The Swing Cast Strategy Benefits Everyone At Your Company
March 18, 2025
Hosted By
Are the people on your team ready to step into any role if needed? If not, why not? Dan Sullivan and Jeffrey Madoff explore the “swing cast” concept, explaining how adaptable, cross-trained teams—like actors ready for any role—drive entrepreneurial success. Learn why prioritizing ample time off for team members and focusing on results builds a high-performing business.
Show Notes:
If you try to work continuously without taking time off to recharge, your overall productivity and performance will decline.
Most Strategic Coach team leaders have experience in multiple roles.
Team members can grow by volunteering for responsibilities beyond their initial job description.
People accustomed to working within large corporate structures may struggle in smaller, more agile entrepreneurial environments, which have fewer support systems in place.
Entrepreneurism is a “Results Economy,” not a “Time and Effort Economy.”
Selling is about getting a sale, not the time and effort you put in to get the sale.
Most entrepreneurial companies begin with the founder acting as the primary salesperson.
We can expect to see more people returning to the office, driven by our innate need for social interaction and connection.
If you want to build a great company culture, you need team members in the office.
Resources:
Casting Not Hiring by Dan Sullivan and Jeffrey Madoff
What Free Days™ Are And How To Know When You Need Them
Give and Take by Adam Grant
Your Business Is A Theater Production: Your Back Stage Shouldn’t Show On The Front Stage
Learn more about Jeffrey Madoff
Dan Sullivan and Strategic Coach®
Episode Transcript
Jeffrey Madoff: This is Jeffrey Madoff, and welcome to our podcast called Anything and Everything with my partner, Dan Sullivan.
Dan Sullivan: Jeff and I are devoting some of these podcasts that we do to the writing of our current book, which is called Casting Not Hiring, which is treating an entrepreneurial business like a theater production, where you don't have jobs, you have roles. So you cast for roles, you don't hire for jobs. Just on a fascinating subject of what are called the swing cast in theater, and that's someone who can fill in for a more leading actor if something comes up. And it's very, very necessary in entrepreneurial companies that you're always double trained, that every position in the company you have a trained person who knows what to do in case the lead person is not available for one reason or another. This is another one of these areas where there's a great resemblance between the theatrical world and the entrepreneurial world.
Jeffrey Madoff: What sort of led to this is Dan was talking about how people get their Free Days and their time off, but there's also people that need to fill in for that. And, you know, when it's a lead performer in theater, it's your understudy. But then there are the members of the ensemble and that ensemble they have to be prepared to jump into a number of different parts. And they're called swing. So they may play a different ensemble member, they may play a minor character who's out who's part of the ensemble, but also has some acting things to do. I mean, it's really fascinating. But the point is that everybody knows more than just their role. And that's, I think, the key about it. So Dan, how did that even come about in Strategic Coach? Did it evolve to that point? Where'd that idea come from?
Dan Sullivan: I came in early. We started the company before 1989. I was just a one-on-one coach, you know, and we had a secretary or someone else because I was the company essentially in terms of the coaching, Strategic Coach. But the moment that we went to workshops where we started, you know, very, very small, we would maybe have a very small workshop for six people. But it was basically the same structure and process that I had been using for 15 years, 1974 to 1989, 15 years, where I was just testing out different coaching structures, different coaching tools. And we had a lot of confidence. This is Babs Smith and myself. We're married and we run the company together. We always said, if you think of Coach as a theater, which we did right from the beginning, Babs is in charge of the entire theater, you know, the operations and all the teams that create the theater, including sales. And I was in charge of what's on stage.
So, first of all, we just started in Toronto and then we went west in Canada, we went to Vancouver, we went to Edmonton and Calgary—fairly large centers, very entrepreneurial in the Western Canada, more so than the Eastern Canada, but still the Wild West a bit in Western Canada. And it just came up that Babs was always a big proponent of Free Days. And that is that if you try to work all the time, you can only work at a fairly low level. But if you get time off, performance jumps. So we've always considered free time, time away from work as a crucial strategic structure and philosophy inside Coach. So that's where it all started. And it's been fixed for 25 years. And that is that everybody in the company gets six weeks of Free Days, 30 days, weekdays, and they get the holidays. There's, you know, 10 or 11 depending on the jurisdiction. We also give them three community days where they're volunteering for some cause, you know, some charity or something they're doing.
Jeffrey Madoff: Is that a prerequisite, by the way?
Dan Sullivan: No, no. And you don't have to take it, but you can take them as Free Days. I mean, we have to have verification from the organization that they're working for that they actually work. We have a team of around five or six that we have a provincial park, like a state park in Canada. You know, these are outdoor parks and they work with the Rangers for three days during the off season. So it'd be, you know, during the winter and they repair bridges and they clean up things. And they've been doing this for 20 years. Even when they leave the company, as some of them have, they still get together, this group, and they go and they work with the rangers and know them. The rangers love them. They get lodging and they get food and everything.
So in the terms, there's about 220 work days. And then if you put all their Free Days together, they get about 145 days off during the year. And we do that so that they don't burn out. You can't stockpile your Free Days. So by January of the next year, you have to have taken all of your, we give them a grace month in January where they can take their Free Day. But here's the condition on it. You have to be double trained for everything you're doing. Someone has to be able to fill in like a swing actor in theater. You have to be able to fill in and to a point where it's not noticed that you're gone from a maintenance standpoint, that you can do everything. They couldn't do it forever, but they can do it for two weeks.
Jeffrey Madoff: Are there people that have actually changed their focus or tried to change their role in the company as a result of being exposed to having to do something for a couple of weeks? Because in a way, I think that could be very beneficial for the company because they develop more capabilities.
Dan Sullivan: Yeah, the leadership group now, and this is leader more than manager, the leaders who really direct the various parts, we have about 12 different teams. If you take everything that happens in the theater, we've broken it down to 12 teams. And each of them has a team leader and assistant team leader. And the vast majority of them are the ones with the greatest experience of working many different roles in the company. Yeah, and they have a volunteering attitude. You know, our entire team right now, we're about 120 and we're in three countries, U.S., Canada, and the UK. The ones who really take over really started in entry-level jobs and then they moved around and they volunteered and they tried this. And if they want any out of the company training, we finance it for them if they can show that that training is gonna be applied when they come back.
Jeffrey Madoff: Are they paid for those Free Days?
Dan Sullivan: Yeah, these are all paid Free Days. And it's a big bargaining chip when you're hiring people. There's an obvious upside to it. Yeah, well, legally they get two weeks. They get six weeks when they come with us. That's a big difference. The one thing we've learned over the years, this will be a topic of our book, why we put the emphasis on the entrepreneurism for what the book is about. And I find that people who have worked for large companies don't do well when they come to a smaller company. So, you know, we have a big bank shares. So we have people who worked at a bank and they say, you know, they get laid off for whatever reason they're leaving from the other and they come in and they, there's just a level of alert and curiosity. We have it in our main tool that we use that's backing up this book called the 4x4 Casting Tool. And you have to really have your wits about you.
And a lot of company people have been slotted into a job, but there's a lot of support systems in large corporations that they don't have to think about anything. They show up, they do their work, and you have to be much more alert, curious, responsive, and resourceful. Those are the things we're looking for. So generally, it's a point against you if you've come from a bureaucratic setting. It doesn't mix well when they come. So generally, a lot of them are individuals who just come out of college. They've just graduated from college, but they've worked their way through college. They've done a lot of different jobs during the summer. Some of them working even while they're going through college or university. And they're just used to showing up and being useful.
Jeffrey Madoff: I'm curious, aside from coaching the entrepreneurs and the founders of the company, do you find that some of these methods, like the Free Days in the way you define those, and other things have been adopted by those companies too?
Dan Sullivan: Yeah, we really push Free Days because we say there's two types of economies. The first economy is the time and effort economy. You put in the time and you put in the effort, okay? And you're paid for the amount of time and effort that you put in. And then there's the results economy. Entrepreneurism is a results economy. It's not a time and effort economy.
Jeffrey Madoff: And just go deeper into that. Clarify that difference for me a bit more.
Dan Sullivan: Well, we can apply it to our own lives here, Jeff, in the sense that both of us are really good salespeople. And selling is about getting a sale. It's not about the time and effort you put into getting the sale. You know, sales actually happen quite quickly. If you just add up the amount of time it took you to get the sale, it's actually really quite quick. It's like that. But there's a certain amount of time and effort you have to put in before. So a lot of salespeople say, well, I work 50 hours, I work at nights and everything else. I say, yeah, but you don't get any sales. Yeah, but I'm putting in a lot of time and effort. I said, yeah, you don't get paid for time and effort, you get paid for sales. Almost all entrepreneurial start with the founder being a salesperson of something.
Jeffrey Madoff: Right. Yeah. This is the idea of the company.
Dan Sullivan: Yeah. Yeah. The idea of the company. And it's hard for a lot of people. They want the security that if I put my time and effort in, regardless of whether I achieve anything, I should get paid. And I said, well, it's going to be interesting to see what remote work does with this whole concept.
Jeffrey Madoff: You know, my belief and it has been even since lockdown and there was all of these articles written about the shift in work to remote and all of these pronouncements, which the only thing I knew was we don't know what the impact of this is gonna be. That's the only thing I knew.
Dan Sullivan: I think it'll take 10 years.
Jeffrey Madoff: Well, what's interesting though is that a lot of more companies are not only requiring people to be in the office now five days a week, there's a lot more people who want to go back to the office. You know, that gets into the whole thing about relationships, about, we were talking before we started recording this, about friendships within the company, that your good friends are also your colleagues, and we're not made to work alone. I mean, some people are, if you're a painter or a writer or whatever, but that's only a part of the process. You gotta get response from what it is you're doing, and that involves other people. And I think there's such a demand for quick answers, which are, in new circumstances, rarely correct. But everybody's demanding what's the answer? What's this gonna change? What's this gonna do? I think that we're going to see a lot more people working back in the offices again, because ultimately we're social animals and we need that. And plus, if you want to build a company culture, you can't do that remotely.
Dan Sullivan: You can't do it remotely at all.
Jeffrey Madoff: That's right. And so I think all of these things in searching for those quick answers, as I said, I just knew that we didn't know what the impact was going to be because it was a new phenomenon and that has changed things.
Dan Sullivan: Yeah. Well, we noticed the same thing with our customers, the entrepreneurs who, you know, it's all in workshop form. So whether it's either a personal workshop with the people there, or it's a Zoom workshop. Okay. And we were wondering because during COVID, it was 100% Zoom, you know, and because of the travel regulations and distancing, you know, everything to do with COVID. And so within about the first six months after COVID officially stopped in the three countries, after the travel restrictions were gone, it was about half and half when they had the opportunity to come. And within three months, it was 70%. And within six months, it was back to 85% or 90%. And most of the ones who still do it remotely really come from a long distance away, like Pakistan or Vietnam. It was beneficial to them, and a lot of people joined during COVID.
It was funny, from 1989 to 1989, to 2023, we had a total of 25 clients, not consistently and continually, but 25 people had actually attended at least a year in Strategic Coach. So that's a long period of time. That's, you know, 34 years. But in the COVID period, 30 more signed up from Australia. Okay, because they could, you know, they could. Well, in some cases, Zoom is the only way to have made us more of a global company than we had ever been.
Jeffrey Madoff: Yeah. And with my teaching and having to teach via Zoom, the downside was I couldn't feel the feedback in the same way and teaching is a performative task, but I had guests from Los Angeles, London, Paris, different places in different time zones that, number one, I could have never scheduled them any other way, plus I didn't have to fly them in or put them up, which we had no budget for in terms of persons, but I was able to expand the people that I could bring into the class as a result, which is a big plus too. But you mentioned something I want to go back into. You were talking about a salesperson who wanted to be paid for their effort, even though they didn't generate any sales.
There was an interesting editorial in The New York Times on Thursday by Adam Grant, who wrote Give and Take. He was the youngest tenured professor at Wharton. And I happened to have met him, which is how I ended up lecturing at Wharton. And Adam has written a number of really good books. His first book, Give and Take, is what launched his career. And he was talking about the culture that we are in that people are feeling entitled to a kind of compensation just for showing up. Now, certain jobs take a while to get into and there's, you know, you don't walk in and start generating sales so easily. But there's something interesting about the, what has become a conflict between the expectation of compensation and expectation and the lack of performance and how that impacts hiring and businesses. How do you deal with someone who says, look, you know, I've worked on this for X period of time. It hasn't panned out, but I think I'm entitled to a raise.
Dan Sullivan: Yeah. If they're just coming on board, we have a very extensive onboarding process. First of all, there's five interviews before they get hired. They will meet up to 10 different people in the company. And we've taken a lot of cues from the Four Seasons Hotel and they have jury hiring. I don't know if you've ever heard about their juries. So when a new person is being, you know, they've gone through some steps, they've obviously got outside filters that bring someone to the Four Seasons, but they have a six person jury for every job that's hired. And everybody in the company has to do jury duty, including the general manager of the hotel. So the general manager of the hotel may be sitting in this chair next to them.
As a person who works in the kitchen, another person might be cleaning up rooms. They interact with a potential employee in their case. And after they're finished, they said, number one, do you think this person would represent the standards and the culture of the Four Seasons Hotel? Do you think that this would be a positive addition to have this person in our space, and they're from the Four Seasons, and they have to get six yeses. And the other one is, would you personally enjoy working with this person? And they have to get six yeses. Well, a lot comes out in that interview, obviously. You know, I don't know the insides of what goes on in one of the interviews, but I've been staying at Four Seasons Hotel. I think I'm up to 30 now of different hotels that are all Four Seasons, and I've never run into a problem attitude with any place.
So I think it's really attitude that you're looking for, you know, the attitude. I think entitlement is an attitude. And I don't think it's difficult to sense. I mean, there's some great parodies on YouTube of the person saying, well, we start at eight here. He says, eight? Oh, no, eight doesn't work for me. I do yoga in the morning, you know, and I have meditation. And you know, no, no, no, 10. I'll come at 10. You know, and of course, the person isn't hired. And as a matter of fact, the person isn't hired. And she says, well, I'm sorry, there isn't a place for you here at this company. You mean you're firing me? You're firing me" I said, no, I'm not firing you. I'm not hiring you. No, you're firing me. He says, you know, I deserve this job. No, you don't deserve this job. I saw more of that two or three years ago than I'm seeing right now.
Jeffrey Madoff: Well, I think two or three years ago, we were in a situation where there was shortages of help. And another thing that I thought was total bullshit was all the essays on the great resignation. You remember that about three years ago? And you know, you got to pay rent. You know, you got to buy groceries. I mean, there's realities that set in and most Americans don't have that much money in the bank. They could afford not to work. It was that brief window that everyone was emboldened in a way that I think was somewhat self-destructive.
Dan Sullivan: But we really take advantage of the first three-month trial. You know, you can fire anyone up ‘till three months, you know. And so they are very, very tightly observed for the first three months, how they interact, how they get their work done and everything else. Then, you know, there's a decision made whether they're hired or not. They're on probation, so they don't get any free time during probation period. That doesn't start until they get it. I don't know. You know, you're looking for a certain type of person. You know, we don't spend a lot of time thinking about who we don't want. We spend a lot of time about who we do want. I'm not trying to prevent something bad from happening. I'm trying to blueprint something good happening.
And that really was the reason why I created the 4x4 Casting Tool. You know, this is how you show up. I don't care how you show up. When you're with me, you have to be really lively. You have to be really alert. You have to be really current. I mean, what you do at night, what you do on weekends, I don't really care. And if you don't do it this way with other people, they'll tell me. And so you won't be able to hide it. The other thing is that the first three months, you're just going to be learning the job. But every quarter after that, we want to see things happening faster because you know how to do it easier, you know, and you're a great team member. We're going to ask you, is there ways that things can be improved? Do you think that there's some improvements that can be made? And we see how they respond to.
I had a production manager because I do a lot of video work. I do a lot of audio work, a lot of print work that I create. And my production manager was really tough. She was a tough person. And she had an assistant, and there was something that if the person had thought through what was going to happen, it happened right, but it happened wrongly. And my production manager's name was Vanessa, a terrific person. She went to law school and she left us and went to law school and she, you know, went on her way. But she was terrific while she was with us. And she says, you got to think, you know, when you see the next dates, you have to think things through. And the woman turned to me, Vanessa. I want to show up at nine. I want to leave at five. I'll do what you tell me to do. Don't ask me to think. So we didn't. We didn't ask her to think anymore beyond that day. We were looking for a thinker, I'm sorry. Our mistake, but this happened within the first three months, you know.
So there's a lot of observation. I mean, our team leaders are really wary. They really, how's this person fitting in? And I know we had these two young men who joined us. They were both British. They were British immigrants to Canada. And one of them had a nose for when the boss is around, you're on your best behavior. And the other one was just really interesting thinking about what he was doing. I knew what the date was when their probation was up. And I said, well, you guys, seven more days, seven more days. But he was always congenial with me. He always interacted with me. But he treated other people really terribly and he was gone. But I didn't see that.
Jeffrey Madoff: So, you know, a lot of people don't realize that when you are auditioning for a job, that when you make the first phone call to the company and you're speaking to the receptionist, when you walk into the room, how you treat that person, all these things that if you're only reserving your good behavior for the person you're gonna be reporting to or the boss, other people talk too. And you and I have mentioned it before, like if you happen to go out for a meal with a client, how they treat wait staff, just different things give you indications this person is going to be a problem, you know?
Dan Sullivan: I mean, we have a pretty big premises in Toronto. We have 40,000 square feet, you know, we have 85 staff there. And the cleaning, you know, the outside, we have an outside cleaning service that comes in and cleans at the end of each day. And I always talk to them, I always talk to them, and they're all immigrants, you know, and for many of them, this isn't their only job. And I sit there and talk to them and, you know, how's it been? Where'd you come from? How'd you get here? And everything like this. And people are people, you know. Where your status is in the rank, that's irrelevant to me. I just, you know, always talk to people who are helping out, always be respectful, always be thankful, always be grateful for them working out.
Jeffrey Madoff: And as you are, and I am curious.
Dan Sullivan: Yeah. You know, who are these people that … what they go through to get here and what's their life like. And one of the things our free time really helps because if you're an immigrant to a new, especially if it's a language issue, you know, you're coming from another country and, you know, you have minimal English and everything like that. Everything of getting settled in the new country takes two or three times longer. Getting your kids into school takes longer. Getting your driver's license takes longer. Everything about the new system. So we feel that them having a lot of free time, I'm talking about those who have been hired, you know, but we've had two or three people who came from outside services, catering services, janitorial services, who asked if they could apply for a job at our company just because of the way they were treated.
Jeffrey Madoff: Oh, that's great. The thing that I mentioned about Adam Grant, what Adam was speaking about wasn't about somebody who would come to work and feel they were entitled, but it spilled over into that. He was talking about at school, and it was something that I experienced also teaching. He taught at Wharton and I taught at Parsons. And it's when a student would, and it's maybe have a parallel to being reviewed at Coach, there would always be a few students who questioned their grade, which is fine. I would say to them, a part of their final exam was, what grade do you think you deserve? And why do you think you deserve it?
So one of the students was very upset because she got a B minus. And I said, what grade do you think you should have gotten? And she said, I should have gotten an A. And I said, why do you think you should have gotten an A? And she said, because I showed up in class and I did the assignments. I said, well, what we call that is table stakes. To show up for the class that you've enrolled in and to do the assignments, that's a C. You're now starting at a C. You're at the table. And if you want to go beyond that, then your work has to take you beyond that. It's not about the fact that you just show up.
Dan Sullivan: Or did the minimum required.
Jeffrey Madoff: Yeah, what it's about is, do you put in the extra time, extra effort so that your work excels and stands out? So if you think you deserve an A, what did you do beyond showing up? And what was good about your work that should take you to that level? And that's where the notion of entitlement came in because they felt just for, these particular students felt just by the mere fact that they showed up, they ought to get an A. And I said, that isn't how it works. Let me tell you something else that wouldn't work. I said to her, you've often came into the class 10, 15, 20 minutes late. And she started to say something, she said, you always had an excuse. Okay, do you know what happens when you're out in the real world and that happens? And she was silent and I said, you would be fired. Why do you think you can show up in class consistently late and there's no consequence?
One consequence is of course you're missing that part of class and maybe something valuable transacted. But the other thing is the whole attitude that you bring to work. And that's not respecting the job or your colleagues. When you think you can come in 20 minutes late and it doesn't make a difference. When you think you can just do the minimum and you should be rewarded beyond that C. And I'm a believer in consequences. Now those consequences have a wide range of application. And so to me, the consequence is, maybe you don't get the grade you felt you deserved. And upon our discussion, you might realize, and it would be a valuable lesson for you to know why you didn't. Because out there in the world, they don't care that whatever the reason is. I think we're going through a shift in many areas of our culture.
Dan Sullivan: You've been in the workplace in your family store since the 50s, and I worked on a farm. I grew up on a farm. But I was aware right from the beginning that you're always a member of a team when you're at work, that you doing your work is necessary for someone else to do their work. And I think the possible problem with the academic and university system is that every individual is on their own. You know, they're not part of a learning team. They're part of, they're being tested. They pass the test that got them into university. And then there's more tests that get them out into the marketplace.
And I think that the biggest culture shock that I think young people get, whether it's at 18 years old or whether it's at 24 years old, the shock is that all their education and training has really been about them, unless they took part in sports, they took part in theater, they took part in extracurricular activities. And you find generally that what we find when we look at the background is that even when they were growing up, they had a lot of work experience, not necessarily paid for, but they did a lot of work, they volunteered, they did this. And that's an indicator of what their bandwidth is for them being part of a team that gets things done. And I was always passionate about teamwork, you know, I was always passionate. I wanted to do my work really well because someone else depended on my work.
Jeffrey Madoff: Well, and it also makes it more fun and more fulfilling.
Dan Sullivan: Well, it's meaningful. There's a purpose bigger than you showing up.
Jeffrey Madoff: That's right. I'd like us to do a little bit of role play and it's about the notion of what you want me to do some thinking.
Dan Sullivan: I thought I was supposed to show up at one o'clock and make it through. Great.
Jeffrey Madoff: Yes, if you want to take a time out to do some exercises. I want us to talk about entrepreneurship and the application of theatrical principles are casting, not hiring, but I'd like you to take the role of—I am going to be the skeptical CEO, and you are going to be you. And I want to hear how you would respond to the skepticism to our ideas of casting not hiring and the theatrical nature of business. So as that skeptical CEO, I might say to you, look, I appreciate creative thinking, but business isn't theater. We're here to make money and deliver results, not put on a show. How is that any more than just fancy window dressing? What's it actually gonna do for me?
Dan Sullivan: Well, the first thing I'm going to ask you, because I'd like to know, because you're making a judgment about me and I'm making a judgment about you, what are your plans for your company that are exciting? What kind of exciting plans? How do you want to grow your company? Is the company just going to be the same as it is now, and everything's automatic? Or are there some really great, exciting projects that your company is taking on right now? And so that's the thing I would like to know. It's not so much about theater, but is this an exciting place to work? Are you excited about being the owner of this company? I don't know.
Jeffrey Madoff: Well, as long as we grow and we certainly have our ups and downs, but, you know, to me, the excitement is in the growth and the profitability of the business. So I want to involve myself in efforts that I think are going to contribute to that growth and profitability. And what I don't really get, other than, you know, jargon about theater, how does that really help my business grow? How does that increase the profitability? What does it actually do for me? Is this a gimmick or is this a real philosophy that's applicable to growing a business?
Dan Sullivan: Yeah. Well, can I ask you a question? Who wants to buy the products and services of this company and why do they want to buy them? And can they buy services from anybody or do you have to do something special to get their attention?
Jeffrey Madoff: Well, I mean, like anybody you're selling to, you got to get their attention so you can sell to them. So, yeah, we do have to do that. We have to be, you know, well priced so that we're in competitive pricing with people that are in a similar market to us. And, you know, we've got to deliver what we say we're going to deliver, you know, best practices in terms of business. So yeah, those are the things that we have to do, but are we really on stage? Are we really creating back stage, front stage situations like you're talking about? Because we know what we need to do, we need to sell more stuff. That's what grows a business, selling more stuff.
Dan Sullivan: Do you have any customers that are elastic in how much they have to pay, or does everybody just want the lowest price? I mean, do you have customers who really, really like working with your company because there's something special that happens with your company, or are you just like anybody else? Because personally, if I'm going to go and spend the time working for something, I want to know that it's a special place. Is there anything special about this company?
Jeffrey Madoff: Well, you know, I mean, we have what I guess is the normal amount of turnover. It's hard to find good people, you know, so we always have turnover and, you know, we're always faced with or often faced with people saying, well, I can get the same thing for X amount less.
Dan Sullivan: I'm just talking about, is there anything special about this company that really good people would want to come and work here? I mean, they'd be excited to come and work. Is there anything, does anything happen here that you sound pretty bored? I should say you sound very bored. How long are you going to last in the company? I mean, are you on your final days or someone new coming in to take over is more exciting than you are? The reason is you're looking, you're looking for good people. Are you looking for great people? That's what I want to know. I don't want to be a good person. I want to be a great person. I just want to know if where you're going as a company and where I'm going with my career is going to line up because you know, I don't want to be disappointed working here that nobody's excited that I work with, nobody's excited, nobody has any goals, nobody has any ambition. So I just want to know what, because, you know, you're a buyer of my talents, but I'm a buyer of my future. And I just want to know if my talents and future are going to be going in the same direction.
Jeffrey Madoff: I mean, eventually, it's years away, but eventually I hope to sell my company. And the only way that I see to increase the value of that company is to grow its profits.
Dan Sullivan: Can I ask you a question about your work as the owner and the head of this company? Is there a part of your work that you really love doing and you wish you could do that all the time? And tell you the reason I'm asking you that question, because if I can be part of the solution that frees you up to do what you like, I'd like to know what that role is, because that seems to me that that would be the best thing I could be doing for you.
Jeffrey Madoff: So here we take a pause. And what you just said there, I think is really important because I think you're hitting a vulnerable point in that role I was playing, which is, you know, how can I help make your life better? What can I do to make your life better? Not about how much money I want to make from you, but, you know, what can I contribute to make this better? Which is, I think, and the 4x4 addresses this to a point, but I think that a lot of people aren't clear on what that is.
Dan Sullivan: I think there's two things here. One is the owner himself, the person who's doing the, this is strictly an employer here. This is not a caster, you know. If the owner doesn't really know what they wanna do personally inside their own company, it's not gonna be clear to anybody else in that company. For, you know, 50 years, I'm just used to dealing with the owner of the company. And I said, you know, are there things about being in the company, being the owner, being the person who's responsible primarily for the success of the company? Is there something that's really, really exciting that if you were freed up from everything else, the company would grow just because of your excitement? Because if there's no answer to that, nothing's going to happen.
Yeah, I was hired to ad agency here in Toronto and it was a personal hire. I knew the half owner of the agency. I met him in social circumstances. He liked my background, thought I might be a good writer, gave me a six-month trial. He says, not everybody can write ads. And so he says, your education doesn't play much in this. He says, you either have a knack for ads or you don't have a knack for ads. And I said, so tell me something: How does the agency make money that you could actually afford to pay me for six months? So I said, where's the money come in that you could pay for me? And when I get here, what do I have to do that lets you sleep at night that you made a good hire? What tells me I'm doing a good job when I come in?
And he said, be excited about any work that we give you. And he said, the other thing is, when you have any free time, go and talk to the veteran writers, go and talk to the layout people and ask them what makes a good ad, okay? And check your work out with them and say, do you think this is a good ad and everything else? So I was hired in June of 1971. After two weeks, he said, let's go to lunch. Let's go to lunch. We go to lunch and he says, your six months are up, you're hired.
Jeffrey Madoff: After two weeks?
Dan Sullivan: Yeah, because I asked the right questions. And I knew the complete financial structure of the agency within two weeks. I know where their 17% came from, because it was media placement that the agencies made money. So I said, I've got to be really useful to the other artists and writers, don't I? And he says, yes, you do. And I said, good. And I got the game plan. They have to get their work done faster for the company to make. Yeah, I said, yeah. I got the picture. Anyway, the problem of entitlement is that you're not seeing anything from any other person's point of view but your own.
Jeffrey Madoff: That's right.
Dan Sullivan: Yeah. If you just go in the opposite direction and you're interested in how everybody else is succeeding, it's not difficult to be useful.
Jeffrey Madoff: And if you're not curious about how does this work from where do we actually make our money from, what do we make our money from, but what is it that we're doing in terms of the ads, in terms of the layouts, what makes, what all the things that you were probing about is going to help you help them. And if that's not in the mix, it's not the right place. And how long did you stay there?
Dan Sullivan: Three years, and then I got this. What happened is that they had a lot of what are called legacy clients and legacy clients, because most ad agencies, if they're the second largest in Canada, came through about five or six mergers along the way, because usually they grow through mergers. They were number two by about 10% lower than the number one agency, but they had big clients. They had Chrysler, they had Kodak, big banks. Canada has really big banks. We had TD, but then they had a lot of small clients that were fee-for-services clients. So I got good enough that they took all the fee-for-services clients, put them in one group, and I was the lead writer. So these were, they just came along. They weren't media placement clients, but they paid fees for the services.
And so I did it, and a lot more family businesses that I was doing the work on. And what I noticed right off the bat, the solution to their future wasn't advertising. The solution to their future was to have a future. So I would ask him, you know, a year from now, two years, how are things going to be bigger and better? And I just immediately went into a coaching role, asking them questions, you know, and, you know, they had succession plans, you know, family businesses are complicated. They had succession plans and everything like that. But I said, I can write great ads for you, but if you don't have a future for the company, you're going to find some way of not growing. That's when I made the decision and he was sorry to see me go. He was sorry to see me go because it's not an easy thing to find good writers.
Jeffrey Madoff: There was a woman that I interviewed who I really liked. And I said to her, you know, I've got some more interviews to do that are already scheduled. I like you a lot. I'm very serious about hiring you. If anything happens between now, that was on a Thursday, now and next Wednesday, let me know because I think you've got a lot going on and I like you. She called on Monday and she said, I took another job. And I said, what happened? She said, honestly, I just needed to know I had a job. And you know, when I got a firm offer, I felt like I had to take it. And I liked you too, which is why I'm calling. And I said, well, have you signed anything? She said, no. I said, what are they expecting you to start? And she said, you want me to come in on Wednesday? And I said, would you tell me what they offered you? And she said, yes, and I said, actually, forget that. You don't need to tell me, because I knew the general ballpark of what it was gonna be.
And I said that I will beat their offer, but I want a yes from you now. I think you're terrific. I have never pursued someone like this. And what do you think? And she said, you'll beat what they offered me? And I said, yeah. And she said, I'll take it. And she was great. We're friends to this day. She's gone on to be very successful in her world. And she wanted to learn all aspects of the business. And it was really interesting because I also think as a business owner, you have to be elastic in terms o,f you know, if you think somebody's really special, then be flexible to try to get that person, because I think finding exceptional people, and she was exceptional, finding exceptional people is really hard.
Dan Sullivan: Yeah, it's interesting. It comes up because our clients, you know, along the same lines that you're talking about here, they look at our team and our team are very front stage conscious. I mean, we put in the, this is front stage. You know, I mean, I've been talking about this for 35 years. This is like theater. You got to show up, you got to put on your best presentation. Anytime you come in contact with somebody who's writing us a check to be in this program and anybody from the outside, you have to show up. You have to be very gracious. You have to be very, very responsive to what they want. And they said, where do you get great people? All your people are great. Where do you get them? And I said, we have this vending machine. We have a great employee vending machine. So we just put our credit card in. No, I said, there's great people everywhere. They just may not be looking for you. Great people are looking for great places to work. And so that's what makes them great, is that they become very, very discerning about, can they really be great in the new thing? The worst thing is to be great and not treated great.
Jeffrey Madoff: Yeah, well, and yes, and to not be recognized for your contribution. But your contribution, of course, has to be real.
Dan Sullivan: And not be challenged. They give you things where you really have to be at your best to actually achieve it.
Jeffrey Madoff: So to go back to the question that I asked you originally with this role play is, I appreciate the creative thinking, but is a theatrical approach gonna really help my business? From our conversation and what it makes me think of is giving a concrete example, Steve Jobs. He presented as Master of Ceremonies, Wizard of Technology, when they presented a new product, the enthusiasm among their own people for his performance, the media's response to his performance, the audience and buyer response to his performance propelled them to the front of the line, beating out Sony, upending the Walkman.
Dan Sullivan: Well, their operating system was clearly so much better than …
Jeffrey Madoff: Yeah, but, you know, the way that it was all presented was pure theater. Pure theater, you know. Apple was a great example, and Steve Jobs, of the theatrical presentation, awareness of front stage, back stage, all the things that they did to build even the narratives outside of that presentation meeting, like when somebody found the newest model of the newest iPhone, that allegedly somebody from inside Apple left at this bar. Do you remember that? And I'm sure that was all a plan to create that narrative and suspense and get a lot of copy and build curiosity and anticipation for that new product. So I think that there are examples that in fact businesses that thrived, you know, Apple also knocked BlackBerry out of the box.
Dan Sullivan: With one iPhone, the first iPhone, they knocked them out. And BlackBerry never recovered. No, no, because they took their eye off the ball. I remember because in the 2000 American presidential election, leading up to it for the year and a half, is that Al Gore was the first person where everybody had BlackBerrys, and they were all communicating with BlackBerrys. So that was going into 2000, and I think the iPhone came out. When did the iPhone come out? It must have come out pretty close beyond that, because they got knocked out. I mean, Nokia got knocked out just like that.
Jeffrey Madoff: Well, you remember before BlackBerry became the thing for a while, it was actually Palm Pilot. And then with BlackBerry, what they did is had the enhanced security and encryption. So that's why governments and businesses were using it and they lost that entire market. And all of that was the seduction of the theater approach, which I think is quite fascinating.
Dan Sullivan: Well, it's everywhere. I think theater is so deep in the human brain, and this is one of the main points in our book, that all of human existence, if it survived and went forward, had better theater, you know, that engendered much more enthusiasm, engendered much more commitment. I mean, there are things where you just didn't have enough troops or you didn't have enough gunpowder, but generally speaking, there was just this enormous theatrical print that's on everything. Just great stories. Somebody's just got a great story. That's great theater, if you have a great story. But I think we're in times right now where one thing is much more important going in 2025, where we are right now, than was true in 2020. And that is person-to-person contact has gone way up in people's estimation of what's really important. See, even the technology exists. That was magic, how you did that. It's all in the front stage.
Jeffrey Madoff: Well, there's a phrase that you use, which I think sums it up, and you were talking about the Four Seasons. It was, systematize the predictable, and humanize the exceptional. And I think that that says it all. That's just such a brilliant summation of what it is, because that human touch is extraordinarily important. There are people that master that, be it Walt Disney who mastered that, Steve Jobs who mastered that. It's quite incredible.
Dan Sullivan: Apple stores, when you go to Apple stores.
Jeffrey Madoff: Well, that's right.
Dan Sullivan: Yeah, that's right. Those are theaters.
Jeffrey Madoff: That's right. Absolutely. Absolutely. And, you know, it's really those are the things that separate good from great from businesses that have a future. To those that are just trying to move towards a future, but they don't really know what future they want other than more money. And so having that vision, I mean, Sony was Apple before Apple was. When Akira Morita died, he was the visionary for the company and they have not recovered yet. And I would posit that without Sony, Apple wouldn't have come into being in the same way.
Dan Sullivan: Yeah, it was very interesting. There's a great story about Morita. And it had to do when Carter was president and his secretary of, treasury secretary was Robert Strauss. So Morita would fly to Washington because they heard that Strauss was flying to Japan. Okay. So he would get to, and he bought two first class tickets, one for himself and then another ticket. I know he couldn't get away with it with the airlines now, but you could in the 1980s. So Carter had this rule that none of his cabinet secretaries could fly business class. They had to fly economy. Not great front stage, not great theater.
Anyway, so Morita gets there first in line, he gets there. He's right in first class and Robert Strauss comes in. He says, Bob, are you flying to Tokyo? He says, yeah, I'm flying to Tokyo. He says, when we get there, can we talk? And he says, well, we can't talk now because I have to go back there. And he says, just a minute. He makes a phone call. He says, my companion wasn't coming with me. Why don't you join me in first class? He had him for 17 hours just picking his brains. Oh, he says, oh, I know somebody you should talk to. I've got this person. And that was total theater for 17 hours with the Treasury Secretary of the United States. And he's plugging him in to everybody. He says, no, no. He says, we can speed this up. We can do this. We can handle this. We can handle that. And he put his entire company at the disposal of the treasury secretary of the United States while he was in Tokyo.
Jeffrey Madoff: Yeah, it's fascinating.
Dan Sullivan: And I say that's great theater.
Jeffrey Madoff: Yeah, well, it is. But what's interesting about it is when the Walkman was dominant and basically, you know, became what it was called at first, you know, that personal listening experience. You walked around, you had your earphones on. And I think, you know, I'd mentioned it in one of our earlier podcasts, I was given a Walkman by Morita, actually his wife, I met with …
Dan Sullivan: In Paris, you were in Paris.
Jeffrey Madoff: I met with both of them. When you look at the commercials, what Sony did, which ended up, I think, being a big mistake, but what Sony did was show you how all the components fit into this very small piece and that the technology, that it was small, that fit into something a little bit bigger than a cassette, which is what they played originally. What Apple did is they had that kind of an animation of a person dancing. And that to me became the example. And when I gave my branding lectures, I would show those things back-to-back because what Sony did is they showed you the technology, but they didn't …
Dan Sullivan: Back stage.
Jeffrey Madoff: That's right. So Apple already assumed that they systematized predictable, which is it works, it plays music. Here's the fun you're gonna have with it. And so that was the human element. They humanize the exceptional. And I think that's how they won the battle for that, how they won the battle for the phone, by doing exactly that. And I think people overlook that insight. And it's so important on every level of business. I think it's incredibly, incredibly important.
Dan Sullivan: There's another story about Steve Jobs that fits in directly with that. When they created the first iPhone, they gave it to him and he says, take the cover off. And he says, well, you know, the cover never comes off. He says, I want to see what it looks like inside. And it was, you know, a jumble of wires. And he says, not beautiful. The inside's not beautiful. And his design team said, nobody's ever going to see the inside. And Steve Jobs says, no, but we'll know. I want it to be beautiful on the inside too, even though nobody's ever going to see it. But that's a whole attitude. That's just a total attitude towards life.
The other thing he would do is that apparently, and I think it was with the first iPod came out, the boxes they came in were so amazing. As a matter of fact, I kept the iPod box 15 years after I got rid of the iPod. And apparently, Steve Jobs said, the person's in the store, how are they being treated? How are they looking at the product? What's the box look like? And he would take them through the whole progression. of what had to happen with the customer, the entire experience of the customer, until they got home and actually took it out of the box and started to use it. He wanted to know what their total experience was, and we got to make that experience. So I think we're zeroing in on something. We're not selling products and services, we're selling experiences.
Jeffrey Madoff: That's right. And, you know, the Apple Store, as you mentioned, is front stage—the decor, the whole setup of it, because people remember and tell stories about their experiences. And when they talk about being an evangelist for the brand, what that means is you're singing the praises of that. They become part of your marketing. And I think a lot of companies don't realize how you have to enlist others to do that in order for a business to grow and be successful.
Dan Sullivan: Yeah, a client that you know, one of our long-time clients from Chicago, Ken Arlen. Ken has bands. He can slice and dice about 20 different presentations. He's got about 70 musicians. He's got a dozen singers and specialty artists and everything. So he was telling a story that he was at a social event in Evanston, where he lives in Chicago. And a nice man came up, he talked to him, and he said, would you do Ken? And they talked about Ken. He says, what do you do, John? He says, John, he says, well, I have the main Lexus dealer here in Evanston. He says, Evanston, yeah. He says, yeah. Have you driven a Lexus? He says, no. He says, but I really like what they look like and everything else. And so, you know, Ken immediately, his shields are going up, it's a car dealer, you know. And he said, yeah, he says, you should drive one. You should drive one, Ken. You'll notice the difference. He really noticed the difference. He says, yeah, I'll come by. He says, you don't have to. He says, and they went over to a window. He says, see that car here? Here's the keys. Keep it for the weekend and come and see me on Monday. And on Monday, who bought a car? Him. I mean, that's pure theater.
Jeffrey Madoff: That's right. And it's also the human touch.
Dan Sullivan: Yeah, well, I trust you. What are you going to do?
Jeffrey Madoff: Exactly. So we've covered a lot of different ground here. What would you say your takeaway is?
Dan Sullivan: Well, I think the big thing I really got reminded because I talked a lot in the role play before I went after the central issue. And that is, how do you need to be freed up to, you as the owner of the company, how do you be freed up to be more excited and enjoying your work? And whatever it is, that's my job. My job has to contribute to freeing you up. It's not about the company growth and that and everything else. It's just how do you have to be freed up?
Jeffrey Madoff: Right.
Dan Sullivan: Yeah, and that's everybody's main issue. How do I get freed up? Because most people are trapped in a lot of things that they don't like doing. And if you could free them up from what they don't like doing, you're great.
Jeffrey Madoff: Yeah, and you are letting them know that you're aware.
Dan Sullivan: Oh, yeah. And wherever I'm hired to help you, I'm not going to stay there long if I'm really useful. I'm not going to stay there long.
Jeffrey Madoff: And for me, it's that and it's also, although we just said it bears repeating because this applies in so many areas or could apply in so many areas, which is systematize the predictable and humanize the exceptional. That's huge. And the combination of those two things can lead to tremendous, tremendous success and satisfaction. 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.
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