#storytellerjewels this episode, I interviewed Bill Caskey listen in as he shares some insights. 

Bill Caskey “If you do content every week, do something every week, you will become a better communicator whether anybody read your content or not. So just by the very nature of writing, producing videos, recording audios, I believe that I have thrown in my ability to formulate sentences and talk about concepts that might be difficult because I’ve had so many reps, you know, contents, just a rep game, it’s just a rep game, just constantly putting out content and every time you do it you get a little better.”

#storytellerjewels Welcome to the telling of story podcast. I’m your host, Storyteller Jewels. And along with my guests, it’s my endeavor to explore the art and science of storytelling, to attract, engage and retain a business audience and to unpack why it works for some and not for the many that try today. It’s my honor to interview. Bill Caskey. Bill is a sales development Leader, an experimenter who has been improving B2b Sales teams and executives since 1990. His philosophies and strategies have fueled explosive growth in sales and profits for his clients and is passionate about sharing his ideas about selling business life money and meaning, but his work expands beyond b2b and individual training and coaching. He is the author of same game new rules, rewire the sales mind and the sales playbook, to name a few. He also co-hosts two podcasts, the advanced selling podcast, a weekly podcast counseling salesforce’s and leaders who seek to improve their business and the Bill Caskey podcast, a deeper dive into achievement. He believes the most important approach to any endeavor is improving one’s mindset. So naturally he enjoys business books, human development, psychology, topics as well as health and fitness books. Bill goes on to say that we owe it to ourselves to make it a lifelong habit of learning how to master our lives. Whether we’re leaders of teams or members of those sales teams our audience relies upon us to bring our a-game to the field every day. It’s incumbent upon us to spend a few hours a week in personal growth so we can be at our best when the time demands. Bill’s success and passions are routed by his family and community service. He spends time with his wife, Jane and their two daughters, Kelly and Kara who work in Indianapolis and Denver. You can find Bill at https://billcaskey.com that’s C A S K E Y or on LinkedIn. And there’s more information in the show notes at https://thetellingofstory.com Bill welcome to the show. 

Bill Caskey That was a long bio that was need to shorten that up a little bit. Thank you, Jewels. It’s really, I’m looking forward to this and have for the last week since we scheduled it. And so I think we’ll get into some cool stuff today. 

#storytellerjewels I’ve been following your podcast for at least a decade now, so it’s actually quite exciting for me to actually be speaking to you rather than just listening to your voice. So welcome and thank you. Tell us, Bill, what is your backstory? And how did you get into training and coaching in the first place? 

Bill Caskey Yeah, well, I’ve been in the training and coaching business now for the better part of 30 years and uh, man, it seems like a long time, but it’s not, still a young man. And I got into it, uh, the Bass Ackwards Way, which was, I didn’t think I was very good at sales actually, more than I didn’t think I was, wasn’t very good. I wasn’t, I just wasn’t very good at sales and, and it was one of those, uh, come to Jesus meetings you have on the side of your bed at night when things aren’t going well and you have that deep conversation with yourself that basically is you got to get your act together here, my friend because uh, there’s, there’s no future outside of a certain narrow, uh, just, you know, a focus in business, You’re not going to be a lawyer, you’re not going to go back to accountant accountancy school, you’re not going to get an MBA, so sales is it? And you better figure it out. And so once we had that we, me and I had that conversation, um, I started to get serious about learning what the truth was about sales because I struggled with it. I was always in the bottom third of the stack rank and I knew I wasn’t good. I wasn’t pretending like I was good. I just was bad at it and yet I enjoyed parts of it. I enjoy the give and take between customers. I enjoyed the freedom, enjoyed the money. I actually did sell some things so it wasn’t a total loser. Uh, but I, I enjoyed parts of it, but parts of it were really painful for me. And so I sat on a quest to go out and, and by at that time you’re too young, cassette tapes and cds and you got some coaching and just, I really was a sponge for everything sales. And what I realized was that a lot of people were teaching it the wrong way and they were kind of teaching sales people how to be clowns, how to be, how to be manipulative and how to, uh, you know, do whatever it takes to get the deal or to get the customer to say yes. I always felt like that just didn’t fit me. It just wasn’t my personality. It felt out of integrity me. So Over the last 25, 30 years I’ve put it to myself to figure out a better way to do it and teach people as I learn it. And so that’s what I’ve been up to the last 25 years. 

#storytellerjewels And at what point did you decide or make the decision to take that to an online environment to a digital environment? Because I’ve been following you for at least a decade now. So you must have been an early proponent of the digital space. When did you decide was it a conscious decision or? 

Bill Caskey Yeah, we had radio show in Indianapolis here, we’re in Indianapolis Indiana in the U. S. Which is the midwest Eastern time. And we had a radio show from 12 to 1 on Saturday At a little am station couldn’t have been more than 500 watts. I mean it probably covered a few neighborhoods around the tower and yet we loved doing it Bryan Neale and I who co-host the advanced selling podcast. We do that together. He and I had this show and we just enjoyed it. We got a kick out of each other on it. We got a kick out of the people who called in. There weren’t many, but occasionally we have a call in. We were able to book guests. We had some killer guests on. We had Jack Canfield, we had David Allen. I mean, we had some really good guests and uh, and so we really enjoyed doing it. And so at some point about 15 years ago I started to hear about podcasting and a friend of mine told me that he would teach me how to do it, set it up. And so after I learned it only took an hour to figure out how to do it. I said to Bryan said, you know, we got to get into podcasting this, we can use it, we can literally do a podcast you’re recording and 15 minutes later it’s out to the world. Australia, Bali, New Zealand, wherever it’s everywhere versus a radio station that is only being listened to by the people in that neighborhood. So we went heavy into podcasting. We’ve done 1000 episodes ish 1000 ish episodes over the last 15 years. And uh, we’ve got 11, 12,000 people in our LinkedIn groups. So we really committed to it. We haven’t missed a week other than the holidays. We, miss two weeks around the holidays, but we’ve been super consistent at it. So 12 years of, no, did I say 12, it’s 15 years 15, 16 years times 50 episodes is up near 1000 episodes, about 900 episodes. 

#storytellerjewels And you have to be commended for that effort because I know the intensity of producing the show and speaking of the show, was there any point in time that you felt like you were spinning your wheels or wasting your time or you feel like throwing it in throughout that process? 

Bill Caskey Yeah, that’s a good question, because I think I have gone through that and I think we’re always it’s always in the back of our mind, Is this enough content? Is anybody listening now? The advanced selling podcast? I know I know there are people listening because of people like you who reach out. But I think, I think with any kind of content production you’re always wondering, well I took a lot of time to do that piece of content only had five people look at it or five shares and Lincoln said there were 600 wait a minute. I got 6003 months ago. Why is it I mean you constantly play that game with yourself, but here’s the way I’ve looked at it and friend of mine Doug Carr, who I just interviewed from my podcast, he said something to me once probably 15 years ago when this whole content things started to come up. He said, if you do content every week, do something every week, you will become a better communicator, whether anybody read your content or not. So just by the very nature of writing, producing videos, recording audios, I believe that I have grown in my ability to formulate sentences and, and talk about concepts that might be difficult because I’ve had so many reps, you know, contents, just a rep game, it’s just a rep game, just constantly putting out content and every time you do it you get a little better. I have clients that uh, I work with, I’ve got a high achievers group called the high achiever mentoring program and I’m constantly on them to do linked in videos. And I said, for those people who have never done one before, I said, do 20, Record yourself 20 times. Don’t you dare let one of those get out. But I want you to record, I want you to watch it and you tell me if the compare the first one to the 201 and tell me you didn’t make 100 x improvement. And of course they always do. But we look at that first. we tend to do, well, I just shot a LinkedIn video. God, I’m embarrassed about this, but Caskey said I need to do it. So, but now don’t do that, do them until you get them right, do a lot of reps and before you know it, you’ll you’ll be able to do them in three or four minutes and you’ll be happy with him, you’ll be proud of them. So I think content is one of those things that you do it for the world, but you also do it for yourself because every time you do something, whether it’s record or produce or write, you just get better. You just get better because you become more skilled at communicating your thoughts. 

#storytellerjewels I mean, the fact that you came from a radio background sort of makes sense to me, you know, leading into podcasting and you’ve got a beautiful radio voice, which is which is part of the, I guess the enticement to keep listening. Do you think it’s important to from, you know, what what’s more important, the quality of the production and the, you know, the way it sounds and the way it looks on video? Or is it the content? Is that the frequency? What are the things that are most important when you’re when coming to producing that type of content and, you know, making people or getting people to listen to that? 

Bill Caskey Yeah, thank you for the very nice compliment. I don’t I don’t think voice quality has much to do with it. I I listened to some podcasts. Listen to a guy named Adam Corolla who has been on the podcasting circuit for 20 years and his voice is awful. The first time I heard him like, I could never listen to that guy. And 20 years later I’m still listening to him every day, but he’s funny and, and I think that the answer to your question is how real are you? Like, I can tell when you did the introduction, when you ask the questions, you’re not scripted. Uh, it comes from your heart, you’re thinking through questions as you’re asking them. I think that’s what people are onto. They are, they are too quick to turn their quick to turn off the person who is overly hyped, who’s overly prepared. Who scripted, who sounds like he’s doing some kind of late night radio show From back in the 70s. I think we’re tired of that. You think retired was like, oh God, we’ve heard that guy so many times before. That lady, we don’t want to hear them again. We want to hear someone who is as they’re answering a question or putting together a thought. They’re actually thinking through it at the same time. That’s really intriguing. Talk about storytelling. Uh telling a story is great. If you’re memorizing it, telling the story is even better if you’re making it up as you go and you’re remembering things and oh by the way I forgot I forgot one important part. And that’s the kind of stuff people love because they want to co create it. They want to co create it with you. And if you’re just telling, telling, telling, they don’t get a chance to be a part of the creation process. And so I I think the podcast success, to the extent we’ve had it is because we literally go into a room for five minutes and we plan out what we’re going to say. And we posed the question and I say, you know what? I’ve got three ideas and he says, okay, I’ve got four, let’s go and we’re winging it, but we’ve done it long enough, it’s we’re not really winging it, we’re just winging the content for that day. So I think that real nous and authenticity is probably a probably a bigger thing than voice quality. 

#storytellerjewels You’ve made an excellent point there on the way you approach your content creation. Has it always been that sort of natural for you? Or was it a little bit more labored when you, when you first began? Did you have to sort of sit down and think about what you were going to produce and less of the winging it? Or have you always just been natural enough that you can sort of make it up on the fly a little bit? 

Bill Caskey Oh, I can’t really remember, it been so long ago that we started um I think we probably thought through it more than like when I sat down to do my podcast, Bill Caskey podcast is where I go into a lot deeper ideas about life and discipline and, and mindset and things like that. Uh I do take notes, you know, I come up with kind of an outline in a sketch of how I want to show to go, things don’t go according to plan. I’m always willing to stop and erase something and start over. Um but with two people, I think that’s one thing that people who are doing podcasting, if there’s a two headed podcast to humans behind the mic, you can play off each other. You don’t need as much rehearsal, you don’t need as much scripting because he’s going to say something that I will want to pick up on, I’ll say something that he does and so before you know it you’re 15, 18 minutes in and but you’re building off of each other when it’s a single headed podcast. It’s hard to do. You better have a script or an outline or bullet points if nothing else. 

#storytellerjewels So what advice would you give? Somebody who’s just starting out and you know, wanting to get their sort of public persona out there a little bit more? Is it better to start with a co-host or is it just like you say, get in front of a video and practice some and get your message out there? What how would you particularly when it comes to a sales, when you’re, when you’re teaching sales people, how do they get their brand out? What’s your advice there? 

Bill Caskey Yeah, I think that the salesperson of today and I work primarily with business to business sales people, not business to consumer, although I don’t know that it makes any difference. What I’m about to say, the salesperson of the future is the person who does have the brand, who is, who has put time into developing their personal brand and by personal brand, if you have a LinkedIn page, you have a personal brand. We’re not talking about color schemes and logos and artwork and Photoshop and we’re not talking about that for now. Maybe someday, I’m just talking about how are you building your reputation online. So that when someone looks at you on LinkedIn and they say, oh, you know what we need to have John in, I followed John, I mean I get a call from people, I got a call last week from a guy who I worked with 20 years or 15 years ago, but he’s been following me on the podcast for 12 years, 10 years. And just now he called I even said, I said, where have you been for 12? You’ve been listening for 12 years. And it took you 12 years to pick up the phone and call me. And he and he didn’t laugh. And I said that’s that is a joke, but thank you for calling. Um let’s see. I think what happens is we don’t we as sales professionals, don’t think about our brand that way. We think about the brand being the company we represent. And it isn’t it is that but it’s also you and if people are looking to you for advice and for resource and for answers to questions and expertise, you have a brand. So now the question is, what are you doing to build it? And I’m not talking about artificially constructing some kind of a schema. I’m not talking about that. Just what are you doing to build your reputation in the market? Are you delivering value? Are you educating the customer? Are you helping your customer base become more sophisticated in how they buy, what it is you sell uh are you helping identify problems that they have that they may not even know they have through video and audio and things like that? So I think the salesperson of the future has to be a brand builder. They just have to be or you’re going to get beat by the people who are Because when you when if I’m I just had a uh for it’s probably a fortune 1000 purchasing manager was in one of my groups. I don’t know how he slept in, but he was one of my groups. And uh he said if somebody calls me today, a salesperson who wants to see me and I go to their LinkedIn page and there is nothing there of value for me. I won’t see him. He says, if they haven’t taken the time to write an article to produce a video, to make a post of something of value, if they’ve done nothing, why would I see them? Why would I entertain seeing them? And when he said that, I’m thinking that’s it, that’s it right there. You don’t think people are looking, People are looking, people are searching on you. People are looking for you to see maybe you call them. And you said, look, I’ve got something I want to show you. And they invited you in before you get there, that’s likely they’re searching for you to find out who you really are. If they see nothing, they may cancel your not positioned properly. Nothing good happens. So I think, I think it’s a huge thing right now to build your brand and I think you can do it through building content. I think LinkedIn video is the best way to do it right now. I think you’ll get more reach. It’s getting a little tougher because You know, it’s only 10-15% of your LinkedIn connections will probably see any piece of content. Maybe it’s less than that, but still it gives you good practice. People will start to recognize you as a thought leader is somebody who’s out there trying to give good quality information. So I think LinkedIn video is a really good place to begin. 

#storytellerjewels I’ve been saying for many years and statistically it’s been shown in many different reports that I’ve read that People will research or are spending more time researching both the individuals that they’re buying from. And also the company that they’re buying from before they pick up the phone. Well before 60, 70% of the research is done before they make any form of content contact. And if you’re not out there, if you are not visible, then you might be invisible because they won’t buy from you ultimately. So it’s great advice. So, can you, after 15 years, I mean, you’ve been doing this for a very long time. You had a sales practice before you got online at all. Can you quantify at all what impact that brand building has done for you and your business? 

Bill Caskey Well, um, I don’t make cold calls. So and I never have never have. I should say that maybe the first month I was in the business I had to had to make a few, but I I hated them. I didn’t. Yes. Like it was just awful. I mean, and I don’t I don’t suggest that salespeople in my program. I don’t suggest salespeople make cold calls. I think there’s a better way to do it. I’m not saying you don’t reach out with something but have something in your in your satchel, have something there for a value to the person when you are making these cold calls. So therefore I I never made him. So I kind of relied on education, Whether it’s an executive previews. We used to do monthly executive previews. I would invite 15-20 people to come and visit and I would talk about some things and sales and you know, 10%, of people would raise their hand at the end say, Okay, I want you to come in and see me. So that’s how we built our business or education, education, marketing. And I think it’s the same way today we do webinars. I’ve always got a webinar at the top of bill Caskey dot com. For whatever the topic is, there’s always one word promoting all of our business comes through personal brand building everything, whether it’s a podcast listener who finally calls or whether it’s somebody who listens to watches our Youtube channel or somebody who comes on the webinar, somebody who signs up for an email, like a freebie of some kind or something that we’ve produced and then they hit they are there, they hit our email list. All of it comes from personal brand building. I don’t I don’t know anything that doesn’t, we don’t have like people walking by the hallway and say, what do you do here? Oh, sales training. Oh, I think I might, we don’t have that. It’s all it’s all virtual. 

#storytellerjewels Has that meant that your sphere of the business that you do and the people that you interact with is that much more global than it would have been prior to getting online or you’re still pretty well contained in Indianapolis? 

Bill Caskey No it’s global. I’ve got a client in Madrid, I’ve got clients in Toronto, I’ve got individual clients all over europe and England. Um I used to have some in Australia but don’t anymore. And then probably half our business is from the U. S. But I only have one client who is in Indianapolis who is physically in Indianapolis and I go see them and we work on the fact that we do only brand building for that company is a construction company. Uh But yeah all everything that we’ve done, I would put under the brand building under brand building. And so it has been responsible for You know, tens of millions of dollars to us over the last 20 years. 

#storytellerjewels Fabulous and Bill, what one of my last questions is, you know, what have you learned about yourself through this journey? 

Bill Caskey I think I’ve learned I’ve learned something in the last three months and it’s been around me for probably all my life. But sometimes those things just pop in and it’s like, well that’s what, that’s why this is working or that’s why this is not working and that is I must really believe in what I do. I’ve got to really believe that if you pay me X amount of thousands of dollars to for me to be your coach for a year or if you pay me, you know thousands to come in and speak to your group or whatever, it doesn’t matter what the money is. But when you’re paying me money, I’m selling something to you of value that I’m going to come and deliver, I’ve got to believe in it. And if I have even the narrowest thought about, you know, yeah, we could do that, but I don’t know, but we’ll go ahead and try to sell it. It never works. It just never works. And so we just released a program for high achievers this year and I committed to really getting into the details and not just glossing over things, but really getting into the details about imposter syndrome and about all the reasons that we can’t scale our business and self limiting beliefs. And I got I went all in on that. And when I talk to somebody now, I know I just reek, I just reeked the value that I’m trying to communicate. Not in a pitching way, just in a way that, look, this is this will be the best program you ever do. I I know it is because I’ve created it and I’ve built it and I’ve researched it and it’s been a lot of time doing it. And I think people just feel that versus trying to make the sale because you need the money. And I think there’s a very, very big difference there. So what I’ve learned about myself is I’m I’ve got to really believe in what I’ve created or what I’m selling or I won’t be successful at it. And on the other hand, when I do believe in it, I can be very successful at it. 

#storytellerjewels So what I hear there is that you’ve got a very strong mindset when it comes to both developing your products and services and delivering them. And the authenticity of actually selling something of value is of huge importance to you, so that both you have that confidence to sell it and deliver on it and maybe even over deliver on it and for somebody to take that on board and actually get value from that. That interaction to you is hugely important and I get that from just even from listening to your podcast, is that The authenticity level is at a 100 because that’s you know, it’s coming from a good place, It’s coming from the heart, but it’s also coming from experience and knowledge that you will be able to add value to anybody who either listens or takes part. Is that true? 

Bill Caskey That is true? You said it, you said it better than I did. It was, it was very well spoken. Um I was listening to a guy the other day and I would I would attribute it, but I cannot think of who it was, but we talk about this mindset, you brought up mindset, so I’ll finish here, we talk about mindset a lot because to me that’s all there is any kind of any kind of success you have in life or in business or in sales or in making money, it begins up here, it begins with how we think about ourselves, our market, our business, our potential, our relationships with our customers are value. It all begins in our mind. And one way that I think you can attract more people is to not need them and to be detached from any and all outcomes. And I get into some discussions with other sales trainers and was like, oh the other sales trends like, oh no, you’ve got to be attached every deal and times are tough and there’s not enough deals and you’ve got to be dark, like you don’t understand prospect doesn’t want that. Do you think the prospect, once you hanging on their shirt color, you know when they get home, just just like dog, just dogging? Do you think that’s enjoyable for prospects to have you dog people? Really? You believe that? And some of them do. I believe it’s just the opposite. I believe that if uh, this speaker that I was hearing talk, he talked about with or without you energy, I’m okay with you or without you. I’m okay. Either way, if you don’t want to work with me, god bless you, that’s great. Next I’m on because I’ve got a good prospecting mechanism, I’ve got ads working, I’ve got good content. So if somebody says, no, that’s cool. Now some people bother. They can’t, they can’t accept that. It’s just too, it’s too, it’s a bridge too far and yet we live in an abundant world. You can, there’s seven billion people on this planet. Now, all those are not prospects for you, but a better percent are. And if everybody always say this to my clients, if everybody showed up tomorrow, who’s in your territory? If you have such a thing, raised their hand and said, I want to I want to buy from you, you couldn’t handle it, You couldn’t handle all the all the sales. So I know the markets abundant. So the question is, is why are you so attached in an abundant market? If the market the more abundant the market is the more detached you should be because if this person doesn’t buy the next one, will. Now, I’m not being a jerk about it, I’m not, I’m not being flippant or cavalier, but I also don’t get attached to any deal. Don’t get attached to a deal because I know that there’s one right behind that one and that gives you a lot of energy. It gives you confidence and I think it’s better for the prospect because now you’re not you’re not dogging them, you’re not persistent and calling and following up and bugging the hell out of people. You’re not doing it. You’re saying, look, I’ll, if I don’t hear from you Friday at five, I’ll just presume that this is a done deal. It’s over. 

#storytellerjewels You and I subscribe to the same philosophy. I think I’ve always said that, you know, I prefer people to buy from me rather than be sold to. So I’d like them to know and understand me and what I do and how I do it and my ethos and my attention and um and if they like what they see and they like what they hear, then they will naturally come knocking and pay dollars to be part of that. And that’s great. And if they don’t like that, then that’s okay too. 

Bill Caskey Yeah. Yeah. And part of that, then it’s incumbent upon us as sales professionals to be really good at understanding the problems they have, understanding what they’re struggling with, where they’re trying to get to understanding how to craft our message and our offer. So we are, it’s incumbent upon us to do things really well in the sales process. We’re not talking here about just sitting back, waiting for the phone to ring and say, well, do you want to work with me or not? Absolutely not. There’s lots of stuff that has to happen. But at the end of the day, if you’re more detached, you are, the more power you have, the more freedom you have to ask. The questions that need to be asked to say. The things that need to be said. And if you’re attached and need the deal, you’re not going to ask them because you’re not free. 

#storytellerjewels Well, my final question for the day and this is something I like to ask all of my interview, guess. Um if somebody paid you $1 million dollars to pick your brain, but you only had a few minutes, would you say? 

Bill Caskey To them a few minutes, wow. Million dollars for a few minutes wow? That’s music to my ears. I like that I should come up with something creative. Um, what would I say? I would probably go to the concept of the map and the map concept. To me. It’s not an acronym. It’s actually a word uh, is where do you want to go? Where do you want to go? And I would help them in a few minutes because I would want to help them for a million bucks. I would want to I would say I’m on the clock. So I’m gonna help you. Let’s craft where you want to go. What do you want to be do see have in 55 to 10 years get crystal clear about that. Even if you think it’s a wild, wild shot, a shot in the dark. Just get clear about it and then build the map to get there. So what are some things that have to happen along the way? We’ll number if the person says, well I want to make a million dollars a year. How much you’re making now? 50 grand? Okay, well one step along the way is you’re going to have to get okay with a million dollars a year psychologically okay. Because you’re not gonna do, you’re gonna go from 50 to a million if you can’t get psychologically okay with having a million dollars come in. So, um, I would want to build, help them establish the clear vision, the clear ideal outcome, clear future and then help them build a map and to me that would easily be worth $1 million dollars to them. 

#storytellerjewels Well, I feel like I’ve got $1 million 30 minutes and I know you and I could talk all day all day and I’ve heard so many podcasts and I’m amazed that every podcast is engaging. It’s useful. It’s positive content. Uh it’s something that I can often take away. So thank you for the years of service. It’s been a pleasure. It’s been a pleasure interviewing you, you can find out more about Bill, that Bill, Caskey dot com. Is there anywhere else? 

Bill Caskey Everything’s there Jewels, it’s all there free videos, audios, and the way that you can connect with me. And also at the very top there’s a webinar button that uh, is promoting our current webinar which is coming up here in a couple weeks. 

#storytellerjewels Bill, thank you so much. Thanks for being on the show. How good was Bill? It was an absolute delight to talk directly to someone who have held with great respect for so many years. My take on all that was if you truly believe you are able to solve a problem. If you’re passionate and knowledgeable in your space, regular publishing of content from you will elevate you as a thought leader and that will ultimately attract, engage and retain an audience who one day might just buy from you. It might not happen overnight, but with persistence and practice, it will happen if you’ve enjoyed this episode, Head on over to the telling of a story dot com, where you will find links to bill this episode and others like it, Make sure you’re subscribed, so you don’t miss out on each episode as they are released. And I always appreciate if you take the time to leave me a comment or rate this podcast on your favorite medium. Much love chat soon