Why Questions Matter More Than Answers In Business

Jeffrey Madoff: This is Jeffrey Madoff, and welcome to our podcast called Anything and Everything with my partner, Dan Sullivan. We were talking about our upbringing and business and how we approach different things. And I thought it might be interesting to explore ideas such as fulfillment and success and values and decision making and all of these kinds of things. And I'll start asking you about the entrepreneurial journey that you've been on, Dan. And is there any difference between your journey and the fulfillment that you've experienced as a result of what you do?
 
Dan Sullivan:Dan Sullivan: I can think immediately of a couple of things. And one was right off the bat, and this is 1974, we're talking about my first real entrepreneurial venture. And I wanted it to be about ideas, okay? And I was never tempted to go into a product industry, you know, like you're selling products and everything like that. One is that I just don't think that I have the mindset for it. But the other thing was that from childhood, I had really discovered that a lot of people aren't good at asking themselves questions. And if you are good at just asking them questions and get them thinking about things that they hadn't thought about before, new ideas pop up for them, and that you know, with some trial and error in the marketplace, I was able to actually get them to pay for that.
 
And in the early days, I just had big artists, you know, artist sheets. I have layout skills. I can draw arrows. I can draw circles. I can draw boxes. I could write. And I think that was really the key to it. I don't think I could have done as well as I did if I'd gone in another direction. So I think the big thing is that Strategic Coach is about thinking and it's about ideas. And from our standpoint, from the Strategic Coach standpoint, we're the askers of questions. And it's really interesting just to put a modern, up-to-date slant on what I've just said, is that ever since AI came out, people said, you know, Dan, people want to ask you questions, so why don't you create an AI bot? And then people can ask the bot, and we can use all the books you've written and all the podcasts you've done, and there'll be a you, it'll be a digital you, and they could answer questions.
 
And I was never tempted to do that. Because when we did a survey, we talked to about 10 clients. Would you actually use, you know, if I created something like this? And they said, no, Dan, we want you to ask us questions. We don't want to ask you questions. And so we could have spent a lot of time on that. And I think it would have been a waste of time. And I think it would have been a waste of their money if they paid us for that. And my sense is that the key skill of our business is that we're asking them questions. They have to really, really think, use their experience in a different way. And they come up with entirely new strategies. They come up with other ideas. And that's really been the basis now for this going on 51 years.
 
Jeffrey Madoff: Well, full disclosure, since I'm a believer in generative AI, I am a bot. And I have been learning from our conversations through our last two and a half years or so doing these podcasts. And I'll see if I can wake up the real Jeff Madoff, so that you can talk to him instead of that bot. But you're good at questions. Well, why do you think that?
 
Dan Sullivan: Yeah, it's like the British. Why do you British always answer a question with a question? And the answer is, do we? Yeah, it's always struck me that questions are exponentially more powerful than answers.
 
Jeffrey Madoff: Oh, I think so too. So you created a business based on ideas, about the thinking, about thinking and so on, which is, one of the things that's interesting about it is that your vision, did you have a vision of success about your business when you started coaching? Do you have any idea of what that would be, or is it something that just evolved? I had the monthly rent in mind.
 
Dan Sullivan: No, I mean, as you've pointed out that from a coaching standpoint, using the word coaching, which we really didn't until I was at it for about 10, 15 years. And it was actually a client who gave me the idea that it should be called coaching. I was coaching, but, you know, I used to do house calls. So when I was a one-on-one coach, I would make an appointment, but I would go to other people's offices and we, you know, we'd have a boardroom and, you know, I'd ask questions and it would be a conversation. There was a time frame for it. So it would be a couple hours. By the end of the two hours, I'd have a drawn-out plan for them that was on a sheet of paper. Then I would go to a blueprint shop and I would get an actual size vellum of what I had drawn out.
 
You know, my handwriting, my printing was really good, you know, and they love these big pictures, came back, you know, and this was done on a quarterly basis. I arrived one day with a client and he had a friend in the office and he said, I'd like to introduce you to Dan Sullivan. He's my coach. He's my strategic coach. Yeah. And I said, bingo, bingo. And I called up the copyright office. You know, we put in a copyright and we got that. But it was actually a client who named us. And that's actually a good thing when somebody who's writing you checks actually nails it. You know, so that was around ‘80, ‘86, 1986. I'd started in ‘74. So I was 12 months in and both years—yeah, 12 years in.
 
Yeah, that's the reason why Babs handles the numbers. You just got a little picture of the trouble I caused myself with Babs, yeah. And the world had changed in 12 years. The biggest, and I'll ask you the question, whether you saw a significant change in your life when the personal computer came along. That was really the difference. I think the entrepreneurial world really broke open around 1980, ‘81 with the first personal computers, and by ‘86 or ‘87, they had software. Software was now becoming really important. Software was becoming more important than hardware.
 
Jeffrey Madoff: You know, the two things that I started my business with, the first thing was an answering machine. You know, so if I wasn't around, I could get a message. So that was the first thing. And that was a few years before computers, you know, personal computers came out. I actually built my first computer. And I knew that I wanted to get one, I knew I wanted to learn. about it. And I decided to build it. And I built this computer, it was an Eagle computer, one of the very early PC clones. Quick sidebar on that is the company went public, Eagle, and you know, it's considered a great PC for its time, you know, looking back quite primitive, but there was a party for the going public where the founder all of a sudden became pretty wealthy.
 
Dan Sullivan: This was New York based?
 
Jeffrey Madoff: No, I think it was, yeah, it was California based. And on the way home from the party, the founder was killed in a car accident. And that was it with Eagle. So anyhow, I had the functioning Eagle computer, and between that and the answering machine, but the answering machine was first. And I would argue in many ways, it was probably more important to have that than a computer if I would have had to make the choice, because I could always get back in touch with somebody. When did you first recognize that your vision of success and what your business was, was very different from societal expectations? And did that at all, what was the effect? Did that at all help shape your path?
 
Dan Sullivan: Yeah, well, I recognized it right away because it was an utterly simple business. I didn't have to do any prep work for it at all. There was no preparation. And it was all just an interchange between myself and the customers and clients. Clients, not customers. And the other thing was, it was very energizing to me because it was just my wits. I was just, depending upon my wits, and really listening to what people were saying and then asking questions. And I actually got the basis of it from someone who was an accountant for one of the businesses. And he had a little structure where he would use three years as the basis. And he says, you know, most accountants, they'll use the next year, they'll use 12 months. And he said, you know, yours are kind of arbitrary. You know, he says, things don't neatly happen in 12 months period. It's really, he said, you have to have a bigger timeframe.
 
Michael Nairn was the accountant's name. And he said, you know, if we were having the way he says, so what do you want three years from now? And I reworked that and I created a terrific question. And the question was, if you and I are having a discussion three years from today, and you name the date, so today's date in this year, but three years in the future, and we're having this discussion, and you're looking back over the three years, what has to happen during that three-year period for you to feel happy with your progress, both professionally and personally?
 
Jeffrey Madoff: It's a dynamite question.
 
Dan Sullivan: Yeah, it is. And it's the future perfect tense. You're actually in the future, but you're treating the future as the present. And then you're treating the actual present as the past. And you're creating this timeline. And one of two things would happen. One, if it was a prospect, they'd say, well, I don't even know you and I'm not going to give you that type of information. And I'd say to them, well, here's the thing. I don't know if I can even be useful to you. And the only way I would know that I could be useful to you is if you told me what you're trying to achieve. And then I see if I've got skills or I know other people who have skills that could actually assist you with that. And since you won't tell me, I think that we've reached absolute clarity that we're not going to work together.
 
Jeffrey Madoff: Interesting, yeah.
 
Dan Sullivan: Because in the service business, in the consulting business, you can waste a lot of time trying to turn a prospect into a customer. But if they did answer the question, it was dynamite. They would just say, oh my golly, he says, what a question. He says, well, I gotta do this. And the greatest one, and I actually put this in a book, I was given a referral And so I came in, and he said, you know, my friend works with you, and he says it's very, very useful. He gets a lot of value out of you asking him questions, and then I understand you sketch things out and everything. So I asked him the question, and he said, well, I tell you, he said, three years ago, I was a complete and total alcoholic. And he says, it's taken me three years just to get back up to ground zero.
 
So he says, over the next three years, I've got to do this. And he talked for 23 minutes straight. I actually looked at my watch. And he said, well, your program sounds really good. I hadn't said a thing. And I learned once you ask the question, you don't say anything. It's totally in the other person's, you know, it's their side of the net to respond. And it was great. And that relationship lasted for 20 years after I did that, you know, but we teach this, like all of our salespeople in the Program now, we have 15 salespeople, and they're asking the question, and I said, it gets rid of the maybes right off the bat. It's either yes or it's no. And I said, yeses reward you, no’s teach you, but maybes kill you, and you don't want any maybes. That question created our company.
 
Jeffrey Madoff: That's cool. That's really cool.
 
Dan Sullivan: I'll just say one thing. I had a really top trial lawyer, criminal trial lawyer, who was a client. And back in, this is 1995, he was getting $500 an hour in 1995. But they were all criminals. They had the money because they'd mostly stolen it. And so I asked him the question. One of the salespeople introduced me to him and I asked the question and he said, I'm a trial lawyer. My life depends upon question. He said, that's one of the greatest questions I've ever heard in my life. But it makes the future. It kind of tells the other person, look, what my program is, is about you, it's not about me. So I'm all ears, I'm just listening to what you say and then I'm going to direct what I know about how you can think about this in a way that I think you'll find valuable.
 
Jeffrey Madoff: So if Strategic Coach ceased to exist tomorrow, what aspects of your identity and sense of success would remain intact?
 
Dan Sullivan: You know, it's trying to think how old I was. You're asking a question that really relates to an important juncture in our company. And I think I had just turned 70. So it would have been 11 years ago. I'll be 81 in a month or so. So I was thinking about it, that Babs and I always fly together. So wherever we go, whether it's a business trip or a personal trip, we always fly together. So they had a little meeting and there was a party to go along with it for my birthday. And I said to them, we were meeting with the top 20 or so of the team members. And I said, you know, Babs and I fly everywhere together. And what if you got the word that we hadn't successfully landed and we're gone? You know, Babs and Dan were gone. And we did an exercise with them as a result of that. I mean, I didn't just hit them with the question and then didn't have something.
 
And I said, we have an exercise for you if that were true and Dan and Babs were gone—we have all the finances worked out. I said, you know, we've thought about the finances and what happens if we're not here. But the big question is, what would you do? And we said, what would you do in the first hundred days? And we had an exercise where they each said what they would do during the first hundred days. And it was a thinking, you know, one of our thinking tools. And two things came out of it, which was really interesting. And they said, in the first 100 days, I couldn't worry about what other people were doing in the company. And these were all team leaders, so they all had teams. Maybe at that time we were 80. And they said, I just have to focus on what the team, what we're going to do.
 
And the other thing is, Dan, we want a lot of your ideas on the shelf, meaning books, etc. Things that we haven't used yet. We just want a lot of material on the shelf. I came around to, what do you want Babs and I to do? And we went through a revolution of new structures, teamwork structures, you know, every activity in the company got defined. We don't have so much as jobs, you know, which is interesting given the project that we're working on. What we have is that the company has made up about 500 separate methods. And each person has maybe 10 or 20 of these, you know, how things get done, how workshops get put on, you know, every activity, how the marketing activities occur, and these were all defined as methods. And they're just a little diagram that says first you do this, first you do this, second you do this, third you do this, fourth you do this, and that came into play.
 
And then the second thing is that I have created enough material that the company could probably create new stuff for about the next three or four years, quarter by quarter for the next three or four years. But, you know, day after I die, I don't really care, do I?
 
Jeffrey Madoff: Probably doesn't even take a day.
 
Dan Sullivan: People ask me, they say, what do you want your legacy to be? And I say, legacy? I said, I don't think legacies happen until after you're dead, do they? I said, what do I care? And everything else. But there's a lot of stuff. The first tool that we had, which was the question I asked, that was our first tool. And now it's diagrammed, nicely printed, and it's an algorithm of steps that you go through and everything. That's the first of 250. We have 250 of them copyrighted. 80% are trademarked, and then we're starting the process of getting patents. So there'd be a lot of me that went on afterwards.
 
Jeffrey Madoff: But I was talking about if Strategic Coach, not you and Babs, but if Strategic Coach ceased to exist tomorrow, what aspects of your identity, you Dan Sullivan, your identity and sense of success would remain intact?
 
Dan Sullivan: I think a lot. I hadn't thought about the question. Our big thing was that the Strategic Coach would go on.
 
Jeffrey Madoff: Right, but I'm not talking about your death. I'm talking about what the business brings to you.
 
Dan Sullivan: I started all over again. Yeah, I mean, one of the thought exercises we do is if something happened that where you are, you couldn't do it anymore. And of course, this has changed a lot with Zoom. And I said, you had to move to an entirely new city. And you had to start from scratch again, just knowing what you know, and how you're doing it. How long would it take you to match what you've achieved so far? And with most of them say it would take us far less time, we could do it. Where it took us 30 years, we could do it in five or 10 years the next time. I'm still not answering your question though.
 
Jeffrey Madoff: You're not.
 
Dan Sullivan: I could tell just by your facial expression.
 
Jeffrey Madoff: Yeah, because I mean, you know, we have our businesses. But who are we without the businesses?
 
Dan Sullivan: I would be creating new thinking tools. I'm so used to it and I've been at it for so long. I've got such a grasp on how you put it together. My sense is I'll be doing this to the day I die. I don't doubt that, but I also… I'm just trying to see what an answer to this that didn't involve the business. How would I spend my day? Who would I be interacting with?
 
Jeffrey Madoff: How would you think about yourself? How would you describe who you are without your business?
 
Dan Sullivan: Well, I think what's happened is that it's not so much that I'm the business, I think the business is me. In other words, that I've become the person I am because of the business we've created. So I don't see any separation between the business and me. Partially because the role, I just play a specific role in the business. I'm not responsible for the whole business. I'm just responsible for my role in the business. And we have, there's a whole team that's already thought through the problem of what they would do without me.
 
Jeffrey Madoff: Right, but that's a separate …
 
Dan Sullivan: Yeah, that's a separate question. I'm sorry, your Honor, I'm just not going to plead guilty to this question.
 
Jeffrey Madoff: There's no guilty or innocence.
 
Dan Sullivan: No, no, I mean, I think the two, the business and me have merged.
 
Jeffrey Madoff: You know, how one's identity and sense of themselves plays out, you know, I think is really interesting. How much are we defined by what we do? And if we had to be, if we had to make that decision of who we are, answer that question without the, you know, if we went to a party and the agreement was you can't talk about what you do, you can't say what your job is, you can't talk about what you do, how do you describe yourself?
 
Dan Sullivan: Well, yeah, well I've got a, I'd be asking questions, you know. Well, I'll just play act here. I'll just play act here a little bit. Somebody will ask me what I do. And I say, I ask people who are entrepreneurs questions that they're thinking about the questions actually gives them a great deal of freedom. Okay. And people say, well, what kind of questions? I say, well, I'll ask you the question and then I'll hit them with a three-year question. And then all of a sudden that they're talking about themselves, you know, so I'm a trickster at a party.
 
The other one is the, when are you going to die question? And I said, well, I've got this great question. And when people answer, they tend to extend their sense of their life by another 10 or 15 years. They say, what's the question? I said, well, at what age are you going to die? You know, how old are you gonna be when you die, at what age? And they said, wow, I don't know, 85. And then I'll say, okay, let's not talk about 85, let's talk about 84. How are you gonna be physically when you're 84? Physically, mentally, financially, quality of relationships, assessment of the life you've lived over the first 84 years. And they'll get talking, and all of a sudden people gather around, you know, they'll answer it, and everybody answers it the same way.
 
You know, I've done this with about 20,000 people individually, and they say, you know, physically I'm in good shape, mentally sharp, financially well off, supportive relationships, feel really good about what I've done. And I said, so if you were that way at 84, what are the chances you die a year later? And they said, well, I wouldn't. And I said, well, if you were 84 in that condition, then how much? And they said, another 20 years. And I said, 20 years? And I said, well, we've just talked for 10 minutes, and you just extended your life by 20 years. Because you had a number before, and now you've changed the number. And it has a huge impact.
 
And I talked to them. And they said, do you have that written down? And I said, I've written books on it. you know, and everything else. I don't know, Jeff, I'm so, first of all, our business is so much not about us. It's so much about the entrepreneurs that we have in the Program that I don't really, it's more how, what happens to the entrepreneurs in our Program when they engage with us. It's not really about us. You know, we're kind of simple behind the scenes.
 
Jeffrey Madoff: No, you're not.
 
Dan Sullivan: I don't mean there's not a lot to it. I simply mean, but the approach is very simple. Our approach is very simple. You either want to talk about this or you don't want to talk about it. So if you don't want to talk about it, then we don't have a relationship. But if you want to talk about it, then we have a whole series of questions.
 
Jeffrey Madoff: So I think back on young Dan, who knows if he goes over to whatever her name's house that lives next door, Mrs. Wetzel, and asks questions, more cookies and milk will be coming. There's a possibility of a business model here.
 
Dan Sullivan: That's right.
 
Jeffrey Madoff: And, you know, we both know people that, we know that their self-worth depends very much on external validation and recognition. And if they don't have that, they strive to get it because they need that external validation. And I guess my question is, does that external validation, that recognition, you know, because people—you have a big following, people know who you are. And in that world, you are a very, very significant player. My question is, how much of your self worth has to do with that kind of external validation or recognition? Or does it come from something else?
 
I mean, we all establish our self-worth. We all want to be somehow acknowledged. And I'm just wondering, because I know it's all, the business is all about them. That's the business model. And, you know, as you and I have talked before, and I said, I don't, you don't consider yourself a therapist, but you do what a therapist does, which is you ask the right questions and hope the person can hear themselves. And that helps determine their direction. Think about how you think about yourself. Think about how you think about your business. So when I'm sitting in the audience and watching a performance of my play, and there's a laugh at a line that I wrote, or the applause or the quiet or whatever, there's an external validation that happens that feels really good.
 
When people say, did you write that? That feels good. As long as what follows is that it's not a piece of shit. It's good. But I also feel like I have a, I feel like my self worth is such, you know, I didn't have the play ‘till relatively recently in my life, but I did other things. And I always felt like it, you know, I had to be my own compass in doing that. And so, I think that, you know, it's interesting, so does, I guess the sense of, I suspect your self-worth, your sense of self and recognition would be, no matter what you ended up doing, you would find a way to somehow receive that. And does that make sense? Do you understand what I'm saying?
 
Dan Sullivan: Yep. It's a combination of factors that are connected to each other. It isn't just one thing, but it's a series of things. And fundamentally, I have control over all these things. Okay? First of all, constantly creating new things gives me a tremendous sense. So I've got a heavy production schedule where it's a quarterly production schedule that every quarter certain things, new things, have to be created. And these are used by other people. They're used by clients. And first of all, I've got myself in a situation, you know, where my relationship with my entrepreneurial clients is that they expect brand new things every quarter. And I've established this, you know, over decades that when we come, there's always going to be new things and Dan's going to produce it.
 
And then I committed myself 10 years ago that I would create a new small book every quarter. Okay, and there's a whole team, our Production team. And again, the clients expect that to happen. And the other thing is that, you know, there have been larger books created and they were good sellers and the books themselves brought new clients to our Program. And that was seen as a real breakthrough in our marketing, that these larger books that are, you know, produced by other outside publisher, really produced it.
 
And the other thing is my teamwork, especially my teamwork with Babs, you know, as creators of the company. And that's a daily thing, like I'm really conscious every day that I have one thing and I think that happened immediately when I met her. I met her, it's more than 40 years now, I met her and instantly I had a sense I would never want this person to think badly about me. You know, and I'm really, every day I'm very, very conscious that you don't do anything today that Babs would think something badly about me, okay, and everything like that. So I'm saying these, that these are all combined, all these different aspects, they're measurements, and she thinks that I'm super, I mean, Babs really thinks that what I do and how I do it is really super.
 
She has that. She would admit that the moment that she met me, she thought that I was capable of doing really, really great things. But as far as outside recognition, I don't really give it much thought at all. Outside of the people I know, I don't have any thoughts about being recognized outside of the community and the network that I'm in. Yeah, I mean, one of the ways that I put it about myself is that … and I think we have that in common, that our sense of who we are is really a function of how we're doing things. It's just a function of what we're creating next and who's involved with us and who we're in teamwork with. And I don't get any sense of outside, external recognition.
 
Jeffrey Madoff: No, I think that, you know, one of my sayings is, look at who's applauding before you take a bow.
 
Dan Sullivan: And why are they applauding?
 
Jeffrey Madoff: Yes, and as Babs is your validator, let's say, and I have Margaret and my kids and my closest friends who I would, that's what's most important. And it's never been tied to my business, which I think is, I guess, now that I'm thinking about it, is maybe why I could go from one thing to the next and didn't feel like I was giving up anything. I was going towards something else.
 
Dan Sullivan: Yeah. I do think the play, you know, the Personality play, though, represents a real shift of gears in your life. I mean, you were creating great productions, you know, for other people, for their, you know, for their life. I think the big thing is that your creative relationship with Lloyd Price was a real fundamental shift when you got to put all your skills together.
 
Jeffrey Madoff: Yeah, and all the things, the culmination of things that I have learned. That's right.
 
Dan Sullivan: And what you loved. And what you loved.
 
Jeffrey Madoff: That's correct. And along with that was the knowledge that I was not going to compromise what it was that I wanted to do. If somebody said to me, I'll write you a check, but you need to do this, and if the this was against what I valued, whether they were telling me that I had to replace somebody that I thought was great or whatever, I would just say goodbye to them. I would not compromise that. And I've had times where an offer or whatever has conflicted. On one hand, it's conflicted in the sense that it could affect my profitability or growth, but that was always a distant second to maintaining what I felt was the integrity of what I did and how I conducted myself.
 
Dan Sullivan: Yeah, I totally get that.
 
Jeffrey Madoff: Have you ever had anything that your decisions or your values were in conflict with what could represent very good healthy growth to your business or let's say profitable growth, but you weren't willing to do X in order to achieve that?
 
Dan Sullivan: Yeah, I mean, we've had a couple long, long time ago, you know, late 80s, early 90s, where somebody said, let's create a new company and, you know, and we'll invest and, you know, we'll be partners in the company because I have all these connections, you know, I mean, there was a sales pitch on their part, you know, to do that. And I just said, no, I'm not interested. And they said, well, you know, you only get a few chances like this in life to really take things where you are. And you're not thinking about this correctly because it's going to remain small as long as you're just doing what you want. And I said, yeah, but we're growing and we've always been growing and my figure will always grow. So anything I might get faster with a situation like this, we're going to get to anyway in the future. And we'll kind of do it our way. That was one.
 
The other thing, I've had some situations, and I haven't done one-on-one coaching for 36 years. So, you know, I just do workshop coaching, it's groups of entrepreneurs. And I've had people who have said like, you know, could you just come to California? It was a California person. And he said, I've got a private jet. I'll send the private jet. You know, we'll bring you out. This is like 19, 1992. And he said, then I'll write you a $50,000 check just to come out there. And I said, no, I wouldn't be interested. I wouldn't be interested in that. And they said, well, why not? And I said, well, I've done one-on-one coaching. And so that wouldn't be anything new for me.
 
And the other thing is that it was going to be over a weekend. I said, it's not, I take time off on the weekend. I wouldn't want to be working on the weekend. And I said, besides Babs and I do every, oh, Babs can come. And I said, Babs would definitely not want to come. And that would be the only situation. And I have to tell you, in 1992, 50,000 went a long way. But as I said, I just don't want to. Look, we got a point that's just going to be workshops, and I don't want to go back to something that I did in the past. Besides, I don't want the word to go out that I do this sort of thing. Well, so you … no, no, no. We didn't need that 50,000.
 
Jeffrey Madoff: Well, but it's also you're maintaining your authenticity and the truth of your path and what it is that you want to do. Because when somebody's response is, look, opportunities like this don't come around a lot, you're gonna stay small, and all that dialogue also, at least to me, would say, you're not a person I wanna be in business with anyhow.
 
Dan Sullivan: Well, the other thing was that he was in the Program and, you know, and a lot of people say, well, you know, if it was just you coaching, people would pay large checks. And I say, but I wouldn't learn anything. It's not, it's not really interesting to me anymore. And I said, being in a room with 50 people who are all smart and watching the interaction, new ideas popping out, that really interests me. Being with one person for a weekend, you know, wouldn't really interest me that much.
 
Jeffrey Madoff: Do you think in your business, because you're dealing with such a range of people, and I think back to when you've talked about Babs, that without her, you have your own phrase, you would be …
 
Dan Sullivan: I'd be a smart drunk worried about the rent.
 
Jeffrey Madoff: Yes, yes. In your coaching, although I know it's all about making good decisions, thinking about what you do and thinking about your thinking about what you do and all that sort of a thing, does empathy play a part in the coaching that you do and somewhere in your past because of the things that you experienced and with your divorce, with starting a new business?
 
Dan Sullivan: Bankruptcy.
 
Jeffrey Madoff: Yeah, the bankruptcy, yeah. That day when the roof fell in and the floor fell out from under you.
 
Dan Sullivan: Two report cards.
 
Jeffrey Madoff: Yes, yeah. Having gone through what you went through, do you think that empathy plays a part in your decision making and how you approach your clients?
 
Dan Sullivan: Yeah, you know, it's very, very interesting. What I can spot most in other people isn't so much their emotional pain. I can spot their confused thinking. A lot of the pain comes from the fact that they had a context, you know, they had a context. And the context is, you're seeing a lot of that today. I'm just, the world is really shifting. This is one of the big periods of big shifting going on. I think in my lifetime, I can't think of a period where there seems to be more stuff moving than it is today. And I could just see that people are, that what was working before just doesn't seem to be working now. And the problem is they've gotten too far out of themselves and they've gotten away from their own capabilities. You know, to a certain extent, they're so fixated with what's going on outside of themselves that they've forgotten who they are.
 
And then I'll start just a series of conversations and I, you know, I'm very, very much focusing on the positive. So I said, let's just do a little exercise. What's working about things right now? What do you have in your life right now? And they said, well, nothing's working. I said, no, no. Some things are working. I said, you're looking. So what's really working? And then they'll say, well, I've got a great marriage. And I said, we'll put that right at the top. And I said, and you're talking and you're supportive of each other. And he said, oh yeah, I don't know where I'd be if it hadn't been good. And I said, and then they said, well, I'm in pretty good health. I said, that's a good one. And if I can get them through five things that are working, all of a sudden some confidence comes back into their life.
 
And I say, okay, now let's talk about what's not working. But they've lost the ability to be confident somewhere along the line. And I think it's because they've gotten too far outside of themselves. The stock market. And I said, well, the stock market is a guess and a bet. You know that. So you were guessing, and you were betting, and it was not the right guess, and it wasn't the right bet. But what have you guessed and bet on? Well, I've got this great idea, and something's developing. You have to get them around where they get local again. They come back to themselves. And I said, just in terms of your relationships, do you have a lot of good things?
 
So yeah, they do. But they're being fixated on something outside of themselves. And they get grounded. They get grounded again. They've lost touch with the ground, and they get grounded again, you know. But the one thing, I mean, you talk about empathy, but I don't feel their pain because it isn't happening to me. The pain is happening to them. And Babs coached for a while and Babs feels their pain. And she coached for a couple of years and she found, I just get too bound up. I said, I don't get bound up with their pain. It's their pain. I'm trying to figure out how they're looking at their pain, and I'm trying to get them to see how they're actually looking at the situation.
 
Last week, I had somebody, a 30-year client, and the game board just changed for him. All the Monopoly pieces went back into the box, and there's a whole new game there. And I just got him talking about what he had to work with. And I had three meetings with him. And at the end of the third meeting, he said, I've got a whole new game plan. I've got a whole new picture. But I don't experience the turmoil that they're going through. I don't experience that at all. So I don't know if he would say I don't have empathy.
 
Jeffrey Madoff: Well, I mean, empathy is the old walk a mile in my shoes. Feel what I feel. And then there's compassion. And compassion can be a desire to take action. You don't have to feel their pain, but there's a recognition of their situation. Do you think you'd be where you are if you hadn't gone through the alcoholism and the divorce? Do you think that that set you up for a kind of recognition of your own innate talents that may have been, you know, not fully formed at that point? Could you have recognized that without going through that difficulty that you went through?
 
Dan Sullivan: I wasn't alcoholic. I just liked wine. Well, what do you mean? Well, you know, the big question is that I think a lot of it comes, I've just had a lot of years of experience, you know, I'm, you know, you and I are, yeah, we've got a lot of experience in the background, and we're interested in other people. And, you know, right from early childhood, we've been very interested. So I've not only got my own experiences, I've got a lot of other people's experiences in my head. And I think the other thing is that as I've gone along, I have this sort of thought that the bad things that have happened to me weren't really that bad in comparison to bad things that have happened to other people. So I've got a sense of perspective, you know, I've got a sense of perspective about it.
 
But the other thing that I'm very, very familiar is that when I did get in a bad spot, how was it that I pulled myself out of the bad spot? Because I always did. You know, I always turned it around. And I'm much more in touch with that than the pain of what happened when I was in the bad spot. I'm more in touch with how I actually got back, you know, with a sense of energy and a sense of purpose and a sense of energy. I think that happened a lot.
 
Jeffrey Madoff: Personal resilience.
 
Dan Sullivan: Yeah, you know, it's like America, you know, is a very interesting culture, is that they're less impressed with someone who came from nothing and got to the top than the person who did that and then took a tumble back to the bottom and then they get real interested. Can the person come back again? America just loves the comeback stories, you know, come back stories. You know, I mean, your play has a lot of that. Your play has a lot that in there. When Lloyd lost Logan and then he went to Nigeria and then he got back in touch with who he was. He got back in touch with not just who he was with a person, but he was an American and everything like that. Yeah, and I don't have a real tragic sense about life in general. I have a pretty transformative sense about life.
 
Jeffrey Madoff: Which is a great survival skill, you know, a great, it's a great survival skill. Do you think that, how has over the years, and part of this is, I think, just as we get older, priorities regarding physical and mental health—you know, I mean, every morning, my goal when I get up is to keep the old man out. You know, so I do what I can in terms of exercise, eating well, treating myself well. And have your priorities at all changed as you've gone through this journey?
 
Dan Sullivan: I wouldn't say recently. I wouldn't say it happened recently. I did have sort of a real flash of clarity when I was 70. So this is a decade ago. And it had to do with the fact that I didn't think I had to improve too much, where the focus is on me improving and everything else. And it switched to teamwork. I said, all the growth from now on is going to be through teamwork. It's not going to be my personal skills. So the big question is, where do my personal skills fit in with other people's skills to create something that's bigger? And I did an exercise. It was about two years ago. It was called Your Best Decade Ever. I had people draw a curved line when they were born and then to break the line up into decades because some of my clients are in their thirties, some are in their fifties, not too many in the seventies and I was 70, I was 78, 79 when I did it.
 
And I said, now let's take the last 10 years and what did you accomplish during the last 10 years? All entrepreneurs. And I said, so tell me everything you accomplished in the last 10 years. And they did. And then compare it with all the years before the last 10 years started. And every one of them said that I accomplished more in the last 10 years than I did all the time leading up to the last 10 years. So I said, will the next decade be the same? So I said, you know, so if you go 10 years in the future, from now until the 10 years in the future, and I said, what are you going to do so that you can say the same thing about all the life you've lived up until now? And they said, well, I don't know if I can pull that off. And I said, well, 10 years ago, you didn't know if you could pull it off either. So here you are. And you've done all this stuff in the last 10 years.
 
And I wasn't aiming towards this, but it came out loud and clear throughout the whole workshop room, big rooms. I did it with about seven, eight different groups. And they said, but our next decade won't be bigger than everything else if we're not in Strategic Coach. And I said, now that's a very satisfying answer. And I said, if we don't have this community and we're not coming back and reporting in every quarter, it won't be as big. And I said, useful thought.
 
Jeffrey Madoff: So what would you say, because I know I don't get a sense that you're looking for the, the only external validation is signups.
 
Dan Sullivan: Yeah. I like signups.
 
Jeffrey Madoff: Yes, yes.
 
Dan Sullivan: I like books sold too, book sales.
 
Jeffrey Madoff: Yeah, it's becoming more important to me too. But what would you say drives your ambition at this point? And is it something different than 40 and 30 and 20 years ago?
 
Dan Sullivan: It's very interesting, I'm starting a new book, a new quarterly book in about two weeks, and the title is Always More Ambitious. And it came to me about a year ago, and people said, what's your ambition when you're 90? And I said, to be more ambitious than I am now. And I said, that's an ambition that you can really work towards. And what I mean by that, I said, we've gotten very, very skillful at collaboration and teamwork in the last, I would say the last 15 years, 15 years, we've just gotten very, very good at finding real capabilities outside of our company, you know, with other people. You're a good example of that. Joe Polish is a really good example of that.
 
And we just do these sort of collaborations where we say great things about you, you say great things, and we put things together. And I said, as long as you define your capability as growing teamwork and collaboration, you can be far more ambitious in the future than you are right now, because it's going to grow project by project, quarter by quarter. And I would say right now, every one of my quarters, from a standpoint of collaboration with other people, is the best quarter I've ever had in my lifetime for doing it. I'm in good health. Mental health is good. My brain is in good shape. So my sense is that I'm very excited about that of being more ambitious in the future.
 
Jeffrey Madoff: It's funny, my focus has changed in the sense that, you know, I have a screenplay that I want to turn into a film. It's a very cool story. I had initially, that's the path I started then when I met Lloyd. I'd raised a little money to develop the screenplay. And when I shifted and wanted to do Lloyd's thing first, I mean, the other one's written. And it was because I thought his story was more important and more timely. The other one's very entertaining and cool. But I also had him by my side for a number of years, which was also great from the relationship that we developed. And now what I want to do, I still want to do that film. But I want to do the film as an executive producer, not directing it, just because if I'm the executive producer, I can do a few projects. If I was directing it, I could only do that. And I don't want to limit myself at this stage. I want to have a few things going on. Like in this case, I can do the play and I can do our book. I would say that's more ambitious.
 
Dan Sullivan: Yeah, I totally understand what you're saying. That's my thing. So there's a whole other—what'd you get out of this so far? You know what I would suggest that is probably common? That who we are is internally generated, not externally.
 
Jeffrey Madoff: Well, I think a lot of people are actually very … Are you speaking about us specifically?
 
Dan Sullivan: The two of us.
 
Jeffrey Madoff: Yeah, I mean, it's hard to tell. I'd like to think that on the other hand, because I'm sure part of the external validation we got when we were younger, and this is true for anybody, shaped who they are. And when a certain confidence became well seated, you didn't need that anymore, because you realize you carry that within yourself.
 
Dan Sullivan: Well, I think you need external proof. I mean, you can think you're, you know …
 
Jeffrey Madoff: Right, that's different, though.
 
Dan Sullivan: Yes, I agree. I mean, that's like science. Science isn't science until someone else can do the same test and get the same result.
 
Jeffrey Madoff: Otherwise, you're talking about the realm of evolution.
 
Dan Sullivan: You know, you're just creating fantasies for yourself, you know, and everything like that. So my sense is that, you know, sell-out crowds, standing ovations, great reviews, there's a test that what you feel inside is being validated outside. I don't see that.
 
Jeffrey Madoff: Yeah. I mean, that's true.
 
Dan Sullivan: That's just proof of concept, you know, basically.
 
Jeffrey Madoff: That's right. Yeah. Yeah.
 
Dan Sullivan: I don't, I see that different as, you know, feeling terrible about yourself if you don't get it. My feeling as well, back to the drawing board, you know, we didn't get the result that we were looking for, you know, I don't really take it personally. I just said, well, I, I guess that this would work. I bet on them, but it didn't work. So we have to rethink, we have to go back to the planning board and come up with something different.
 
Jeffrey Madoff: Yeah, you know, it's funny, last night I was reading some stuff and looking at certain film grosses. And there was a movie that got tremendous hype, and big star, and it tanked. I'm talking about the movie Maestro, starring Bradley Cooper, about Leonard Bernstein. And I saw, I was shocked actually, that it's worldwide gross was $383,000.
 
Dan Sullivan: Wow.
 
Jeffrey Madoff: And thought about, you know, that's the first film that he also directed. And, you know, it was a very, audacious vision that didn't get the external validation that it needed. And you know, years in the making, and there had to be a, no matter how wealthy you are, and how much celebrity you've got, when you take a blow like that, it's not so easy to just slough it off. You know, and I know people, I'm sure you know people, that in spite of what they've accomplished and in spite of what they have, it's never enough. And they can't comfort themselves with what they had done before. They stay focused for a while on that, what they consider to be failure.
 
And, you know, and it depends on just, you know, I think it's really interesting because I've experienced this with people that I know that have done incredibly well, but when something didn't work, the not working was much more painful than the joy they got from something that did work. I'm fortunately constructed that I can, you know, I can take the blow, and then, you know, that's the resilience I guess we were talking about a little bit before. And I'm not saying they're not resilient. They'll come back, but it's coming back, I guess the phrase that comes to mind is coming back with a vengeance as opposed to, you know, their fuel becomes something else.
 
Dan Sullivan: Yeah. Well, it all depends on what they thought it was going to mean if it was a big hit.
 
Jeffrey Madoff: Yeah. Yeah. Yeah.
 
Dan Sullivan: I mean, it seems to me that they bet their identity on it for a while.
 
Jeffrey Madoff: Oh, I think you're right. Yeah.
 
Dan Sullivan: Yeah.
 
Jeffrey Madoff: I mean, that becomes the real devil's bargain.
 
Dan Sullivan: I don't think that's a good bet. I don't think you should ever bet your identity on something.
 
Jeffrey Madoff: I agree. Yeah. You know, what did you get out of today?
 
Dan Sullivan: Well, first of all, your questions were really great questions, and I'll probably convert these into tools, get patents on them, and I'll make millions of dollars off the contract. But it really brought, for me, first of all, I think why we connect is because we have the same operating system, completely different lives, but same operating system, that the activity that we're really good at, as we move forward, keeps telling us new things about ourselves. And it's really gratifying. It's a very gratifying activity. And it's also the reason why age doesn't mean anything to us, because it never did. You know, when you're a certain age, you're supposed to have confidence. I never thought in those terms. It was just that this is as good as I am right now. Now I can take a leap and I can do something more and I'll get better in the future. So that's it. But I think the other thing was that I really, really feel that I've made good use of my life to be doing what I'm doing right now. And that as I look at it, we're in the early stages of what it's going to be.
 
Jeffrey Madoff: Yeah, I think if you truly feel good about who you are and what you've done or the effect you've had on others or whatever, because I think for a lot of people, immersion in their business can be an avoidance of pain. And, you know, that can become as much of an addiction as alcohol or drugs.
 
Dan Sullivan: It's an addiction.
 
Jeffrey Madoff: Yeah, it's interesting. Well, I'd like us to maybe do a part two to this, because I've got some more to explore in that. And I think that possibly we've hit a milestone today, which is we've been the most focused,
 
Dan Sullivan: Now that worries me. Yeah, we gotta do a number two to see that we didn't get out of hand here.
 
Jeffrey Madoff: Yeah. Do you want to wrap us up?
 
Dan Sullivan: Yeah. Well, what we're looking at here, first of all, we're talking about entrepreneurism and we're talking about the kind of thinking that entrepreneurs go through. And one of the things that all entrepreneurs have to ask is, why did I take this particular route in life instead of following what a lot of the people you knew when you were in your teens and twenties, they attached their career to an external activity that wasn't self-created? And I think that the thing that I find is that people were you know, when I was growing up, they always said, you know, that what you want is a safe job with someone else. And as I look at things in the world right now at age 80, I said, I really did choose the safest job. Because a lot of other people aren't even doing their job anymore at my age. And I think that the real distinction between the entrepreneurial life and where someone else has created your profession, they've created your job for you, is that what you were looking for was the answers. But I think that entrepreneurism is really about the questions that you're asking yourself.
 
Jeffrey Madoff: I would say life is about the questions.
 
Dan Sullivan: Life's a good, yeah, yeah, life, yeah. Yeah, I didn't want to get too profound here. Anyway, I really enjoyed it. It was really great. And this is Dan Sullivan, and I'm reporting in from Buenos Aires, Argentina. Over to you.
 
Jeffrey Madoff: And this is Jeff Madoff reporting in from the Upper West Side of New York City.
 
Dan Sullivan: And we'll see you on the next episode, Anything and Everything.
 
Jeffrey Madoff: Thanks for joining us today on our show, Anything and Everything. If you enjoyed it, please share it with a friend. For more about me and my work, visit acreativecareer.com and madoffproductions.com. To learn more about Dan and Strategic Coach, visit strategiccoach.com.