Answer Tough Questions

“Take the chance to have as many experiences as you can. They really are educational—it’s like going to school.” Notable Moments [00:01:33] Reflections on opening Disneyland Paris [00:03:02] Why young professionals should embrace global experiences [00:06:00] The long list of cities Lee lived and worked in [00:08:36] On not letting comfort or homeownership prevent career moves [00:10:43] Why Orlando became the family hub (and how the "stuff" piles up!) Retired Executive VP of Walt Disney World, Lee Cockerell, shares personal stories and lessons from a career marked by saying “yes” to big opportunities, including when it meant moving cross-country (or across the world). He reflects on the launch of Disneyland Paris, how moving shaped his family, and why young professionals should pursue new experiences early and often. This candid conversation offers timeless wisdom about growth, change, and choosing adventure over comfort. Read the blog for more from this episode.  Resources The Cockerell Academy About Lee Cockerell Mainstreet Leader Jody Maberry Travel Guidance Magical Vacation Planners are my preferred travel advisors. Reach out to have them help plan your next vacation. You can reach them at 407-442-2694.

“Life is about service. When you help people, they don’t forget.” Notable Moments 00:50 – Staying grounded when your title changes 02:29 – Why relevance is fleeting and what matters more 03:55 – The power of knowing people’s names and stories 05:59 – Fame is short; service is lasting 08:10 – People remember how you helped, not your title 11:30 – Traits of a leader who earns lasting respect 14:33 – Upcoming October Mastermind event info In this episode, Lee Cockerell explores what it means to stay relevant as a leader and why lasting influence comes from service, not titles. With personal stories and wisdom from decades in leadership, Lee offers a heartfelt reminder: it’s not about being the star, it’s about being someone others can count on. If you want to create a lasting legacy, start with humility, consistency, and helping others grow. Read my blog for more from this episode.  Resources The Cockerell Academy About Lee Cockerell Mainstreet Leader Jody Maberry Travel Guidance Magical Vacation Planners are my preferred travel advisors. Reach out to have them help plan your next vacation. You can reach them at 407-442-2694.  

"Don’t be afraid of tough questions. They bring out the last 20% of truth that everyone needs to hear." Notable Moments 00:01:24  The importance of answering any question 00:03:14  Why tough questions build trust 00:07:00  How to tackle big problems as a team 00:10:21  Roundtables over rectangular tables 00:13:02  Living your values in real time Lee Cockerell, retired Disney executive and leadership expert, shares why leaders must welcome hard questions and answer them truthfully. He recounts a leadership session where every question was fair game and explains how this builds trust and unlocks the last 20% of truth people usually withhold. He discusses practical ways to create psychological safety, handle big issues like AI, and why getting everyone in the same room beats endless meetings. Lee reminds leaders to know what they stand for. After all, your reputation depends on it. Read the blog for more from this episode on answering the hard questions.  Resources The Cockerell Academy About Lee Cockerell Mainstreet Leader Jody Maberry Travel Guidance Magical Vacation Planners are my preferred travel advisors. Reach out to have them help plan your next vacation. You can reach them at 407-442-2694.  

“You’re either going to deal with it now or deal with it later. That’s how time works.” Have you ever noticed how easily we get used to things that aren’t working the way they should? It happens at home, like my garage door that only works if I hold the button, and even more often at work. Fixing what’s broken, no matter how small, sends a message. It reinforces standards, builds morale, and improves the guest and employee experience. You don’t need to do it all at once, but you do need to start noticing again. Read my blog for more from this episode on why you don't want to get accustomed to average.  Notable Moments: [00:03:30] — "It’s amazing what we get used to and think is okay"  [00:06:00] — How we set emotional priorities [00:07:40] — Importance of walking the floor and modeling high standards at work [00:13:00] — The small details that matter [00:15:38] — Creating habits by giving teams clarity and preparation Resources The Cockerell Academy About Lee Cockerell Mainstreet Leader Jody Maberry Travel Guidance Magical Vacation Planners are my preferred travel advisors. Reach out to have them help plan your next vacation. You can reach them at 407-442-2694.  

"Nobody knows you have low self-confidence but you. And chances are, most people in the room feel the same way." Notable Moments 02:19 – Advice on breaking free from negative environments 04:16 – Why moving to a new city helps build self-confidence 07:46 – Choosing to return home vs. never leaving 08:54 – How to grow confidence without leaving your environment 10:21 – Becoming an expert to grow credibility and demand 11:26 – Track your wins and evidence of progress 12:09 – Morning Magic Planner and the power of daily focus Lee Cockerell dives into the real root of self-confidence: action. Lee shares personal stories from his early years in Oklahoma and explains how moving away and changing your environment can unlock new levels of self-worth. They explore how expertise builds confidence, the impact of negative feedback from family, and how to get unstuck when you can’t leave. This episode is full of practical and motivational advice to help you build confidence and take ownership of your life. Read Lee's blog for more details from this episode on building self confidence.  Resources The Cockerell Academy About Lee Cockerell Mainstreet Leader Jody Maberry Travel Guidance Magical Vacation Planners are my preferred travel advisors. Reach out to have them help plan your next vacation. You can reach them at 407-442-2694.  

“You are the problem… or you can be the solution. Manage yourself first.” Lee Cockerell answers a listener’s two-part question on handling emotions in the workplace and at home. He shares strategies to stay calm, cool, and collected, even when tempers rise. Lee emphasizes the importance of managing yourself first, creating psychological safety, and learning to anticipate your emotional triggers. From family squabbles to workplace frustrations, Lee offers personal stories, practical advice, and simple tactics to become a steadier, more trustworthy leader. Read the blog for more on managing emotions in the workplace and at home.  Notable Moments [00:00:42] – How to “park” emotions when tensions rise [00:02:37] – What to do when you know you tend to overreact [00:05:54] – The value of stepping away to regain composure [00:08:09] – The importance of creating psychological safety [00:10:36] – How to keep emotions at home from following you to work [00:14:43] – Managing yourself is a full-time job Resources The Cockerell Academy About Lee Cockerell Mainstreet Leader Jody Maberry Travel Guidance Magical Vacation Planners are my preferred travel advisors. Reach out to have them help plan your next vacation. You can reach them at 407-442-2694.  

“If you don’t ask, you don’t get. It’s that simple.” Notable Moments 02:28 – Why you should be asking for what you want 03:36 – The origin of Jody and Lee’s working relationship 04:54 – Why most people don’t ask and how it limits them 06:22 – A story about a student who asked Lee just to be known 07:58 – How to ask without seeming selfish or overreaching 09:36 – Introducing yourself to company leaders 11:52 – Don’t say no for someone else. Ask and let them decide 13:19 – Challenge: Ask for something big and tell us what happens One of the simplest yet most overlooked success strategies: asking for what you want. From professional promotions to meaningful connections, Lee Cockerell explains how powerful it can be to speak up and ask. Whether you’re early in your career or a seasoned leader, this episode will challenge you to be more intentional and courageous in pursuing opportunity. Read the blog for more on how people miss out on great opportunities simply because they don’t speak up.   Resources The Cockerell Academy About Lee Cockerell Mainstreet Leader Jody Maberry Travel Guidance Magical Vacation Planners are my preferred travel advisors. Reach out to have them help plan your next vacation. You can reach them at 407-442-2694.  

"What helped me the most was, leaving home and going out on my own and getting experiences." Jumping into the unknown is rarely comfortable, but it’s where true growth happens. Stepping outside our comfort zone reshapes our perspective and how we lead, work, and live. That is true whether it’s traveling to a foreign land or saying yes to an intimidating opportunity. After hearing Jody share his whitewater rafting adventure in Chile, it struck me how bravery really is progressive. Every time I took a leap in my own career, the fear was real. Moving countries, taking new positions, even getting fired at one point. But with each jump, I came back stronger, wiser, and more confident in my ability to handle whatever came next. It’s amazing how we talk ourselves out of risk because of fear of not knowing or the fear of what others might think. But most people are too busy worrying about their own lives to be focused on ours. Experience is the best teacher. You can read about whitewater rafting all you want, but nothing compares to being pulled under and coming out the other side. Setbacks like getting passed over for a promotion, or losing a job, often become stepping stones to something even better. The more we say yes, the easier it gets. Don’t be afraid to trust yourself, and surround yourself with people who support and inspire you. Remember, courage and leadership don’t appear all at once. They grow with every brave choice you make. The key is to take that first leap. You never know where it might lead. Resources The Cockerell Academy About Lee Cockerell Mainstreet Leader Jody Maberry Travel Guidance Magical Vacation Planners are my preferred travel advisors. Reach out to have them help plan your next vacation. You can reach them at 407-442-2694.  

"We all have our own thing, and we all have to make that decision every day about what's in it for us, is it worth it, and is it worth my time." Notable Moments 00:36 When to Say Yes or No 03:22 Invitations Increase with Familiarity 08:02 Facing Life's Tough Challenges 12:14 Managing Life's Responsibilities 14:17 Get Organized for Success Sometimes, the most powerful tool you have is a simple “no.” During my years at Disney, I learned that it's okay to not say yes to every opportunity. The more important thing is knowing which doors to walk through and which ones to keep closed. Success isn’t about overloading your calendar. It’s about making conscious choices so your time and energy add up to something worthwhile. I’ve seen leaders rise by grabbing big opportunities. Djuan Rivers seemed to say yes to challenging new roles again and again. He didn’t accept every little invitation though. He chose the moves that advanced his career and expanded his world. On the flip side, I said no to a lot of late-night banquets and endless committees so I could be ready for what really mattered the next day. It comes down to this: “Is it worth it?” That’s the question I challenge myself with all the time. The best use of your time is investing in things that help you grow, personally and professionally. Say yes to the adventure, the project, or the role that stretches you, but don’t be afraid to save your time for when it counts. And here’s another secret: A big part of making your life easier is tackling the hard things head-on. Write down the tough conversations you’re avoiding, make a plan, and just get it done. Don’t let the easy distractions pile up and rob you of bigger opportunities. Master the art of yes and no—your energy, focus, and future will thank you. Resources The Cockerell Academy About Lee Cockerell Mainstreet Leader Jody Maberry Travel Guidance Magical Vacation Planners are my preferred travel advisors. Reach out to have them help plan your next vacation. You can reach them at 407-442-2694.  

"When you start doing what everybody does, it's hard to be noticed any longer. Professionalism gets you noticed." Notable Moments 00:40 "Stories That Work" Event Recap 04:57 Embrace Professional Etiquette 07:34 Professionalism Over Expertise 11:16 Importance of Professional First Impressions 15:20 Encourage Open Conversations Time and time again I see people underestimate the power of professionalism. Unfortunately, it ends up stalling their careers before they’ve even hit their stride. During our latest conversation, I shared how critical it is to set expectations for professionalism, whether you’re running a classroom or leading a workplace team. I believe that professionalism is showing respect, being reliable, and paying attention to the details. Those can make or break first impressions, as well as shape your entire reputation. I learned this early on in my own career, thanks to mentors who stopped me before I made missteps in dress and behavior. The classroom example we discussed hit home. Students weren’t waiting their turn, interrupting others, and leaving early. My advice: lay out the rules clearly from day one. Make professionalism just as much a part of your teaching as the subject matter. It’s the same in the workplace. If you don’t make it clear what’s expected, chaos creeps in and opportunity slips away. Remember, your reputation starts with the small things, the details others notice but never mention. If you’re a leader, teacher, or even a parent, don’t shy away from the tough conversations about professionalism. It matters more than people realize, and it’s often the reason some move ahead and others get left behind. Teach those soft skills such as reliability, courtesy, and awareness. By doing that you are setting people up for real, lasting success. Remember, being just “one of the herd” won’t get you noticed; professionalism will. Resources The Cockerell Academy About Lee Cockerell Mainstreet Leader Jody Maberry Travel Guidance Magical Vacation Planners are my preferred travel advisors. Reach out to have them help plan your next vacation. You can reach them at 407-442-2694.