Episode 13 | Part One: The New Rules

Gregory Shepard, an entrepreneur who's built and sold 12 businesses, a recipient of 4 private equity awards, TEDx speaker, and Forbes author. This is The Boss Podcast with Gregory Shepard.

Welcome back to The Boss Podcast. If you're enjoying the show, please tell a friend. When you get a chance, tell us what you think. Leave a review on Apple, Spotify, or wherever you listen to a podcast. Now, let's get into this. Every entrepreneur can't do it all, but you need a particular set of skills to succeed. Joining me this week is a business coach that helps executives and sales teams prosper by developing new skills for their success. He's the author of Same Game, New Rules and the host of the Bill Caskey Podcast. His name is Bill Caskey. Bill, thanks for joining me today.

Well, Greg, ever since your people asked me to do this here a month or so ago, I've been listening to your podcast and I really, really like it. You're very good at what you do. This is also— I'm grateful to just be here. I think it's going to be fun.

Oh, that's generous. Thank you. That's very generous. Bill, I've always been fascinated by business coaching. I'm really interested in how you became a coach to start out with.

Yeah, I got out of college a long time ago. And the only thing— A long time ago. Yeah, the only thing I really had on my radar, everybody said, you know what, Bill, you need to get in sales. You should be in sales. Try for a sales job. And I really didn't want to go back and get an MBA. I wasn't smart enough. So I started hunting around for sales jobs and I found one with a Caterpillar dealer in Indianapolis. And it was kind of an entry level and you'd go out and call on contractors. And I had such a bad taste in my mouth because there was no training, there was no coaching, there was no nothing. And I really struggled for, you know, for several years at that. And it wasn't until I finally, it was almost like an awakening. One night I said, you know, Kasky, if you're going to be successful in anything in business, you'd better get some training. You'd better get some, some knowledge and some wisdom. So that kind of set me on the path of trying to learn all I could about selling and business and strategy and marketing and all those things. So that was back in the, in the '80s. And then in 1990, I started my own training business because I felt like, well, if I'm going to learn this stuff, the best way to learn it is to teach it. So that's what I did.

That's true. That's true. It does work that way. I love your humble beginning because I have a very similar background, you know, starting with nothing.

Yeah.

And moving my way up.

Sometimes I'm afraid to tell the story because it feels like, well, if I'm going to hire you to be a sales trainer for my company and a coach, you didn't like sales, you weren't good at it, why would I hire you? But I think we all have a transformational experience from the time we're young or the time that we didn't do something well and we knew we were awful at it. At some point you just decide, you know what, enough. I got to get good at this. Yeah.

And, you know, I always think there's a difference between intelligence and experience, you know? So, you know, what you have is you have the ability to have the intelligence to understand, you know, the little algorithms that have to do with sales. But then you have the experience and the wisdom because you've been doing it for so long. Right. So you can't— you can't teach experience to somebody unless you have a class environment like you do with your firm. One of the things that caught my eye, I wanted to ask you about this. One of the things that caught my eye on your LinkedIn profile is mindset plus mechanics equals results. Can you walk me through that a little bit?

Yeah, I'm a pretty simple guy. At least that's what my wife and family tell me. And I need to block things down and make them simple. And so over the last 20, 25 years, I've written a lot of content. And 2 or 3 years ago, I looked at all the things that I had done and ask myself, is there a way to simplify this a little bit? Because, you know, having 17,000 things that I'm going to teach someone doesn't work very well. So I, I came up with this concept. I think there's the, there's the mental game or the emotional game, and then there's the mechanical game. There's everything that happens outside and everything that happens inside a salesperson or an entrepreneur. And I think the inside is every bit as important as the outside, and yet not too many people really teach and train and coach much on the inside stuff. And when I looked at my clients over the years and went back and, you know, kind of assessed how they were doing with the material, every— almost every one of them said, Bill, you know, you have good sales techniques, but it's all the mindset stuff that has changed my world and changed my life.

Uh-huh.

And so as I started to hear that, I started to dive even deeper into the mindset And it's fascinating because it's like another dimension of growth when you start talking about mental constructs and frameworks and points of view and things like that. It never ends. Whereas there's only so much technique you can teach to somebody. If you get good at asking questions and positioning yourself, there's 5 or 6 other things, you're kind of at the end of that line. But mindset, it just never ends. And there's never a lid on how high you can go. If you keep working on it.

So, so mechanics is like tactic, like tactical stuff, right? And so, and maybe strategy also, right? And then, but mindset is like how you feel about what you're pitching and what your internal sort of mindset is on, on the customer and how you're approaching the process. And you see these things as being different things.

Yeah. Here's an example. If I have a coaching call, let's say I have one coming up and the person in my coaching program says, okay, Bill, I've got this situation. I'm going out to see this prospect. It's our last meeting. We've had 5 meetings and this is kind of the come-to-Jesus meeting. And I really need this business. So I need some help in how to position, blah, blah, blah. Well, once he says, I really need this business, I stop listening. Because once you have identified that you are more okay with a piece of business than you are without the piece of business, you're in trouble. You're operating from a one-down position. So, that's an example of—

So, in your mindset, so you're saying you've now basically reduced your internal leverage the way you feel about your own—

That's correct.

Oh, okay.

That's correct.

That's just an example, maybe not a great one, but an example of how our thinking gets in the way. So now when I suggest something to that person to go do in this last meeting, only certain suggestions are going to be open to him because he's in a desperate situation.

Mm-hmm.

So I might say, here's what I think you need to say, and he'll say, okay, and then he'll get in the meeting and he won't do it unless I address this neediness, scarcity mentality, mentality of lack. Until I address that, My coaching is not going to land.

You know what, this is— it also reminds me of like when you're doing a transaction and when I'm selling a business and I'm in a deal, like I invest in a company and it gets down to the end of the road and I'm doing the negotiation, I always have this mindset of like, I'll walk from this deal anytime. And so, that's what you mean by the mindset. That's really interesting. I think it's really effective, not just for selling a deal, but even selling a company or raising capital or even just raising capital for your company.

Or dating. I mean, yeah, because there's always another— there's always another deal. You know, Greg, you— if you don't get a deal, I suspect you have them lined up 3 or 4 deep. So there's always another deal. Now, if it's— if it's my only prospect and I've got nothing else in the funnel, well, guess what? I'm going to— I'm bound to be desperate. There's no way I can walk in with confidence there because I need this deal too much. So that's where the mechanics come in, because it's not just a mindset game. You have to have the mechanics, you got to generate the leads, you have to understand how to pitch and position your product. So it's both, but I have found that mindset and mechanics is an easy way to frame everything so that people who are simple like me can say, okay, I get this.

Yeah, I love that. I love that. And you've said that the customer doesn't have time to connect the dots of your complex solution. So you got to get good at explaining The complexities, because a confused buyer just doesn't buy anything.

Never buys. Yeah. I don't know who said that, Greg. A confused buyer never buys. I love that line. I never know who to attribute it to.

I thought it was you.

Well, maybe it was. No, I've said that before. Whenever I hear something, I always like to attribute it because I think, you know, it's only the right thing to do. But I've never figured out on that one. And then sometimes you have a saying and it turns out there's like 19 people and everybody's fighting for the mantle to say who said it first.

When you sit down with your folks, right, and you're coaching somebody and you're sitting there going, listen, you need to make sure that you connect the dot, you explain this to them in a way that they can get it. So, you know, because of the fact that a confused buyer just goes, look, I don't understand it, I'm not going to buy it, right? And this is the same with an investor. Like when I look at businesses to invest in, if I don't understand the business, I don't invest, right? I have to understand it. I'm assuming this is a mechanics thing more than a mindset thing.

I agree. Yes, it is.

So how, how would somebody sort of go about— what would be the process that they sit down? Is there 4 bullet points or something that they would go through to understand that? Or do they read Same Game, New Rules, your bestselling book, in order to get that?

Well, of course, you know the answer to that, Greg. No, I think you said the key word there, and that's process. There is a process to communicating And unfortunately, what we have tended to do, and I think entrepreneurs are kind of bad at this generally, I'll probably lose 90% of your audience by saying that, but we entrepreneurs are so damn proud of our value and the product and the service and how great we are that we never think, okay, well, how am I going to take that value and really communicate it properly to a person who's either going to raise their hand and say yes or walk away and say no. So this packaging of the content, packaging of the message is really important. I was on a call yesterday with one of my coaching people. She sells to the public sector here in the US, to federal government and military. And she was having trouble getting the second call. So she would call an Army major up, National Guard or whomever, and say, look, I've got this product. And this person would say, well, let me pass you on to my lieutenant colonel and they'll see if they like it. You send him some information, and if we like it, we'll set up a call. And guess what? Nobody ever calls. And so I said, what was your message? When the person said, well, tell me what you do, what did you say to that? And it was some— I wish I'd have had it recorded, but I'm not trying to belittle her, because she just never thought about it before, but it was basically a we message. We, we, we, we do this, we do that, we do this, we're going to be awesome for you. And I said, what are the circumstances that that major, colonel, Commander, is going through in his life right now in absence of your product? There must be some pain, there must be some frustration, untenable dilemma that they're in. And she goes, oh, that's easy. She goes, these people have a problem with 3 things. Number 1, security. They're never sure whether their stuff is secure or not. Number 2, migration, blah, blah, blah. Number 3— I didn't understand what she was saying. But the point is that those 3 things were emotional circumstances that would speak directly to this person.

Mm-hmm.

So rather than make these messages— and that's probably the number one lesson here that an entrepreneur listening can take— is, okay, when I go out and deliver my message, is it about me or is it about them? And it's got to be about them because they have no way of connecting the dots if your message is all about how great you are. They just have no way of doing it. They're not going to spend the time to do it.

Yeah. I mean, I think about that sometimes too because when you're— I get pitched probably, I don't know, 100 times a month, a business.

Wow.

And it's very rare that the entrepreneur on the other side tries to understand my perspective as an investor, right? So, you have upside and downside and they don't do that, right? They go, this is our business. This is what we do. It's exactly what you said. That really resonates with me.

Here's our return, here's where we're going, here's what we're anticipating— nothing about you. And you're the guy that is going to make it or break it for them, possibly, with investment. So it's just a— I think it's hard for us though, Greg, because we are so used to looking through our eyes all day long. It's hard for us to shift gears and look through the eyes of another. And that's really what core key messaging is, what's my customer facing? What are their dilemmas each day? How is their life not so hot because I'm not in it?

Oh.

And boy, if you can isolate and write down 5 to 10 things, now you're building your message. And that's how you get someone's attention is you say, look, we work with VPs of sales who struggle with 3 things basically. Number one, they look at their sales team and they know their sales team could be better than they are. There's good people, but they're just not generating the new business they know they should. Well, I'm just giving you an example. That would be an example of something that I would say to a VP of sales. Well, there's no VP of sales alive that doesn't have that feeling somewhere, like, yeah, we could do more. Yeah, we're good, but we could be so much better.

It's like mile in their shoes kind of thing.

Yeah. So if I can tap into a little bit of that emotion, now they know That's fantastic.

Do me a favor, Bill, and hang on for one moment. Coming up in the second part of my chat with Bill Caskey, the author of Same Game, New Rules, Bill talks about the importance of shifting your mindset when it comes to making a pitch.

I think if you get your mind right, and you— and by that I mean you think abundantly, you don't think scarcity, you don't think scarcity. You think about bringing value to a prospect or to a customer versus what can I get out of the deal.

Learn more about the BOSS Business Operating Support System at bossstartupsience.com, or you can reach Gregory Shepard at gregoryshepard.com. This has been a production of Forbes Books.