Tips for Cold Calling

Cold calling is often overlooked by most business owners. However, Wendy Weiss believes in using all the tools available to acquire potential clients, and cold calling is a sharp one!

In this episode, Wendy Weiss – a sales trainer and coach – explains an effective method to make connections with clients.

After moving to New York to become a professional ballet dancer, Wendy discovered a gift in business development within herself when she took a day job at a telemarketing agency. She soon started her own business to help others grow and become successful in their businesses.

In this episode we discuss:

  • Cold calling tactics that are working right now
  • Proven techniques to build connections with clients
  • How to hire a good salesperson or appointment setter


Josh  0:00

Welcome to the Work The System podcast where we help entrepreneurs make more and work less by managing the systems of the business. And today I’m very excited. I have Wendy Weiss here today, and Wendy Weiss is known as the queen of Cold Calling. She’s an author, speaker and sales trainer and a sales coach. She was recognized as the leading authority on Lead Generation, Cold Calling, and new business development. Her clients typically 3x the number of qualified appointments, they can schedule with a corresponding increase in sales revenue and a shortening of the sales cycle. Clients include Avon products, ADP, Sprint, and thousands of entrepreneurs throughout the world. Alright, Wendy, why don’t you give us the background? Tell us how you become the queen of Cold Calling?

Wendy 0:48

Well, thank you for asking that question. And I’ll begin by saying I was never ever supposed to be the queen of Cold Calling. I was actually supposed to be a ballerina. I grew up in Pittsburgh, Pennsylvania, I moved to New York City where I still live at work. And I moved here when I was 17, to dance. I studied at the Joffrey Ballet School. And then eventually, like every artist in New York City, I needed a day job. And I waited on tables for a while. And that got kind of tiring quickly. And then I got a job with a telemarketing agency that did business development. And it turned out I was really good at it, which was a complete surprise. Because ballet dancers, we don’t talk, we just dance, we don’t talk. So I did that day job for a while. And then I started my own business where I had clients that I would represent. And I did business development for them. And it was actually one of those first clients that dubbed me the queen of Cold Calling, because I found so many opportunities for him. And then from there, I segwayed into the business that I have today. And the business that I have today is that I work with business owners that are looking to grow their business faster, more easily, more profitably. And I want to say one more thing. And I know we’ll probably get into it, Josh. But for those of you that are struggling, or don’t like the idea of Cold Calling, you know, I was really lucky. I knew nothing about business. But I got that day job. And they taught me this skill. And learning this skill enabled me to build a business. So the really good news for any of you that might be struggling with how to find new clients is what we’re talking about today is a communication skill, and it can be learned and it can be improved on.

Josh  2:50

Well, let me start with maybe the elephant in the room first. Because everyone is aware of Cold Calling. And I think there’s probably no one who really likes doing it. Maybe you do.

Wendy  3:01

I’ll take issue with that.

Josh  3:04

Is it still the same as it used to be? You know, you got email, your texts, your social media, Facebook, all that sort of stuff? Does it still work?

Wendy  3:13

It absolutely still works, it doesn’t work the way it worked 20 years ago, or 10 years ago, or even five years ago, everything evolves. And by the way, I am a believer in using all of the tools that are available to reach out to potential clients. It’s not either or, or just pick one, it’s really all of them. And one of the most powerful things that you can do is speak with another human being with that prospect on the telephone. There’s actual research, it was done at the University of Chicago Booth School of Business. They tested written communication, and spoken communication, written communication could be an email, social media text, a letter, spoken communication, when you’re face to face with someone or on a zoom call, or on the phone or even a voicemail. What they found out was that if people hear you talk, one, they think you’re smarter. And two, they’re more likely to take action on whatever it is you’re talking about. So the phone is a very powerful tool.

Josh  4:24

So what about the answering rate of phones? So and you mentioned several different things. So is there like a system or a strategy and I’ll just use our company as an example. We collect phone numbers and we have email addresses. Is there a way when you would try to engage them by email first and then phone or just directly to phone? Or you send them a voice file or how do you know where you begin to actually make connection with someone who maybe is not expecting to hear from you?

Wendy  4:54

Well, we teach you like this Josh, we teach a very step by step system for This because the cliche or the myths about cold calling is you open up the phone book, call anybody just start dialing the phone with your fingers crossed, and maybe somebody will say yes. But what we actually teach is a very step by step system that includes reaching out by phone and sending emails. And I always start with a phone call, because you know what? You pick up the phone, you call someone they may answer. Then you have the conversation. So start with the phone call. But what we do is a series. I call it a voicemail campaign. It’s like a drip campaign for voicemail and email. So it’s a series of voicemails and emails that you leave over time. And I can walk through the process, you want to get more granular with it with a charge. But that’s that’s what we do. And I have a business development person. Her name is Gail. And she sets appointments for me and one of the things that I always hear when I speak with a prospect, she sets up the appointment, they say to me, she’s so persistent. And it really makes me laugh, because it’s really easy to be persistent. If you have a system you’re following.

Josh  6:22

Actually, I do want to get to the granular because it is perfect for me, but also I think anyone listening, it’s gonna be a lot of value. And because most people are afraid to do it, because they think, well, it’s not going to work. And I and they’ve done it before they’ve called 100 numbers, nobody really picked up and there’s a way that doesn’t really work. I think, seeing there’s a system that works, makes people believe they should probably put the effort in. So what is it like a 10 day cycle, a 15 day cycle, or what is the system?

Wendy  6:51

We usually start with a month long cycle and before I walk you through this, I am going to say that it’s really important to micro target who you’re reaching out to and to have messaging that’s relevant to that’s really going to resonate. Otherwise, it’s not going to work. So put that aside for a moment. There is research that shows that on average, it takes somewhere between eight to 12 touches to get someone to respond. And so we usually excuse ourselves, we start with eight touches. And we track it’s really important to track what you’re doing. And then we let us know: Do we need more touches, can we do it with fewer touches. But a touch is a phone call, a voicemail, it’s an email, it could be a text. So we do week one, call the prospect. If you get voicemail, leave a voicemail number one and immediately send email number one, they mirror each other, they say exactly the same thing. You wait about a week. If you haven’t heard back, you call again, if you get voicemail, you leave voicemail number two, which is different from number one. And you’ll immediately send an email which is the same as voicemail number two, they mirror each other. You wait about a week, you haven’t heard back, call again. If you get voicemail, it’s voicemail number three, different from wanting to, but the same. Then you send along that email, email three and voicemail three are the same. Now these first three voicemail email combos have to be about challenges that prospects have that you can help them with and it has to be relevant. The last message you wait about a week, voicemail email combination number four, I call this the move on message. The move on message goes like this. Josh, I tried to reach you a number of times to discuss filling in the blanks. I haven’t heard back from you. I know you’re busy. So I’m figuring this just isn’t a good time for us to talk. I don’t want to be a pest. So I’m going to cease and desist. And we’ll check back with you and you name a timeframe. Could be three months could be six months could be a year that’s really just contingent on how many leads you have. And then you say, but if you’ve been meaning to get back to me and just haven’t had the chance, I’d love to discuss filling in the blank with whatever it is you want to talk about. This is actually the most returned message. And this is why it works. There are people that are in the market today. Whatever it is you do there are people in the market. They’re looking for it. But here’s the thing. They think you might be a business owner, you might be the CEO However, you know, whatever title you use, they think you’re a salesperson. And they think because you’re a salesperson, you’re gonna keep calling them. What most people do is they call once, maybe they call twice, maybe they didn’t call three times, and then they just stopped. They never say, I’m not gonna call you again, they just stop. But your prospect thinks you’re gonna keep calling them. So you might be on their list, they want to talk to you, but you’re down at the bottom, because they think you’re gonna call them again. So when you say, I don’t want to be a pest, so I’m going to stop, the people that want to talk to you will respond. And there are people that are in the market today that will respond, there are people maybe they’re not in the market today. But they know, at some point in the future that they will be. And because you, you have to love some good messages previously, to make them want to talk to you, they will also reach out. And one of the things that we have also seen, you will get more of a response by email, it’s easier for them. And we have seen this, we’ve seen it internally, we’ve seen it with our clients. But sometimes you say, Oh, I’m getting all the responses by email, I’m gonna stop calling. When you do that the response rate goes down. So you still continue to leave voicemails and send emails.

Josh  11:25

Makes me feel really good. This is good, this is the process that we’re actually doing right now. Similar, but I got a few little insights here. Now, what is the way to deliver a voicemail that actually gets responded?

Wendy  11:51

Well, it’s about your tone, about your energy, about the things you say, how do you leave a voicemail, it actually gets responded to? Well, it’s certainly about tone, it’s certainly about energy. But most of all, it’s about saying something that’s relevant. The goal when you leave a voicemail is to get someone to respond because quite frankly, even if they respond, and they say take me off your list, they just get you a huge favor. You don’t have to spend any time calling them. You can now go call somebody that’s gonna say yes. So what we’re looking for is the response. And you want to script these messages. I know people don’t like the idea of scripts. But my definition of the word script is if you think before you speak, that is a script. So what is it you want to convey? What is the challenge that your prospects have, that you can help them with? And how did they talk about it? Not how do you talk about it? But how did they talk about it? And I can give you an example. We had someone in our program, a while back, she was a consultant. And she worked with nonprofit agencies. And she helped them produce their fundraising events. And so I said to her, okay, well, why should a nonprofit agency be interested in working with you? And she said, oh, well, we have a very special proprietary process. And I said, okay, so much. Tell me about your process. She said, oh, well, we met with the client. I said, Okay, so what? She said, Well, we ask a lot of questions. Okay, so what? Well, we analyze the answers. I said, okay, so then she said, Well, we make recommendations. And I said, Okay, so how is your client better off? Do you meet with you, ask your questions, analyze the answers, you make recommendations, are they better off? She said, oh, they’re fundraising events to make money. Bingo. So we helped her put together a script about helping nonprofit agencies raise more money on their fundraising events. And when she got someone on the phone, they would talk to her, they would set an appointment with her when she left him a voicemail or send them an email, they would respond because the ones that wanted to make more money on their fundraising events needed that kind of help.

Josh  14:27

So, it makes total sense to me. Now, with the micro targeting, you mentioned in the beginning, do you have any techniques or wipe in order to actually micro target your, your target? How do you do that? Are there certain tools? What would you consider a good micro target?

Wendy  14:47

Well, you have to look at what I call this the ideal prospect profile. What a lot of what a lot of businesses, a lot of businesses are just Really reactive, they work with whoever comes in the door. What I like about this process is you get to choose, it’s, it’s really very powerful. Who do you want to work with? Which companies would be the best fits for you in your market. And that’s really where you start by defining what makes an ideal, not any old kind of prospect that maybe is going to do some teeny tiny little thing with me, but who are the ideal ones. And so that is looking at the size of the company on it by revenue or employee count, maybe it’s a particular industry, maybe they need to be in a specific geographic location. You know, people come to our program, we actually called our program 3x appointments is our core program, because people participants in the program, triple the number of qualified appointments, they can schedule. And you often what they do is I’ll say, tell me describe an ideal prospect. And they’ll say, oh, any company that has five to 50,000 employees. And I’ll say, well, we need to narrow that down a little bit. Because when you narrow it down, and you really micro target, first of all, it makes it easier to find them. Second of all, and really importantly, it helps you create, it’s so much easier to create the messaging, an introduction, is really going to resonate, so that they want to talk to you.

Josh  16:43

That’s changing gears a little bit, but I’m thinking of all the reasons people don’t do it or excuses to not do this. And one of them that comes up is compliance, where they’re afraid they’re gonna get in trouble calling, emailing, texting, and there might be some kind of lawsuit or GDPR. Are there any compliance things that people need to be aware of before they start embarking on this kind of technique?

Wendy  17:09

Well, I’ll begin by saying I’m not an attorney. So this is not legal advice. And I am only talking in the realm of B to B. Because B to C is different. The, the big thing that you have to if somebody says, take me off your list, take them off the list. Don’t keep calling them. And I think that’s really the biggest thing. If you think about this call, it’s a business call. It’s an introduction. That’s all it is. you’re introducing yourself to a likely prospect. And so in that context, there’s really no issue. But again, if somebody says, Take me, take me off your list, take them off the list.

Josh  17:58

Now, how do you find a person to do that? If I’m a business owner listening to this conversation, I’m saying, you know, that sounds great. But I really, really, really don’t want to do that myself and unlikely a business owner shouldn’t do it themselves. And they likely don’t have anybody in their team. Who has the, I guess the fortitude or the skill or the backbone to do it. So how do you find someone like this to do this kind of work?

Wendy  18:26

Are you asking me how to hire someone internally, there’s certainly lots of agencies one can outsource to do that

Josh  18:34

What do you recommend finding an agency to do for you? Or do you recommend finding someone who just is a hard worker and training them? Like what is the best way to kind of get someone in this seat?

Wendy  18:47

Well, the best way to do this is to take a step back and before you hire anyone, to have a system in place that is benchmarked, so that when you hire someone, whether it’s you, you hire someone internally or you go hire an agency, you know what to expect. And one of the big mistakes that I see so many business owners make is they say, oh, I’m gonna hire a salesperson. Or, I’m gonna hire an appointment setter. And I say, great. What do you have in place for them? And the answer, unfortunately, is often nothing. And so then you’re aside from the fact that it often does not work, you’re really saving your power to someone else to define your message. So how do you want to be represented in the marketplace by this call, or whoever whoever they might be, and that’s, that’s really the first step is putting that system in place. And one of the things We often do with business owners, we’ll work with them, we’ll help them set up that system, and then they’re in a place. Sometimes we’ll have them prove they prove the model themselves, but then they’re, they know what their numbers are, they can, they can go hire someone, or they at least have this system in place. And they can hire someone to prove the model, but what we know what the numbers should be. So if someone’s making the calls, we can then tweak what needs to be tweaked.

Josh  20:31

So then, what about the profile? Like, Is there like a Myers Briggs profile or disc assessment or some kind of assessment that would tell you, okay, this person would be good at this, because I feel like this is a position where, when you hire somebody that their success rate or their chances are low? So how do you boost the chances of having a successful appointment setter?

Wendy  20:56

you boost the chances by training them, okay, you can train someone to set an appointment in a matter of months. Okay, now what? What most businesses do is they hire someone, keep them around, especially if they hire a salesperson, not just an appointment setter, then it might take a number of years to find out if they’re actually going to sell anything. If you have a long sales cycle. And that as an appointment setter, you can train someone to set appointments on your behalf in a matter of months, three months, four months. And if you have hired someone that is not setting appointments, in that time, with some good training, they’re probably not going to be able to do it for whatever reason, there are some people that just won’t pick up the phone no matter what you do. But for everybody else, you can just, it’s a communication skill. You can learn it.

Josh  21:56

What are some good benchmark numbers? So if you can bring someone and say, Hey, here’s a list, go for it. Maybe give him some more structure? Are there certain numbers where you say, hey, you should be doing this many calls this many emails, this much conversion, this many appointments that are kind of standard in the industry? Or does it vary quite a bit based on the list quality?

Wendy  22:16

Well, list quality is really important. And we actually look at at three numbers, it’s, you know, one of the really stupid, dumb things that people say about cold calling, and there’s a lot of them. But people will say it’s a numbers game, and you just dial the phone 100 times. And if that doesn’t work, dial the phone 200 times, and that doesn’t work dial the phone 300 times. But we actually want to look at conversion. And that is the conversion of dials, you dial the phone dials into conversations with the right person with the decision maker,  not with the gatekeeper with a decision maker. And then the conversion of those conversations into appointments. So if you look at the conversion of dials into conversations, that number is a little trickier. Because it does depend on the list, the better the quality of your list, the higher the conversion is going to be there. But also, depending on the market, you could have, you know, if you’re calling CEOs, fairly large companies, it could be as low as 3%. It could be as high as 25%, depending again, depending on the market. But the other number that we look at that is vitally important is what is the conversion of the conversations with decision makers into qualified appointments? And we want to look at a minimum of the 20% conversion. So you get 10 people on the phone, two of them, at a minimum should say yes to an appointment. Now we have conversion numbers that are much higher than that. But that’s that’s minimum number. So that’s the real numbers game conversion.

Josh  24:15

So you get a list you call 100 people, and you get, let’s just say 20% on the phone after calling them a few times. And then at that point, another 20% of those, you should hope are actually qualified to actually have sales compensation.

Wendy  24:34

Is that right? Well, they should be qualified before you call them. Okay. So I, I mean, it depends on your definition of the word qualified if your definition of the word qualified is they’re ready to get me my, their credit card. Debt, it’s gonna be a much lower number. But if the definition is that they’re qualified, that they meet the criteria of what makes an ideal product spec, they’re in the right industry the right size, I’m talking to the decision maker, not to a manager who’s going to say I have to ask my boss, you know, if all of those that they are open to having that conversation, then that’s that’s that would be a different number.

Josh  25:22

Yeah, I feel like, Wendy, I could talk to you all day about this. A lot of questions. I know that time is kind of running out for this particular podcast, I’m about to have you on again, with either this group or another group. So I want to get to some of our standard signup questions. And one of them is to wonder was always about a system. And he already told us about a system. So I’m going to jump to the next question, which is, why don’t you tell us one thing that I forgot to ask you, but I should have asked you during this conversation?

Wendy  25:53

Okay, well, I’m going to combine your two questions, and it’ll be my system that I learned in ballet class, okay. Because everything I know, in life, or in business, I learned in ballet class, this is what I learned in ballet class. Warm up, rehearse, perform. That’s what we do. And we did when we’re the answers that the first thing you gotta do is you warm up, so you don’t get hurt. So when you’re cold calling, the first thing you have to do is warm up, which means getting that micro targeted list together, putting your scripts together. So you are saying something that resonates. If you’re a dancer, you don’t just run out on stage and start dancing. You’ve been rehearsing your practice for months. So this is why sales trainers, we love role playing, but you’ve got to practice. Because you just want that automatic muscle memory. So when you’re speaking with a prospect, you just say what you have to say, and the words come out of your mouth because you’ve practiced. And then when you’ve done those two things, that’s when you get on the phone, that’s when you do the performance. The problem most people have is they jump right to the performance. They don’t warm up. They don’t rehearse. And then the performance, not good.

Josh  27:16

Yep, no, I believe it. Owners of companies have a way of being impatient. Yeah, wanting to get that ROI in a couple of days instead of a couple bolts. So I understand that. So what is the way people find out more information about you, and how to get some help?

Wendy  27:35

Hey, well, a few different places. First of all, I invite you to download my gift to you. It is the business owners guide to getting more qualified sales appointments when the prospects are all completely freaking out. And the guide is it’s 1212 ways to find more sales opportunities now. And you’re going to post that link below. Okay, you can also visit us website is And one more thing, you can call me on phone at 866-220-4242. I bet you’ve never had a guest give out a phone number before, right?

Josh  28:22

It’s very rare, very rare.

Wendy  28:24

866-220-4242 That’s my phone number. You leave me a voicemail, leave me a message. I’ll call you back.

Josh  28:35

Awesome. I think that’s great. It gets right down to the point in the world of all these automated emails and all of these automated funnels, just getting on the phone gets right to the chase, and people don’t have time to mess around with that sometimes. And so that’s great. Well, good. Wendy, thanks again for being on the show. Thanks, everybody, for joining us live on this podcast. We stream these pretty much every Friday. So you can join us on the Work The System Facebook page for that. Or maybe you’re listening to this on iTunes or some other podcast player or YouTube or Instagram, we’re all over the place. So again, thank you for being here with us. And then if you want a copy of that book right there, work the system, the one behind me on the video. You can get that for free. At work the system comm is a download but if you want the physical copy mailed to you leave us review once a week and grab a name out of a hat and we mail that person. a free copy of the book I like to do is take a picture of that review and send it over to [email protected] and we’ll send it out your way. Again, Wendy thanks and we’ll get you ready soon.

To share the podcasts on social media, note the buttons below.

Subscribe to our newsletter

Sign up to receive updates, promotions, and sneak peaks of upcoming products. Plus 20% off your next order.

Promotion nulla vitae elit libero a pharetra augue