EPISODE 487: Demystifying Sales Cold Calling with Nancy Calabrese

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[EDITOR’S NOTE: This is a replay of the Creativity in Sales virtual learning session sponsored by the Institute for Excellence in Sales on February 11, 2022. It featured an interview with Nancy Calabrese, the author of The Inside Sales Solution.

Find Nancy on LinkedIn.

NANCY’S TIP: “Pick up the phone, hold yourself accountable to making a certain amount of dials a week, get it going. I’m telling you, I’ll be the next person to get that piece of business if you don’t do it.”


Fred Diamond: Today, Nancy, we’re going to be talking about probably the hardest part of sales for most people, which of course, is prospecting. We have Nancy Calabrese, she’s with One of a Kind Sales and she is a guru, she loves cold calling. Let’s just get started. Why do people not love cold calling?

Nancy Calabrese: Oh, my God, they think they’re bothering people. The biggest thing is they don’t like rejection. But you know, it baffles me because sales is about rejection. All a cold call is, is a conversation. A conversation that should be non-salesy.

It’s like a discovery call. The purpose of making cold calls and outbound prospecting is obviously to hit your target audience and also, to get a decision maker on the phone. If you’re properly prepared, and you know what you’re going to say, and that’s really key in calling, you sound natural, you sound non-threatening, and you sound curious. Their fear is the rejection. And I will say this in the beginning and I’ll say this at the end, if you’re not cold calling, you’re leaving money on the table.

Fred Diamond: Absolutely. Let’s get a couple of definitions out of the way. Cold calling versus prospecting. Is it interchangeable, or is there a distinct difference? Give us a definition there.

Nancy Calabrese: Well, cold calling is part of prospecting. There are multiple marketing channels and I think everyone should apply all of them. We just did a survey and we asked people what their favorite prospecting method was, and I am happy to say picking up the phone came in second. I was really surprised. LinkedIn came in fourth, but emails came in as number one. Now, I don’t know about all you folks out there, but I get so many emails every day and frankly, I don’t look at them. I delete, delete, delete, but the ones that catch my attention are deliberately written differently.

Most of the emails that you’re getting in your inbox, it’s very features and benefits. “Oh, I want to set up a time to speak with you.”  And I’ll just, delete, delete, delete. But what would catch my attention and what we do in picking up the phone is to deliberately sound different. I’ll give you an example. How many times have you gotten a call and, “Hi, my name is Nancy Calabrese, and I own One of a Kind Sales, we do lead gen and prospecting. I want to get on your calendar tomorrow or Thursday”?

What happens is when you go in and you introduce yourself, and you provide your company name, can you guess what happens? You have any idea Fred? The sales wall goes up. They know immediately it’s a sales call. By not using your company name and sounding different, what you want to do is catch their curiosity and ask their permission for 30 seconds. And I will tell you, 99% of the time they allow you to speak.

Fred Diamond: One of the big things that you’re a proponent of is what you call conversational selling. Let’s get deep into this a little bit. What exactly is conversational selling? What is it that makes it different from some of the other types of sales techniques out there?

Nancy Calabrese: It’s all about discovery. In my business, every call is a discovery call. First, we have to determine, are they the decision maker? We do that through conversation. The next thing we determine do they have a need for what we sell at the time of the call?

You all know timing is everything in sales. They could be your target, they could be the right decision maker, but if they’re not experiencing an issue that you can solve, our position is no pain, no sale for most of our clients. Some of our clients want to do meet and greets, which is fine. However, they have to understand the likelihood that they’re going to close soon may not happen.

We identify they have an issue, and then the conversation pivots because we want to hear Fred talk about his issues. That’s where we become really actors and actresses, because we have to match their communication style, we want them to talk about their issues so they’re in pain and that allows us to pivot to the qualified appointment. It’s just conversation and frankly, we will say, “It just seems like we can’t help you at this time.” And you always end by asking for a referral.

Fred Diamond: Nancy, I want to talk about a couple of things. You mentioned a prepared call. There’s so many things that we talk about all the time on the Sales Game Changers podcast, and one of them is preparation. Give us your specific things that you and your team does to really prepare for a call.

I’m curious, how long do you spend? How much work do you do? We have a great friend named Steve Richard who’s been on our podcast a number of times. He would talk about how some people are librarians, they would spend three hours preparing, and then some that would get all they need in three minutes. Give us some of your insights into, what really does preparation mean?

Nancy Calabrese: I think that it starts with the script. It all starts with the script, and you become the actor in delivering that conversation, so you have to internalize it. That’s number one in preparation, number one in preparation is having a script that sounds different. When we make calls, I encourage my people to spend maybe one minute in between calls to do quick research.

That means go on the company website. You’ve got the name of the person. The reality is, most of the time we go into voicemail land. If you’re spending three hours preparing for a cold call, you’re wasting your time. Truly, in every call, believe it or not, you don’t have to be an expert in what they do. You don’t, because they are going to teach you what they do by explaining what their issues are. I always say, a cold call should last anywhere between four and nine minutes, max.

If you go beyond nine minutes, you’re probably going into sales mode because the goal in conversation is to set the qualified appointment and not be the expert. When they start asking questions, it’s a buying sign. So, you ask, “Well, why are you asking this?” And you get them to talk and then you go to the appointment because you want to put them in front of the expert. It’s human conversation. That’s all.

Fred Diamond: We have a couple of questions that are coming in here. Again, we’re talking to Nancy Calabrese with One of a Kind Sales, she loves cold calling. She has no fear. She has her people who do a great work getting through and like you just said, it’s designed to get to the next stage.

You’ve talked a couple of times about a qualified appointment, whatever it is, it’s next stage. We have a question here that comes in, “Can Nancy speak about the right time and the best time to do prospecting or cold calls?” That question comes in from Marty. Let’s talk a little bit about that. It’s interesting, a lot of people are home still, because of course, we’re doing today’s interview in the middle of February, in 2022. A lot of people are still not back to the offices, some are but not all of them are. Talk about those two things. When is the best time? Do you guys have some rules, and what about calling people at home?

Nancy Calabrese: Okay, great question, Marty, thanks for asking. If you go online, you’re going to read several different recommendations. It really depends on who you’re looking to reach. If you’re looking to play in the C-suite, earlier in the day is a good time, mid-day when gatekeepers are out to lunch is a good time, and also end of the day. The larger the corporation, the longer it’s going to take to get to a decision maker because you are going to have to go through gatekeepers. C-suite, those times. If you’re dealing with smaller business, say for instance, owner operators, then a lot of times again, good in the morning, good at the end of the day, but there’s really no time.

I’ll tell you the best days to call, Friday afternoons. Also, Monday’s work because many people don’t call on Mondays so they figure everybody’s going to be so busy. You always want to do something that other people aren’t doing. Businesses shut down, producers play golf on Friday afternoons. Well, guess what? Somebody is out there calling your prospects setting the appointment. Calling at home? It’s not likely you’re going to find a lead with a home number. You may find it with a mobile and you call that, but if you’re in the B2B space, I wouldn’t call at home. If it’s B2C, yeah, you can call them at home, you could text them, and I wouldn’t text C-suite people, people that you don’t know.

Fred Diamond: A lot of people are fearful that they’re intruding. We talked about that, you must come across it all the time, which is why companies hire One of a Kind Sales to do this hard work for them. Talk about not preparation from a research perspective, but do you recommend any things before you physically dial? Do you recommend that people meditate for 20 seconds or listen to pumped up music? I’m just curious.

Nancy Calabrese: First of all, we like to have a lot of fun here. I’m the big believer in putting stupid GIFs on the group feed and we celebrate an appointment. Everybody celebrates every day, I put something about sales in the group feed. However, and I’ve heard this before, it’s not an interruption if you do it the right way.

All you’re doing is asking permission to have a conversation. If you sound professional, and that’s key, you have to sound professional and you have to know what you’re going to say in advance. I go back to the script. For anyone that doesn’t believe in the script, I’m guessing you’re missing opportunities. That prepares you, that grounds you, because, think about this, our biggest challenge is handling objections. If you go in with the script that you have up here, you don’t know what they’re going to say afterwards. That’s where the real research and study goes.

Fred Diamond: We have a question here that comes in from Brian. Brian says,” I’ve heard that it’s good to call the C-suite before the day starts, like seven o’clock in the morning. What does Nancy recommend?” Here’s the thing. We’re trying to get to these people, because we want to have this conversation and sales is basically about getting to the next conversation in a lot of ways, right? Hopefully, you get to the point where you’re able to ask for the deal and the business, etc. Talk a little bit about that. We’ve heard this a lot of times, but if you want to really get to the C- suite, they’re going to be at their desks at seven o’clock. They’ve probably been working late and they’re not going to have their gatekeepers usually. We’ll talk about gatekeepers in a second, too. What do you recommend? Do you recommend people call C- suite cell phones at seven in the morning?

Nancy Calabrese: Well, if you have their cell phone, again, I have no problem with that. I feel like 7 to 7 pm, fair hours. I don’t require my team to call after that time, but we want to give them some flexibility. You have to use your judgment, too. Going back, if you get somebody on the phone at 7 am and you’re professionally prepared to have a non salesy conversation, they’re going to listen, that’s all you want. You want them to stay on the phone.

Here’s another thing about reaching the C-suite or any business owner, you have to have a repetitive process, and a lot of salespeople fail. They’ll try three times and nothing. You want to build into your system, if you would, a repeatable professional process so that if I can’t reach Fred Diamond in my first attempt – and our attempts last for four weeks – then I’m going to recycle him for three months. At some point, he’s going to become familiar with me. If it’s a no, well, he’s back on the phone with me because we were professional. I go back, it’s all about timing. You want to be top of mind and if you have that system in place, you will be top of mind at the right time.

Fred Diamond: We talked about gatekeepers a second ago, talk a little bit about gatekeepers, because to the C- suite, especially, the CEOs and CFOs, there is somebody who manages their schedule. Give some strategies on how to get them enlisted in what you’re doing.

Nancy Calabrese: We think of gatekeepers as the receptionist. Executive assistants are a different story. Now, our recommendation when you get a receptionist on the phone, and think about this, everyone. Who do they naturally put through in a call? Do you have any ideas, Fred?

Fred Diamond: Family members?

Nancy Calabrese: Yeah. How about clients?

Fred Diamond: Clients.

Nancy Calabrese: Right, friends, so it really is your tone. “Nancy Calabrese for Fred, is he around?” You sound like you belong, and they’ll push back, “Well, is he expecting your call?” “You know what? I have a meeting in five minutes, can you just patch me through?” “Where are you calling from?” I usually say Jacksonville, which is true. Here’s another thing. If you can’t get through that gatekeeper, go to the sales department, or go to another department to get patched through. That’s one.

With the executive assistants, you really want to ask for their help. They tend to be a good resource, they will direct you to the right person. If you can’t get through the CEO but you can get to the COO, you’re starting somewhere. That would be my recommendation.

Fred Diamond: One thing you talked about before, you said,” If you’re not getting anywhere, you at least want to get to a referral.” I want to talk about follow up, because one thing that we found time and time again is that you’d be amazed at how many people don’t follow up. Let’s talk specifically about some things to follow up. What could you be doing? Do you want to get somebody on schedule and the call? So tell us what optimal follow up looks like from your perspective.

Nancy Calabrese: Our process, as I mentioned, we start with a batch of leads month one, and we reach out for four weeks. That means voicemail, emails, and if it’s a B2C, texts. If we don’t speak with the decision maker, the respite cycled for three months. Then in the course of the month, we’re going to have conversations with decision makers that have known me, they get recycled for 90 days, and the goal is to engage the right person to schedule the appointment.

That’s month one. We always recommend to our clients in month two and three, touch them, either send them a blog, connect with them on LinkedIn, so there’s touches. We come back to month four, now we’re back in front of those prospects and you just repeat the process. If you think about a whole year, you’re going to be in front of your prospects four times a year, each time for four weeks, 16 weeks. In addition to that, there should be some other touches so that they’re at least familiar with who you are, and can follow you on LinkedIn.

Fred Diamond: Talk about LinkedIn for a little bit. Again, we have some good mutual friends who are great at LinkedIn, but give us some of your advice from a prospecting type perspective on what are some things that you have. How do you tie in to LinkedIn?

Nancy Calabrese: LinkedIn is great. As a matter of fact, we’re just going to start another search. So we use Sales Navigator, we have certain verticals that we go after, and then we have an email sequence . We go to connect and if they connect, we have, I want to say four or five emails. The first one, I have a video of me, and video marketing really gets the attention. I have gotten business from LinkedIn leads doing that. They’ll either say, “We’re not interested at the time,” that’s fine, but they’re following me. And then there are people that come through that are interested, we just signed an insurance agency up through LinkedIn. I really recommend doing that, in addition to the cold call outreach.

Fred Diamond: Once you get the person on the call, talk a little bit about how quickly you need to get to the business at hand. We’re all going still through the pandemic, we all have personal stories that have happened. Is it a successful call if you spend 15 minutes talking to a prospect about state of the world, or is that a bad use of time? Or is it like, make some small talk and get right to business? Tell us your perspective, what does an ideal call look like once you’re engaged?

Nancy Calabrese: My first-time calls are 30 minutes. Again, we start with the script. I have it in my head, but I thank them for making the time with me. I reconfirm that we booked it for 30 minutes, “Does that work for you?” And I go into business. “Naturally, I want to be able to answer any questions you may have about our company and our process. Right now, for me, I’m real curious, what motivated you to take this call. If it’s okay, I’m going to ask you some questions.” And then I end it with, “Fred, usually there are one of three outcomes and I just want to assure you that if at any point you feel that what we do isn’t going to be a fit, are you going to be okay letting me know that?” Everyone says, “Oh, yeah, I would do the same.” And who knows? We may both decide to take next steps.

It’s like a contract. And then we begin, I turn it over, “Well, why are you on this call?” And take notes. You’ll learn a lot when you allow them to speak. The 70/30 rule, you want to hear them talk and at the end, I’m always mindful of the 30 minutes. I ask permission if we need to stay on longer and we make a decision there. What would you like to have happen next? Or I would say, “Why don’t we get on each other’s calendar again? I’m going to send you some information, we’ll continue the conversation.”

Fred Diamond: We have a question here from Erica. Erica says, ” How many completed calls does Nancy accomplish a day?”  Nancy it’s great question. What’s the metric? Is it three calls, 10 calls, 50 calls? What’s reasonable? I know Erica, she actually comes from a relatively large software company, that is a billion-dollar company.  I’m not going to mention the company name, it’s a well-known company name. Her team is tasked with just literally trying to make calls and get through. So, what’s a reasonable amount. Is it one? Is it 10? Is it 50 per day? What are your thoughts?

Nancy Calabrese: Well, it really depends on the role of the person. If the person is just responsible for setting appointments, they should be making 160 to 200 dialers a day. For me, I run my business so I have other responsibilities, but for me, I set goals of outbound prospecting. But the calls I make are to people that I’ve spoken with in the past, they’re not cold, cold. It’s a little different. Some organizations have their callers also do account handling. You really have to look at what their role is. But I will say Erica, you want to hold everybody accountable to making those dials. That’s the trick. If it’s consistently done, then you’re going to get the results.

Fred Diamond: Absolutely, and Erica says thank you to Nancy. Nancy, before I ask you for your final action step, you’ve given us so many great ideas here. Is there anything we missed is there anything thing that you want to bring up before we get to the action step? We talked about a lot of things here today. Is there anything that you tell your team every day to make them more successful that we might not have discussed?

Nancy Calabrese: Well, first of all, I tell my team they’re great every day because they are. They deserve to hear that. But, I am a big believer in setting myself accountable to doing certain activities. Whatever those activities are for your team, make them accountable. I have like a cookbook. Every day I look at it, and you know what? When I see I’ve done things, I go, good, I’m headed in the right direction. Cookbook and have a script. Have a script that sounds different.

Fred Diamond: I want to follow up on that and Rima says, “That is a great point, thank you.” Louisa says, “Thank you so much, Nancy, for that point.” What would be your advice for someone who’s new as a sales manager, who now manages, let’s say, an SDR team, or a team that’s responsible for making the appointment? We see this a lot. The hardest job in sales, of course, is the first-time sales manager who was probably promoted because they were very strong, and the company sees something in them.

Especially over the last few years, Nancy, when people haven’t really been in an office together, when everything has been virtual, if you will. What would be your advice having done this so successfully for so many companies over the years? I like the idea of, be nice to your people, motivate them, tell them that they’re great, have the script, and the playbook and all those things. But what may be some of your advice to a new sales manager who might be struggling right now?

Nancy Calabrese: Great question. Being a manager is challenging, especially being a new sales manager, especially if they were promoted from the ranks. Let’s assume we have the right person on the seat, and one of the first things that I would do is obviously, you have to observe the performance of your team. You have to know what the metrics are, what kind of goals they were given in the past. Have they achieved those goals? Once you get a sense of that, next step for me would be to do one-on-ones with my team. Get to know them, let them get to know me as a leader. Then my next step would be to have them be accountable to me every week about their performance the week before, and you can identify certain metrics.

I don’t know what kind of CRM everybody uses, but CRMs will help provide the metrics. How many dials are they making an hour? How many first-time conversations are they having? What’s their conversion ratio? Your goal as a manager is to be a coach and a mentor, and to get them to the place you want them to be. I go back to look at the metrics that currently exist. Get to know your team, and let them get to know your style of management. It’s so important.

Look, people are hard to come by these days, so you have to be appreciative of their role and supportive. Frankly, if somebody is not cutting it, you have to be prepared to have a conversation and it can be non-confrontational, but just factual. That would be my recommendation. If anybody wants to talk one on one, you can always reach out.

Fred Diamond: We’ re getting a lot of nice comments here Nancy. Marty, who asked a question, says thank you. Rima says thank you again. Once again, I want to acknowledge you, Nancy, for the great insights today, the great thoughts. I’ve referred some of our customers to you and I know you’re going to do a great job for them. I want to applaud you for really taking probably one of the hardest topics in sales and making it embraceable, making it something that people can enjoy and do. I want to acknowledge you for that. As we like to end every Sales Game Changers episode, if you have a final action step – you’ve given us so many great ideas, but one thing specific people should do right now to take their sales career to the next level.

Nancy Calabrese: Pick up the phone, hold yourself accountable to making a certain amount of dials a week, get it going. I’m telling you, I’ll be the next person to get that piece of business if you don’t do it.

Fred Diamond: Absolutely. People ask me what have I learned running the Institute for Excellence in Sales. I always say, “The number one thing is the best sales tool is the phone.”  Once again, thanks everybody for listening and thanks to the great Nancy Calabrese.

Nancy Calabrese: Thank you.

Transcribed by Mariana Badillo

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