On this week’s episode of Conversational Selling, we speak with Shari Levitin of The Levitin Group. She helps teams bridge the gap between beating quota and selling with an authentic, heartfelt approach. Throughout her career, she’s helped create over a billion dollars in increased revenue for companies in over 40 countries. She’s also the best selling author of Heart and Sell: 10 Universal Truths Every Salesperson Needs to Know and is a contributor to Forbes magazine, CEO Magazine, and Huffington Post.

Shari says, “You have one or two choices in life: you can look for the rare talent in people, and in situations, you can look for the good, or you can look for what’s wrong. And the more you look for the good in people, in situations, the more successful you’re going to be.”

We chat about connecting emotionally with our customers, as well as:

  • The right questions to ask yourself to keep your edge in sales
  • The best skills to develop to improve your sales
  • The delicate balance between competency and empathy
  • The surprising good to be found during the pandemic
  • And more

Listen now…

Mentioned in this episode:



Nancy Calabrese: Hi, it’s Nancy Calabrese. And this is Conversational Selling. And as you know, it’s the podcast where sales leaders and business experts share what’s going on in sales and marketing today. And of course, it all starts with the human conversation. Today we speak with Sherry Levitin of the Levitin group. She is an energetic, wickedly funny sales guru, who helps teams bridge the gap between beating quota and selling with an authentic, heartfelt approach. She’s helped create over a billion dollars in increased revenue for companies in over 40 countries. She’s the best-selling author of Heart and Self, is a contributor to Forbes magazine, CEO magazine, Inc, magazine, and Huffington Post. And today, she graces us with her presence. You know, Sherry, I saw you speak outbound last year, the first time I heard you, you were fantastic, full of figures. So you did not disappoint. I’m so excited to welcome you to the show.

Shari Levitin: Thank you, Nancy. It’s my pleasure.

Nancy: You know, we spoke before the program, and I’ve, I’ve been following you, you have so much content out there. And most of it is humorous, you know, kind of in your face stuff, which is so refreshing. How did you get to be so funny?

Shari: Oh, god, I’m glad you think I’m funny. No one in my family thinks I’m funny. You know, I think I feel that there’s so much information out there coming from salespeople and sales leaders. And when we can be entertaining, I think it’s actually the way the brain works. When we get people to laugh, and we’re entertaining. And when we emotionally connect, they’re much more likely to learn it actually opens up the learning centers in the brain. And so I always try to think about where’s the analogy here? And actually, I’ll tell you a secret. I never used to do videos like that. I would do them kind of stuffy, and I get all made up and be in a suit, you know, in a studio. And it was about four years ago, when a millennial on my team, Daniel said to me, you know, you’re not connecting with people my age. I said, Excuse me, you said you’re just stuffy, you’re inauthentic. Like, if you really want to connect with a new generation. Just be yourself.

Now you have to know while I was talking to him, I was hiking up a mountain. Because I loved the outdoors. I live in Park City. And he says No, really, like you should just you know, be yourself and do it without makeup. And I said yeah, yeah, he’s like, like, just do one now do a Facebook Live. I said I meant doing one now I don’t have any makeup on. He goes exactly. I dare you. I Double Dare you. And I kind of got mad at him. So I said, Okay, fine, I’m going to do it. So I was literally on top of a mountain and I thought I’m going to draw a parallel between how sales people get on top and how they fall down. And I just didn’t have bad hair like fuzzy hair, no makeup, you know, I’m kind of a wreck right in my mind. And I put it on Facebook. I was like, Oh my god, like 12,000 views. When I have a blog, I’m lucky if I get a, you know, very low single digit percent open rate, you know, of people that actually read it. And I thought this is a much better way to communicate. And from then on, I just started, you know, wherever I was, whatever I was doing, if I’m cleaning out my storage locker, I would think, Well, what does that have to do with sales? Oh, our sales presentations become junk drawers.

Let’s pick up our camera. I live with my husband and my son, and they love shooting guns. I’m like, Okay, fine. I’ll learn to shoot a shotgun. I thought, ooh, there’s a lot of shotgun sellers. So I just started having fun with it. And I thought, wow, people really liked the craziness. And I can think of humor and the analogies. Because really, you know, you can find analogies and parallels in anything. And I think the best stories and the best sales stories come from everyday life. So it seems to resonate with people. So Ah, yes.

Nancy: Well, you’re genuine. People like people that are extremely genuine and you did something to stand out in the crowd, right?

Shari: Yeah, it wasn’t intentional, but I’m glad that it worked out that way. Because I also feel that you know, when you give away content and you give away yourself whether it’s online on LinkedIn or through your newsletters, you know, people come to you. And I really hate it when you know people try to connect with you. And the first thing they do is they lead with their product instead of leading with either giving you something, giving you information or helping you and there’s just too much content out there today, and people will delete you and forget about you. So I try to think and I tell sellers, you know, if you want to connect with your target market on LinkedIn, don’t just like, you know, throw up on them. Like, hello, it’s not all about the product, do your research, take 5-10 minutes, learn a bit, a little bit about them. I call it show me you know me. Find out what’s important to them, give them value, give them something, and you’ve earned the right to get people’s time today. You’ve earned it.

Nancy: I agree. I agree and show me you know, me, that’s probably something I’m going to steal from you. So I’m just giving you a heads up. Okay.

Shari: I think I saw it from Jill Rally. So let’s give her credit. Okay, thank you. Yeah, you do?

Nancy: Well, speaking of feel, I did some more homework. And, you know, as I said earlier, we share your content, especially when we’re allowed to steal and borrow and one in particular jumps out. You talk about the biggest deal you ever landed and I’d love you to share it with the audience. What did you do? That was so amazing.

Shari: Oh, was that when I couldn’t get Simon’s attention? Yeah. Oh, okay. Yeah, this was years ago. This was actually back in the days of fax machines. And now that I’ve brought up this strategy, I have had people use it and land similar deals. I’ve gotten four different emails on exactly that. So wow, you know, it’s hard to get a hold of decision makers today. Right? Even if you have a relationship, even if you know them, you know, people are so overloaded, so busy. I think in some ways, now that we’re locked up in the pandemic, more of them are home, but there, it’s so hard to get to the right people, right. So I have defined a gentleman named Simon, the head of sales and marketing, or I don’t remember if he was out or the CEO at the time, but I knew he was the perfect client for me. You know, we had met a couple of times at a conference, I just, I could not get the guy on the phone. I couldn’t get in front of them. I did all you know, the gatekeeper, called the Secretary and made friends with her, you know, and every time I call her she’d say, Oh, I’m sorry. Simon’s in the meeting. Oh, I’m sorry. Simon’s in the meeting. Now, like months later, I’m thinking, like, God, like doesn’t ever like get out to like, go to lunch or, you know, see the ducks in the park. Like course Simon is always in a meeting.

So one day I called her. I called every couple of weeks ago, I said, Hi, is Simon in? No, he’s in a meeting. It was about 11 o’clock there. And I said, I have an idea. She said, Yeah, I said he had lunch yet. She said, No. I said, what’s the best pizza place around? She says, Paulie’s, why? I said, Okay, tell you what I’m going to do. I’m going to buy two large pepperoni pizzas. I’m going to send them there. And then I’m going to fax you this was a while back at the poem. And if you don’t mind, that’s the poem on top of the pizza box. And I’m gonna buy you a pizza as well. She starts laughing, she says, fine. So I wrote this funny little poem that said, um, is it sunny? Or is it raining? It’s always a good time for online training. I know you’re busy playing businessmen and banker. But isn’t it time we sat down our anchor? So when you’re done with that last pepperoni, pick up the phone, and let’s make some money? Oh, so about 90 minutes later.

Nancy: Wait a minute, you should patent that?

Shari: Well, I helped a friend of mine who works for a big software company. A month ago, she got a $750,000 deal. Because I wrote her a poem. I know, I should go into the poem writing business, right? Like it was so so I get this call from time and he is laughing so hard. It turns into a million dollar deal. Now as a new training company, it was a big deal. It’s still a big deal. Right? So, you know, it ended up being you know, they got our online learning, we created custom content for them. And it ended up being a multi year relationship that really kicked off my career back then. But I wonder if all of this is, you hear so many SDR sales people, consultants, whatever they are, I left a message I called they didn’t call back Really? Like, are you surprised? You know, it’s it. You don’t have to be better but you do have to be different in what’s going to get them. I have a girlfriend Karen Keating that I told you about a top, top seller. She is so creative. If she can’t get like let’s say she’s trying to get two stakeholders together.

And this was pre COVID. Right? But within a company, she’d send a bottle of champagne. to one and two champagne glasses to the other, you know, and I’m, whatever it takes. And I love doing this exercise in seminars and saying, How can we be creative? What can we do today? There’s so many things that you can do. But the bottom line to all of this is it takes effort. It takes up creativity, and it takes courage. And these are the skills that every seller needs to develop. And I say courage because we think, oh, what’s everybody else doing? Well, if you do what everybody else is doing, you’re going to get the results everybody else is getting. And right. Those are good. Let’s sales reps aren’t hit quota. So you better think what can I do? And yes, do you risk looking like a dumb Gumball yet? I don’t even know if dumbbells at work. But do you? Looking silly? Yes, you do. Do you risk looking silly being on a mountain? Yes. Do some of my messages backfire? Yes. Yeah. And I’m not telling you to imitate near imitating video.

But think like, what can you do? What is unique to you to get in front of your decision makers? How can you make the process fun, because it’s not always so much what you say, it’s how you make other people feel didn’t Maya Angelou famously says, people will never remember what they say, they remember how you make them feel. So I like to have. I like to have fun. So I want my customers to feel the fun and the levity.

Nancy: Well, I am doing the fun right now. If everybody were in front of you, they would be applauding right now. So what is your unique idea you bring to the table that really sets you apart besides fun?

Shari: I think the one that resonates with people the most is I like to talk about, you know, what’s more important in selling competency, knowing your product or empathy, knowing your customer and I always do this live. And if we were on a chat right now, I’d have the audience chat. And what’s more important, it usually comes right about down the middle. And people say, Well, you know, you know, some people say competency, some people say empathy. And then we cite a Harvard Business Review article that says, it’s actually a trick question. Because you need both. In fact, competency and empathy are 90% of influence, and of course, influence in sales. By the order matters. Empathy gets you in the door. It’s competency, reliability, and integrity that keep you there. And I guess what’s unique about it is we all know, at some level, we need to lead with empathy. But I haven’t heard a lot of people juxtapose it with competency, and then realize that, yeah, you may know it in your head. But you’re not doing that. That’s why we’re generally selling virtually right now, when we get in a time crunch. Because time is different, virtually, right?

We don’t have the benefit of serendipity where, you know, a 10 minute meeting turns into an hour and two hours in the signing of a contract, you’re usually in a 30 or 60 minute segment. And then that’s it. So what happens is, when our time shrinks, particularly in a virtual call, what do sales reps do? Well, well, throughout that empathy piece, we won’t get to know them, you know, and when in fact, you’re better off doing the opposite. Get them to trust you, show them, you know, then build a relationship, and then at the end of your time block, then you can book another poll. That’s way more effective than jumping into the demo, which I’m telling you 90% of sellers.

Nancy: I hear you. I don’t understand. I don’t understand it makes no sense to me. We call that features and benefits. Wow. Yes, feature Duncan thing. Yeah. Oh, yeah. So you know, I asked you also earlier, I love storytelling. What story would the audience find interesting. I mean, we’ve heard a few are already. I don’t know if you can top that.

Shari: Well, I, I think there was a moment that really changed my life. And I was a mediocre salesperson. When I started in sales. I wasn’t the top and I wasn’t the bottom. I remember one day I just wrote a contract. And my mentor called me into his office and he shut the door. He looked me in the eye and he said, You know, I’ve been watching you for years. And you have a rare talent. Like, yeah, if you keep it up and work harder and study more, I think you have the ability to be number one in this industry. Well, you have to understand I’d never been the top so I’m thinking wow, I’m really something. So you know, the next morning I got up early, and I started listening to tapes and watching videos. Okay, I got all this talent. And at the end of the year, sure enough, I became a top seller and I remember I got this huge bouquet of flowers.

That said, congratulations, you have a rare talent. In fact, I did so well that I ended up getting a promotion to work longer hours and make less money. They made me a manager. And I was a horrible manager, like I just sucked. And a lot of sales people don’t make good managers. And I remember going into his office to quit and to say, you know, I need to go back to sales. And he says, How come when you were in sales, you asked me for help every day now that you’re a manager, you think you’re supposed to know it all? And I’m crying? And he says, aren’t you want me to teach you the trick to being the world’s greatest manager? Like, yes, yes. He says, When you find a sales person, even if they’re not that good, but they’re hungry, and they want to learn, what you should do is bring them into your office, look them in the eye, and tell them they have a rare talent. Because, to this day, I never knew if I had any talent, or any more than anybody else, and I still don’t, but what I do know is that he taught me perhaps the most important lesson that I’ve taken with me my whole life, and that is this. You have one or two choices in life, you can look for the rare talent in people.

And in situations, you can look for the good, or you can look for what’s wrong. And the more you can look for the good in people in situations, the more successful you’re going to be. And I take that with me every day. Yeah. And I think what’s good about this pandemic, God, there’s so much book I have connected with so many people I wouldn’t have had time to connect with. I just connected with you. I’ve Yeah, you know, time more time to be with my family. There’s been these serendipitous moments, there’s been more time for reflection and introspection, and I just feel like a choice. Look for what’s right.

Nancy: Yep. So what would you like us to, for me to spotlight on your behalf? What’s important to you right now?

Shari: I would say, be careful when you set goals. And this is probably counterintuitive. Pardon me, I got Siri yelling at me. Oh, be careful. When you set goals. I think a lot of times, we set goals. And we lose sight of who we are. And what’s important, I noticed is very counterintuitive. I’ve gotten to a point in my life where I set goals. But I have to look at there have been many times in life where I have set goals. And I’ve run ragged, I remember 10 years ago, I had these, I had a 40 person company, I had migraines every day. And I hit my goals. But I lost a lot. And I just think it’s important for people to know what’s important and why and to create what I call the triangle of happiness. And I learned this from a dear mentor. Because so often we think if we hit this goal, then we’ll be happy. And then we’ll run fulfilled.

But we lose something along the way. And I think that it’s important to look at not just what your financial or your work goals are, but what your life goals are. And I will leave you with this. The triangle of happiness is that we need to have strong loving relationships. You need to have great health and wellness, spirituality. And we need to have a sense of purpose. This is the trick in life, right? How do you balance the three and if we’re chasing some, you know, material goal, we lose our health, or we sacrifice our relationships will never be fulfilled. So instead of just thinking about what you want to achieve, ask yourself a more important question. And that is Who do I want to be?

Nancy: Wow. You know, we could go on and on but we’re running out of time and I know that you have a time crunch. How can we find you?

Shari: You can follow me on LinkedIn and see some of my silly videos. Or you can email me at Shari@sharilevitin.com and or you can buy my book on Amazon, Heart and Sell. I’d love that.

Nancy: All right, well, everyone out there. You just got a dose of what Sherry is all about. I highly encourage that you follow her on YouTube. I want you back to talk more about Heart and Sell and continue with some of the funny observations you’ve made in sales. I have so enjoyed speaking with you and I hope this is the first of several to come. Thanks so much.

Shari: Thank you Nancy.