How to Send the Best Sales Emails

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like, we have to start from scratch. I'm Jason Pfeiffer, the editor-in-chief of Entrepreneur Magazine.

2:21wisdom of that, but it got me to open the email. So fine. And it starts with this. It starts, Hey, Jason, I'll save you the fake personalization and get straight to my question. All right. And then it goes on. If you're curious, the next thing is, are you running monthly promos for your consulting offer? If not, you're leaving significant cash on the table. That said, I can help with this. Working on a pure commission basis, dot, dot, dot. Okay. Anyway, so this is not a service that I needed. So unfortunately, I could not give the person who sent me this business. But let's just linger for a moment on the genius of that first line.

2:59Hey, Jason, I'll save you the fake personalization and get straight to my question. The reason I love that is because so many emails start with fake personalization. So many. I mean, I get them all the time. I realize that I'm in a unique position where people are emailing me constantly because as editor-in-chief of Entrepreneur Magazine, people mostly want coverage in Entrepreneur Magazine. And so they're reaching out all the time and they are fake personalizing emails. But I am sure that you get them too. I am very, very sure. How do I know? Well, because I posted about this on LinkedIn and a ton of people chimed in that they also hate fake personalization.

3:42Fake personalization is terrible. It takes so many forms. People say, I love your work, but clearly they've never read my work. None of the references that they're making are of my work or of knowledge of my work, where they open up an email and they say, I noticed you're an editor at Entrepreneur. And what is even the point of that? Look, I get it. Personalization creates better connections. You should make things personal. But true personalization, that requires time and effort. And if you won't put that in, then your fake personalization is basically saying, hello, I want you to trust me. So I'm going to start by lying to you.

4:24And is that really the right way to start a relationship? I say no. Today on Problem Solvers, once again, no guest, just me talking to you about this thing that I think we need to think more about, which is how to really meaningfully connect with someone else. There is some reason that you are doing this right now. Maybe it's sending sales emails. Maybe it's sending what you hope are going to be good introductions to people. Maybe it's finding partners. Maybe it's finding customers. Whatever it is, we are reaching out to people all the time. People we don't really know, but people we're taking a guess might want our thing, might be useful to us, might something.

5:01And if we can just get a little bit better at doing that, at reaching them, at connecting with them, well, then business soars. It won't happen from fake personalization. So what will it happen through? I'm going to give you an answer coming up after the break. Hi, I'm Emily Washkovic, Yelp's small business expert and host of the podcast Behind the Review. We're back for season two, and this time we're keeping everything you love and adding so much more. Get ready to find out what happens behind the scenes at those businesses that everyone raves about. You know the ones. Learn how owners swallow their pride when getting critical feedback and what they do to turn around that unhappy customer.

5:52And don't forget the reviewers. We'll find out what inspires them to leave those rants or raves in the first place. Get ready for buzzy new guests like restaurants from Yelp's famed top 100 lists and new short BizBite episodes. Just a few minutes of advice on how to set your business up for success and create connections with customers, both online and off. Subscribe, like, and follow the show to hear new episodes every Thursday. All right, we're back. So today we are talking about how to connect with people when you don't have all the information to stand out in a truly personal way, which is a real problem.

6:32I mean, look, I've sent plenty of emails to people hoping for things. I reach out to see if somebody wants to bring me as a speaker to their convention. And I don't have a ton of personal information about the person I'm reaching out to, or sometimes even the organization and their needs. So I do my best, but it's not that personal. I get it. I get it. I get it. We don't always have the information and we have to reach out. So how do we do it? Well, I'm going to offer three things in this monologue. Number one is how to do it well in a non-personalized way. Number two, how to get some sense of who you're reaching out to.

7:14And then number three, a conversation that you can have that's not salesy, that can really inform your sales. All right. So let's talk about how to do it in a non-personalized way. I posted, as I told you, that really funny email that I got where the person said, I'm going to skip the fake personalization. I posted that to LinkedIn and oh boy, people responded. They themselves have been the recipients of fake personalization. They did not like it. Here's a funny comment from a woman named Amanda Ross. She wrote, in a DM, someone said to me, I really love your work. I asked what stood out to her the most.

7:55She said, you know, your websites. Oy vey. Then she tried to sell me something because of course she did. Yes. Yes, of course she did. They didn't know. They didn't even have an answer for that. I, for what it's worth, wrote back to the person who sent me the fake personalization email. And I said, I said, look, I don't need this. It was service, but I do appreciate your opening line so much so that I posted about it on LinkedIn. I sent him a link to my LinkedIn post. And this person wrote back, hi, Jason, glad you like the opening line. And thanks for sending me the LinkedIn link. In keeping with my overall philosophy, I won't attempt to personalize this reply to you either.

8:34But your reply and post did make me smile. Cheers. I appreciate that. I appreciate what this person is doing. And what I appreciate the most about it is the way in which it is just so knowing. It's so knowing. And there's real value in knowingness, in acknowledging the thing that we both know, which is that I'm sending you a sales email, you're receiving a sales email. I know that this is not magic. I know that most of these are not going to land. I'm playing a numbers game here. But I hope it's useful to you. And if it's not, no hard feelings. You know, There's just something kind of wonderful and human about that.

9:11I think part of the challenge that we have when we're sending emails out to everybody all the time or letters or whatever, it's just that it can start to feel not human. It can start to feel purely transactional. And I think that there's something a little wonderful about pulling the curtain back a little bit and just saying, hey, look, I'm a human being. You're a human being. Hopefully, there's something here. If not, all good. When I sent out email, I just sent out, let's tell you something that I just did that was sort of not that personalized. I had an idea for how to get speaking gigs because I do a lot of trade association work.

9:42Trade associations hire me for their annual conventions to speak. So I decided to identify 20 trade associations that have upcoming events and to find the marketing manager, who I'm just guessing is the person who might be involved in developing the event, and then to send a copy of my book along with a semi-not-really-personalized letter, which I printed out and signed to them, mail it to them. And in that letter, I open, let's just say that I'm emailing, I don't know, the American Dental Association. I open by saying that I imagine there's a lot of change happening in the dental industry right now, and that the ADA, American Dental Association, is surely guiding its members, but that I would love to help where I could because that is an area of expertise of mine.

10:34It is. That's what I talk about. That's what my book is about. And then I pointed them towards something in the book that I think that they'll find valuable. And the reason I know that is because it's often the exercise, the advice that I have in my talk, started my book, and then I moved it to my talk that people respond to the most. So I sort of road tested it. I know that people like it. So I'm pointing it out to them so that they read it and hopefully it resonates with them. And then a little bit later, I say, I say to them, I say, look, I'll be honest, I am not a dentist and I would never profess to tell dentists how to do their jobs.

11:10But I do feel confident telling them about one of the most important skills of their job, and that's to be adaptable. And that's what I want to help with. Now, this is not really personalized, right? Actually, you know what? It's funny that I use the dental example because that was one of the rare moments where I actually could add a small amount of personalization because my dad is a retired dentist. And I mentioned that in the opening line, bolded. But when I wrote to the Architect Association or the Financial Planner Association, I didn't have that. And so I didn't lie. I just didn't include any kind of personal detail at all.

11:44But I did do the same thing about, there's a lot of change happening in the financial planning industry. There's a lot of change happening in the architecture industry. And what I'm trying to do here is really to my point number one, which is to just be human. Look, I'm not a dentist. I don't know your people. But I do know my thing. But also, and this pivots into point number two, is that I am working off of the best information that I have about how I am relevant to them. I ultimately want to try to identify their needs and concerns and what great outcomes look like for the people that I'm reaching out to, and then show them how I can create that outcome.

12:25because ultimately that's the thing, right? People don't care about your solution. They care about the outcome of your solution. Nobody wants a keynote talk. What they want is something that their audience can learn from, can take away. Ideas that they will be mulling over for quite a while. That's the thing. I can't just live in, hey, you need a keynote speaker. I'm a great keynote speaker. That's not exciting to them. I need to understand the outcome, the thing that they want to happen as a result of the solution that I provide. This is something that I learned from my friend, Rochelle DeVoe, who is a consumer insights research expert.

12:59And she always focuses on the outcome, not just the solution, but the outcome to the solution, the thing people get as a result of the solution. If you understand that, if you can do some research, either on how people respond to your product and the way that they understand and articulate the outcome, or if you want to get a little more personalized, you can individually research the people that you're reaching out to and try to understand their outcomes, now you're somewhere. Now you're building something that isn't exactly personalized, but is on the path towards where they likely want to be.

13:35And that leads me to point number three, which is how to have interesting conversations that can help you reveal that stuff. This is where we can start to get personalized in a real way, but without the whole song and dance, let's say. Okay. To explain this, I want to tell you about, I'm going to have to be careful about this. Just a couple of days ago, here's some context. Just a couple of days ago, we at Entrepreneur were talking about an interesting sales program that we were developing. We were going to go out to some large companies and see if they were interested. And I said, I think that we should probably have and conversations with people at these large companies to make sure that we understand how they're thinking so that we can best match what we are about to offer to the way that they're thinking about their budgets and their priorities.

14:27And so I proposed this. I said, look, if the sales team reaches out, it instantly becomes a sales call. And now everyone's in sales mode. And I don't think that that's the right way to have this conversation. So why don't I reach out? Why don't I see if I can get the head of sales somewhere on the phone with me, and we will have a conversation. And I will start by saying, I don't have anything to sell you. I'm not in sales, but I would really like to understand how you think. So that is what I did. And the person I got on the phone, well, again, I wasn't interviewing them. This was just an off the record conversation.

15:03So I will not tell you who they were, but I will tell you that they are the head of marketing at a very, very large company, a company you've heard of. Head of marketing, very, very large company. This is the person who is making a lot of the decisions, I guess probably all the decisions, I don't know, about how they're going to spend their money on places like Entrepreneur to advertise. And this person told me something so interesting. I had an AI note taker going during the call, so I have the conversation. I'm just going to read you like a tiny bit from the transcript. This person tells me, all right, I'm literally reading from the transcript, says, if you want buy-in from the brand, the way that we're talking to other brands, whether it's magazines, other publishers, it's like the big question is, where's the need, right?

15:51So what he means is that the publishers or whoever should be asking this of the giant brand, where's the need? Where's the need within your world? What's the business challenge, the business opportunity? And then how can we apply our technology, our data, our AI, our capabilities, our reach to solve that need for you. And when we have that conversation, we can find a way to tell a shared story. And that to me has been the flip because for years, it's been so transactional. It's like, I've got this ad space. I've got this thing. Do you want to sponsor it? Do you want to put some ads in it? And you can get all the vanity metrics you want.

16:29But this whole concept of a value exchange, that's where we're really good. Okay, that was from the transcript. And as I was reading, I had to take out some details. So maybe it sounded a little weird. But the takeaway from that conversation is this head of marketing is very interested in having conversations before there's a sales pitch where he gets to articulate this large company's needs. And oh yes, they have needs. They may be a very large company with a lot of money, but they have needs. He was telling me about some of them. the brand awareness in particular arenas and consumer confusion.

17:08And there's all sorts of stuff that they want partners on. And they have identified needs that they're willing to put money behind solving. And I said to him, are you interested in having these conversations about your needs? And he said, yes, absolutely. Because that's the only way we're going to find great partners. And it made me realize that I had stumbled into something really valuable, something that I think is scalable, which is have the non-salesperson or have a very non-sales conversation about people's needs. Don't start with the sales pitch. Start with trying to learn what they need.

17:46Because when you learn what they need, you can create the solution that drives the outcome. The outcome that Rochelle DeVoe just a few minutes ago, I was telling you about Rochelle taught me. We have to understand the articulation of the outcome. And we only know the outcome if we know their need and we have a solution that gets them to their outcome. And the more that we can do that, the more we can then turn around and not even have to have an email at all, an email that might be fake personalized or not, because now you're just in dialogue. And the dialogue so importantly, again, I just want to stress it, I couldn't stress it enough, didn't start in sales.

18:21It didn't start with the sales call. It started with the needs call. And how do you get a needs call? Well, look, I mean, sometimes this is going to happen because you are already some kind of trusted partner or you're in some position like Entrepreneur Magazine where, yeah, entrepreneur, we'll take the call. But it can also happen by meeting people somewhere, by going to events, by having casual conversations, by working your way up a ladder, by connecting with people on social media, by doing something where you're having the casual conversation that eventually leads to a solution. And can I say, doesn't just immediately go there.

19:03That is a thing that is, I think, often what people really miss. As I go back to thinking about that woman, Amanda Ross's comment on my LinkedIn, she said in a DM, someone said to her, I really love her work. She asked what stood out the most. The person just said, you know, websites, and then just tried to sell her something. I get stuff like that all the time. It's so annoying. Actually, as I'm talking, I'm going to pull up a DM that I got on Instagram. So here's this person who says, he DMs me, he says, loved your interview, double exclamation mark. Jason, your episode with Kara Golden, Kara has a podcast.

19:40I was on the podcast recently. Jason, your episode with Kara Golden was straight up fire. Dude, thank you for the work you're doing and for continuing to inspire. And people people do send me notes like that when they just hear me on a podcast. And I really appreciate that. So I, so I wrote him, I said, Hey, thanks. Glad it connected. And he said, yeah, you nailed it. You're looking to get on more shows. It's what I do all day. LOL would love to help you get on big podcasts. Let me know. And I didn't respond to that. And so the next day he replied, he replied, Hey brother, did you get my messages?

20:09I, uh, Instagram can let me down pretty badly sometimes or whatever. And so anyway, I said, I'm not in need of the services. I don't like that. That is, man, that is even worse than fake personalization because it started seeming like it was real personalization. It started feeling real, but it turned out that it was, he was basically like he dropped a hook, like he was trying to catch a fish. And I came over to the bait, which was him being nice and personalizing something. And then immediately just started trying to reel me in. It doesn't feel good. I wouldn't, I don't respond to people who do that.

20:44Right? I'm trying to reveal some of my emotions to this stuff because people don't want to feel like they're walking bags of money that you can just somehow kind of trick into giving you a little bit of that money. People don't like that. So be real. That's ultimately the thing that I'm getting towards in this whole thing, right? Whether or not you're just not personalizing it, but being kind of honest about it, about the non-personalization, or you're trying to understand their needs, even if you haven't been in touch and just do your best to lead with value, or you're having true personalized conversations that aren't sales that will lead to potential sales.

21:25Either way, what this is about is about being real and being human and honoring the connection and the time and the just personness of the person on the other end of that line. That is what it means to be the opposite of fake personalization. It's real personalization or even just get rid of the isation. It's just about being a person. And if you do that, you'll find other people who want to work with you. And that's our episode. I would love to hear what you think and maybe even about a problem that you solved. You can find me at my website, jasonpfeiffer.com. J-A-S-O-N-F-E-I-F-E-R.com. Also, I have some more useful stuff for you.

22:07I write a newsletter about how to future-proof yourself and become more adaptable and optimistic. I would love for you to sign up. It is at jasonfeiffer.bulletin.com. Also, check out my other podcast. It's called Build for Tomorrow. In each episode, I take on some belief that we have that holds us back from progress and show you why it is not as bad as you think. Problem Solvers is a production of Entrepreneur Media and comes out every Monday morning. So make sure you're subscribed so you don't miss an episode. Thanks to Deepa Shah for production. My name is Jason Pfeiffer. See you next week.