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Generational Selling: The Different Ages Of Selling With Shawn Casemore [Episode 75]

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Are you confused when you’re selling to different generations?

You’re not alone. The good news is that, with a bit of insight and communication, it isn’t quite as complex as you may think. In this episode, Doug C. Brown discusses how to maximize selling to different generations with Sean Casemore, the author of The Unstoppable Sales Machine. Doug and Sean also discuss different social media habits, why you need to follow up, and more tips to successfully navigate generational gaps between you and your clients.


In this episode you will learn:


Episode’s guest – Shawn Casemore

CSS 75 | Generational Selling

Shawn Casemore is an expert in sales, driven by a passion to help business owners, executives and sales leaders accelerate their sales results. As a keynote speaker and virtual speaker, he enables companies, their leaders and teams to accelerate their sales results. A prolific writer, Shawn frequently writes about best practices and proven strategies to generate more sales. His insights can be found online in publications such as Fast Company, PLANT Magazine, and INC magazine to name a few. Shawn is also the author of “The Unstoppable Sales Machine” which was released in 2022.

Visit his website: www.shawncasemore.com


Generational Selling: The Different Ages Of Selling With Shawn Casemore

I’m bringing you another amazing guest. His name is Mr. Shawn Casemore of ShawnCasemore.com. He’s from Canada. We’re going to talk a lot about generational selling. Generational selling means you’re one generation, you need to sell and must sell to a different generation. How do you do it? Somebody who’s in their 20s wants to communicate and maybe talk on a different level than somebody who’s in their 60s, 70s, or even their 50s. 

We grew up with different technologies and embraced certain ways to communicate. When we tread upon those ways to communicate, especially when we’re prospecting, we don’t get the opportunity to have that next longer conversation because the approach takes it out. We’re going to talk a lot about how to make that approach, the steps and stages of doing that, and some of the dos and don’ts of selling to multi-generations.

If you don’t understand and you’re growing up at my age, we grew up in a different way than my daughters, who are in their 20s. We had different technology. We only had a few ways to contact people. Now there’s a multitude of ways, and they shift a lot. Certain people used to use Facebook. Now they don’t use Facebook. Certain people used to use LinkedIn. They don’t use LinkedIn. Some people prefer email. Some people prefer phone calls. Believe it or not, people over 40 still prefer phone calls in many ways.

Texting is becoming much more of an abundant method that people like to communicate, WhatsApp in different places. If you’re international and you’re doing business internationally, these methodologies even become a little more involved because certain countries like to use things like WhatsApp. In the United States, we don’t use it as much.

Pay close attention to this episode. There are a lot of gems here that we pull out. If you get your prospecting and communication down right, you will definitely sell more. Your revenues will grow. Your profits will be higher because you’ll see fewer people but you’ll make more sales. The reality is your marketing spending may come down, which increases your profitability. Your prospecting may come down, which gives you more time to prospect if you get your prospecting time cut. Without further ado, let’s go talk to Shawn.

We have a nice gentleman here. His name is Mr. Shawn Casemore. Shawn, welcome to the show. Thanks for being here.

Doug. Thanks for having me.

We’re going to talk about something that you and I had a good conversation about. I love that we were talking about are we becoming our parents. We’re talking about generational selling. How do you run sales teams and accelerate that now through a multi-generation process? I know it’s important, but why do you think people need to pay attention to it now being 2022 almost into 2023?

If you’ve taken a look at what has happened in the last few years and what happened in 2020, I’m committed to not talking about what happened because I’m tired of hearing about it. What happened is it pushed a lot of people, Baby Boomers specifically, who are on the cusp of retirement into retirement. In some cases, it lasted so long that they said, “Forget about it. I’m not coming back to the working environment.”

What I’ve found in the teams that I’m working with all across North America and beyond is that it’s regardless of age. There are two sides to this to look at. It’s the age of the person selling and it’s the age of the person buying. What has happened is a lot of the people who are now buying or who are the prospects that we’re pursuing, they’re suddenly much younger because the people that have retired have moved out. They were maybe in their 50s or 60s, and now they’re replaced by somebody in their 20s or 30s.

If you look at the demographics, there are a lot more Millennials out there than there is any other generation. It’s more Millennials than there ever were Baby Boomers. We’re being taken over and that’s a good thing. Nonetheless, as sales professionals, what we tend to focus on is the process of selling, “Here are the steps I need to take in order to make the sale.” We do think about the person when we get a chance to interact with them.

What we have to do is think about what is the age of the person we’re pursuing. As a result of that, what are all the factors I need to consider when it comes to connecting with them and communicating? I think the example we shared earlier is if I’m 25 or maybe even into my early 30s and I was going to reach out to somebody, it may seem very comfortable to me if we met up at a trade show and I happen to get your business card or your cell number to drop you a text.

If you’re in your 50s, you may or may not appreciate the text. Your preference might be to get an email from me first. Why? It’s because of your demographic, how you’ve grown up in the working environment, and how you expect salespeople to connect with you. That’s a long-winded answer to your short question. It’s something that if we want to be successful in sales, we have to start to think about the age and the demographic of the people we’re selling to and the influence our own demographic has.

If we want to be successful in sales, we have to consider the age and the demographic of the people we're selling to and the influence our own demographic has. Share on X

I totally agree with you and I’ve noticed this. I have a 21-year-old and a 23-year-old, so they’re on the Gen Z side, but a lot of Millennial friends. When I was selling, I remember the ’60s, ’70s and ’80s selling was very different than it is now. I’m sure somebody who was 50 years old back in the ’60s said, “These crazy kids are doing this,” and going into the ‘70s. I think there’s another factor here that has even accelerated this far more than previous generations, which is technology. I know you’re not, but I know I’m old enough to remember when dial-up came in.

In those days, we were saying that speed dial was how quickly when you have your finger in the hole and you’re dialing. Speed dialing is when you force that dial to come back and your finger or whatever has a red circle around that.

For those of you who don’t know what Shawn and I are talking about because you never grew up with this, those are called rotary dial phones. You used to have to put your finger in, dial the phone, and it would spin back. If you wanted to go faster, you pull the dial back as quickly as you could. When the touch-tone phone came in, that was lightning speed. That was like texting today.

You could actually make songs because each number had its own tone, and you could make different songs on your phone.

I remember when dial-up came in and then DSL was the next biggest thing. I used to tell people back then, “This is going to change selling forever.” They would say, “You’re crazy.” I’d be like, “Think about it. You can get information quicker than you ever have before.” This has happened long before, but here we are now where if you want to know something, what do you do? You go to your favorite search engine and there it is.

It has made sales change because the people now who are the buyers grew up with this. I’m still a Baby Boomer at the cusp, but as the old traditionalist, they wanted to go play golf or meet at the country club or whatever. I remember in the days, I would drive an hour and a half to go meet a client one way to meet at their office, at the restaurant or wherever. Now, it doesn’t seem that way anymore. They don’t necessarily want to get together for coffee anymore. Let’s go to the older generation. How do you sell to the younger generation and what do we get to pay attention to?

You’ve hit the nail on the head. What I tell people is the obvious thing that you can always do here is ask. When you connect with people regardless of their age, what is the best way that you want to connect at this point? You don’t always have that chance if you haven’t actually met them at an event or run into them somewhere. Nonetheless, if you can, you should always ask because if you have an opportunity to take a shorter path, such as texting, usually that’s a little easier to use.

It comes back to we have to think about the person we’re selling to. We have to draw some assumptions based on their age as to how they would prefer to communicate. Something came to mind as you were talking about the changes and differences that have happened for sales professionals. It used to be that a sales professional needs to be a master communicator. Back then, it was all about the language that you used and how you present yourself. That’s still the case. If there were any skills you need to work on aside from those, it was how quickly can I get to my discussion questions on a phone call because they’re going to hang up quickly.

Now, we got all these different methods and means to communicate. While we were having a conversation earlier, I mentioned that I’m a fan of a BombBomb. It is one of the main tools. It’s a video platform. You can shoot a video on it, send it by email, and track those emails. It integrates with a lot of CRM systems. I’m not a fan of taking that right out of the gate because if I haven’t met you or connected, it’s weird to get a video from some you’ve never known. If you go to your LinkedIn messages, you’ll see people doing exactly that.

As sales professionals, we have to think about the age of the person we’re selling to. Think about what their preferences might be and how we communicate. If we’re not sure we get the opportunity, we should ask. I also think that it’s important that we test these different methods to figure out what works. I had this conversation with somebody who likes to send emails out. That’s their first step. I’ve said, “You shouldn’t do that.” Regardless of generation, I’m a fan of calling first. All it means is if they’re a little bit older, they’ll probably pick up the phone. If they’re younger, they definitely won’t but I’m ready with my voicemail.

That message is simply to say, “Doug, I haven’t had a chance to connect with you. I was going to send you an email but I wanted to make sure you knew there was a person behind that before I do. If you’d like to call or text me, here’s my number. Otherwise, watch for that email.” The intention of that approach is because so many emails are going to spam now that we’re not off and breaking through.

I challenge this person to say, “If you’re comfortable sending emails as the starting point, what is the age of the person that’s receiving them and what’s their preference because that’s what matters.” It doesn’t matter how you prefer to start your sales cycle with a new prospect. What matters is the preference of the person on the other end, and their age can play a significant factor in that.

It’s interesting to me because even my girls, they’re 21 and 23, I was talking with them and I was mentioning Facebook. They’re like, “Dad, we don’t use Facebook anymore.” I’m like, “It’s called Meta now.” They’re like, “It doesn’t matter. We don’t like Facebook. Most of our friends don’t like Facebook.” I’m thinking, “How quickly this changes because Facebook used to be the all big in that everybody was on.” I’m not saying Facebook goes away. I’m just saying that they prefer not to use it, so they use other methods now.

It’s great that you brought it up. Even if we know their age, you got to ask. I used to teach this. I’ll be like, “You’ve got direct mail, phone call, email, and in-person.” Those are pretty much your four options. Why don’t you ask the person how they want to be communicated with? Just because you think you should pop in their building, it doesn’t mean they want to entertain that. Just because you think they want to hear a voicemail, it doesn’t mean they want to do that. They might want to communicate in a different manner.

When we would do that, close rates would go up because it comes down to we’re communicating with human beings, not CEOs and whatever title you want to throw at it. I think you brought something up that’s really important. I didn’t want people to gloss over it because I wrote it down. It was the intention. What is your intention for this particular call, conversation, or something that you’re doing? That intention can be followed up with the right methodology for communication.

Let’s say that’s the older guys and gal for Gen Z and Millennials, how do the younger people work with me because I’m old? I got some friends who still run their companies. They’re in their 80s, going into their 90s. They’re not using social media. They’ve got teams of people who are using social media. How do they communicate with that age group? They’re still big buyers. Some of these guys own $500 million companies.

It comes back to exactly what you said. For the audience, regardless of age, let’s draw some assumptions for them and set this up so that they’re not walking away wondering. If you are reaching out or trying to connect with somebody who is in their 40 and up, it’s a good assumption that you could probably connect with them via telephone, leave them a message, or send them an email. Maybe even text them if you get to a point where you get their number and they’re open to receiving your text. You do not want to send text straight out of the gate.

On the flip side though, if I’m selling to somebody much younger, as you suggested, they’re not necessarily using those same platforms. It means if I call somebody who’s 25, they’re probably not answering the phone. My youngest is quite a bit younger than that. He’s about thirteen. The phone he has now has TikTok. That’s all the kids in his class are using. I’m not saying run down the road and sell in TikTok.

I can tell you a quick story. I had a client of mine and we were having this very same discussion. They were trying to figure out how to connect with their buyers. Their buyers were younger. They said, “Shawn, all the younger kids are on TikTok. We got to get on TikTok.” They were trying to find a firm that manages that. I’m like, “What are they using TikTok for? Where would they expect to connect with you?” That’s the other side of this. There are the preferred channels by which they want to communicate. Of those channels, which are they expecting or comfortable with communicating with you on?

CSS 75 | Generational Selling
Generational Selling: There are preferred channels by which people want to communicate, but also those channels they expect are comfortable with communicating with you.


TikTok might be something they enjoy watching in their spare time and communicating with their friends. It doesn’t mean you want to be the guy that pops in and say, “I’m selling knives and you should buy these knives.” You have to be cautious. I would say in the retail market, the closest thing for younger generations would be Instagram. You can use that as a way. Keep in mind, from a sales perspective, our goal is to create a connection. That connection often begins with the ability to get people to connect with us.

Maybe it’s through the questions we’re asking and the content we’re sharing. When they do connect with us, we always want to follow up. I’m shocked at how many people I know that use LinkedIn and when a connection request comes in, or if they send a connection request and the connection happens, they don’t do anything with it. They don’t send a follow-up message. I’m like, “What are you doing? You lost the opportunity.”

Keep in mind, if I connect with you on social media, that platform is owned by somebody else. I want to get you as quickly as I can off that platform and into my world, which might be telephone or face-to-face. If you’re trying to sell to somebody younger, take a look at the platform they’re using. Ask yourself the question, are these platforms they would expect to hear from me or not?

If the answer is no, then keep going down the list. To build on what you mentioned a minute ago, it used to be that we had a telephone, email, direct mail, and in-person. Now we have all of that and a variety of social media platforms from Meta, Instagram or TikTok, you name it, depending on what we’re selling, to video conferencing type solutions like BombBomb and that kind of thing, texting, instant messaging, or WhatsApp, the list goes on and on. I had a client who was trying to sell into Mexico. I went and traveled with them. If you’re in a meeting, the first thing you’d say to somebody after you say hello is, “What’s your number so I can WhatsApp?”

They will happily say, “Here’s my number.” You send them a WhatsApp right then and there to get them to confirm because they will not focus too much on their email. If you send them a WhatsApp, they’re going to respond. It is looking at what their preferences are. The best way to do that is in the moment with them. I tell people if you go to a conference or a trade show and somebody says, “Do you have a business card?” Say, “I’m out of business cards, but what’s the best number to reach you?” While you’re staying there, you put the number in, or if they give you an email, put the email in and say, “I’ll send you a text right now.” You’ll be shocked at how many people wait for it, “I got it.” “Awesome. I’ll send you a note after the event.” Now you’ve got a direct channel in the means that they prefer.

There’s a lot to unpack there. What do they expect? It’s extremely important. You don’t expect somebody to show up at the front door of your home at 7:00 at night and go, “I’m here to talk about the big contract.” You wouldn’t expect that or maybe you would, but you want to ask them as you were saying. The expected channel is important because we can make assumptions because we don’t know.

The other thing is that follow-up is a key component. When you said that about LinkedIn, I couldn’t tell you how many times I’ve had that happen to me where people reach out, I’ll connect with them, and I never hear from them. I can tell they’re not somebody who is going to be long-term. In the old days, the most beautiful girl in school, you had the nerve to ask her, “Can we go out somewhere?” She goes, “Sure.” You go, “Okay,” and then you never talk. It’s like, “What did you go through all that effort for to get to that place?”

Follow-up is extremely important and not just one time. You and I both know this. Follow-up is a common courtesy, but people don’t look at it that way. They look at it as, “This is another chore to do.” Think about it. When we’re dating somebody, we follow up all the time when we’re initially dating. We send them little cards, messages, voicemails, flowers, or whatever is what you’re into, but we’re constantly following up to bring the relationship closer.

People don’t think about follow-up that way. They think, “I got so much going on.” Work harder, not smarter if that’s what you want to do. I have a question for you because you’re the expert on this. It’s multimodality. I don’t know. I can’t ask. Could I try multimodality? In other words, could I try an email, LinkedIn, or a phone call? Do I put it into a cadence that way to see what their preference is? What would I do?

Let’s run that in a scenario to back up what we said before. What if you can’t ask somebody what their preference is? What if they haven’t told you? What do you do then? You have to make some assumptions based on their age and where they might expect to find me. Once you’ve figured that out, then you do some tests. I had a call prior to our discussion here with a coaching client.

What we walk through is what their progress has been in reaching people over the last month. What has been the most successful based on the age, demographic, and profession of the people that they’re trying to reach? If they’re trying to reach somebody in HR, they’re going to be a little bit different than trying to reach a business owner, an entrepreneur, or a production manager.

They all have different roles and as a result, those roles can mean different priorities in their day, etc. Taking a look back at what have been your own personal best practices, and then replicating those is the best way to find what works if you can’t ask directly. Here’s what happens a lot of times in reality and again, somebody said this to me in a call. He said, “I like email for prospecting.” I said, “Why is that?” “It’s easy. It’s cut and paste a message, blast a bunch off, and see if I get any.” I said, “That’s fair.”

Let me tell you a quick story. I’m not a fisherman. I find that putting the worms on the hook is gross, and getting the fish off the hooks is even more gross. It is not my thing. I will eat fish, but that’s it. When it comes to fishing, I can put a worm and I can cast a worm. Over time, the worm loses its energy. It slowly dies in the hook, bits and pieces are gone, and nobody bites the worm anymore. When it comes to any outreach, whether I’m sending you an instant message, WhatsApp, an email, or whatever, it’s got to be somewhat personalized to you.

CSS 75 | Generational Selling
Generational Selling: When it comes to any outreach, whether I’m sending you an instant message on WhatsApp, an email, or whatever, it has to be somewhat personalized.


If I make it too cookie-cutter, a lot of people pick up on that. People are now uber-sensitive to personalized experiences. You mentioned Meta earlier. All of these social media platforms and all of us here know that they have algorithms in place that identify our behaviors and habits on the platform and otherwise, and then they give us information that they think you are looking for.

It’s the very reason why you Google something and all of a sudden, you go to Facebook and there’s an ad for it. The indirect outcome of that is it has taken all of us and trained us that we get exactly what we want. As a result of that, when we’re trying to reach out to buyers, we don’t want to be cookie-cutting anything. It doesn’t mean I can’t replicate what works, but I want to make sure I’m making slight adjustments and tweaks based on the person I’m going after to personalize it and try to add value because that’s what’s going to get their attention.

Otherwise, I look like every other salesperson out there that’s blasting an email to them or sending a voicemail. You got to ask yourself. Once you pick that modality, you do some testing, and you figure out what works. The next step is to make sure you’re personalizing this to some degree and you’re adding value in those interactions because that’s how you’re going to set yourself apart from all your competition that’s doing exactly what you’re doing.

It’s sage advice. We’re speaking with Mr. Shawn Casemore of ShawnCasemore.com. Shawn, I imagine people going, “How do I get ahold of this guy?” Let’s cover that here. How do they get ahold of you?

The best way is you can visit my website, ShawnCasemore.com. There are all sorts of resources, newsletters, you name it. You can route around. There are ways to connect with me there if they want to reach out directly. You can also connect with me on LinkedIn. I spend a lot of my time there. If you sell in the business world, I would highly recommend anybody of any age spend some time there. That’s another way you can connect with me. Send a message or whatever is easiest. You can Google me because I seem to have a number of pages now that are scrolling out. All good though.

Thank you. If people didn’t realize what we did, I asked you your preference for contact. The question was, where would you expect me to contact you?

Let’s play this out a bit. I told you where I would expect it. I gave you my website. I said, there’s a method to contact me there, which probably goes through email. Most websites do. I mentioned LinkedIn. If you were to come to my Facebook page and message me, I may or may not get back to you because I don’t check that often. If you’re to come to Twitter and message me, I’d be shocked because I don’t see there much going on Twitter these days.

If you were to come to me at TikTok, you wouldn’t find me. To your point, in that conversation, when I give you the preferences of where you’ll find me and how to reach me, that opens up the avenue. It’s the way that shared them with you. What is happening is usually that’s the priority with which people want to be connected with. That’s what you should make note of.

The website was first and then LinkedIn was second.

What you can do when you’re doing this with a prospect is I always suggest transparency. Let’s say for a moment you say, “I’m going to reach out to Shawn. I’m going to go to his website.” You go to the website and you reach out but you don’t hear from me. If you decide, “That’s funny. I’m going to try LinkedIn.” Always refer back to the other contact points you’ve made. You might say, “I tried to connect with you on your website. I didn’t hear back, so I thought I’d try here.” You want to create that transparency because I find that when we don’t do that, it can seem we’re trying to attack them from a multitude of angles and not focus on their best interest.

It makes sense because sometimes email doesn’t get through. I know people have been like, “I’ve been trying to get ahold of you.” I’m like, “I look at my spam and my deleted stuff. I got nothing. It didn’t come through.” I think you bring up a good point. People always want to increase their sales and I have found that the master prospector will always outsell the master closer. What we’re talking about is being a masterful prospector at this point. You can be a good closer and a great prospector and you’ll outsell master closers every day. I’ve never seen it not happen.

There are more options to work with. You can be choosy about who you are close to. You bring this up and I have to say it. For years, I’ve said it’s not the ABCs or Always Be Closing. It’s the ABP, Always Be Prospecting. That’s what high-performing sales professionals do. They’re prospecting no matter where they go, 24/7.

It's not the ABCs – always be closing; it's the ABPs – always be prospecting. Share on X

It’s innate or they develop that sense that makes it look innate. I’m starting out. Shawn, you blew my mind. I can tell right now, seasoned sales professionals are going, “I get this,” but what do I do first? Can you give me 3 or 4 steps or whatever?

If we take a look at everything we’ve said here and put it into a package, we apply it back to the prospect. People have done their homework to identify a list of people they want to pursue. They’ve made sure that those people are the right people to pursue, the right title, the right position, etc. With that aside, then what I’m going to do is say if I have no history here and I’m not sure the best way to reach out, draw some assumptions relative to the demographic and the people I’m trying to reach, which is their age and how they would prefer to be connected with. If I’m 20 and I’m pretty sure they’re all in their 50s, I’m not going to go to TikTok and send you a message.

I’m probably going to resort to an email and/or call. I prefer the call than an email if I don’t know you, so that warms up that email a bit. Step one is you take a look at the people you’re pursuing. The demographic and age, and identify the best way to connect with them. Once that’s in place, then you launch your testing ground, which I always like to say voicemail then email, and then you create those touch points that we hear so much about.

I’ll add a tip in this in a second about touch points. That second step is the outreach, which you space out on an accelerated method, not a decelerated method. Here’s what happens most of the time. You get a name and you get excited, “This is awesome. I’ve got Doug’s name. I call Doug. I email Doug. I call him again. That’s today. If I don’t hear from him tomorrow, I’ll email him. If nothing, on Wednesday one more time, then forget about it. If I didn’t hear from Doug, he’s not interested,” which is completely wrong.

What we want to do instead is accelerate. If I reach out today, maybe a quick email or a phone call, then I wait a week, then I wait 5 days, 3 days, 2 days, then I go twice on the following day. Psychologically, it creates this means by which you believe that “I’ve heard of this guy, and all of a sudden, I hear about him more. It sounds like he has something to say.” It tends to create that connection. After that second step of reaching out, make sure to accelerate your reach, not decelerate. Once that’s done, after you do this for about 30 days, take a look back and ask yourself, “What has been most effective at reaching these individuals I’m trying to reach? What has been my most effective way?”

Make sure to accelerate your reach, not decelerate. Share on X

You’re going to have to change it up a little bit to create that test. Go back, take a look at your results, and then start to replicate those results that tend to work best and again, in 30 days, revisit. I find as sales professionals, we don’t ever sit back and say, “How am I doing? What is working? What’s not?” We go on to the next thing and we keep doing the same thing and we’re frustrated we don’t get different results. That’s the third step that I think is crucial.

That is, without question, crucial because you’re right. As sales professionals, they don’t. We’re always on the go, “Next deal.” Marketers will say, “You got to test.” Truth be told, most of them don’t test like that either. I can hear all the hate mail coming in now from marketers. The testing component is important because too many sales channels look at things short-term.

The reality is this is a longer-term play. It’s a 90-day play. That’s basically what I heard you say, and I agree with you. Tony Robbins once said, “Success leaves clues.” I always remember that. It doesn’t for this because there are certain things that are successful and there are also blind spots that you’re going to go, “I didn’t expect that. That’s successful. I tried this and I’m being shot down left and right.” You want to pay attention to those and grade them like you would in marketing. Whatever you gave, a letter which is grade A through F, a number system, color system, or whatever works.

Folks, personalize this stuff. As Shawn said, personalize this. The thing is, I get so many lame stuff that comes in. It’s like I check the company out and I look at the offer or whatever on the website. I’m like, “This is pretty cool stuff,” but the approach is like walking up for a first date and going, “Do you want to get married?” They don’t know who you are and they’re going.

I suspect you probably got those too. I don’t know how it is in Canada. You’re a heck of a lot more polite than the Americans but it’s like, “Shawn, this is Doug. I’m great. My company is great. Here are the reasons why you should pay attention to me.” It’s those types of messages as well. I get those sometimes in voicemails. It’s like, “Why?” Can you give a couple of tips on what you should do in personalization?

Here’s what tends to happen. When we say personalization, people think, “I put their name in it. I spelled it correctly.” You check the personalization box. You have to think of your opening line, whether that’s an email, a message, even if it was direct mail, and then a letter. That opening line has to resonate for them to read anything else. All of the studies show that anything that we read typically, and a lot of this goes back to how social media has influenced us, we look at the top line and the bottom line. If those seem interesting, I might touch on some of the rest. I’ll jump through. You want to be verbose, but that first line has to resonate with them.

It can’t be something that’s generic like, “I think you need a higher return on investment.” It’s got to be something that grabs their attention. You can figure that out by looking up their company or if you know something already about these people that you’re trying to sell to, if you’ve been in the role a little bit or if you know some of their pain points, test out and say, “I was recently talking to Bob at ABC company down the street, and Bob is challenged with whatever the case might be. I’m wondering if you’re facing similar challenges.” That opening line is either going to get you or not, but at least I know from trying that a few times, if it gets you and gets others, now I have an opener that’s going to work, and then I focus on my closer.

It’s grabbing the opening and closing lines to get people’s attention. I’m a fan of using some CRM that you can use to send emails and make calls. You could do it in one platform, especially since I’m a big fan of HubSpot. I don’t get paid to say that but that’s my personal preference. When you can see if somebody opens an email or they open it several times, that gives you the impetus to say, “There’s something grabbing them here but they’re not biting it. The fish is not on the hook yet. Why is that?”

CSS 75 | Generational Selling
Generational Selling: After the opening and closing, make sure there are some questions in there or a question that grabs your attention and makes them want to respond.


I’m a fan of using a provocative statement. I emailed a gentleman that I had met. We had a good conversation and he says, “I want you to reach out. We should have a coffee. I want to ask you a couple of questions.” I said, “No problem.” He got back, I had his business card and sent him an email. He opened it but nothing. I sent him another follow-up email and left a message, “I’m just following up to make sure you got the email.” A couple of more opens but nothing.

This is the provocative one where they haven’t grabbed a whole list yet. I replied because I knew he is opening the email, so I knew he is getting it. I’ve left him a voicemail. None of this has worked. I sent him a message back that said, “Typically, when somebody doesn’t respond to email after we’ve met, it’s for one of three reasons.” I then put in two that were serious and one that was a joke. The first is because they’re too busy with X, Y and Z. The second is they’ve gone on vacation and whatever the case is.

The third is the problem that we were discussing at the time has now been completely solved and doesn’t exist in the organization. Which one of these three is most relevant in this situation? You’d be shocked when you ask people pointed questions and how many people respond because they want to correct you. After the opening and closing, make sure there are some questions in there or a question preferably that grabs the attention that makes them want to respond. I’m breaking this down into micro points here. That’s how I would use this approach in order to make sure I try and get a response from the person I’m reaching out to.

I loved what you did in the last. It’s the old go for the no type process. I would love to have you back on another episode. We could talk about questions and what you’re supposed to be asking. Many people are worried about hearing the word no. Folks, I promise if someone says no, you won’t dissolve like sugar into the water. It won’t happen. Your life is not going to be over. The reality is that if you don’t go for the no, they don’t respect you enough anyways at that point. When you go for the no, I’ve sent stuff out like that and I like to use humor a lot at the end.

I’ll put in something like number 1, 2 and 3. Number three is you’ve been kidnapped by dolphins and they pulled you out to sea. Usually, people type back something or respond back and go, “That was funny. It made me laugh,” whatever it might be. Don’t be afraid to challenge these people. Your time as a sales professional, whether you’re the owner, CEO or whatever you’re selling to, they will respect you when you respect yourself and you let them know where you’re coming from.

If you position yourself as a subordinate, you’ve already lost your position in the process. I love what you did. Thank you for sharing that. Shawn, I could talk to you all day long but there’s a certain time on this show and people go, “It’s too long.” I’m going to thank you for being here. I welcome you back on another episode if you would like to be. Any last-minute closing or anything?

CSS 75 | Generational Selling
The Unstoppable Sales Machine: How to Connect, Convert, and Close New Customers

I’ll tell you the third point I actually put in that email, and this is something you and I discussed, but my latest book, The Unstoppable Sales Machine came out. What I said in the third point was, you’ve read the book that I provided you and your sales are suddenly no longer an issue. I haven’t gotten a response yet, so we’ll see. Nonetheless, if people are interested in furthering some of these ideas that I’m sharing, they can go to Amazon. Unstoppable Sales Machine is the name of the book. I would love it if they wanted to grab a copy. They can reach out to me and I’m happy to send them a personalized copy if that’s a preference.

I got to tell you something here, Shawn. When no one knew John Maxwell, I didn’t know who he was, I happened to be at an event and he had a book. I walked up and said, “You seemed like a pretty smart guy.” He was a preacher turned leadership guy. He said, “I appreciate you telling me that.” I said, “I would like to get one of your books.”

He goes, “Let me take the book and if you get a course, I’ll personalize it and I’ll sign it.” He did and that thing is worth a heck of a lot more money now. I have a personally autographed book from him and different people. I recommend to everybody, contact Shawn and get the personalized edition. Shawn, thanks for being on the show. I look forward to another episode together.

Sounds good.

I got a lot of notes here. There’s so much in this episode that’s cool stuff. I love the fact that people have a preferred method that they expect communication. Not only do we have like this person tends to use this platform or that platform. That doesn’t mean that necessarily is where they’re expecting you to contact them. You want to qualify for that. You must actually, otherwise you’re breaking rapport. They don’t like you as much if you’re irritating them because you think X and they’re thinking Y.

Remember, when we’re prospecting somebody, it’s more about equal share, but it’s got to be a fair share proportionate to what they’re seeking in addition. Don’t forget to test and measure everything. I thought Shawn did a great job on that. Ninety days, test and measure everything. You’re going to adjust. People are going to say no or yes. They are going to give you ideas and feedback. Take that information. Don’t forget to follow up. I can’t tell you big of a challenge that is. It’s a huge challenge for people. They don’t follow up over and over again.

They do all the work to get there, and then they don’t follow up, which is expected from us approaching someone else. Try multimodality. Meaning, if you don’t know what to do, try different methodologies. You’re testing and trying to figure out like you would in marketing. Where are these people and who are you hyper-responsive? Hyper-responsive are those people that you reach out and they go, “Let’s talk.” Those are the people who are qualified to talk with you. If you bring those in, your numbers go up.

If you like the subject matter that we had, reach out and let us know. If you have some type of subject matter that you are interested in but you’re like, “I don’t have an expert to talk about it,” reach out to us at YouMatter@CEOSalesStrategies.com. Let us know what that is. If it’s in line with leveraging your sales and creating business growth, maybe we’ll run an episode on that and we can bring you that expert in. We’ll source it and do all the work, you get the information. If you think you could be a good guest, reach out to us and let us know. We’ll evaluate that. If so, we’ll have you on the show.

If you love this show and you want to share it with other people, I would be grateful if you would do so. If you want to give it a great review, please do so. The more reviews and the more people comment on these things, the better it is for us and the better it is that we could keep sharing this type of information. If you want great information to talk about this episode, reach out to Shawn at that point.

If you know anybody that wants to be in the top 1% of sales globally in their industry, maybe yourself, someone who works for you, someone you work with, or someone you know, have them reach out to me at Doug@CEOSalesStrategies.com and we’ll help them take it to those levels that they’re seeking. Until next time. Go out and sell something. Sell a lot of it and sell it profitably. Don’t discount when you don’t have to. Play win-win and make people happy. You win. They win. It’s a better world in that case. Thanks so much.


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