Stay On Top With Dan!

Listen to #36 episode to learn what it feels like to leave Disney after 27 years of work, what Dan has learned from working at Disney, and how he organizes his work!

Dan’s first experience working for Disney was as a participant in the Walt Disney World College Program in Orlando in the summer of 1989, when he worked as a front desk host at the Contemporary Resort.

Upon graduation from Boston University in 1991, Dan moved to Florida and participated in the Disneyland Paris Management Trainee Program.  In January of 1992, three months before the opening of Disneyland Paris, he was transferred to France, where he remained for five years in various management roles. 

Dan has held various management and executive operations roles at the Walt Disney World Resort, both in the theme parks and resort hotels, and was the sixth executive to hold the position of Vice President, Magic Kingdom since the park opened in 1971, leading  TWELVE THOUSAND (12,000) cast members.

Dan retired from Disney in May 2018, and now runs his own consulting/speaking company.

Keynotes of this episode:

  • How does it feel to live Disney after 27 years
  • Running your own business after the career at Disney
  • Why having talented people on your team is the key to success
  • Dan’s ucoming book
  • Why Dan takes care of himself first

Books and people mentioned:

Listen to us on iTunes!


Podcast Transcript

Welcome back to the 36th episode of Stay On Top of Your Work Podcast. I’m Kate your host and this time I’m talking with Dan Cockerell.

In this episode, you will find out what it means to leave Disney after 27 years of work, what Dan has learned working at Disney, and how he organizes his work. He’ll also talk about the books he reads.

Dan’s first experience working for Disney was as a participant in the Walt Disney World College Program in Orlando in the summer of 1989, when he worked as a front desk host at the Contemporary Resort. Upon graduation from Boston University in 1991, Dan moved to Florida and participated in the Disneyland Paris Management Trainee Program.  In January of 1992, three months before the opening of Disneyland Paris, he was transferred to France, where he remained for five years in various management roles. Dan has held various management and executive operations roles at the Walt Disney World Resort, both in the theme parks and resort hotels, and was the sixth executive to hold the position of Vice President, Magic Kingdom since the park opened in 1971, leading 12,000 cast members. Dan retired from Disney in May 2018, and now runs his own consulting/speaking company.

[00:01:46 – 00:05:23]

Kate: Dan, thank you so much for joining me here. I feel very honored and very happy to have you here.

Dan: Thank you for having me on, I’m excited to speak with you today.

Kate: So Lee Cockerell was also the guest on this podcast and I decided that you would also be a perfect person to be here. So I’d like you to say a few words about yourself, if you could.

Dan: Sure. I grew up… my dad was with Marriott for 16 years so we moved a lot as I grew up. When you work at the hospitality industry, hotel industry, you end up moving a lot to different places. And we settled in Rockville, Maryland, outside Washington, DC when I was 12 years old and I grew up there. I went to Boston University and studied Political Science in my undergrad.

And I didn’t know what I wanted to do from a career perspective so I chose Liberal Arts. And I actually worked at Walt Disney World on a college program my sophomore year of college. With about 6 thousand college students that worked at Walt Disney World at a given time and it’s a great opportunity to get the Disney name on your resume. You learn a lot about structure, service, and it’s a great way for Disney to get, you know, younger people to come in for a short period of time to work there and build up their reputation and a lot of people end up staying.

So I went back to school for two years. When I graduated I still didn’t know what I wanted to do for a living so I went back to Disney, and I joined Disney internship program. So this was in 1991 and they were opening your Disney in 1992 in April. So I went down to Walt Disney World and got a work Visa through school. And I trained for 6 months. And it was about 300 of us from a lot of European cast members and some Americans that had Visas. And I worked at the parking lot Epcot at Walt Disney World, and then January 1st 1992 I flew over to France, and that was about 3 months before the park opened and I was a management trainee in parking.

And we opened the park on April 12 which was a very exciting day for us and I learned a lot in the first few months working there. And I was supposed to come back to the States in April of ’93 but I met this girl on Florida and she was from France and so we decided that things were going really well and so we had a 5 week engagement and we got married quickly. So I could get my work Visa and stay over in France. And so we worked there for 5 years, I worked in operations as a Front Line Manager for 5 years and our son was born over there. And then in 1997, the two of us moved back to Florida and I worked for Disney for 21 years right up until 5 months ago when I left and started my own consulting company and I’m doing keynote speeches now and consulting, and I’m doing some work in Croatia with the hotel company and I’m working with some online universities. And just… we’re sort of on an adventure now, after 27 years at Disney, my wife asked me last year, what are we gonna do next? And it took me about a year to decide to leave Disney since it’s a very, it’s a great place and you really get emotionally attached to it.

But we decided that, you know, our younger son, we’ve a daughter who’s in a college, we’ve a younger son is a senior in high school so he’ll be going somewhere next year. And so we decided we have an opportunity for freedom right now to go do whatever we wanna do. And so I left Disney 5 months ago and now we’re on an adventure, we’re selling our house in Florida. We’re moving to Boulder, Colorado, and we are going to see what happens next.

[00:05:24 – 00:07:04]

Kate: Amazing! That sounds really great! So how does it feel to actually end that career at Disney with so much experience and to start a career at some different point in your life? How do you feel about that?

Dan: Well, the first word that comes to mind is “terrifying.” It was pretty scary. You know, when you work at Disney for so long, you get used to working certain way and there are so many resources, so many talented people and you’re just not sure what else is out there in the world. But, you know, my dad did the same thing. He retired 12 years ago, left Disney and has had a great second career writing books and doing speeches and he’s helped me a lot. He’s given my advice and just giving me, introducing me to people and so that was a big help.

But as my wife said, she said, “I feel like we’re in college again except that we have a lot more wisdom and we have little money in our pocket.” And so it’s going to be very exciting. Having learned more in 5 months than I think have learned over the past 5 years. When you’re running your own business, there’s a lot of things you gotta start thinking about you never had to think about before – marketing, networking, your income touch write-offs. I mean you have to be super organized and pay a lot of attention to a lot of things because there’s no big team around to help you with all that.

So I went from leading 12.000 people at Magic Kingdom to now it’s my wife and dog and as I tell people, the dog has to go in and out all day so I’m even working for the dog now. But it’s been fun. I think the idea of having the flexibility and freedom for us to do whatever we want to do is certainly worth the experience at Disney that I worked for so long.

[00:07:05 – 00:12:50]

Kate: That’s great, that sounds really fantastic. And your dad, Lee Cockerell, who is a really inspiring person,    has a method of managing time. How about you? Do you have a method to stay organized? Because when you work like that and you’re flexible, you actually have to be able to somehow organize your time. How do you do that?

Dan: Absolutely! Now I have to admit, I’m not as organized as Lee is, I don’t think anybody is. For him it’s an art and a science all wrapped into one. But I’ve learned a lot from him. I took a time management course when I was 16 years old. He taught time management course. And I had my Day Timer when I was 16 and it helped me. It helped me get organized and I sort of adopted a lot of these principles along the way.

But I have a system. I think… He likes to have a paper book, he writes a lot of things in and I think today people look and say, “How can you use paper, everyone uses iPhones, everyone has the technology now.” And what I’ve come to realize is, I don’t really endorse any particular system, I just think people should have a system.

But I believe that no matter what you use, it really for me it’s not as important as making sure that you have a system and process to handle things in life. A lot of it is… I think you need to start out with your purpose. What are your values and what’s important to you and what are you trying to get done. And the way I’ve explained it to people I have come up with methodology when I think about my own life and I kind of have three big pillars. These three big themes I think about all the time. And I kind of judge myself every day and every week and every month and every year on how I’m doing.

And the first thing I’ve focused on is, I’ve learned this reading some books and hearing a lot of great speakers, my number one priority, and when I ask the audience what their number one priority is, people always say family, right? Because that’s what you’re supposed to say, your family is the number one priority. But that is not my number one priority.

I’ve come to learn that I am my number one priority. I have to take care of myself first. And I think people sometimes say, “Well, that’s kind of, you know, it’s not very nice, it’s kind of greedy and self-centered.” But what I’ve come to learn is, if you take care of yourself, you’re much better dealing with your family, you’re much more productive, you’re much better dealing with work and career and everything. And so I’m a big advocate of focusing on yourself first. It’s like they say when you get on an airplane, the oxygen mask comes down, and they always say, “You put it on yourself first before helping others. Because if you pass out, you can’t help anybody.”

And so I really think a lot about… and these are very basic things but I don’t think people always have a good bid on these is, you know do you know what your health is? Do you take care of yourself? Do you go to the doctor once a year? For women, do you get a mammogram on a regular basis? Do you get your prostate check? Do you know what your blood pressure is? Do you have resting heart rate and your blood sugar and all the things that are gonna help with quality of life as you get older. I think it’ important to keep track of those. And you have to be organized. It’s important to have systems and processes in place to remind yourself to do all those kind of things. Exercise, extremely important. What kind of exercise do you do? You don’t have to be tri-athlete to be fit, all you need to do is something physical.

But as I’ve noticed in the world now, everything is becoming automated now. You know, all the things we used to do to get our work muscles, aren’t there anymore. I mean, what was the last time you rolled the car window up and down. A lot of the cars now have automatic windows and doors, a lot of doors now you press a button, the door open. The sliding doors and escalators.

So I think you really need to focus on, make sure your body is getting the right amount of exercise. Not only is it good for our health but it makes you feel much better. It’s a great way to deal with stress. And then all the other themes – diet, sleep, hydration, emotional intelligence, you know we stress ourselves out a lot of times by thinking and getting upset over things and people say and thinking about things, so can you learn to control your emotions and how to listen and manage your stress level?

And I think time management is right in there with all those other things. When you’re organized, you have less fires you need to put out. You’re surprised less often, you’re able to do the things you wanna do because you thought ahead and you plan things. And it takes discipline but I’m really big advocate of do everything you can to take stress out of your own life before you focus on anything else.

And then after that, you know, you can go out and take care of your family, you can take care of your career or you faith or whatever your other priorities are. But that time management piece is way underestimated by people, how important it can be. When you’re organized, you just get to do more things. Because how often have you showed up at the restaurant, you just forgot to make a reservation or you wanna go see a certain show you saw an advertisement for and you didn’t have a system to write it down to remind you what day the ticket sales went on sale.

They’re just little things. But life is much better when you’re organized and you’re kind of ahead of the curve. So that’s kind of how I think about balance. For me, I use a combination of things. I have an iPhone. Siri’s one of my best friends, she reminds me of all kinds of things. When I need to be reminded to pick up something from supermarket or do something. And I have a few different apps I use. I’ll try different things at times but basically, what I’ve learned is, anything I asked anyone to do or anything I need to be reminded of, it goes into my desktop or my iPhone or goes somewhere.

I realized I have no memory anymore. There’s too many things happening. And so I have to really focus on system and a process so I can use my mind freed up to do other things.

[00:12:51 – 00:15:32]

Kate: We all need that second brain that holds our appointments and all the things we have to do. So, Dan, you worked at Disney and you had to deal with many people. So I’d like to ask you, when you talk about people and giving their time. Leading people is also about managing their time. What do you think about implementing time tracking to kind of monitor people and their work? Do you think it’s efficient? Because people are very often so afraid of it and that they will be spied on but you know, it’s not true. So what do you think about it?

Dan: Yes, I’m a big fan of role modeling. And so you can tell people what to do all day long but I think it’s much more powerful when you can role model. So if I tell my team that is’ important to have balance in life and make sure they’re spending time with their families I have to role model that. And some days I’d leave work early. If my work was done, I’d leave early and would hang around and tell them, “Hey, I’m leaving for the day, my work is done, I’ll be at home if you need to reach me.” And by doing that, they see that it’s also okay for them to do that. I think people get nervous that if the boss doesn’t leave, you can’t leave.

So I’m a big fan of delegating and trusting my team and letting them schedule and do what they need to do. But also there’s a term that we use often, “trust and verify.” So you wanna let people what they wanna do but you need their processes in place to make sure that things are getting done. And I have different people on my team. Some people are extremely organized. And other people aren’t as organized. And I said, you know if you need to figure that out or learn that, you know, get an assistant who’s gonna help you do that or take a class on it. I’m more interested… my focus was on the results. And so it wasn’t my place to tell someone how long work will take. It was up to them to figure that out. And I was a thought partner with them. And they were never alone. I always told them you’ll never alone. You can always come, let’s discuss. Always reach out to people to help you think about those things.

But everyone approaches things differently. Some people are better in delegating work than others and they get a lot more done. Other people like to do thing themselves because they wanna make sure it gets done right and what I’ve learned is you move up in the organization, you have to delegate more and more. You just don’t have the time and day to do everything yourself. And I asked my team to do certain and projects or certain things done, I would have a system to remind myself to follow up with them, ask them how things were going, make sure they had tools they needed and support. And then make sure they can reach those deadlines.

[00:15:33 – 00:18:15]

Kate: Okay, it sounds good. So what else have you learned from working at Disney in terms of managing people? Maybe one thing that really goes so deep into your memory that you think changed your work or attitude to people.

Dan: That’s a great question. I read a lot because I need to keep learning. And so I don’t really have any original ideas. I just keep learning from smart people and try to adopt that in my life. And the thing that I’ve realized over time is if you do nothing else, make sure that you have very talented people working on your team. Because talent is so important and when you get a talented person, they just get great things done and they’re proactive, and they’re creative, and they’re really good at what they do. And they’re passionate, they solve problems.

And the people who are highly talented on my team, they would identify problems I didn’t even know where problems, they come back to me with a solution even before I asked about it. And if I had a team with people like that, I wouldn’t even have to go to work anymore. But it’s hard to find people like that. But I think sometimes we settle for people that are good or very good and we don’t push hard enough to get people who are great.

People can do a lot more than they think they can. When I was growing up, I played lots of sports. And I had certain coaches who would push me to beyond pass the point I thought I couldn’t ran faster than I ever thought I could. I run farther than I ever thought I could because they knew how to motivate me and push me.

And so I would just challenge people and make sure you have great people on your team and you’re taking time to hire the right kind people because once you do that, you have more time to work on other things, you don’t have to worry nearly as much about things. And it just makes your life a lot easier. You see that happen all the time in sports. It’s easy to see because we can measure athletes pretty easily because you can see how fast they run or how many goals they score or how high they jump. The problem is in business, it’s not as obvious. There’s no this statistics. We’re always being asked, “Are you good problem solver? Are you creative? Are you resourceful? Are you productive?” And it’s not always easy to measure those things and so you gotta get a little creative doing that. Yeah but at the end of the day you can pay people a lot of money, you can create clarity for them, you can reward, you can build relationships with them. These are all extremely important.

But if you have the right talent, everything gets easier.

[00:18:17 – 00:21:40]

Kate: That sounds like a good trick at work, to have the right people, talented people. Are there any tricks or tips you could give to our audience that you use in your work and that really help you?

Dan: Yes, I think one of the things that I’ve done is not as exciting but every time I work with the new team, there’s a couple of things I do. The first thing I do is I sit down with each person reporting to me and we meet for a couple of hours. We may have lunch together or dinner together or coffee together. And 90% of the discussion is not about work. All we talk about is where they grew up, where they’re from, what jobs they’ve had, what experiences they’ve had, if they’re married, what their kids do, what they do on weekends, what hobbies they have, what they career goals are. We talk about very broad topics.

And I tell them I wanna do this because at work we hardly ever have time to talk about personal things because we really talk about work all the time, that’s what we do. And I think when you establish a relationship with people, you get to know them on a personal level, you build trust inevitably, when you make a mistake or you say something that may be offensive, they’re more likely to forgive you and you’re more likely to forgive them because you have a friendship.

And what I’ve learned, with friends also, these relationships, they’re never the same. What I found stereotypically, stereotypically, it’s not everyone but it’s what they stereotype is, in France, if you wanna get to know somebody, people are very closed, they don’t share nearly as much as Americans do, you know, they won’t talk about their family, there’s a lot of things they won’t share, and that’s not good or bad, it’s just the culture and you have to learn that.

Now, generally, stereotypically, in the United States, if you ask someone, they will tell you their life story, and they’ll tell you every detail they can’t wait to sharing with you. Not everyone’s like that. So I’m not saying that getting to know people and forming a relationship, it’s not the same in every culture, it’s not the same with every person, but taking the time just to get to know people on personal level, just outside professional I think is really important.

And then the second piece is clarity, setting clear expectations. When I started working with a new team, I had a memo I give them. It’s about five pages long and it’s just a list, I say, “Hey look, I don’t know you, I don’t know how this place works but let me tell you how I work. You know, once a week I’d like a one page recap from you on what you’re working on, what I can help you with, what ideas you have. IT can be a voicemail, it can be an e-mail, I don’t care what the format is but just keep information flowing to me so I know what’s happening. It makes my job easier.”

And I tell them, “If I give you feedback, if I’m wrong, I expect to get you push on me and if you accept the feedback, you need to put an action plan in place to correct the behavior. And if you do that, we’re gonna work great together. And I don’t measure your success in the amount of hours you work, I measure it on what you get done. So don’t think if you’re twelve hours a day, six days a week you’re automatically performing because maybe you’re just not organized and can’t get things done.

So I really value results. And I like to leave people to manage their own time. I think when people feel empowered, they manage their time on their own, that they’re much more productive and they get a lot more done. So I think those are the two big ones, the relationships, and clarity of expectations. And if you can get those right and you can get talented people, it’s incredible at the results you can get.

[00:21:41 – 00:23:35]

Kate: Okay. Dan, I’ve heard in your podcast, “Come Rain or Shine”, which you’ve just released, that you said you are working on a book. Could you share with us what’s the book going to be about or maybe it’s still a secret?

Dan: No, it’s not a secret! I’ll share it with you. Actually, the funny thing is, my wife is… I asked her if she’d help me write the book and the way it’s turned out  is I think I’m helping her write the book because she’s a really good writer. So we’ll sit and talk a lot and we’re each take a chapter, and she’ll write, I’ll write, we’ll proofread each other, we keep working on it and hopefully we’ll get it done at some point.

The working title, I don’t know if this is gonna be the title of the book, it might be, but the working title is How Is The Weather In Your Kingdom? So the idea is that the weather, the culture of a company or the culture of a family is like the weather, it’s all-encompassing, environment you walk into and in some cultures and some weather is violent, some is stressful, some is peaceful, some is supportive, and so as a leader or anyone, anyone working in an organization has the ability to control and influence the weather. And it’s how they interact with people, it’s how they feel about themselves, it’s how about they lead and manage others, if they watch each other’s back, if they help each other.

And so I get into all the details around that and it’s very much summing what I’m talking about in this podcast. You lead yourself first and once you’re feeling comfortable leading yourself, you can lead your direct reports and your team. And once you get there, you’re an extension of you. And once you feeling comfortable leading your team, then you can lead the organization.

But it has to be in that order. And I get into a lot of tactics and stories about how I did it at Disney and how some of the people I worked with did that. And I just wanna share those stories so people can take some of these concepts and hopefully apply them to their own lives.

[00:23:36 – 00:25:45]

Kate: I think it’s a great title and I’m hoping the book will come out soon. I can’t wait for it!

So what books do you read? Because you said you read a lot. Do you have maybe favorite titles?

Dan: Yeah, recently there’s a few I’ve read and I read tons of articles also. There’s just so many great articles out there today. But recently my father and I did a presentation in Zurich. They really wanted to talk about how to give effective feedback. It’s something that people are not very good at, people are nervous about giving feedback, they’re getting emotional. And so they wanted to talk about that. So in order to prepare for that I watched some videos and read some books. Some two great books that I’ve read, Crucial Conversations was one book, and I forget the author’s name but it really broke down sort of scientifically how to think about how to have a difficult conversations with people.

And then another great book was called Radical Candor. It really talked about how if you care for people and you’re direct with them, you can build up trust and really strong relationship. And that was a really good book.

One of my go-to favorites is The 7 Habits of Highly Effective People. That’s been around for a long time by Stephen Covey but I think that what he has in there, you know this idea of sharpening the self, you should always be improving yourself. The concept of emotional bank accounts, you know, when you interact with people you make deposits and withdrawals. And if you take too many withdrawals, you lose their trust and the relationship is damaged but if you keep making deposits, then you can ask someone for tings and it’s sort of an exchange system that we have in our minds with people.

Those are some of the good ones. StrengthsFinder 2.0, the Gallup organization route, I love those concepts that Gallup uses around. They really have a lot of concepts around talent and making sure that you get the right people and you get in the right fit jobs and they do it really nice so you can do your personal own strength assessment, find out what you lead there.

So those are three or four that are on my shelve that I pull out pretty frequently.


Kate: Great! So I have one last question to you, related to the name of this podcast, Stay On Top Of Your Work, how do you stay on top of your work?

Dan: The way I stay on top of my work, I go to bed early, I get up early. I found out that early in the morning there’s not many distractions. Everyone’s sleeping, I can get a lot work done, my mind is fresh and so I can knock out a lot f things.

And then the other thing is just discipline to track what I’m working on, when things are due, breaking large projects into smaller pieces. I think a lot of people get intimidated when these big projects come, they don’t take the time to think and plan and they get overwhelmed as opposed into breaking it into smaller pieces.

And something my dad taught me and I’m sure he talked about this when he did the show is, you should always in the morning just take a few minutes to plan your day. The investment of time, you know, you’re gonna spend eight to ten to twelve hours working, why wouldn’t you take ten minutes, fifteen minutes just to think about what the important things you have to get done for that day are. Because a lot of people don’t have a plan and they just get up and go to work and whoever calls them becomes what they’re working on. It’s not a good way because if you do that, other people are now managing your time. You’re not controlling your own time. If you don’t do that, you’re never gonna work toward your goals.

And so you really have to take control and you have to think. And it’s hard today, we just don’t always have time to think. So you have to block some time and make sure you have a plan.

Kate: Exactly. That’s what your dad talked about here as well and it’s a good advice.

Dan: Oh I know, we talk often and I think it’s a great advice. Oh I meant to mention on books, I love Creating Magic, that’s my favorite book that he wrote.

Kate: I love the one on time management, it’s actually helped to change my life a little bit and my time management.

Dan: Well, good thing I think Lee did with the Time Management book, he just doesn’t talk about technical part of time management. He really talks about why it can change your life and how you’ll get more done and you’ll be happier and won’t have regrets and you’ll take care of things and your health will be better, your relationships will be better, you’ll get better results. And then once he talks about that then he dives into very much the tactical, you know, the different approaches to it. I think that’s why it’s been so I guess popular for people.

Kate: Yeah, and it’s a good book to read I do recommend it to everybody.

Dan, thank you so much, it was an honor to talk to you. Thank you for taking your time to be part of this podcast.

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Kate Kurzawska

Author Kate Kurzawska

Marketing Assistant at TimeCamp. Freelance translator, proofreader, copywriter & content writer, software researcher.

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