suggest your clients track when they’re looking at their buyers and creating their profiles?

Shiver: Yeah, I think in our world — less from a marketing or a segmentation kind of persona perspective — but more feet on the ground — I think, Kevin, one of the things that we see consistently — even outside of the generational perspective — is there’s a lot of sales teams out there that are successful in spite of a lack of basic mastery of the fundamentals, right?

In terms of just pre-call meeting prep, having a meeting — especially where there’s a team-based sale involved — and then doing some structured debrief. So to answer your question, what we’re really looking at is — again, this is just one piece of the equation.

But when you go into a meeting, and you’re doing your prep, who do you think’s gonna be in the room, what’s their buyer persona, what’s the setup for the meeting, and what does victory look like from us?

All the basic kind of 101-, 201-level prep questions. You go into the meeting — and I think in this case, again, like most solid sales teams would do — it’s always nice to have one person in the room — part of your team — that’s really observing behavior, body language, engagement, questions that are asked.

Trying to understand buying criteria and role. All the classic sales decision-making theory and analysis. And then have a debrief and talk about that. And again, I think the generational piece could be a little bit nuanced in this case.

But we’re asking them to look at things like, who are the decision makers? Where does the “power,” quote unquote, lie in the room and in your sales process? Is that distinct in a generational way from [tenure], right? Or distinct from title in terms of the influence involved?

So really taking some of the classic — I mean some of this goes back to the Neil Rackham, Mike Bosworth-solution selling type sales approaches that have been around for 20, 30 years. But updating it with some of the generational concepts and also concepts, in terms of style, again — like back to the disk, HBDI. So that when you’re going back in front of that prospect — and certainly in a more complex, lengthy sales-type process — how are you matching up against that?

How are you presenting information — both the content of information and how you’re communicating the information — in the most appropriate ways? Again, where some of these generational nuances are just one piece of the equation.

But certainly, increasingly, an important piece. Depending on your buying audience.

Bova: So for the sales leaders that are listening to this podcast, what would be your kind of Monday morning advice to them on how they could first maybe identify what they have in their stable of sellers — first to kind of look and observe and do those things? And then what actions would you advise them if they felt like there was some opportunity for improvement? What are those best practices?

Szen: So if you think about an organization in terms of what they’re facing, they’ve got to think about a few things. They’ve got to think about recruiting, meaning, “Who are we going to bring into the organization in key sales or sales leadership roles?”

Compensation gets into that discussion. Onboarding is part of your consideration. Onboarding and training would fit together as part of that overall thing you have to think about. So the first thing, to answer your question, is, let’s look at who we have. And that’s going to be a mix across the three different generations. In our opinion, that’s gonna hit a couple things. That’s gonna hit coaching, and it’s gonna hit ongoing development.

And the things that people have to think about is, “How do we deliver education to people?” And that’s a balance of some face-to-face training, some in-field coaching, potentially some online modules.

But education comes in a bunch of different varieties, and generations will have preferences for how they like to take in that information. I still — just because of what I do every day — I still fall back on experiential style development and in-field application — where they can see it live and in front of customers — tends to be your best friend.

Because you get to see how people behave when they’re under a little bit of pressure. And that’s really important to consider when developing sales talent. To me, that bridges all generations. The second thing, especially with recruiting, is — that’s really where we start to see some issues pop up, depending on what type of a role you’re recruiting for, if it’s an entry-level sales position or a more tenured, strategic-level seller.

They’re going to have to make some important decisions about who you look to recruit, what their compensation looks like, what type of person it’s going to attract, and how to get people in the right roles to be successful. And then that’ll also touch on training and ultimately what their development path looks like.

The important thing to remember is what type of customers they’re going to call on. So that you’re setting them up for success. But that is worth looking at as well.

And then long-term, I just think it’s an awareness thing. To think about — ultimately, how do we develop top talent and get people to want to stay in these roles as long as possible. Because organizations — it’s expensive when you turn over people in key sales roles.

So it is definitely something worth considering when companies consider their future as to end-sales professionals and leaders.

Micalizzi: I want to ask you both our lightning-round question before we wrap up here. If you could take all your knowledge and experience, go back to the beginning of your sales career and give yourself one piece of advice, what would you tell yourself? Warren, do you want to take it first?

Shiver: So, yeah, Kevin, great question. I think if I could go back to my younger self, circa 22 and getting a first job in consulting and selling, I think I would tell myself to just take a pause and take a deep breath. I think we — and certainly I — would put a lot of pressure on myself in a [younger] way. Especially before going back to business school to try to develop a deep level of business acumen that — certainly — I just didn’t have.

So I think I would focus on relaxing, focusing on what I could drive in terms of professional persistence. But also doing even more of leveraging the team and senior resources that seemed relatively inapproachable at the time, given their age, experience, expertise. And I think I would tell myself to take a breath and try to leverage the team in a better, holistic way.

Micalizzi: Sounds good.

Szen: All right, so this is David. I think that’s a fantastic question. And if I had to roll back to the start of time in my professional selling career, I would say something really simple: “It’s not about you.” And what I mean by that is, sales tends to be a little bit of a self-centered sport. And we all think about victory or think about making ways for us to become more successful.

And I think earlier in my career, if I had really focused on, “The more you know about the customer, their buying process, what they’re going through, walking in their shoes, and also understanding that I could learn a whole lot from a lot of people that had been there a little bit before me, I think I would have saved myself a little bit of pain earlier on in my career.

Micalizzi: Love it. So I just want to say, thank you again, guys, for joining us today.

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