How Anyone Can Become A Great Salesperson

Tom Kelly is a Master Certified Business and Executive Coach specializing in working with salespeople, entrepreneurs, small business owners, and corporate executives. He has over 18 years of coaching experience and has coached for some of the most well-known names in the coaching industry, including Ken Blanchard, Tony Robbins, Brian Tracy, and Jack Canfield. He’s personally coached thousands of business clients, helping them significantly grow their businesses and improve their leadership skills. 

Episode Summary 

  • Having a systematized approach to selling will make things simple 
  • A 4-step process to help anyone become a better salesperson 
  • Find someone who knows how to do the things that are holding you back 
  • Why taking a consultative approach to sales will lead to more success 
  • A salesperson is a great investment for a new company 
  • How to reframe your mind around cold calling 



“People don’t buy products and services; they buy solutions to their problems.” 

“If you boil it down to just basic human behaviour, we do things for one of two reasons to avoid pain or to gain pleasure.” 

“If you had cancer, right? You wouldn’t try to cure cancer yourself? No, you go to the doctor, right and you go find a specialist that’s an expert at this.” 


The Complete Idiot’s Guide to Cold Calling by Keith Rosen 

The Go-Giver by Bob Burg 

How to win Friends & Influence People by Dale Carnegie 

Guest Information 

Website: https://www.businesscoachchicago.com/ 

Facebook Page: https://www.facebook.com/businesscoachchicago2/ 

Twitter: https://twitter.com/chicagocoach 

LinkedIn: https://www.linkedin.com/in/businesscoachchicago/ 

Episode Transcript

Chris Ippolito 01:16 

Hey, Tom, welcome to the “Get Coached Podcast.” It’s great to have you here, thanks for joining. 


Tom Kelly 01:23 

Awesome, Chris. Thanks for having me, I’m appreciative of the opportunity. 


Chris Ippolito 01:26 

You’re welcome. I think I say this a few times, but this one I’m really excited for. One of the things you coach clients on is sales, and you even have a four-step process that you walk them through to teach them or empower them or whatever it is, I’m going to get you to explain that a little bit more. 


I’ll add just some brief context as far as why I’m so excited about it. I, in my working career, have basically been in a sales role of some sort for probably 20 years, close to 20 years. I’m hungry to learn what you have to share and see where that goes. If you don’t mind, I’ll just throw it over to you and maybe you walk us through that four-step process and why sales is so important for really every business owner. 


Tom Kelly 02:19 

Yeah. It’s interesting, as a business coach I work with salespeople, entrepreneurs, small business owners, even corporate executives, and one of the things that I find that people constantly struggle with is sales, right? I mean if you lined up 100 business owners right now outside of your office and said, “Hey, what’s the biggest business challenge you have right now?,” 99 hands would go up in the air and say, “How do I get more business?,” right? “How do I bring in more customers? 


And I think, too, it’s even exacerbated because of the bad salespeople that we have out in the world, right? We’ve all experienced the annoying sales guy, the used car salesperson, the guy that’s telemarketing right in the middle of dinner, that sort of thing, right? I think a lot of my clients, entrepreneurs, all the way even up to veteran salespeople like yourself that have been doing this for a long time, have a lot of mindset issues around, “Hey, I don’t want to be perceived as the annoying sales guy, I don’t want to be the aggressive sales guy. I really am concerned about how my customers and prospects view me, especially if I’m a business owner,” right? Because their relationship with their customer is really important to them. 


One of the things that I’ve done, and I’ve had sales experience myself as well for 28 years and also 18 years as a sales coach, I think it’s important to really boil down sales to a real simple process. And over the years I’ve not only coached veteran salespeople on this, but also people that are new to sales or have never sold before. And it really comes from the context of having a systematized approach to how you sell, and making it simple and easy for people. And really what I start with is, number one, the thought process that people don’t buy products and services, they buy solutions to their problems. 


Really step one in the four-step process is just having a conversation with someone and asking them some great questions about exacerbating and understanding what the challenges are that they’re trying to solve, right? The first question that I always ask, and I call it my signature question, because I’m a business coach, when I’m talking to someone about coaching I’ll say, “Well, what’s your biggest business challenge?” And really what that does is that opens up a dialog around the things that they’re challenged with, and then we start digging into that. 


For my clients I encourage them to think about what is their business and what are the types of customers that they’re dealing with, and what is their signature question, what is it that they can ask to start a conversation with a prospect, or even if they’re networking, around what that person’s challenges are. And what that does is it just starts a simple conversation to better understand what that person is thinking about, what maybe they’re consumed with, what’s causing them not to sleep at night. And it’s really a great way to understand, first of all, what the challenge is, but also, “Hey, can I help that person solve the problem with my business and my solution that I have?” That’s the first thing, right? 


And in my experience also, and you can probably relate to this as well as a salesperson, is people buy when there’s pain. The next step in that process, that’s the first step, and underneath that first step is really digging into that a little bit. If I were to ask you, for example, what your biggest business challenge is, what would you say to me? 


Chris Ippolito 05:33 

Currently it’s the technical work that is required that goes into building a site, producing podcasts, creating content to promote it, all that really technical type stuff. It’s not my favorite thing to do, it’s necessary and a requirement. What I enjoy is the strategic side, sitting down with a prospective client and actually doing exactly what we’re talking about. Though I don’t see it as selling, it’s solution-oriented, right? “Let’s solve the problem.” But in a sense it’s selling. That part, that’s what I enjoy. But for me my current biggest pain is all that technical work that goes into the business I’m launching. 


Tom Kelly 06:17 

Awesome. Now that we’ve identified what that is, right? The next part of that first step is what I call digging deeper. And what that’s really about is just asking more questions to really understand what kind of problems and issues that pain is causing that person. If you and I were having a conversation, I would dig into that. “Okay, great, the technical things are really causing you some problems, what kind of issues is that causing in your business?,” and digging deeper on that. 


Chris Ippolito 06:44 

What it is, I think it’s the fact that I feel like I’m stuck in the business as far as I’m working in the business versus working on the business. Though I’m so early on that I try and reframe it for myself, this is personal coaching for myself. I reframe it in the sense that this is required work. Though it may feel like I’m working in the business and stuck in the weeds of it a little bit, it’s required work. I always reframe it that I am working on the business, but I do aspire and look forward to the day where I can either delegate or outsource some of this type of work so that it can free up my time so that I can do the things that I know I can add the most value. 


Tom Kelly 07:28 

Oh, absolutely. And what else is it costing you to have to focus on this technical stuff that you really don’t find enjoyable? 


Chris Ippolito 07:34 

It’s so draining as far as my energy. When I’m doing the things that I truly enjoy, I get energized doing it and time flies by. Whereas when I have to do the few things where I go into it and I’m just like, “Ugh, I’m not looking forward to this.” 30 minutes later and I go, “What, it’s only been 30 minutes?,” it felt like hours that I was doing that work. It’s mentally exhausting, it’s a little bit stressful because some of the work is things that I’m not great at or I’m not proficient, I should say. It takes me a lot longer to do it compared to somebody who’s an expert in it or a professional in that space. 


Tom Kelly 08:24 

Right, exactly. Just to sum this up, the technical issues of your business are really causing you to work in the business versus on the business. It’s not something you’re passionate about, it’s draining a lot of your mental energy and also your physical energy, and it’s also adding to your stress a little, right? 


Chris Ippolito 08:39 



Tom Kelly 08:39 

And I’m sure that’s probably causing some other issues outside of your work, as well. 


Chris Ippolito 08:43 

Yeah, possibly. Like lack of sleep. Though having a newborn, I could easily attribute it to that. Just things like that. And I would assume that a lot of other entrepreneurs and business owners feel the same, like the end result, the pain is probably going to feel a little similar. It’s what is it that’s getting them to that pain that I think is the most valuable part as far as what you’re sharing. We can all assume that everybody has got similar pains, but it’s what’s causing that pain. 


Tom Kelly 09:21 

Absolutely. And we’re going to get to that in a little further on in the process here, step number three is going to help us really identify that. But now what we’ve done is we’ve identified what the pain is and we’ve exacerbated it a little bit, right? And what I would continue to do is continue exploring that with you to really amp up that pain factor so that I understand what it is, that you also understand what it is. Then we can move on to the next step, which is step number two. 


Chris Ippolito 09:50 

Can I ask a quick question on two then, when you mention exacerbating the pain? 


Tom Kelly 09:55 



Chris Ippolito 09:57 

A different way of saying it is really getting that person to almost bring that pain back into them, in a sense. 


Tom Kelly 10:05 

Exactly. Bring that to the surface, right? 


Chris Ippolito 10:07 

Right. You’re mentioning it like, “Tell me how does it feel when you have to,” like you asked me. And then I actually started feeling it, “Ugh,” the anxiety was almost building up a little bit in me. Yeah, okay. 


Tom Kelly 10:21 

Well, people, actually if you boil it down to just basic human behavior, we do things for one of two reasons, to avoid pain or to gain pleasure. And sales is no different, right? If you have pain and you want to get rid of that pain, you’re going to be looking for a solution for that. I don’t want to tell you what your pain is, I want you to tell me. By asking great questions, just having a conversation, like a consultant would do if they were troubleshooting a problem, I’m doing the same thing in this first step. It’s really just identifying what is that pain, and then let’s dig into that and bring it forward so that I can really understand what you’re going through, what your feelings are, what your emotions are, and what kind of other issues that’s causing for you. And as I fully explore that, what happens is that becomes more and more real for you and it goes up from 10, to 20, to 30, to 100, right? 


And when you’re up in that 100 level, that’s when you know it’s time to move to the next step in the process, which is simply asking you, “Well, what would you like it to be like?” Or what I like to often say is, “Hey, if I could wave a magic wand, Chris, and make that problem go away, what would that solution look like?” 


Chris Ippolito 11:26 

I’ve used that line, too. 


Tom Kelly 11:28 

Absolutely, right? It works pretty well, right? It’s like you’re a magician or something. But the point is what you want to do, and step number two is explore the fun part. What would the solution look like, right? Going on with our theme here of the technology in your business and that pain that you’re experiencing, what would you like it to be like? 


Chris Ippolito 11:46 

What I would love it to look like is having other people do it that are much more proficient at it so the quality and the speed at which they’re able to output is significantly better than what it is that I can do. And just being able to guide them and give them direction and let them run with it. My most positive experiences when it came to working for somebody else was that basic scenario of they taught and guided, but then eventually they said, “Okay, now run with it, go. I’m trusting you. And I know you’re going to make mistakes, but you’re going to learn from those mistakes and I’ll help you learn from those mistakes as far as what was the mistake, what could you have done differently, what did you learn from that.” Being able to build a team of, whether it’s, freelancers or employees or whatever it be, but having them take on that kind of work because they like it, they actually love that kind of work. Whereas my strength is somewhere else, and then just building this, I like the term, Avenger team of superheroes that are just awesome at all these very different skills sets. But when you get them together, they just kick butt, right? 


Tom Kelly 13:15 

Perfect. You want to have a great team that’s able to do that for you. 


Chris Ippolito 13:18 

Yeah. That would be the desired outcome I would like, yeah. 


Tom Kelly 13:22 

Awesome. And if you had that, if you had that in place today, what would that do for you personally? 


Chris Ippolito 13:27 

It would just really free up my time to focus on growing the business and working on the business. If they ran into a bunch of roadblocks and obstacles that were preventing them from taking their roles to the next level, I would come in and work with them like, “Let’s get that roadblock or obstacle out of the way,” including if it was even myself. Like, “How do we optimize and systematize your process so that you’re enjoying your job and it starts freeing up your time so that you can maybe start exploring other things?” 


For me a big thing, as I grow a business and start working and building a team, is I’ve always had this vision of bringing on people, but telling them from the get-go, “I actually don’t expect you to be with me for a very long time because I want you to go out there and do your own thing. But while we’re working together, let’s learn and teach each other, and then we’re going to create this thing together. And then eventually you’ll have the skill sets that you’ll be ready to go and do it on your own. And I’ll support you in that, as well, however we figure that out.” But that’s the kind of person I would want to add to the team. That’s what I’m aspiring for and looking for eventually. 


Tom Kelly 14:53 

Awesome. Really you’d be able to elevate yourself as more the entrepreneur, the person working on the business, you would be able to spend time working on things you’re passionate about and empower these other people to work on things they’re passionate about. And then almost be a coach for them, right? Helping them grow and reach their potential, and then eventually kicking them out of the nest so they could go do their own thing and moving forward from there, right? 


Chris Ippolito 15:15 

Yeah. Because I think the types of people that I like to surround myself with, coaches, entrepreneurs, they’re the types of people that are always working towards improving themselves. The term I use is leveling up, you’re always looking to level yourself up. And I’m going to bring that kind of person into my world and we’re going to work together, but I want to see them level up and get to a point where they’re at a level that they’re ready to go out and adventure on their own. But we’ll have that lasting partnership hopefully for life. 


Tom Kelly 15:51 

Wow, that sounds pretty powerful. 


Chris Ippolito 15:53 

Yeah. I don’t know, that’s maybe pie in the sky optimism, but that’s the vision I have as I grow this. 


Tom Kelly16:01 

Great. For you it’s more about not just solving the technical problems and the things you don’t like doing in your business, but it’s about empowering other people and working in your business and building that team of Avengers, as you said, to go out and conquer the world, so to speak. 


Chris Ippolito 16:17 

Pretty much, yeah. 


Tom Kelly 16:18 

That’s awesome. Okay, great. We just accomplished step number two, which is really understanding, “Hey, ideally what would you like the situation to be like?,” right? And we learned a couple things. Number one, we learned that you want to build a team of people to do the technical stuff. But at another level from that it’s really about helping those people and empowering those people to do what they do and helping them get better at what they do, and leveling yourself up while you’re leveling them up, as well. There’s lots of advantages and stuff there, which is great. 


Now that we’ve explored those two things, I know what your pain point is and what that’s costing you, I know what you want it to look like and the benefits of that. The third question here is really what’s preventing you from having that. And that’s, what I like to say, what the real issue is, right? The real issue is not that you’re having to focus on these technical things, the real issue is, the question now is, what’s preventing you from doing that. You just told me what your problem is, you told me what you want the solution to be like. 


And by the way, what’s interesting is that when you have this conversation with people, it’s very valuable because most of the time they’re not thinking about those things. Now you’ve helped them identify what the challenge is for them, and now they really understand what it’s costing them. You’ve helped them understand what they really want, which most people don’t know, by the way. As you walk them through that process, there’s value to that. And now we’re getting to brass tacks of, “Okay, what’s the real issue here, what’s prevent you from being able to do that?” I’d like to ask you that question, what’s preventing you from solving that problem? 


Chris Ippolito 17:49 

I made a commitment to myself. And this was actually one of the episodes I did with, his name is, Ari Meisel. He owns the Less Doing brand, a productivity coach. And in our conversation he had mentioned something because I’d asked him a question and he said basically until you reach a certain, well, I’ll just share it because it’s in the episode, but until you reach a point of $300,000 in revenue in your business, he’s like, “You should not hire a person.” He’s like, “Figure it out yourself, grind it out.” And he’s like, “You can do it, because there’s a lot of people that have done it. And until you get to that point, it doesn’t make sense to start hiring because,” and this was the reason he gave, “you haven’t quite figured out your system yet and your processes and all the key things that go into when you start hiring people. In a sense you’re duplicating yourself. But if you’re duplicating something that’s broken, well, that’s only going to exacerbate the problem eventually,” right? 


Tom Kelly 18:53 

Sure, absolutely. 


Chris Ippolito 18:54 

That was his recommendation and that’s something I’m going to stick to, and just grind it out. And I’ll learn a lot of lessons along the way, which those lessons will be incredibly valuable once I start building that team because I can then share the personal journey. It might take longer, but the value I feel that I’m going to get is worth it. 


Tom Kelly 19:20 

Great. I certainly find value in that, right? And that’s probably good advice for a lot of people, but I want to challenge you a little bit on that. Is that always true? 


Chris Ippolito 19:30 

I would agree that it’s probably not always true because there could be circumstances or situations where if it’s a big enough bottleneck that by simply just finding the right partner and bringing them in early on in the process, and then just working very closely with them on making sure that it’s done at the way that it needs to be done and there are no broken systems, broken processes, it could accelerate and just bring the business as a whole to just that next level much, much faster. 


Tom Kelly 20:05 

Absolutely, right? And the thing I’m thinking here is an analogy in my mind, right? That’s just popped in my head, right? If you had cancer, right? You wouldn’t try to cure the cancer yourself. You would go to the doctor, right? And you’d go find a specialist that’s an expert at this. And it’s the same thing about the technology in your business, right? Probably the fast track way to do it, you could certainly do it yourself and learn how to do that, and then bring someone into your business and teach them how to do that, or you could say, “Hey, you know what? I’m going to bring in an expert that I know is already an expert at this, that’s been there, done that,” and they could probably help you rapidly get to where you want to go, right? 


Chris Ippolito 20:40 



Tom Kelly 20:41 

That would be my challenge to you there, is to maybe rethink your belief system around that. Maybe that’s true for you, but maybe it’s not. And if it’s not true and there might be something else true, another avenue for you to go down, perhaps that’s worth exploring to speed up that process to $300,000 so you can get faster up to the next level and level up, as you said before, more quickly, right? 


Chris Ippolito 21:05 

Yeah, that’s true. 


Tom Kelly 21:06 

But really, based on where you’re at now, what’s preventing you is really getting to that $300,000 level, right? 


Chris Ippolito 21:12 



Tom Kelly 21:13 

If I could show you a way to quickly get to that $300,000 level by doing it yourself in your paradigm and your belief system here, would that be valuable to you? 


Chris Ippolito 21:25 

Yeah, of course. 


Tom Kelly 21:26 

Okay, great. Do you see what I did just there? 


Chris Ippolito 21:29 

Yeah. Solved, I’m solved. 


Tom Kelly 21:33 

Yeah, hey, the problem isn’t your technology, the problem is how you’re thinking about this. And we identified that the real issue in your business is, hey, you feel you need to get to $300,000 before you can get to the next level. Knowing that, and as a business coach, I could probably help you get there a lot faster, right? That third step is really identifying what’s preventing you. 


And then seguing to the fourth question, which is what I just said, “Hey, if I could show you a way to get to where you wanted to go to that $300,000 level faster than you’re doing right now, what value would that have to you?” Because here’s the truth, right? People are looking for a solution to their problem, but they have to see value in that. And as long as the value that they see in your solution is more than you’re going to charge them, you’re usually going to make that sale. If you said, “Well, Tom, that’s worth $100 to me,” and I charge $5,000, well, that’s not going to work, right? I have to go back and go back through those steps, exacerbate the problem, exacerbate the solution so you see the value in that so that you see more value in that. 


And that’s why, by the way, it’s so important in the first two steps to do your due diligence and spend enough time on those things so that when you get to the portion of talking about what the solution looks like and what’s preventing and working with you, that they see the value in that. Because if you skip over that too quickly, then when you get to ask them what the value is, they don’t see any value in that. 


Really the fourth step in the process is asking them that question, “What is that value?,” and then having them articulate that. I’ll ask you that question. If I was able to show you a way to solve that problem so you could fast-track to $300,000 and get to the next level, what value would that have to you? 


Chris Ippolito 23:23 

Oh, jeez. Well, there’s the number I’m willing to pay, and then there’s the number that I am able to pay, right? 


Tom Kelly 23:31 

Okay, sure, absolutely. 


Chris Ippolito 23:33 

For me, if I could, I would pay $10,000, $15,000. I would pay a pretty significant amount of money up front, knowing that with that support system, that product, that service, that whatever it is is going to get me to a result of something like $300,000 in annual revenue. Because obviously that’s a pretty solid return on investment, right? 


Tom Kelly 24:03 

Absolutely, right? You can do that equation. You say, “Hey, I invest $15,000 and I get to $300,000.” Let’s just assume you’re at $100,000 today, that’s $200,000 of value, over whatever period of time that is. That’s a great investment, right? You have 20 times that investment. That makes sense and you’ll do that most likely all day long. And that’s really what we’re looking for in that fourth step, is evaluating what the value is. 


And really if you come at this, you can come at this one of two ways. You can come at it from a sales perspective, like the aggressive sales guy, like, “Hey, I need to convince this guy there’s value.” Which I don’t recommend. But if you come at it from a consulting perspective, right? Of being detached from the results and just really coming from the heart and saying, “Hey, I’m looking for a great match here for my business, and I want to really understand what this person’s issue is and see if I can help them.” And really understand that you’re exploring it from that perspective, and you’re sincerely exploring that value proposition with that person. They’ll sell themselves. If you ask the right questions and explore that with them deeply, then you’re not going to have the issue about moving forward or using ugly closing techniques or any of that used car salesman person stuff, right? 


What’s interesting, too, Chris, about this process is that it will work with someone that’s brand new to sales, it will also work with somebody that’s been in sales for 20 or 30 years, like yourself. Because oftentimes as salespeople, and I’ve been there too, we forget how simple the process is. The other thing in sales, as you know, is there’s a syntax to things. And what I mean by “syntax” is there’s an order of steps. And if I put the steps in the wrong order or if I skip the steps, then the likelihood I’m going to make the sale is zero. Because if I skip the first step and just go to what do you want the solution to be, and then I can’t do the what’s preventing you from having that because we didn’t explore the pain point. And then also you’re not going to see value in that because you haven’t connected to the pain that it’s causing you in your business, right? 


You can’t skip the steps and you can’t do them in a different order. Because if you do, it’s not going to get you where you want to go. It’s like baking a cake, right? If you skip the steps or you mix them up, you’re probably not going to get the cake right. It’s the same thing in sales. Does that make sense? 


Chris Ippolito 26:26 

Yeah, that makes a lot of sense. Just a couple of thoughts that were popping into my head and it was like “oh, hold on to it and don’t forget.” I don’t know if you would call him a sales coach, he sells courses on what he calls becoming a high-ticket closer. And one of the big things that he’s really pushing as far as to promote his course is the fact that selling is such a, when you think about it, very low barrier of entry type career to get into and it can be incredibly lucrative because of exactly what you shared at the beginning. Which is there’s a lot of businesses, business owners, entrepreneurs, whatever it be, that either feel they’re not good at it, don’t want to do it for whatever reasons, they just don’t want to touch it. And that’s actually, I would say, probably the number one type of role that a company would be more than willing to either outsource or bring somebody in early on for the reason that most of the time sales type jobs are compensated through commissions. 


Tom Kelly 27:46 

Absolutely. It’s one of those things in the business, and it’s always one of the first places that I would have someone invest in their business when they’re trying to grow, right? Because it’s a low investment price, most of the time you can give someone a commission or a low base plus bonuses, and it’s a win-win situation. If they go out and kill it and bring in a bunch of sales, your business grows quickly. If they don’t sell anything, then you’re not paying them anything, it’s no loss to you. It’s a win-win, it’s an easy investment to make early on in your business because it’s not really too much of an expense. But also what you said, it’s easy to get into sales, sales can also be attractive for people because of the big-ticket dollars you can make. 


Oh, and the other thing that exacerbates this issue, as well, is there’s not a lot of training out there. You don’t go to college to become a salesperson, right? And even when I got into sales, I have an engineering degree and I got into sales by accident. I wanted to be a construction manager when I grew up and there was no jobs in that when I graduated because we were in a bad economy. And one of the jobs I was offered as I went through on-campus interviewing and stuff was a sales position. And I had zero interest in being a salesperson, but my dad was a salesperson, he said, “You should take that job.” And I said, “Well, why would I want to do that?” And he goes, “Because you’re going to be calling on construction companies, building relationships with those people. And then when they’re ready to hire a construction manager, guess who’s going to have an inside track to do that?” And I’m like, “Wow, that’s genius,” right? 


And just by accident I took the job thinking that I would be in the job for six months and leave, and I loved it. But one of the things that I learned growing up in sales, and you maybe have a similar experience, is that all the knowledge I have was self-taught. I started reading books, my boss would teach me how to sell, I learned from other sales guys in the office. 


What that leads to is a lot of people getting into this because they think they can make a lot of money that aren’t trained, and they sometimes learn sleazy sales techniques and things like that. And that’s why we have the annoying sales guy, right? Or the used car salesperson that people are like, “Oh, I don’t want to be that person,” right? And I think it’s an opportunity also because if you’re good at what you do in sales, you can rise to the cream of the crop pretty quickly. But a lot of those salespeople that don’t quite know exactly what they’re doing or are doing it in an unethical way give everyone a bad name. I think you have to overcome that stigma a little bit sometimes. 


Chris Ippolito 30:13 

Yeah. Very, very true. I mean there are so many industries out there that a few bad apples start creating a very negative perception of the entire industry. But I would say sales is probably one that has, for a very long time, a very negative perception. They’re like, “Oh, you’re a salesperson?” They instantly think that you’re going to try and sell them something on the spot, and you’re like, “No, I don’t know what you need so what can I sell you?,” right? 


Tom Kelly 30:45 



Chris Ippolito 30:46 

You mention books. I was wondering if we could dig into that a little bit because I’d love if we could, maybe together, recommend a couple of books that the audience could dig into if they’re looking to shore up those sales skills. That could be one of the action items maybe that we assign to them. 


Tom Kelly 31:06 

I’ll give you one actually right here, one of my favorite ones in my bookcase here, I’ve got this right next to me. 


Chris Ippolito 31:13 

I’ll grab mine, too. 


Tom Kelly 31:14 

Yeah. This one right here is one of the sales books I recommend to a lot of people, it’s called The Idiot’s Guide to Cold Calling. 


Chris Ippolito 31:20 

Oh, interesting. 


Tom Kelly 31:20 

And strangely enough it’s written by a coach that I worked with early on in my coaching career, Keith Rosen. When I first became a coach, I was looking for somebody that was already a coach that was where I wanted to go, and Keith was that guy. He had been a coach for probably 10, 15 years and was making really good money and was really good at what he did. And he’s a sales coach mainly, but he helped me get started in the coaching business and really ramp up my business from nothing to six figures in about a year. 


And one of the things I love about this book, and it’s an interesting story. When I was working with Keith, one of his goals was to write a book. And he got approached by the Idiot’s Guide people and they said, “Hey, we’re looking for somebody to write the Idiot’s Guide to Cold Calling.” But what’s interesting is that Keith was never a big cold calling guy. I’m like, “Well, what are you going to do?” And he goes, “Well, I can’t pass up the opportunity, right? I’ve got to take this.” He ended up writing the book from a standpoint of coming from the sales coaching perspective of someone that really didn’t like to do cold calling and really didn’t advocate for that. 


What ended up happening is this book is like a Bible on how to, number one, manage your mindset and get your mindset right as a salesperson, and then also a step-by-step process on how to prospect people when you’re calling them cold and how to do it in a professional way that really works. And it’s really a how-to guide on how to sell. 


I recommend it to a lot of people. There’s a whole chapter in here in Chapter 10, it’s called The Anatomy of a Prospecting Conversation. And he breaks down step by step how to prospect with somebody. And it’s a great resource that I highly recommend to people. That’s one that I recommend a lot, that would be one of mine. I’m curious as to what some of yours are. 


Chris Ippolito 33:07 

Let’s see. Oh, jeez. I have a few on my shelf, I’m trying to think. I want to pick one. While I’m thinking about that, I want to mention something real quick about cold calling. If people are reluctant about selling, which a lot of people are, they’re, I would say, 100 times more reluctant to do cold calling. 


Tom Kelly 33:34 

Yes, very true. 


Chris Ippolito 33:35 

And even myself, having been in a very long career of sales, even at the very end, well, I shouldn’t say “at the end” because I’m technically still doing selling, but there’s always that bit of reluctance. But the one thing you had mentioned that I think is the number one thing to help with cold calling, it’s really the number one thing to help with a lot of things, but cold calling in particular, is mindset. If you go into it like, “Ugh, I hate this,” you’re just never going to have success. 


Tom Kelly 34:07 

You’re done. Yeah, absolutely. 


Chris Ippolito 34:09 

The biggest change for me was reframing what that initial call was all about and what defines success. 


Tom Kelly 34:18 



Chris Ippolito 34:18 

And for me what it was was as long as I can get the name of the decision maker, of who am I trying to actually get a hold of. I was doing cold, cold calls. I did all the research online and couldn’t find who the actual decision maker was. I would call the front, the receptionist, whoever it was, and my sole purpose on that call was, “Who’s the person I would want to talk to about,” blank, whatever the services. 


Tom Kelly 34:50 

Exactly, right? Yeah. 


Chris Ippolito 34:51 

And if I could get that name, bang, that was, “Check,” that was a successful call. 


Tom Kelly 34:57 

Exactly, and that’s so true. Because there’s a company down in North Carolina called Yankelovich Consumer Research, I think the name of the company is. And they did a study back in 2012 on consumer behaviors. And what they found was that the average person gets bombarded with 3,500 to 5,000 marketing messages every day. 


Chris Ippolito 35:16 

Every day? 


Tom Kelly 35:17 

Every day. And it’s up anywhere from 7 to 10 times what it was in the ’70s and ’80s. If you think about it, I mean if you just think about it, we’ve got Internet, social media, radio, telephone, text message, everyone is trying to get at us, billboards, all the traditional stuff that we typically get ads and marketing from. But what they also found that’s interesting is that it takes 26 impressions to move someone from complete apathy about your product or service to ready to buy. And I always remind my clients that because that cold call or that first introduction or that first handshake in a networking meeting or whatever, that’s impression number one. 


If your expectation is that, “Hey, I’m going to get on the phone and make a cold call and make a sale,” you’re going to be horribly disappointed. Same thing if you go to a networking event. If your expectation is, “Hey, I’m going to walk in, I’m going to meet 10 people, we’re going to be doing business tomorrow,” probably not going to happen. But if you look at it and say, “Hey, this is the first step of 26 steps that I’m going to have to take to build a relationship with this person and get a sale,” then what you just said is really important. Because it’s like, “Hey, my goal here is to just get a name or have an introduction or have an initial conversation or leave a voice mail,” whatever that is, right? And I think if you think about it like that, you’re going to have a more effective career as a salesperson. And also, if you’re a business owner trying to sell, having that perspective, you’re going to be a lot more successful that way. 


Chris Ippolito 36:52 

Oh, 100%. I think I’ve picked the put that I would recommend. 


Tom Kelly 36:56 

Okay, great. 


Chris Ippolito 36:57 

It’s not actually a sales book, but it really helped me out in just changing my approach to building business in general. I don’t want to necessarily say selling, but just growing business, right? And the book is called The Go-Giver, and I think I may have mentioned this in another episode. 


Tom Kelly 37:17 

Oh yeah, Bob Burg, right? 


Chris Ippolito 37:18 

Bob Burg, yeah. Yeah, that’s right. Actually, Aaron Walker, I had him on the show and he’s actually good friends with Bob Burg. When I read that book, it just really changed my approach to selling in that it was all about, as you mention, still doing that, but like, “How can I give value up front without having to even ask for money in return?” And once I started doing that, and also just, I learned this quite young, but remembering that selling is really just about relationships and people, right? Like getting people to like you because they buy from you and not necessarily like the company or whatever it is. 


Tom Kelly 38:08 

So true. 


Chris Ippolito 38:08 

But yeah, I took the approach of The Go-Giver and just, “Okay, now I know their pains, I know what their desired outcome is, and maybe right now is not the best time to make that final purchasing decision. What can I do that’s going to add value to them now, but that’s not really costing me a whole lot?” And sometimes that was, “You know what? I know you’re struggling with this and maybe financially you can’t do the transaction right now, but let me send you a couple articles that you might find some value in,” or, “Let me recommend a book or send you a video,” or whatever it is. 


And it’s just these small little gestures of adding value that build a stronger relationship, and then ultimately when they are ready you’re already top of mind, right? Hence the reason why prospecting and going out there and talking to as many people and engaging as many people as possible is so important. I think I used this analogy before, it’s just planting a whole lot of seeds. And you’re nurturing it and nurturing it and nurturing it, and eventually a harvest comes. 


Tom Kelly 39:16 

It’s so true on multiple levels, right? And I have a saying in my coaching practice when I’m coaching business leaders and salespeople, I say, “Everything is done under a blanket of rapport.” And what I mean by that is that if you don’t have rapport with someone, if you and I don’t like each other, if we don’t connect on a certain level, then I can’t influence you. And sales is all about influencing, leadership is all about influencing. You always want to come from a perspective of the number one thing I need to do when I’m with someone is build rapport with them. And also, the number one reason people buy is because they like you. 


When you couple that with what we just talked about a moment ago around the 26 impressions, right? If you can add value for somebody every impression you have with them, then you’re going to stay top of mind, like you mention. But also, they’re going to remember that. And see, nowadays that’s critically important because we’ve all done this before, we’ve all gone to a seminar or something like that and we come home and we eagerly subscribe to somebody’s newsletter or something like that. And maybe the first couple months we get the newsletter and it’s lots of value to it, and then all of a sudden the articles in there don’t connect with us anymore. And pretty soon we’re hitting the “spam” button, and then we’ve forgotten about that person. 


What I always teach people is, hey, keep in mind that 26 impressions and keep in mind that you have to add value at every one of those steps, right? If you’re adding value and always coming at it from that Go-Giver perspective and you’re thinking that way, eventually not only is that person going to hire you, but they’re going to constantly remember that you’re an expert at what you do and you’re going to build all of that deposit into their bank account, so to speak, so that they want to work with you and they want to give back to you. And that’s so important nowadays because we are getting bombarded by all these different messages and things like that, it’s hard to stand out from other people. And the best way to do that is just add massive value for people. 


Chris Ippolito 41:08 

Yeah. Very, very true. Another thing that there’s that added benefit of, as you mention, people buy from people they like. If they like you, they’re more open to hearing from you 26 times. 


Tom Kelly 41:22 

Absolutely they are. 


Chris Ippolito 41:24 

I don’t want to hear from somebody I don’t like 26 times. By time number five I’m going to be like, “Buddy, drop it. You’re driving me crazy right now and your chance of getting that business has gone to negative,” right? I’m actually going to tell people, “Don’t work with this guy, he drove me bonkers.” 


Tom Kelly 41:46 

Exactly. Well, on the flip side it works with that, too. I mean, like you said, maybe you’re not ready to work with that person, right? Or you don’t have the funds to do it or whatever, you’d like to. But if they’re adding value for you and you like that person, you’re going to refer that person, as well. When you run across someone that has an issue, you’re going to say, “Hey, I know this guy, he could really help you with that,” and you’re going to get referral business from that, as well. It’s just about putting that good vibe out there to people. And if you do that and you have that reputation of adding value for people, you’re always going to win in that situation. 


Chris Ippolito 42:15 

Yeah. Man, that was a good conversation, I really like that. 


Tom Kelly 42:19 

Oh yeah, absolutely. 


Chris Ippolito 42:20 

I think sales is so, so important in all aspects of life, not even business. Because a lot of people forget that you are selling yourself constantly, even in a social setting. Right? You’re making impressions, you’re influencing, you’re getting people to buy why they should want to build a relationship with you, whether it’s an intimate relationship, a friendship, whatever it is. You’re constantly selling. And I think what we both shared as far as the approaches and how you go about it, that’s how you do it, right? You add value, you do things that people are going to want to like you, and then they’re going to want to spend more time with you. Which is the currency of a relationship, is time, right? 


Tom Kelly 43:10 

Absolutely. Yeah, it’s so true. 


Chris Ippolito 43:12 

No, that was really, really good. Let’s wrap it up, what’s the one thing though? Out of everything we talked about, what would you say is that one thing that the audience should really focus on to improve their sales skills, or their capacity to sell? 


Tom Kelly 43:30 

Right. Well, the one thing, out of all the stuff we talked about, I mean I think the four-step sales process is great, right? Because it simplifies things and it makes it easy for people to sell and learn how to sell. But the biggest thing I’ll leave you with is this, is that thought process of everything is done under a blanket of rapport. When two people have rapport, whoever has more certainty about the outcome will influence the other person. And if you want to be a great leader, if you want to be a great salesperson, if you want to be a great business owner, you have to be able to influence people. And you cannot do that unless you build rapport with people. 


That’s the one thing I would leave the audience with, is that if you can learn how to build rapport with people and people like you, that’s 80% of the battle right there. And that would be the one thing, if you’re going to take one nugget away, work on your rapport building skills, it’s so important. 


In fact, I’ll share a story with you. I was interviewing for a coaching position for a CEO of a large company. And it was a female, actually. And I was supposed to have a half-hour with her. And I called her for the interview and she got on the phone and she goes, “Look, Tom, I don’t have a lot of time, I’ve got 10 minutes. Convince me why I should hire you as my coach.” Which is totally against what we just talked about, right? Here I am, I go into panic mode and I’m trying to sell her on why she wants to work with me, and it was failing miserably. And I was sitting there and I was in my head and I’m like, “What am I going to do?” And I thought to myself, “Everything is done under a blanket of rapport.” 


I just stopped the conversation and I said, “Hey, you live in New York, right?” And she says, “Yeah.” And I said, “Well, what do you love about living in New York?” And she just paused for a second like, “Why the heck is this guy asking me this?” And she started talking, she said, “Well, I love the restaurants.” We have something in common, we both love food, right? We start talking about that, and we started talking about her daughter, and then we ended up in a 20-minute conversation. And she was having fun and I was having fun. And then she says, “Tom, I hate to do this, I’ve got to go, I’m late for this meeting. It was great talking to you,” hung up the phone, I thought I lost the opportunity. Next day got an e-mail from her, “Hey, Tom, just want to let you know, I interviewed a bunch of coaches, you’re the guy.” 


And when she hired me, I asked her, I said, “Why did you hire me?” And she goes, “I just liked you.” And I was like, “Okay, there you go, that’s the lesson right there,” right? Sales call gone totally awry, I’m doing everything I preach not to do, and then I turned it around just by building rapport. Again, people buy from you because they like you. If you’re a likable person, if you ask great questions, if you care about the other person and you’re really there to figure out, “Hey, what are their challenges and how can I help them with that?,” you’re going to be great at sales. That’s really the bottom line. 


Chris Ippolito 46:21 

Yeah. I agree. I’m going to add to that and say read How to Win Friends and Influence People. 


Tom Kelly 46:29 

Absolutely, great book. 


Chris Ippolito 46:30 

Start there, because that’s going to help you build the rapport. And the rest of it, like when you want to learn the four steps and the more technical stuff, that will enhance it. But if you can influence people and basically turn them into friends, you’re like 80% of the way there. 


Tom Kelly 46:51 

Yeah. I could teach you all the other stuff. But if you can’t build rapport, you’re dead in the water, you’re not going to be able to sell. 


Chris Ippolito 46:57 

Yeah, so true. So true. That was great, I think that was good advice. If the audience wants to learn more about you or connect with you, what’s the best place for them to find you? 


Tom Kelly 47:08 

Great. The easiest place to find me is on my website, businesscoachchicago.com. You can also find me online, I’ve got a Facebook page also, Business Coach Chicago. You can find me on Twitter, @chicagocoach. And on LinkedIn, as well. Any of those places, but the easiest place is businesscoachchicago.com. There you’ll find all sorts of resources, I have a blog with like 400 or 500 articles on sales and marketing and business and leadership. People can find lots of free resources, I’ve got some free downloads and stuff like that. And also, they can find a place there they can sign up for a complimentary coaching session if they want to experience coaching with me, as well. Reach out to me, my e-mail is up there, as well. If you have any questions or anything, as they listen to this or want to learn more, feel free to contact me. 


Chris Ippolito 47:53 

Awesome. Yeah, I’ll make sure to include all that in the show notes. 


Tom Kelly 47:56 



Chris Ippolito 47:57 

Yeah. Because I’m sure there are a lot of people out there that are like, “Man, I don’t like sales. But if I had a coach, maybe.” 


Tom Kelly 48:04 

Oh, sure, absolutely. And that’s one of the biggest things, too. When I first started getting in this business, one of the first things I did at the prompting of somebody else was to hire a coach. And it was the best thing I could do because that really fast-forwarded my process, it helped me build a six-figure business in about 12 months. Which was great because had I not done that, I probably would have really struggled and I might not be here talking to you about it, as well. I think it’s really critical and important, it’s worth the investment. 


Chris Ippolito 48:32 

Great. Well, that was a fantastic conversation, I really appreciate it, Tom. 


Tom Kelly 48:37 

Awesome. Yeah, this was fun. 


Chris Ippolito 48:39 

And looking forward to future conversations, because I have a feeling we may talk some more. 


Tom Kelly 48:43 

Absolutely, absolutely. Yeah, one of my goals eventually here is to do a podcast, as well. Maybe I can return the favor and interview you a little bit. 


Chris Ippolito 48:51 

That would be great. All right. 


Tom Kelly 48:52 

Yeah, do me a favor. Let me know when this goes up and stuff, I’d love to promote it and get it out there and get people, eyeballs on what you’re doing. 


Chris Ippolito 48:59 

Will do. Thanks, Tom. Take care. 


Tom Kelly 49:00 

Awesome. Yeah, you’re welcome. You too, bye.