EPISODE 502: The Mindset That Will Raise Your Sales Success with The Chutzpah Guy Mason Harris

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[EDITOR’S NOTE: This is a replay of the Optimal Sales Mindset virtual learning session sponsored by the Institute for Excellence in Sales on February 24, 2022. It featured an interview with Mason “The Chutzpah Guy” Harris, the author of The Chutzpah Advantage

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MASON’S TIP: “Chutzpah is very complicated. It’s one of those things that you may have trouble defining it, but when you see it, you know it. Unfortunately, with what’s going on right now between Ukraine and Russia, an example of very constructive chutzpah from a leadership perspective. President Zelenskyy, who is offered the opportunity to leave the country, urged to leave the country, take his family, and set up a government elsewhere, responded with, “I need ammunition, not a ride.” That’s an example of chutzpah we can relate to. It’s a type of courage, standing up for one’s principles, stretching boundaries, and putting at times others in front of or certainly equal to our own needs.”


Fred Diamond: Mason Harris, you’re the author of The Chutzpah Advantage. Good for you. I talked to you about the book as you were processing it and it made so much sense from so many ways. Again, here we are in March of 2022 and we’re seeing chutzpah all over the world, some good, some not as good, but we’re going to be talking about how sales professionals can implement it today. It’s great to see you, congratulations on the book. It’s a fantastic read. It’s definitely a different book. It’s something that not everybody is familiar with, but you do a great job talking about some of the characteristics. For people who don’t know, let’s get right to it. What is chutzpah?

Mason Harris: First, thank you. It’s also a pleasure to be here because our audience is comprised of people who are card-carrying members of the Chutzpah Institute. They’re in sales, they train salespeople, they motivate, they persuade. They use the principles of chutzpah, whether or not they call it that. As far as the definition, chutzpah is, from my research, very complicated. It’s one of those things that you may have trouble defining it, but when you see it, you know it.

I’ll give us a good example from the news right now. Unfortunately, with what’s going on right now between Ukraine and Russia, an example of very constructive chutzpah from a leadership perspective. That is basically where you have the president of the Ukraine, President Zelenskyy, who is offered the opportunity to leave the country, urged to leave the country, take his family, and set up a government elsewhere, responding with, “I need ammunition, not a ride.” That’s an example of chutzpah we can relate to. It’s a type of courage, standing up for one’s principles, stretching boundaries, and putting at times others in front of or certainly equal to our own needs.

I’ve run across easily 60-some definitions or synonyms for chutzpah over the days. Many are positive, constructive. We think in terms of boldness, persistence, grit. Some are negative, rude, arrogance. Some are kind of in the middle, like audacious. Chutzpah is a skillset, and like any skillset, it can be used for constructive or destructive purposes.

Fred Diamond: Today on LinkedIn, I posted a poll asking people if they’re familiar with the term and we discussed what it means. Half the people were familiar and 20% had no idea of the term before. But what was interesting is we have people all over the world who are connected to on LinkedIn and someone said, “There’s a Finnish term for chutzpah.” Someone said, “There’s a Spanish term for chutzpah.” Before we get deep into it, talk about the etymology of the word. It’s a Hebrew word, or a Yiddish word, which is it?

Mason Harris: Well, I believe it’s a Yiddish word, but as you said, it’s kind of global in its understanding. I’ve spoken to people around the world, and although they might say, “Huh, it’s about grit.” The Finnish word I believe is sisu, I don’t remember exactly. Well, I don’t know how it’s pronounced, but I thought, “That’s interesting.” As soon as I saw it on your post, I looked it up, and sisu translates to guts, stoic determination, a tenacity of purpose, grit, bravery, resilience. That’s chutzpah.

There are terms in Japanese, in German that we understand, regardless of our background, because we see it in people and we understand that they’re doing something different. The challenge for me was to identify not just grit, determination, boundary-stretching, but rather look at what are the key behaviors, the key characteristics that contribute towards this chutzpah skillset, this chutzpah mindset. Because I know that it contributes to success, particularly in certain fields, but through life as well.

Fred Diamond: We’re going to talk about the eight behaviors and characteristics in a second, but we have a couple of other questions coming in. A lot of times, Mason, people will ask, “Are you born a great salesperson? Or is it something that you learn?” Let’s apply that to chutzpah. Is chutzpah something that you’re born with? Interestingly, on our LinkedIn post today that you contributed to, we had a number of people who said, “I’m from New York. I naturally have chutzpah.” Is it genetic or is it learned?

Mason Harris: The answer is yes. Probably not the answer we’re looking for, but there is a piece of it. We’re born with some personality characteristics. Think of the child that’s constantly asking questions, challenging, “Why are we doing it this way, mom and dad? Why is that person doing that?” Now, some parents encourage that. Others get tired, they’re exhausted, and they say, “We’ll talk about it later. Stop with the questions. Okay? Just eat your meal.” That personality characteristic may have been there at birth, but what happens afterwards is more critical. Do we encourage these behaviors, these characteristics that leads towards a chutzpah mindset or a chutzpah skillset, or do we squash them when they’re younger?

But my premise, and from what I have learned is we all have some level of chutzpah. We all stretch boundaries at some point or another in our lives. There’s more than just stretching boundaries. How comfortable are we with failure, for example? Which gets into one of the chutzpah characteristics. If you are a trailblazer, as an example, you get that you’re going to fail. You understand that not everything you try as a trailblazer is going to work out. But you learn to accept the failure, grow from it, and move on.

We’re all in sales, we’re all in the business of persuasion, of influencing people. Even if we don’t have a quota, we are in sales because we’re human beings. We relate to others. A lot of what we do is about listening, understanding, handling objections, learning, and then moving towards a goal that’s in alignment. For us, it’s hopefully creating enough value with the products and services that we’re offering, that people understand why they need to make that very difficult decision and change vendors.

Fred Diamond: Let’s get into the behavior. People are asking us, “What are the behaviors that Mason refers to?” Again, the whole purpose of this, and we talk about this every day on the Sales Game Changers Podcast, it’s how you, as a sales professional, can go bigger, go bolder, do better, and that’s some of the theme that you have in the book. You have a unique way of talking about the eight different characteristics and behaviors. Let’s get right to it.

Mason Harris: I’m also New York born and bred. I have a deep appreciation for the best of all food, which is what I consider to be pizza. Not that a lot of you are sitting in your home office watching this, but if you are, and you’re curious, you can think in terms of a pizza and eight slices, and eight letters of the word chutzpah going in each of the slices. Even if you’re not there, you can think in terms of a model now, because each of the letters of chutzpah will remind you of a different characteristic.

The first characteristic, which is the C, I want us to think of what the opposite of procrastination is. Because as salespeople, as sales managers, as company builders, we know that procrastination is the enemy of progress. What’s the opposite of that? Carpe diem. Seize the moment, seize the day. We know we have quotas. We know that making that quota, which is a very large number at the beginning of the year, and hopefully we see it dwindle as we work through the year and have our successes, but it’s a large number. It’s easy to think, “You know, I’m going to put off those prospecting calls till tomorrow. I’m going to finish up a little bit of research,” which becomes a lot of research as opposed to calling, to reaching out, to checking in with clients. The first C, the first principle, the first characteristic is carpe diem.

Fred Diamond: Seize the day. Okay.

Mason Harris: As we move clockwise, next to it, we know that there’s something like death and taxes, it’s going to happen to us every single day. We’re going to hear it from prospects, from customers, from colleagues, from our kids especially. These are objections, objections to what we’re trying to get across. Too often people object before they even understand where we’re going. They object just to have a response. They’re not listening to understand, they’re listening just so that they can sense there’s a break in your breath and then respond to you.

The H stands for handling objections. As salespeople, it is one of the most critical elements, but also one of the ones we can best prepare in advance of meetings with clients and with prospects. How do we handle objections? What are the objections that might come up? How do we even prevent them from coming up by providing a story about a client in a similar situation so that they don’t have to feel that the objection is valid for them, because they’ve seen how somebody else has done it? We know this because we’re exceptional listeners, and because we’re smart enough to realize that there are some benefits of our products and services that apply to a lot of people, whereas a lot of the benefits and features don’t apply at all. Just repeating what we’ve learned is a terrible mistake, actually, to be made in the field in front of a client, because we lose their interests when we keep spouting features and benefits that have no application to them. Handling the benefits is that second one.

Fred Diamond: To be a great sales professional, you need to do a lot of things. You need to be prepared, you need to have empathy. There’s so many things that we talk about every day and I’m beginning to see a trend here, Mason Harris, where you’ve applied this concept of chutzpah to not really the icing on the cake per se, but like a top layer to bring a lot of these things that you need to be good at to be a sales professional, to take those skills, you as a professional, to the next level.

Mason Harris: Yes. I appreciate your saying that, because we’re all trained in the technical side of sales. We’ve all read books, sat through training sessions. We all get what we need to do at certain times. Where we sometimes fail is our motivation begins to diminish, we’re not as inspired as we were, and chutzpah brings us back.

Fred Diamond: All right. Let’s go to U.

Mason Harris: U. Creating value to me is the most critical thing we need to do to actually close a sale. Without value, people don’t move ahead. How do we create value? I’m a big fan of the SPIN selling questioning model from years ago. To this day, I think it was the first and best in terms of showing that it’s not just asking questions, open ended versus close ended, it’s using the questioning strategy to move the sale forward. SPIN is a lot about uncovering need and pain. People don’t buy because they need something necessarily. They may not even take a better solution from you just because you have the better solution. But they will buy if they understand that that need has become a pain, that it’s not something they can put off, that staying with their current vendor is going to cause them potential problems down the road. Well, I’ve added to that.

The U stands for uncover need, pain, and opportunity. Because one thing to share or have shared with you somebody’s needs, a second to understand how that develops into pain and make them aware of it. But then the opportunity comes about from being able to close to show them that there is an opportunity to change their situation.

Fred Diamond: That makes a lot of sense. We talk about value every day, it’s so critical for sales professionals to be able to start off with showing value, and you need to uncover that before you even get to the customer. We think that you don’t have the luxury anymore of being in the room to discuss what some of their pains might be. You need to come to the table with some ideas on what they’re probably dealing with, and here’s the thing, it’s out there. You can go on LinkedIn posts, and blog articles, and even watch the business news, and you’ll see the pain that your customer’s dealing with. There’s nothing to stop you from communicating this. We’re up to T.

Mason Harris: For many of us, people we know, and sometimes ourselves, we follow the safe path in life. The safe path in prospecting, in closing deals. Partially, it’s because we want to minimize our failure, and partially it’s because that’s what we’ve been taught to do. People with chutzpah, one of their key characteristics, and I mentioned this earlier, is trailblazing. In trailblazing, you take more risks. You fail more frequently. What we learn when we have this skillset is that it’s okay to fail. It might be painful, but you get used to it, and you also grow from it.

It’s interesting. I had a friend who was talking about they went with their kid, it’s not a sales example, but their first grandchild was getting vaccinations. Boy, she said, “The fight between the child, and the parent, and the doctor about having a needle stuck in her arm in this case was terrible.” But then she talked about, “They get used to it. After a while, they don’t mind it. They know that it’s going to hurt, but it’s temporary, and they move on.”

Well, it’s the same for people with chutzpah as opposed to without. People who are scared of failure, who fail once, fail twice, get rejected constantly, give up more quickly. Trailblazers continue on exploring new paths, new opportunities for their products and services, things that other people haven’t thought of. If everybody tells you that, “Well, you’re an event planner, you should be focused on this group.” Then you’re thinking, “Well, I’m an event planner, but I see that there’s a niche developing over here because of the pandemic, and more people doing things internally, and they don’t have the skills necessary to set up a Zoom conference. I can do that for them.” Those are what trailblazers do.

Fred Diamond: We do a show on Friday called Creativity in Sales. We started calling it that when the pandemic kicked in, because you always had to be creative to be successful in sales, but now you really had to be creative. Now, Mason Harris, two years after the pandemic, you have to be even more creative because the value that you’re bringing, if it’s not there, the customers aren’t necessarily going to need you. One of the interesting developments over the last two years is everybody has been affected by the pandemic, which means everybody has had to figure out, “How do we, as a company, figure this out? Then how do we figure it out because our customer and our customer’s customer are also struggling with this?”

If you’re not going to be helping them achieve those things and being creative and coming up with new ideas, then as a sales professional, ladies and gentlemen listening to this podcast, there is no reason for you to be in the profession. The customer’s not going to need you if you’re not bringing that value. I loved that one. It makes a lot of sense when you think about chutzpah. It’s taking a stand. When you think about people, not just in sales, but in other professions, entertainment, politics, business, that have the chutzpah, they saw things and they train themselves to see things that other people didn’t see. All right. We got four more to get to. We got Z. This is going to be an interesting one. What’s Z?

Mason Harris: Z actually is interesting. In the book, I refer to the game that many of us know from our youth, the electronic game called Pac-Man, but Z stands for zigzag. We discussed handling objections, learning how to overcome objections, which is critical during a call. Sometimes the call is going nowhere. What we don’t know is that the prospect’s brother-in-law has the exact same service and they just allowed you to come in so they can learn your pricing and maybe learn something new about where technology is going, but they’re not changing to you.

Zigzagging is the concept that we run across roadblocks. Some roadblocks are truly impenetrable. What do we do? We go around them. We find other buyers, or we find another buyer in the same organization. It’s HR says they’re not interested in your office equipment. Well, what about marketing? Perhaps they’re looking at doing some new brochures and they could use those new color printers and their enhanced capabilities. Zigzag is saying, “Okay. Obstacle. I’m going to go over it, under it, to the right, or to the left.”

Salespeople encounter this frequently, but too often, having fortunately succeeded in sales but also trained salespeople, I know that people come back and say, “I just can’t get past this person. I’m going to move on to another prospect.” That might be the wisest way to go. But I will also say, “Have you explored other groups within that organization who also could use our services, our products?” That’s where zigzag takes you. It’s interesting. On the book publishing side, we’re probably all aware of the publisher whose work was turned down. By the way, if you’re an author and you want to go with a traditional publisher, you have to learn how to sell, because you’re meeting with people and you’re saying, “This book has the following appeal. This is the audience.”

Well, this particular author was rejected by 12 publishers. The 13th said, “I’m not really sure that this is going to work for me. It’s not my audience. But I’m going to give this to my kid, because it’s a kid’s book, and we’ll see what she says.” Well, two days later, the kid comes back and says, “This is the best thing I’ve ever read. Is there going to be another one? When can I read the rest of it?” The author, for those in our audience who are thinking, “I wonder who that is,” It’s J. K. Rowling. Zigzag meant that she wasn’t giving up in pursuit of her objective, of her dream. She was going to go around obstacles. She got a no here. She went to somebody else, and somebody else. The best example that I heard of from the publishing side is Jack Canfield’s book, Chicken Soup for the Soul, turned down by 142 publishers before somebody said yes. Today there are 200 subtitles or derivatives of that original book.

Fred Diamond: One of the examples that we think about here is they say sometimes that it takes 40 connections to a prospect to get them to be a customer, but some salespeople will stop after three calls. It’s like, “All right. You’re not going to get to that 40.” But it’s if you’re committed and passionate. On the Sales Game Changers Podcast, one of the themes that comes up a lot is you have to keep going. You talked about that with handling objections, the H, and then of course, with zigzag, that you need to be passionate about what you’re selling, you need to believe in it, and you need to keep going. All the people who we’ve had on the show who are successful, Mason Harris, they all have kept going during challenging times. All right. We got P, A, and H. Let’s get to P.

Mason Harris: P stands for a characteristic that we see out there, that we talk about. It’s critical for getting us through the toughest situations. What gets us to work in the morning? Okay. We have rent to pay. But what truly gets us moving when things are at their toughest? That’s our purpose. Our purpose gets back to inherent elements of who we are. Do we work as hard as we do because of our family, our kids?

I remember I did a presentation for a sales team in, I think it was in the Philly area. I know the company, but I worked for a number of their divisions. The sales rep of the quarter who they announced before I came on, the sales VP spoke glowingly about this person and what he had to overcome. Two small children, and his wife had just passed away a year ago, unexpectedly. Young couple, young children, and how hard it was to get his life back together. Yet we can understand, we feel, but we understand, “Well, two small children, you can’t give up. You have a purpose, and that’s giving them the lives they deserve.” Purpose is that piece that gets us through. It doesn’t have to be as dramatic, as drastic, but it’s the piece that gets us moving. By the way, there’s a lot of luck that interferes with our activities. I discuss this a lot in my book, the luck factor.

Fred Diamond: I’m excited to hear that. All right, we got two more. We got A.

Mason Harris: A. This gets into the piece as to how we allocate our time. Has to do with decision making. There are lots of prospects, lots of opportunities, lots of people who need our help, our mentoring, our training. What can we do to minimize that ambiguity? Decision making is about ambiguity minimization or elimination, make decisions more quickly. The really big, critical decisions, you take a little more time, the small ones you fly through in essence. You also recognize that most of your decisions are reversible. As Jeff Bezos said, one-way door decisions and two-way door decisions. You make a bad decision on a two-way door, you go through, you come right back. On a one-way door, you’re kind of stuck, because that door is sealed behind you. It’s a lot tougher to get through. That’s why we have to consider our decision making differently.

Fred Diamond: We’re at H. Again, carpe diem, handling objections, uncovering need, pain, and opportunity, trailblazing, making the zigzag, having purpose, and allocating your time most effectively. All right. People are wondering what H is. Let’s get to that.

Mason Harris: H is the one that surprises a lot of people. Because when they think of somebody with chutzpah, they don’t think of humility. Well, I believe we’re all in sales. This group, we get that. We know that life is about persuasion, moving things forward, obtaining agreements, being in alignment with others. But humility some people see as, “Well, they’re kind of soft spoken. They don’t have the urge or the desire to upset people and ask for what they want.”

Well, humility is not about being soft spoken. Rather, it’s about accepting responsibility for your failures and sharing the successes with the people that helped you get there. Every sales position I’ve been in, there was a team of people behind me who worked. They might have been in operations, in shipping, in delivery, in training, in support, but they were there, and I made the sale. But then they made sure that it was implemented correctly, which made my follow-on sale that much easier. I made it a point with all my sales to reach out to all these people in departments that were not mine, to thank them for their help and let them know how they contributed specifically. Humility is about sharing the successes, it’s about apologizing when you screw up, and it’s about owning failures.

Fred Diamond: All the eight that you just said here, like I mentioned before you described them all, a great sales professional has a lot of things going on. They care about the customer. They’re prepared. They’re passionate. They give thought. They work with the team. They bring in tech support, they bring in operations ahead of time. One of the great lessons that we learned, Mason Harris, during the pandemic was the great organizations were one step ahead. As customers were trying to figure things out, they already thought through, “Here’s what you need to be a customer of ours. Here’s what you need to be successful without having to wait for it to happen.” As I listened to the eight characteristics of someone with chutzpah, they are great salespeople and this puts a nice bow on it to show all the things that go into being a top sales professional.

Well, listen, again, the book is called The Chutzpah Advantage. Mason, I just want to acknowledge you. It’s an interesting idea that you came up with to write the book. I remember you spoke to me about it early on and helped me think about a bunch of different things. You’re right. In the very beginning, my thoughts were that chutzpah wasn’t a great characteristic. It’s rudeness, it’s some of the negative things that you referred to before. It’s not really caring, it’s only caring about yourself.

When I read the book, I realized I was so far off. Someone with chutzpah is passionate about the customer. They are passionate about their family. As I’m listening to you describe these eight words, the last one of course was humility, the other word that’s apparent there is love. Love of your company. Love of your customer. You’re doing this for your family. Love of your family. Love of your coworker. Chutzpah brings it all together. Kudos to you on your success.

I’m going to ask you a slightly different question. Usually at this point, I ask for one final action step. But I’m going to ask you if there’s any story that stands out from the book that may be able to tie this in a bow and give us the final lesson that our listeners should hear.

Mason Harris: Well, there are a lot of stories in the book, because that’s my style. I think we remember things best because of the stories. But here, again, let’s go back to New York. Two small businesses. One is a person who had very little formal education. He was basically a street kid doing odd jobs. Yet by the time he was 19, he was clearing over $2 million a year for himself and he had a number of people working for him. The bad side of that is he was a drug dealer. I’m not talking about pharmacies or your local drug store, I’m talking about illegal drugs. By the time he was 20, he was in jail and his life was in jeopardy.

Second story is about someone who had developed, again, also little formal education, but was in exceptional shape and had created his own training platform that he had shown to others and enabled them to lose weight and to get in the best shape of their lives. When he came to New York, he figured out that, “If I’m going to grow a business and compete with multi-billion dollar companies that are in this space, Equinox, LA Fitness, then I have to do something different.” He creates business cards and he gives them out to, as he says when he started, women in yoga pants. From that, he started with one-to-one training. Then because he didn’t have a facility, he was doing training in the parks. That led to a small facility where he grew and now he offers live training, recorded training. His single location is known.

Now, as I think about this, I’d probably be reluctant to have coffee with the first person. I saw Shawshank Redemption. I’m sorry, I’m a little fearful. Yet the second person, fellow entrepreneur, fellow salesperson, I wouldn’t mind having coffee with. The interesting thing, and it goes back to what you said about constructive and destructive chutzpah, how it’s good and how it’s bad, it’s the same person. After jail, he couldn’t get a job. But while in jail, he lost 70 pounds, and he helped other inmates lose weight. When he came back and nobody would hire him, he decided he was going to do what he had learned and what he knew. Why? He had a child.

When he went to jail, the child had just been born. Child was now six. He was not going to go back to jail. He created an honest living. As a nice side note to that, he only hires other ex-cons. The name of his company is called CONBODY. You can see the story on a TEDx or on the internet, but it’s an interesting story about a chutzpah skillset and how it serves people to do good things and bad things.

Fred Diamond: Once again, thank you so much to all of our listeners today. If you’re listening today as a Sales Game Changers Podcast listener, thank you so much. Mason Harris, again, thank you so much for exposing people to concepts that many people probably aren’t familiar with, at least to a word that a lot of people are not familiar with. I love the way you tied it all back into how they can take their sales career to the next level.

Transcribed by Mariana Badillo

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