BreadBox Leadership



Conversation with Lee Cockerell - Executive VP of Operations at Walt Disney World

Recently, my family (Nick's) visited the most magical place on earth: Walt Disney World in Orlando, Florida! My family has always vacationed here because we've always loved how excellent, clean and magical Disney is. A few months prior to our trip, I sent a letter to the former Executive VP of Operations at Disney world Lee Cockerell (full story here), who has written multiple books and hosts an engaging podcast. Through a series of conversations with him via email, I had the opportunity to schedule and meet with Lee during my stay in Orlando, Florida.

While sitting in a Starbucks 20 minutes away from Disney, I asked Lee a handful of questions and engaged in conversation with him for over an hour. Here are some of the questions I asked him, along with a few snippets of his response (paraphrased from notes I took):


NICK: What actions can I take to become better at delegating?

LEE: Well, I'd start with the basics: know the people you're delegating to and their capabilities. Are they capable to do what you need them to do? Can they do it? If the answer is yes, sit down with them and talk about deadlines. When do you want the project done? What are the outcomes you desire? It's important you put people in their sweet spot so they can love what they do. If they love what they do and you're clear with them about what you're delegating to them, they'll get it done. The thing that will make you and the people you delegate to successful is clarity. Be as clear as you possibly can with your people

NICK: What strategies do you suggest for providing clarity?

LEE: Say you'll check-in with them. Weekly. Monthly. Whatever works for your schedule and theirs. Take the time to show you care about them, their contribution to the project, and be sure to check-in with them so you can hear from them and remind them of the vision. Another thing I like to do is ask people to repeat what I said back to me. Repeat the desired results that I want, that needs to happen for this project to work. If you're going to be clear with people, you have to set up time to meet with them. Find unique ways to remind people of the end goal, and clearly communicate it to them constantly. The biggest thing I've learned through my life is clarity is key. If you're clear, honest and upfront with people, it gives them no reason to wonder of add their own assumptions about you, a project or their performance.

NICK: That's something I'm not good at: being upfront with people or having difficult conversations. What advice can you give about having difficult but necessary conversations?

LEE: Make it a priority to have difficult conversations with people. Schedule it in your calendar. Don't give yourself an excuse to not have a difficult conversation. Be honest with the person upfront and tell them why you are meeting with them. "Jim, we are meeting today because of your poor attitude toward me and your colleagues," and proceed to share with them the issue. Something you should always say is "I am talking to you about this for your own sake and so you can be successful here." Never make the conversation about reprimanding them or demeaning them. Seek to understand why they are lacking or doing something undesirable, then be honest with them. Again, the most important thing is clarity. Be clear with your expectations, and be clear with your intentions. Make sure you always show that you care about them and want to know why their work or attitude is undesirable.

Something else I'll add to difficult things is that you should make it a priority to do one difficult thing a week. Make a list of difficult things currently on your plate, and prioritize them so you do someone hard once a week. Maybe it's a difficult conversation, or maybe it's rethinking a project strategy. Whatever it is, do one difficult thing each week. Schedule it. Stick to it. This gives you the ability to rethink what you're doing and become better. Always work your hardest and try to improve yourself and the people around you. It's not easy, and that's why so few people actually do it.


Our conversation took a few turns I didn't expect, but all of it was extremely beneficial for me and hopefully you as well! Here are the summaries I made of our conversation:

  • Know the people you're delegating to and their capabilities
    • Put them in their sweet spot!
  • Always be clear
    • Check-in with people you manage
    • Ask them to repeat the desired results
  • Have difficult conversations that are not demeaning or reprimanding
    • Let them know you want them to be successful
  • Do one difficult thing a week

If you enjoyed learning from Lee Cockerell, you'll certainly like his podcast and books! Check out his website and podcast links below:





**Written permission from Lee Cockerell was granted for the release of this content**