Why Sales Deals Die and How to Keep It From Happening

Speaker 0    00:00:01    Coming to you from Orlando, Florida, Orlando, Florida, and streaming around the world around the world. You're not tuned in to the sales samurai podcast. The only B2B sales podcast, providing unfiltered unapologetic views and tactics directly from the sales trenches. Here's your host, Sam Capra.  
Speaker 1    00:00:30    Welcome to episode five of the sales samurai. Thanks for listening. Before we begin, do us a favor, take a moment to subscribe and download on today's show. We're going to be discussing why sales deals die and how to keep it from happening. And I have a very special guest to help us tackle the topic Mr. Bill Caskey. He is a sales development leader and experimenter who has been improving B2B sales teams and executive since 1990. He is also the author of same game, new rules, rewire the sales mind and the sales playbook to name a few. He actually also co-hosts two podcasts, the advanced selling podcast and the bill Caskey podcast, both geared to B2B sales from an individual contributor onto leadership. Hey bill, welcome to the show. Happy to have you on man,  
Speaker 2    00:01:16    Sam. Thank you. And thank you for what you do for the profession of selling. I think there's a lot of podcasts out there. We all need to thank the people who do podcasts like you and I do a couple and a lot of people do, and I think it's really helping the profession to be honest. Well,  
Speaker 1    00:01:31    I appreciate that bill. You know, it's funny, you know, as we kind of hop into this, one of the things that really drew me to you, bill was actually a piece that you had in your LinkedIn profile. I think I shared it with you that they know BS look at current reality. And I thought that was that's exactly what we're all about. I there's a lot of holistic cool methodologies out there, but nothing really tactical that we want people to be able to take away from each podcast. That's why I'm so excited to have you, man.  
Speaker 2    00:01:56    Well, good. Well, thank you. I appreciate it. Well, yeah, let's get into this and see where it takes us and uh, we might talk tactics. We might not. Let's just see what unfolds, how about that. We might learn  
Speaker 1    00:02:06    Something that knows. Hey, so before we kind of hop in, I know we've kind of talked about this offline, but can you give a list of just some little bit of background about cast chief and strategies kind of what you do and then we'll kind of go from there.  
Speaker 2    00:02:17    Yeah. Thanks Sam. We have been in the training and coaching business for almost 30 years, primarily with business to business teams. I don't work with B2C too often, although we have, but my niche, if there is a niche is business to business, I started out by, in the profession of selling, not being very good at it. And I realized pretty quickly after a few years of being at the bottom of the stack rank, that I'd better figure it out. And I didn't have any mentors or coaches and I didn't have a framework or a full, I had nothing. It was just a book of customers. And I was selling heavy equipment of all things like caterpillar equipment. And I had no idea what I was doing. And so it really is just about going out, playing golf and buying cigars and getting drunk with clients.  
Speaker 2    00:03:01    And they love to drink that cat group. And at some point I realized that, uh, this ain't going to work. This is not a good long-term solution for me. So I started to put together some things that I felt the profession needed. And so that's what I've kind of devoted my life to over the last 20 years or so is creating content that really empowers the sales person rather than just content to try to hack and tactic your way to a sale. I just feel like there's so many trainers out there who all they do is teach hacks and I never felt good about that. And my clients don't like that either. And I think there's a big need for, I don't know if I'd call it holistic, but just the idea of look, we sales professionals, we're human beings. And if you treat us only as a way to get revenue into the company and don't take a look at our whole self and our confidence level, I think we sacrifice a lot. So that's kind of been, my focus is wholesale confidence, the inner side, the mental and psychological side of selling, because I think it enters into every part of the sales process,  
Speaker 1    00:04:02    You know about. I'm glad you said that. Because another thing, when I did some research, I was doing some background on ya thing that resonated me as well. Was you put there, you know, before you got into this, a sales coaching, mentoring kind of professional, you've been for the past 30 years, you said there was a scared self-conscious young man starving for approval. I think at some point, and maybe even today, every salesperson has kind of felt that, that, Hey, am I good enough? You know, I'm behind quota that confidence just keeps taking a beating if that's the right terminology. And I truly believe you're right, man. I mean, I think confidence is the leading indicator. If you don't have that piece of it, it's an uphill battle.  
Speaker 2    00:04:40    Yeah, it is. And I have come to the conclusion that sales professionals today don't get enough of what we just talked about. They don't get enough of the, of the mental side and of achievement, not just of selling, but of just personal achievement. You know, we just don't get enough of that. And so then when I introduce this to my clients, they eat it up because they don't get it. They don't get it from a shrink, they don't get it from their spouse or their family or their they're definitely not their sales manager because sales managers, they got one job to make the numbers yet. I think at the heart of making the numbers is taking care of the sales professional and making sure that their, their confidence level is up and they can take risks and they don't get so attached to things. And so we can get into some of those details  
Speaker 1    00:05:21    Without a doubt. I'm curious, what got you into sales in the first place? Bill was like a dad or kind of a family member. What made you get into the sales profession in general? Yeah,  
Speaker 2    00:05:29    That's a good question. It was probably a default. I don't know that I was prepared for anything else. I mean, I went to four year private school and wasn't going to go to accounting or MBA. All my buddies were going to MBA school and we couldn't afford it. I mean, just my family couldn't afford it. And so I kind of got thrown out and some guy said, Hey, you ought to get into sales. You seem to be a pretty fun loving guy and you can talk to people. And you're a nice dude. So, so I thought, well, that sounds like a good qualification. So let's go at, but there was a lot of times in my twenties where the alternative to sales, I didn't have one. And so I thought about getting out of the profession. I thought, well, this is no fun. I just wasn't having any fun and I wasn't achieving, but then the question is, okay, well, smarty, what are you going to do then? And I really didn't have any kind of a backup plan. So I had to make it work.  
Speaker 1    00:06:18    Uh, it's funny. I always ask that question and I've yet to hear anyone say, Hey, I grew up all my life as a kid wanting to be a salesman.  
Speaker 2    00:06:28    Yeah. Sometimes their, their father was successful or their mother, they said, look, this is a profession. You can be free, make a lot of money, help people. But not very much.  
Speaker 1    00:06:37    Yeah. I don't know how successful my dad was, but he just did it all his life. And I saw him and during the summer he'd let me sell whatever he was selling, make it a couple extra bucks that got to it. But I think growing up, it was never, I think I kind of fell on your side. I didn't know what I didn't want to be adopted or anything like that. And I saw that I knew how good I am. I can earn what I want. So I naturally fell into, but I truly believe kind of what you brought up earlier, especially coming up. I think when we both came up, I don't know, from an age standpoint, but there wasn't a lot of resources coming up. Like you had to go find it. Like it was a manual, not like it is today. Right? Bill, am I on the line and saying that,  
Speaker 2    00:07:15    No, I mean, we didn't have, you know, back in the old day we didn't have podcasts. We had cassette tapes, we had cassette tapes and we used to, and then remember when they used to get off track and they not unravel. And then you're there with a pencil tray. I mean, I bought a lot of those and they were helpful. They were good, but it seemed that. And I still think this is the case today, Sam, I think a lot of the content is just refurbished and repackaged stuff from the seventies. And it's like, we're in a different era, we're in a different world. And so you're right there wasn't much. And there wasn't much corporate training or coaching either. I mean, we had two days of Xerox sales skills when I was at one of my jobs two days and we never opened the book again. And I'm sure it was good stuff, but there was never a reinforcement. It was never really training. And coaching was never something that companies committed to, I think more are now, but it's still kind of rare, but I think more companies are saying, look, we need to spend a hundred grand on our Salesforce. We've got 25 people. If we can spend a hundred grand and get 10 million back, that's a pretty good trade, but it's still an 80, 20, 20% do it 80%.  
Speaker 1    00:08:22    Hey, I'm curious because I think this does segue nicely into our conversation in what we're going to be discussing today is, and this is near and dear to my heart. Leading a sales team is, you know, why sales deals die? You know, it really goes sideways. They stall out, they get stagnant. And really what we can do from a sales leadership standpoint, from a sales professional standpoint to either prevent that from happening as much as possible, or to resuscitate them and get them back to life as much as possible as well. But I think this goes into it. So my initial question for your bill is like you brought up corporate training. What part of your self really should fall on you as an individual versus the corporation? Just curious, like when you land on that 80% should be on you as an individual. You want to get better at something go after. Like where do you fall? Cause I've seen two different schools of thoughts on that. Like corporate should be doing that. Other people say it's all about learning.  
Speaker 2    00:09:11    Well, that's a good question that I probably don't have a clear cut answer to. I always default to, if you want to get better personally than why are you waiting on your sales manager to find budget for training? I mean, that seems so idiotic. It seems stupid. It seems so backwards. And I find that I've got a couple of high achiever programs, people in 50,000 or more to be in this program and I don't check their W2's, but generally I can tell. And those people are not afraid to invest in themselves. Someone who's making 35, 5, 23 years old, just got out of school and they don't have the kind of money. So they kind of have to either borrow it or they have to depend on their sales manager. But I think if it's going to be it's up to me, kind of the old worn out Dale Carnegie phrase, and I think that's the case. And if you don't get any training or if you get sporadic training, go find somebody, go find a coach, go find somebody or an online webinar series or something. I just think personal agency, our ability to prosper in life is up to us. It's not a budget that's set arbitrarily by some HR person.  
Speaker 1    00:10:17    Yep. You know, the, the reason I asked that question, because I know we're going to get into this is that I find in today's day and age, access to information, free information as well, not all pay, but there's some great stuff like your content that's paid for. And I highly recommend it. I'm willing to spend a thousand dollars on myself. That's a no brainer, but even the free stuff, just Googling YouTube. I mean, there's so much at your fingertips that you can just allocate 10 minutes a day, 15 minutes a day. So I'm going to watch two videos. I want to listen to one podcast. Like there really isn't any excuse to doing that in today's day and age where there might've been that barrier back when we got started, if you will. But also just curious.  
Speaker 2    00:10:56    Yeah. I th I think there's no shortage of knowledge. There's no shortage of expertise and wisdom out there. Unfortunately, sometimes that can be overwhelming too, because I can learn something from you and then I can go to somebody else and then go to Caskey and then go to somebody else. And before you know, it, it doesn't fit. There's no through line of the theme. Like there isn't a movie, there's no cohesiveness to it. I think that's a challenge in this. So then you're just looking for the hack of the day. However, I do agree with you that go and search some things and find somebody you really believe in and really sees the world the way you do, and then buy from them instead of trying to capture it free from 17 different sources. I think you'll find people who really speak to you. And that would be my recommendation. Yeah, that's great.  
Speaker 1    00:11:40    So let's jump into this whole, you know, sales process, how sales deals go sideways. How do we prevent that? How do we resuscitate it? But I think maybe a good starting point, because I know starting out when people used to say sales process management, some people you'd think that was intertwinable. I mean, they're, they're intertwined other people that there were two separate things. Can you kind of help the audience kind of define what you view as a sales deal, opportunity processed, all that kind of good stuff. You'll notice a little bit  
Speaker 2    00:12:06    In a bit. Well, there are, there are, there is the sales methodology. There's the sales process. There's the selling system. There's all the ingredients underneath each one. Here's something that I have found works. And that is, I think companies need a sales philosophy. I think a sales philosophy is not step one, step two, step three. It's how do we think about our customers? And how do we think about the process of landing clients, a sales philosophy? There's a guy who you might've heard of. His name is Michael Jervais. Michael has a podcast called finding mastery and he's a sports psychiatrist or psychologist. Never. Sure what, which one is, which, but he works with the Seattle Seahawks and he's done a lot of work with Olympians. And he says, the first thing he does when he takes on a client and he's working with high performers is he establishes their personal philosophy on performance, on life, on discipline, on practice, because he says, if you don't have a philosophy that includes practice and the amount of time you're going to devote to self-growth, then I don't want you as a client.  
Speaker 2    00:13:11    And I think sales philosophy is the same way. And I think companies have, have not done that very well. I think the philosophy is make our numbers. Well, that's not a philosophy. That's just a goal. It's an objective. And so sales philosophy to me could mean things like how do you treat clients? Uh, at what point during the sales process, do you say, you know what, Sam, this is not going to work I'm out. Unless I hear differently from you that you've got to have a philosophy of how we go about selling. And if you do, then it becomes a lot easier to say goodbye when it's time to say goodbye to keep persisting, when it's time to keep persisting, to say what needs to be said to do what needs to be done. But if I don't have a philosophy, I'm just wandering around the sales process. And I think that's kind of at the heart of your first question, there is, well, what is the sales process? And I say, well, it is what you say it is, but you've got to have the thinking right first,  
Speaker 1    00:14:06    Right? So the philosophy should not dictate, but educate what the process is as a whole. Was that fair to say?  
Speaker 2    00:14:13    Yeah. So here's an example of a philosophy or the point of philosophy. I teach organizations that you have to have an attitude of abundance. Okay? You have to believe that the market is abundant, not infinite, but abundant. And what makes markets abundance? Abundance is the amount of pain and desire and goals that the customer has that are unrealized the problems, the goals. That's what makes a market abundance. You don't look at your pipeline and say, well, this market is not abundant. Your pipeline has nothing to do with market abundance. That has to do with your work ethic probably three or four months ago. So I think number one philosophy is when we get up in the morning, we have to say, our market is abundant and plentiful. And now the question is, how do we best attack and pursue that market? Knowing that it's abundant.  
Speaker 2    00:15:03    Because if your philosophy is the market is abundant and a customer is dragging you along and pulling you and lying to you, then it's easier to say thanks, but no, thanks. I got to move on. If you think the market is scarce, you can't say no to those people. Right? And so the answer to the question usually is whenever I hear people say, I'm struggling with this client. I always want to coach them say, well, are they more interested in solving their problem? Or are you more interested in selling them something? And usually it's well, yeah, I'm very interested in selling them something, but that's not a good philosophy. That's not a good flow.  
Speaker 1    00:15:37    That's a good catch. I used to one of my old mentors back in my Cintas days, he used to always say, you gotta know when to keep fishing. You got to know when to cut bait. That's a tough thing for sales. It's the toughest thing. I think it is for like, if you see that bill as a routine and it's hard, we're overly optimistic if that's the right terminology.  
Speaker 2    00:15:55    Well, that's why we got into sales. Probably if we were pessimists, we probably wouldn't last a day. So the optimistic side of us is extremely valuable. The challenge is that sometimes we bury our head in the sand and I've done this before. I did it three months ago, I had a client who wanted to do some more work. And I, we talked and we went through the whole discovery process and we did a proposal. And then they said, look, we're going to do this for sure. Well, whenever someone says, you're going to do it for sure. I should have just then said, well, we're done then because you're not going to do. And it went on and on. And I didn't feel like I could just say we're done because they were a client on other things. So I kind of let them drag me along.  
Speaker 2    00:16:32    And finally I said to, the guy said, look, I've got to have an answer by Friday. If I don't get it, then we're done on this. And I hope you understand. I'm not trying to be a jerk about it. And he called me back two hours later and goes, we're done. And I thanked him because now I'm released, I'm released. I didn't try to talk him back into it. If I made an error, it was earlier in the process. But also I was trying to sell to somebody who didn't have a problem with that. Or they realized at some point that the problem is not worth solving. I think they still had a problem, but the point there is I needed to detach earlier. And I didn't. So this is a you're right? It's hard. When you have something that's big or just sitting right there waiting for you. It's hard to knock it off the tee and say, now I'm not going to do this anymore, but you must, because time is all we have. All we have is time in an abundant market where lots of prospects have problems. You've got to make sure that you're generating discussions and leads with those other people so that when it's time to pull the plug on somebody, it's easy to do because I got 19 other prospects without  
Speaker 1    00:17:33    A doubt. And I think that's a great catch. So philosophy, which I think is a good way. It's an attitude about abundance. You know, if your market can support it and there's a lot out to them, why waste your time with this one too? Your time's better spent somewhere else. Right? But people are going to say yes to you. And I like what you said there, because I was always a big believer in I'm fine hearing. No, cause no allows me to move on to someone else. So I, 100% agree with you. What do you think opportunities cause you as a sales leader, I'm talking to sales reps all the time, or we're deep diving into opportunities. I mean, this is a great opportunity, Sam, we're doing this, this, this it's making progress. At what point do deals really start breaking down? Was it early on in the process? You didn't ask the right questions, the whole stakeholders, the budget, like where do you really believe that deals? It didn't start there. Right? Bill just didn't go dark for no reason. Something led to that point. What's your thoughts around that?  
Speaker 2    00:18:26    Yeah. Well it gets back to philosophy. Again, is if my philosophy is correct, then I will probably do a better job upfront in finding out what the problem is. And talking to all the stakeholders who care about the solving of that problem or the gaining of the advantage, or however you have found a customer's wanting to proceed, you know, is the process clear to them? I think sales process a lot of times is we don't share it with our prospect. We have one, but we don't, it's a map. I always say that you're a guide on the customer's journey and a good guide will always tell their campers or their hikers. Look, this is what we're going to do in the next hour. We're going to come up here to this little place and it's a cliff off to the right. I want you to hang left.  
Speaker 2    00:19:09    I want you to hug it. You know what the map is. And I don't think we tell our prospects that. And if we do, I don't think we really believe it. So I'm convinced and I've got a client who does this really well. He's in the engineering business. I don't even understand what he does, but he sells big engineering consulting companies to mining operations. And he's really good about saying, okay, look, here's where we are. Now, here are the next three or four steps and he doesn't lay out the entire, but the next three or four stones to step on, he's a really good guide. I don't think we do that enough. And if we do it, it has to have teeth. Because if we say, look, I'm going to need an answer on this by Friday. And then we'll go to phase two, which is where we include other people. And if they don't give you an answer by Friday, you've got to have the courage to say we're done. But again, it gets back to do we have enough lead flow so that we can make that move easily. And most salespeople don't, we have three or four things on our funnel and it's going to be hard for us to let go of one, because there's only two left while you're not operating from a place of abundance or confidence then.  
Speaker 1    00:20:14    Okay. It makes perfect sense. And you know, one of the things that you brought up in that conversation is I find as a sales rep, when you're going through those deals and you're really kind of being optimistic versus pessimistic and being real, I call that a mutual action plan, right? Hey, here's what we agreed to. I think I fall victim in this bill. I know why I'm doing this. Just as much as anyone else I'm trying to get better is we forget that the customer doesn't always know how to buy and people assume the customer like they do have their mind process. Don't get me wrong, but they don't know how to your specific solution. They know who bought it before. Maybe they've bought it once, but it was someone that, you know, 10 years ago, 20 years ago, and we forget that we need to help them by this look. Here's what we typically see other people in your space. Here's how they buy from us essentially. And I liked that for the simple fact that if you can't get them to collaborate and buy into that, then it's not a real opportunity  
Speaker 2    00:21:10    To begin. No, no, the word opportunity. I know what you mean by it. And I'm on board with that. But I, I also feel like we always talk about our opportunity. The question is what's their opportunity. They have an opportunity to solve a problem. That's costing them $10 million. Are we ever talking about that? Or are we just talking about it from our perspective of what's our opportunity? I say that the best kind of sales process you can implement is one where the prospect should be a title of the book. But I haven't. The best sales process is when they need you worse than you need them to when they need you worse than you need them. And then the question is, well, how do you make that happen? Well, you make it happen by engineering a process where at some point they realize, oh my gosh, I can't let Sam go.  
Speaker 2    00:21:55    Right? And most salespeople and most sales managers have no clue how to do that. So what we do is we push and we persist and we harass and we harangue and you know, 11th hour. And we, you know, I can do this if you're a discount at 20%. And we had never gotten to the point where they see our value in us more than we see their value to us, it's a subtle tweak, but it makes all the difference because now you are, you're talking about their problems and their issues versus your issue of needing the sale. That's perfect.  
Speaker 1    00:22:26    Hey, so what's your thoughts. And I know this kind of ties into things. So, you know, I, you know, my old mentality is your mentality, budget, authority, need timing, all that fun stuff. If you don't have those and that's probably a good indicator, your opportunity. That's not a real opportunity. I don't know if I believe like budget. Isn't always established in today's day and age. There's a lot of budget is being created. So where do you kind of fall in that? Are those leading indicators? Hey, Mr. Rep, you don't have budget. They haven't given you budget, kick it out. And it's not a real deal. Like where do you fall in that? Because some of those are not as linear as we try to make them be. We  
Speaker 2    00:23:00    Love the acronyms. And I've heard that one before and I don't disagree that acronyms are helpful to get us to frame where we are and things. And it's almost like a checklist. You know, budget is one of the checklist points, but budget is something that's many times arbitrarily arrived at through what we did last year or the last time we bought it or what's available in somebody else's budget. Or what's what we just say, you know what? Let's go out and buy training for $3,500 this year for our whole team. And it's like, did you really research it? Or is this budget just an arbitrary, random number? And of course, many times it's a random number. Here's how I look at budget. I think there's two budgets. There's the small B budget, which is what the company is willing to set aside funds like the traditional budget.  
Speaker 2    00:23:48    But there's also the big B budget capital beat budget, which is what's the problem cost. How much is the problem, costing them not to do anything about that's the number we need to be focused on and understand. And in many times they don't know. So it's not a simple matter of saying, well, what's a cost you Sam, not to have this problem. They're going to say, I don't know nothing, a hundred dollars. That's where professional salespeople are good at diagnosing the problem and the economics around the problem. And if you don't know how to do that, you're always going to be compared to doing nothing. And if their best decision is to do nothing and not buy and not proceed, and you've done a terrible job upfront of helping them understand the problem and helping them understand is that it's not just helping you understand.  
Speaker 2    00:24:34    It's helping them. I have a client is in the dental consulting business. And when I first started working with them, they were so excited about their pitch and their offer. And they were closing 12% of the deals. And so we establish an engineered, a survey or assessment process where they wouldn't even propose to the dentist until they really understood what the problem was, costing them not to have their Mo it was a marketing solution. So it was pretty easy to figure out we're generating 12 clients a year. We need to be degenerating 200. The average client buys $5,000. That's $10 million. It's a lot easier to sell a $30,000 package. If they believe it's going to result in 10 million. But if you don't know how to do that, or if you just arbitrarily ask the customer, so tell me, Sam, what does this problem costs you to have? They're not going to know. They haven't thought about it. They should have, but they haven't  
Speaker 1    00:25:26    To piggyback off that. So for lack of better, just to level set, I don't think we're saying that any of this in its own, well, maybe it can't be, I guess, is like, there's a lot of layers to why deal with doubt, right? There's Hey, you didn't diagnose the pain. You didn't reverse engineer. What was a real problem with the savings or with the, you know, from a revenue standpoint, whatever. That's a huge one. And I find that that's always a challenge because if you're talking to someone that can, most people to your point can articulate, that's a $50 million problems, right? It's up to us to help get them there is that right?  
Speaker 2    00:26:00    That's right. That's right. And if you don't know how to get them there and they don't know how to get themselves there, then you're going to close 10% of the business. And it's sales is too hard today to only convert 10% of your proposals to business. It's just, you're wasting 90% of your time. And yet the average closing rates, 10 to 15% in business to business that's as best I can tell. I haven't done it yet, but I've seen Gallop. And some other boardroom did a survey a few years ago, and it was like 12 and a half percent closing rate. That's a recipe for a whole lot of work on a whole lot of little income at the back end. So my goal with my clients is you need to be closing 50 to 70% of the deals. What that means is you may be working on fewer deals, but oh, well, that's time. You have to spend on the deals that you're going to get in that are going to help you. So I think one of the key indicators is what is your closing percentage? And if it's not 50 to 70%, you're probably spinning your wheels in the sales process. You're either not sharing the process with them. You're not creating the atmosphere where they believe they need you worse than you need them. They don't know what the next steps are. You're not talking to the right people. You're right. There's a lot of different layers.  
Speaker 1    00:27:10    It's a great segue is because stakeholders has gotten more complex. And that is one thing I will say, you know, Jim, Bob can sign off for the uniforms. Whereas today no one wants to raise their hands. Say I'll flip the bill or no one wants to be on an island by themselves. It's more consensus by. So how does that impact the whole sales deal, philosophy, whatever you want to call it, but roles out playing right now.  
Speaker 2    00:27:34    I leave it to, I think it's a huge role. We interviewed a guy named Brian Gray, who has a company called revenue path. And he's done a lot of research on this, about the buying influences inside a company for a B2B sales and B2B selling. It used to be that there were four and a half people involved in it. On average. Now it's up to almost seven and a half people. So the buying process has been complicated by more and more people being involved in it. Maybe not, you're not talking to them, which is a problem, but someone's signing off on it or okaying it or approving it or saying no to it. And so you've got to figure out, and that's why I always ask my clients to draw a map of the organization that you're selling into and try to identify who cares about this and figure out a way to go see them.  
Speaker 2    00:28:21    And I remember this was hit home to me years ago when I had a guy, a VP of sales that came to one of my programs and we got talking afterwards and he said, look, I'd like to put together something for my seven salespeople. It was a small team, $10 million, $20 million company. And I said, I will do it, but I need to talk to the CEO first, because at some point it's his company. He's a sole owner. He's going to be writing this check at some point and say, what the hell are we paying five grand a month for this? So he goes, well, you're not going to get to him. His name was Al. I still know him to this day says you're gonna, you know, he, he doesn't care about sales training and sales, coaching, and sales. And I said, well, he probably cares about revenue.  
Speaker 2    00:29:01    Doesn't he? Oh yeah. He cares about revenue. He goes, let me see what I can do. Well, Al sat in for a year. He sat in on every training and coaching session we had. He was our, my most involved, eager. Every time he would come, he would have a story of something that he would use. And that was an example of had I not asked to see Al we never would have done the deal, or he wouldn't have been involved in the training. And so therefore the training wouldn't have been as impactful because the owner wasn't there. When the salespeople see the owner there every day or every week, month taking notes, it changes the whole dynamic of the training and coaching. And so that was just an example of what hit home to me is you don't think you can get to these people.  
Speaker 2    00:29:43    You can get to these people, you can get to it, but you almost have to be detached when you ask, because if you're hoping to get to the, and I'm not saying to call the CEO, you can't get to the CEO of Oracle. I don't think, but you need to look at the map of your client company and say, who else cares about the solving of this problem and create an online or a virtual meeting? I mean, that's the beauty right now is it's not too tough to get a virtual meeting with people, but you've got to get the people inside the company who care about the solution on board. And that's a tough nut for salespeople without  
Speaker 1    00:30:16    A doubt. And I think that dovetails pretty nicely into where I've been doing some analysis on the deals that really go the right way fastest from a momentum standpoint, bill are the deals that have a very good champion, very good influence, or someone that can help you or chart to give you the inner workings of those. Do you think salespeople do a good job with developing champions? Like what's your thought around the champion influencer? I know that's a big topic in a lot of trainers conversations. These days, you gotta develop that champion that influencer or your success rate goes down astronomically.  
Speaker 2    00:30:48    Yeah. I think I totally agree. You can call it whatever you want to call it. It's the idea that person that you have the relationship with has the courage and the stamina and the power to go to other people and organize even a meeting, even organize a meeting with you. And I just had a call Friday afternoon. I wasn't even going to pick up the call. Another guy from Chicago has this. He's a VP of sales with a large organization, and we're going to talk this week. And he says, I want you to meet our CEO. And I want you to meet a couple other of my compatriots so that we can talk about this upfront. Well, that's what I was going to suggest. Anyway, he's going to be a good champion for me because he's thinking about the process of selling it through inside his organization versus just getting a quote from me. Yeah.  
Speaker 1    00:31:35    Without a doubt. So one of the things that I've, and I try to put my head around this is you're right. I found it. And I think it differs by the industry. I happen to be in the SAS space. It's a complex sale. So there's a lot of stakeholders involved in our deals. Sometimes they'll be quite candid with you. I feel like we're hurting cath. Like, I feel like we're constantly, oh, we got to pull him in. Well, he's not really involved, but, but can he say no? Well, yeah, can't so let's, we need to have a conversation with them. Like those type of things. And then you're jockeying. Well, that department really doesn't care for that department, but they need to work together. Like there was a lot of things as a sales rep that are not just the basic blocking and tackling of closing. Right. That's a learned skill. Do you agree that that's a learned skill? That's something you should just know.  
Speaker 2    00:32:22    You mean the herding of cats,  
Speaker 1    00:32:25    Managing all those different pieces and moving that part to get to that part, asking that question, to get to that person, like to your point earlier, do you think that's something that sales reps are just, it's not a learned skill or is  
Speaker 2    00:32:38    That something? Yeah, my philosophy when I do a deal with the company is to engage as many people as I can, because I want to make sure, you know, in my business it matters whether people have bought into this concept. And if they haven't, I don't stand a chance in hell of helping them make changes. So if the VP of sales is fighting me from behind the scenes, because I'm training his people or coaching his people or her people, and they're fighting me well, you know, Caskey is good, but I don't pay attention to that. I mean, that's, that's not right. So I have to. And so you've got as a sales professional today, I think you need to get right with this idea that the more people you talk to, the better the implementation is going to go. And if you do that, if that's your mindset, then it becomes a lot easier to say to your buyer or your initial relationship. Look, here's how I work. I know that the most important part of this is you getting your problem solved. That's really why we're even doing this in order to do that. Implementation is important in order to do that. I need to have some conversation with some other people, if you're uncomfortable doing that, I don't think I can propose if you are. Let's talk about what that looks like.  
Speaker 1    00:33:48    It makes perfect sense. I think there's also, I think this goes back to our original conversation, built around confidence, that confidence to ask that question like, Hey, I need to get to this person. They can say no. Or there could be a hesitation that we need to address with them. It's a fair hesitation. I think that goes back to confidence. That goes back to that mutual action plan we were talking about. Here's the typical things we hear here's who typically gets involved in some challenges that we typically hear. It's advantageous for us to flip that off. Now I think that kind of boils back down to that whole confidence level. Yeah, it  
Speaker 2    00:34:20    Does. It does. And a lot of this, the confidence level is funded. If that's the right word in part by what's your lead generation strategy, do you have an abundance of discussions happening every day, every week, every month so that you know that if you start 10 discussions, four or five are going to end up in business, it becomes a lot easier to make the demand of look, here's who I need to talk to. If you've got a bunch of people who are waiting to work with you, and that's where social media, that's where marketing comes in, personal marketing plans. You're right. It all works together because if I only have one client in my funnel, and this is the person I'm talking to, and I got a demand to talk to the president, I'm not going to do it. It's too shaky. I'm on shaky ground. Yeah.  
Speaker 1    00:35:06    So let's kind of reverse engineer this a bit like, okay, we made some missteps early on in our process. We didn't pull in the right stakeholders. The good news and kind of elaborate on this from your bill is it's never too late. It's not linear. Right. It's never too late to basically, I don't wanna say start to your point. We either cut it. If it's just not the right deal. That is an option. But maybe we didn't do our part. It's not a bad thing to take stock and say, well, maybe if I go back and basically redo that step, should I ask for the stakeholders? Is that so much blocking and tackling that a no brainer or what's your thoughts around that?  
Speaker 2    00:35:40    Well, that's probably the only path forward. Sometimes let's just presume that we've jacked it up somewhere. We've messed up because we didn't ask the right questions or didn't find the cost of the problem. We've got to take personal responsibility to take that on ourselves. And so the way I would always recommend people is just do a reset. And sometimes you have to go to the prospect and say, look, I've messed up and I've messed up because I didn't involve the people who I thought might need to be involved. And that's all on me, but I can't go any further unless we, whatever the thing is, we either have a conversation about that. Or we engage some more people. You have to do it in a nice way, or you're not going to look. If you don't do that, I'm going to take my ball and go home.  
Speaker 2    00:36:25    But we have to be straight into the point. And we've got to be articulate in how we communicate that. And it's got to always be with the customer's end goal in mind. It can't just be about we're going to make the sale easier. If we talk to more people that can't be it. It has to always be framed around their solution, the implementation. I want you to love this and you're not going to love it. If we don't make it happen and we don't get more people involved, it's not going to happen. So you have to frame it properly. And that's where language comes in. I don't like the whole language thing where we talk about, well, if he says this, you say that if she gives us her objection, you'll give that response. It's like, oh, come on. But it is important to have language when you're framing something, especially when you're trying to reset the whole process. I'm not for cutting bait. When I say you leave. That's not my first option. My first option is always to let's see if we can salvage it.  
Speaker 1    00:37:18    I think looking at deals that went south and closed loss, I was closed loss stuff for did not close. It did not convert into a customer is trying to do a deep dive on those. And where did we miss? What are we seeing as the commonalities were, were missing? Like, Hey, we only have one stakeholder involved in there. You know, 90% of deals that we have one stakeholder do not close. Well, then that should educate us on. We're only having one stakeholder, how do we get more people involved? Right. And that's that to our conversation about self-education right and learning.  
Speaker 2    00:37:48    Right. Exactly. I would even say that that's probably more important if you can be rigorously honest with yourself here and not hide something. Well, you know, we were talking to the right people, but they just didn't like our website, you know, crap like that. I think that's more important than going and asking the customer, why did we not get the business? Because you may not get the truth out of that. Well, you didn't get the business because you're 20% high. Well, what are you going to do? Lower your prices 20%. Of course not. Yeah. So I think some self-reflection, there is a better strategy than going to the customer and asking them why, because a lot of times the customer heard they've gotten that call before. And a lot of times that call is designed to reinvigorate things. So we're really not just doing research. We're trying to find out what did we need to say that we didn't say, and then we'll say it and see what happens and people are onto that crap. So I agree. I think self reflection, and I think your example is perfect as we close 90% of the business, when we're talking to the CEO, the VP of sales and a sales marketing person. Well, in these 20 here, we didn't talk to those people. Right. It was a pretty easy solution then,  
Speaker 1    00:38:54    But then also educate how you begin the training process and education process and those types of things. Right?  
Speaker 2    00:39:00    Yeah. I think who to call on inside your prospect organization is frankly, more a function of your mindset and your confidence than it is trickery or, or some kind of attack. I think it gets back to who do I deserve to call on? Do I deserve to call the CEO? Do I deserve calling the VP of sales? Is my value big enough that a VP of sales would say, yeah, come on in. I want to talk to you about this. And if we don't see ourselves in that context of value as being worth much, then we're not going to make that move. And that's where self-worth self-value we give that. We say, well, that's soft skills. Yeah. But that's all there is. It's all there is to it. I mean, if you want to grow your business to X in the next five years, you need to work on your confidence level. That's all, you know, you can work on your hacks and what kind of questions you ask. Okay. But it really gets back to mindset.  
Speaker 1    00:39:53    You know, the other piece of that puzzle here with these hacks is the one thing I've learned in sales is there is no universal truth, right? There might be one universal truth that there's no universal truth, right? I mean like what works for you versus me? Because there's one common denominator. Everybody's different. Every prospect's different. Every conversation is different. Me knowing what Sam said that. So I gave him this answer, but bill said like, it would drive someone insane to try and predict every minute, answer Cuban.  
Speaker 2    00:40:23    You can't do it. So the answer to that for me, and it may disagree with this or other people I know other people do because I was at a program once where I, I espoused these things and they obliterated me. We still laugh about it. There, there are a lot of naysayers here about mindset and I'm one of the people out there who says, that's where it all begins. Now you need no language. I need to be able to articulate your value. You need to be able to ask good questions, of course. But if you don't have the courage to get in front of the people who are actually going to influence the decision and because of that, you don't get the deal. You've wasted their time. You've wasted your time and you're not going to grow your income. And so confidence and mindset and all the things around that are just, they're critical. And I think they're more critical today because we have so much market chaos and there's so much change in the market and, you know, jobs and people that you called on a year ago are not there anymore, or they've taken on seven times the workload. And so they don't have time to, I mean, just all this stuff that came from the pandemic, you're starting to see it here  
Speaker 1    00:41:27    From a sales leader. I know we kind of talked about it from a deal like from a sales leader, how should they get their head around really coaching training, making sure deals are deals and fact, and moving the deal forward, like, what is their role? What is your recommendation on really helping your sales rep either become more realistic, not so optimistic or helping them identify those gaps that they're missing your recommendation. Get on that.  
Speaker 2    00:41:50    Well, the sales manager, they're the linchpin to all this. And I do a program called a world-class sales leader, and it's a mastermind for sales managers and sales leaders have been running for a couple of years. And I always say that you're the linchpin, you're the person that makes it all work. And you've got to bring your best game to the field every day. And if you let the CEO start both threats at you and all you do is throw threats down to the sales team. They're not going to grow and by threats, I mean, Hey, there's going to be layoffs. If we can't make our number and that kind of crap just doesn't, it doesn't fly. It doesn't fly. It might fly for a quarter. But at some point you've said that so many times like, okay, whatever. So I think it's up to the sales leader to take stock of, okay, I've got to inspire my people and I've got to instruct my people.  
Speaker 2    00:42:42    And in a way his or her people are his customers. They are his client base. So just like your sales team is trying to inspire and instruct your client on how to buy your sales leader should be doing the same thing for the sales team. And I find that sales leaders generally are more into the numbers. That's all they look at. Not all, but 90% of the time they're looking at the numbers. And when you have a sales meeting, it becomes a forecast meeting. Okay. Have you got John Smith there? He's been in the funnel for 90 days. When are we going to close that? Well, it's about a 75% chance that it's going to close now. Okay, John, what about, oh God. I mean, do you know salespeople hate those meetings? They absolutely hate them. And so they're just mailing it in. If you have a meeting where you spend, maybe you spend 15 minutes on the forecast, but you spend the next hour and a half on how we can all get better looking at funnels where there's not enough in.  
Speaker 2    00:43:40    It is not inspiring to people. I did a podcast here a few months ago and I just gave it to sales leaders. And I had so many of them write me, email me, LinkedIn, and say, you're exactly right. They can handle it. They can handle this kind of criticism and this kind of change of thought. And they all said, yeah, you know what? I find myself, because the CEO is always down my throat saying, when's that going to close? You know, we've got a factory. We need to keep busy. And then I just pass that onto my people. Sales managers know when they're doing that, they know their stuff.  
Speaker 1    00:44:11    It's a fair assessment. You know, I'll fall on the sore. Like I find myself, I laugh because I can play back some of my calls. And I I've heard those. This has been sitting in this stage for 90 days. Why the closing not move? It's all very linear type of things. W w I said, if I dating, okay, let's go to the next one and you check it off and okay, let's this one. And you're right. It's fine to have those competencies necessary for the world and forecasting and all that. But that's not where the coaching, that's not coaching. That's, that's not helping your team at the end of the day. It's giving them some transparency maybe, but it's not actually helping them move the needle around getting those deals  
Speaker 2    00:44:48    Over the goal line. Yeah. And if you're a sales leader and you've just heard what we talked about here, have a checklist, have a filter say, are we talking to the right people? Because you know, 90% of the time we close deals, it's because we're talking to these three people have it. And then when you have a deal that comes up, get the checklist out and say, let's see how we're doing against. We know our philosophy. Our philosophy is talk to everybody in the organization who cares about the solving of a problem. And if we're not following that philosophy and we're not closing deals, then don't harass people for not closing the deal, instruct them on how to better follow them philosophy.  
Speaker 1    00:45:20    So just to kind of boil that down, I know we're bumping up against it. It start with the philosophy. That should be your guiding light. Well, what is your philosophy? And then as a result of that lot, like you were saying, abundance is your philosophy. I'm just picking that because that's what you said. If you approach it from that, you get a lot better at cutting bait when there's just really nothing there, because I don't have time for something else. I know you said that that's not your first option. I know that that fair. Yeah.  
Speaker 2    00:45:45    Your philosophy should dictate your sales process. Your philosophy should always dictate that. So if one of your philosophies is we aim to engage the client in a way where they become crystal clear about what their problem is. Not just us, but them and all the stakeholders need to be clear, then make sure that's part of your sales process. But if you don't start with the philosophy, then you're, you build a sales process where you're trying to get their money. And people can feel that. I know that we're going to have listeners to this say, well, that's what sales is all about. Getting their money. I don't think it is. I think it's about helping people solve the biggest problems that they have in their business. The money will come, the money will come. It'll probably come and barrel falls versus cup falls. If you're only interested in what you're going to sell. So it's part of that overall mindset shift that I think shows itself all the way through the process  
Speaker 1    00:46:34    And bill, I think you would agree with this, cause I know it goes right alongside with what you said, is this going gotta be a win-win it's not a win lose for the customer. Like, Hey, I tricked you into buying something. There's not going to be a long-term customer. They're eventually going to wake up to it and there's going to be a high churn. And that's another issue you're going to face from a customer success standpoint. Like you should always approach this as if this is not the right deal for both parties, having this conversation  
Speaker 2    00:46:58    And think about the freedom that comes with that attitude and that philosophy. The freedom of look, I'm going to ask you questions. I'm going to share with you how we work. I'm going to share some testimonials, we're going to get into this. But at some point, if either one of us says, you know, I'm just not sure this is the right time or the right deal. Or I don't feel like you're committed. Let's both have the agreement that will, but it's not a trick. I know there's one trainer out there who is always into the trick mode, you know, probably know who it is. There's always a trick behind it. There's always like a card that they're not playing. I don't think you need to do that because I think that screws up your karma. Number one. But I think secondly, the prospect can feel that they feel that when you're sincerely saying, look, if this doesn't fit after our second call, let's both agree. It's not right. If you believe that, sincerely, they're going to say, yeah, this is a person I can trust.  
Speaker 1    00:47:48    Yeah. And I think that, you know, outside of confidence level, and I know this is old school Zig Ziglar, but he was a big proponent in, if there's no trust, there's no deal. They've got to trust you. People buy from people. They don't buy from companies. There's got to be trust at the foundation level. And I always try to approach us. And, and, and this might go against some philosophy here as well, but just have a conversation. It's not all about an interrogation. It's not about it should be around learning. Hey, I'm just naturally curious about this, this, if it happens to tie into our business, fantastic. If there's not a fit there, okay. They think that's where we kind of lose sight of them. We start doing these tactics, these ploys, these kind of these carrot and sticks mentality type of deal.  
Speaker 2    00:48:32    Well, think about the amount of data that's available. If you're in a software business or a SAS business, all sales people are managed by the data. And when we know if you have 17 calls an hour and 17 of those convert to three, this and that converts to one, this, and it's all about data. And we live in a data rich world. But unfortunately I don't think the data is the root cause of anything. I think it's a reporting mechanism. It's good to know, but I want to get back to the basics of how are you may feel during that first call. You're making them feel like on edge and resistant and like, oh God, this person, or you making them feel comfortable where they will share some of their issues. And I think it's becoming a lost art. I hope hopefully some of the work that we all are doing is helping, but you know, in a world of data, there's no emotion in data. It's all intellectual. We always say, well, buying is 70% emotion, whether it is or not, who knows what the number is, but customer doesn't give a damn about your data. They care about their world.  
Speaker 1    00:49:33    Well, without a doubt, so final thoughts, but I know we've talked about a lot of different things. Nope. Kind of final thoughts, wrapping it up like tips, techniques, just final thoughts in general, to leave the audience. As it relates to the subject at hand around kind of managing the deal, understanding of philosophy, adopting a philosophy, having that just in general,  
Speaker 2    00:49:53    I'll give you five things that real quickly we have what we call the fundamental shift. The fundamental shift is the shift required in thinking to go from where you are today, to whatever that next level is. Number one, you've got to think abundantly. We've talked about that. You've got to see abundance. When you look out and again, the abundances of pain that people have. Number two, you have to have high intent. The intent has to be about creating an environment where they want you worse than you want them or need them. The intention is all about their issues. Number three, detachment. You've got to that. You've got to become detached to deals. I'm not saying disengage. I'm saying you can't make the deal more important than them getting their problem solved is important to them. So there's an element of detachment for thing, as the buyer seller interaction, we've got to change our rules around that.  
Speaker 2    00:50:44    It can't be constantly a convinced and persuade and hammering them and calling them 17 times the buyer seller interactions volatile. And you've got to understand that. And then the fifth thing is who are you? Are you a salesperson or are you creating content? Are you publishing content? It's really helpful when you shoot a LinkedIn video? Is it just about how great you are? Or are you saying, look, there's three trends that are facing people. Like you, let me share these with you. And if you want to talk further, we can do that. But are you educating people? And when you do your status changes, you're no longer that cheap Weasley sales person, you're a go-to resource. And so those five elements of fundamental mental shift and psychological shifts, I think would help people. You can learn more. I know you're probably going to ask that if you want to, we're doing a, actually a webinar here in a week or so a couple of weeks called the five week and you don't have enough clients. And I'm taking things that we've talked about today. Going a little bit deeper. If your audience is interested, it's complimentary. They can go to bill Caskey, CA S K E y.com. The very top banner. There's a, you can click that link and jump on the wait list for the webinar and we'll send you an invitation, but that would be good if you want to take this a little bit  
Speaker 1    00:51:56    Further. No, that's fantastic. And we'll add that to the show notes as well. Happy to do so. And I'm excited, you know, cause a lot of the things that you shared bill w was good. You know, as a sales leader, you've got to reassess and you've got to figure out where are you spending your time with your reps? How are you actually helping them get to the next level? And you know, two things I took specifically, a lot of things I took, but I'm a big believer in the intent of a podcast is not to agree with everything is to take one or two things and say, I'm going to drive that home. I like the philosophy piece. You got to have a core philosophy that drives that. And then from there with an a part of the philosophy is if you need to get deep in why you, if that's a philosophy is we're going to talk to you. Every stakeholder then adopted. And that's what you drive as kind of the leading indicators, as you're doing deal, assessments, deal evaluations, whatever. And that little checklist you said, Hey, Hey, we know 90%, boom. We only have one stakeholder in this one. This is going to go south. Like if you do nothing else, those three things jumped out at me. So I hope that that resonated with the audience  
Speaker 2    00:52:58    As well. Synopsis Sam, I think you've nailed the three most important things there. Another sometimes a little harder to get there. The checklist I think would be pretty easy for people. That's a quick win. Your sales leaders should have that with them. Anyway, the philosophy piece and the confidence is it takes a little bit of work, but start, you've got to start somewhere. So start now.  
Speaker 1    00:53:18    Well, bill, just once again, I know, let us know how the audience and just get that web address one more time and then how they connect with you potentially on LinkedIn. Just any other ways they can connect with you,  
Speaker 2    00:53:27    Bill. Yeah. Thank you. Go to bill caskey.com. There's plenty of free resources. There links to my podcast. I've got two of them and uh, the links are there. And then if you want to connect with me on LinkedIn, just search on bill Caskey, C a S K E Y. And I shoot a lot of videos. I publish a lot of content on LinkedIn and so that might be a way that we can connect personally. So those two web properties are probably the best bet.  
Speaker 1    00:53:51    Awesome. Well, thanks again, bill for your time. Sincerely. Appreciate  
Speaker 2    00:53:53    It. Thank you, Sam. It was a great interview. Thank you.  
Speaker 0    00:53:58    Thank you for listening to the sales samurai podcast with your host, Sam Capra. Be sure you subscribe to our podcast and visit sales samurai.io and join the conversation. Access show notes and discover bonus content. <inaudible>.