A Coincidental Conversation™ with former Disney Executive Dan Cockerell about Courage, Curiosity and Being the "Youngest Door-to-Door Salesman Ever"

A Coincidental Conversation™ with former Disney Executive Dan Cockerell about Courage, Curiosity and Being the "Youngest Door-to-Door Salesman Ever"

Every time I interview someone related to Disney, I find myself looking for the traits they share with Walt Disney. Insofar, of course, as much as I actually “know” Walt.

I didn’t have to look far when it came to Dan Cockerell, an author, consultant, speaker, and coach who, before starting his own company in May 2018, had a 26-year career with Disney, which included starting in their college program, managing Disney’s All-Star Resort and Disney’s Wilderness Lodge Resort and Fort Wilderness Campground, and being Vice President of EPCOT, Disney’s Hollywood Studios, and the Magic Kingdom Park at Walt Disney World in Orlando.

No, I didn’t have to go digging for those traits. With Dan, they’re right there on the surface, smack dab in the middle of everything he does and says. Curiosity. Positivity. A believer that we make our own luck. And that the best way to face that “great, big, beautiful tomorrow” that Walt so often talked about, was to be open to it, with a smile on your face.

Like Walt, Dan is curious. Like Walt, he is not only open to change, but his life seems to demand it. And, like Walt, he has shown courage since he was a kid, as I learned how he became the youngest door-to-door salesman I’d ever met, selling the most important product as a kid– himself as a friend.

So, with that, below are 14 takeaway quotes from our conversation (slightly edited for length and flow). And I’m guessing that, after you read them, you’ll want to watch our full conversation.

Takeaway Quote #1: On why he embraces change and how he became a “door-to-door salesman” as a child: “Growing up, my dad [Lee Cockerell, also a former Disney executive] was in the hospitality industry, and we moved to a new city every year and a half. When we’d get to a new neighborhood, my mom would encourage me to go door-to-door on my own and knock on people’s doors to see if they had kids. Of course, that wouldn’t happen now.

“My dad always said that a big part of life is doing things to get exposure and experience. Also, as we travelled, my parents would take me different places and expose me early on to be curious and want to know about cultures, try different foods, meet people, and so on.

“Finally, it’s also part of my personality. It was kind of wired into me that I was just really interested in the world and experiences.”

Takeaway Quote #2: Curiosity did wonders for Dan. “In her great book, Mindset, Carol Dweck talks about growth mindset and fixed mindset. I seem to be attracted to people with a growth mindset, who are curious and willing to try new things. Those people who say, ‘OK, I’m going to go try something. And if it doesn’t work out, it doesn’t mean I’m a failure. It means I didn’t get that thing right.’ And what I found is that, in my life, in my career, I’ve tried to do some things that I couldn’t master. But I’ve had many wins and many other doors opened when I was willing to go ask about things I didn’t understand or talk to that person next to me on the plane or go travel somewhere that I’d never been before and not get stressed out about it.”

Takeaway Quote #3: Luck favors the bold. “Luck is also part of that growth mindset. So, for example, if you can see opportunities around you all the time, you’ll have lots of opportunities. But if you put blinders on, you’re not going to see all those things. So, I tell young people in their careers to be open-minded and don’t judge moments. That every time you learn something new, you’re adding a piece of the puzzle to your life. And those are all going to pay off in the future. Of course, the future may be tomorrow, next week, or 20 years from now. But all those things come back to bear, which again shows that value of experience and exposure. So, it’s that idea of getting yourself out there and treating things as an adventure.”

Takeaway Quote #4: On what he tells entrepreneurs to help them move past any fear they might have: “I’ve learned that you can’t change people very much. People are kind of set at who they are, their personalities and their risk tolerance, or as I call it, their ‘thermostat.’ They may go up and down a bit, but, if they say, ‘I’m afraid to take risks and do public speaking,’ well, they’re probably not going to be doing base jumping. So, I tell people, ‘You just have to figure out how to operate with the skill set, passion, and talents and competencies you have.’ If they’re concerned about taking risks, I suggest taking it slower, or maybe first spend time talking about all the variables. Everyone comes at it differently, and that’s where you just have to understand how people process information.”

Takeaway Quote #5: On how he was introduced to Disney. “I had been to Disneyland as a child while my dad was working in the hotel business. But then I didn’t go to Walt Disney World until I was 19 years old, when I entered their college program. I never planned on having a career at Disney, but once I experienced it, I was hooked. One reason was that I loved the structure. And, when you have 20 million people visiting your theme park every year, you better have a plan every single day of how you’re going to handle that. Plus, Disney wants people who are interactive, who like working with people. I know it sounds kind of obvious, but people have asked me before, ‘How do you hire so many friendly, warm, hospitable people to work at Disney? It seems like everyone is so nice.’ And I said, ‘Alright, here’s a secret. Don’t tell anybody. We do it by finding people who are warm and friendly and hospitable, and then we hire them.’ Probably the most important part of leadership is getting the right people on your team to begin with.

Takeaway Quote #6: Even though he loves structure, he also does well with ambiguity.Yes, as an example, I always say that when I ran the Magic Kingdom, I didn’t control anything, but I influenced everything. Just because you’re the vice president of a theme park, that place is still running 24 hours a day. There are 20 million guests and twelve thousand employees. So, you’re not in control. You can make sure things do or do not happen. But the thing you most do is create the environment, the expectations, and the vibe – and you reinforce them. And you hire the right people and then stand back and let the thing go. Then you help shore up the areas that need shoring up. But that’s one of the hardest things about leadership. It’s about letting go of things, delegating and trusting people to make the right decisions.

Takeaway Quote #7: On how companies, like Disney, keep a vision embedded in the organization long-term. “The big differentiator at Disney is the common purpose, which is different from the vision and mission. It’s what everyone should be thinking about when they come into work every day, no matter what job they have, and no matter what level they are. Even though their roles are different, the purpose of everyone that works there is the same.”

Takeaway Quote #8: On what the purpose of Disney was. “There are many ways to say it. At Disney, we’d tell people, ‘Your purpose is to make magic. And while you’re doing that, you’re going to be selling Mickey bars. And while you’re doing that, you’re going to be checking the heights of guests coming on to the attraction. And while you’re doing that, you’re going to be checking people into the hotel. And while you’re doing that, you’re going to be a housekeeper cleaning the rooms.’ That’s why every day you’re coming in saying, ‘How do I create magic for guests?’ After all, we knew we had the big stuff already, the castle, the attractions, and so on, and we’re going to keep building those. But what it really comes down to is ‘Are the guests going to walk out of here with an emotional connection? Are they going to have a story about how they were treated or an experience they had?’

“You know, we seldom got letters saying, ‘We went to Disney and really love Space Mountain.’ Instead, the letters we mostly got were, ‘We got back to our room at the hotel and the towels were folded like animals all over the room” or “All of my daughter’s plush animals were propped up on the bed and Mickey had the remote control in his hand, watching the Disney Channel,” or “I was in the Magic Kingdom and one of the custodial cast members painted a picture of Goofy on the ground using water from a pan. Or ‘We were walking in the park and a cast member saw it was my son’s birthday.’ So he took us and said, ‘Do you have five minutes? And we got to meet Jack Sparrow in person.’ So it’s this idea that everyone, no matter what job they’re doing, they’re always looking for opportunities to do things that only are done at Disney. It’s an ‘only Disney’ moment. Only at Disney, would a housekeeper create these scenes in the room to discover when they get back, knowing they likely won’t ever meet the guests in person. Only at Disney would the bus driver do a singalong on the way to one of the hotels, resorts, or parks. So, once you rally people around a common purpose and you hire the right people, you’re basically empowering them to be creative and go figure stuff out.

Takeaway Quote #9: On how the apple doesn’t fall far from the tree. “My Dad,Lee Cockrell, retired from Disney in 2006 as executive vice president of operations, reporting to the president of Walt Disney World. Now, he’s a consultant, does keynotes speeches and podcasts, and has written four books. He’s a powerhouse.” [Editor’s Note: Hmmm, sounds like someone else I know, Dan.]

Takeaway Quote #10: When there was the whole furlough with the pandemic and Dan worked together with his wife, Valerie, and Dad, Lee, to give back. “After hearing that Disney employees were being furloughed because of the pandemic, we wanted to help. So, even though we’re not with Disney anymore, we still know a lot of people there obviously. It was tough enough for me to leave Disney after twenty-six years that I couldn’t imagine what emotions they were going through. So, we thought we were uniquely positioned to be able to get on a call and talk to them about life after Disney because we lived it. So, we put on a free webinar to talk about our experiences, what we’ve learned along the way and give them encouragement. It was extremely fulfilling.”

Takeaway Quote #11: On his work with the Disney Institute. “My wife was a facilitator there for seven years. And I was a regular guest speaker there for about 20 years. When they offer their programs, they usually bring a manager or executive to speak to the groups. So, when they were looking for speakers, I raised my hand. I also wanted to get better at speaking. So, I got to train and practice public speaking for 20 years before I had to go do it for a living. If you’re going to be in a lot of roles today, you need to be good at public speaking and you have to be able to speak to groups of all sizes and have a presence.”

Takeaway Quote #12: On why he supports Junior Achievement of Central Florida. “I did Junior Achievement in high school. It was a club where you’d come together with other students after school and create a company. You’d pick a product and a price, market and sell it, do all the financials, and so on. And, at the end of the semester, you’d liquidate the company. Today, I think you donate the money to a non-profit. Back in the 80s, everyone just would divide the money and keep it. We weren’t quite as thoughtful about the community as kids are today, but you really learned about the free enterprise system. So, when I moved to Florida, and became a general manager, I wanted to get involved with non-profit work and give back. Junior Achievement had a board position available for Disney, so I joined the board and served on it for about 16 years. It was incredible.

“You know, there are so many organizations out there to help. I just hope people pick one and do something. If you’ve been lucky enough to have a successful career and gotten a lot, it’s time to go help people.”

Takeaway Quote #13: On where Dan calls “home,” since he has moved around so much.I’ve concluded that my home is where I’m with my family. Right now, home is my wife and me. Then, this Christmas, for the first time in two and a half years, we’re going to have my parents and all three of our kids together. So, that will be home, whether it’s a rented Airbnb or wherever we’re going to be. You know, I looked back at my childhood homes, about ten of them, and I also visited some of them. I have great memories from all of them. So, home for me is where I where I am with the people I love.”

Takeaway Quote #14: On how Dan would finish the quote often attributed to Walt Disney, “It all started with the mouse,” if talking about his career. “It all started with a passion for adventure. And when I say ‘adventure,’ it doesn’t mean it’s always easy, or comfortable, but it means you’re going to go out and you don’t know what’s coming next. That’s been a big part of what I’ve done over my career, and I’ve really enjoyed it.”


And wait, there’s more…


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