The insurance company I worked for (then American Bankers, now Assurant) was based outside Miami Florida.  I was head of IT for a small division located in Southern California.  Corporate had named a new CIO, Michael Ray.

On his first visit to our CA office in his new capacity, we were told to plan to have dinner with him in groups of four to six team members each night, Monday through Friday to let him get to know our team.  We arranged our groups , picked our nights to host, and selected the restaurants.  I picked Friday for my group and checked the restaurant list to assure we didn’t take him somewhere he had already been earlier in the week.

All the restaurants were generic chain places to eat.  I felt my group should give Michael a more unusual experience.

A friend of mine, who was a part-time Disney employee, got us a reservation at Disneyland’s Club 33.  Club 33 is not open to the public and is the only restaurant at the park that serves alcohol.  It sits adjacent to the Blue Bayou restaurant and above the Pirates of the Caribbean ride.

Friday after work, the four members of my assigned group plus Michael drove to Disneyland.  We didn’t tell Michael where we were going.  Once in the Disneyland parking lot, he knew Disneyland, but still had no idea where we would be eating.  Our park tickets were waiting at will-call and we entered and were following signs to the Pirates of the Caribbean.

Insurance company folks dressed the part back then. Suits, ties and perhaps a vest for the men.  Skirts and blouses, dresses, or suits for the women.  We did not look like tourists.  On our way to the restaurant, Disney guests and employees alike assumed we were Disney execs. We got deferential treatment from the employees and random questions about the park from our fellow guests.

We found the entrance to the restaurant.  There was a big number “33” carved into the dark windowless door, outside of which stood a single Disney person holding the traditional clipboard.  I gave her my name, she opened the door and were soon at our table.

Michael did not know Club 33 existed and he seemed to be okay with my choice of restaurants.  Dinner went well enough; he asked his questions, we gave our answers.  But Michael was more subdued than I expected. Perhaps it was fatigue from this being the fifth dinner he was having with his employees this week.  But perhaps he was not happy with our having taken him to Disneyland.  Had I made a career-limiting move?

Dinner was over and we were making our way to the exit when we heard the music that announced the soon-to-start Main Street Electrical Parade which marked the park’s closing for the night.  Packed in with the thousands of guests we continued shuffling toward the exit when Michael asked, “Can we stay for the parade?”

No career-limiting move this!  We took our positions at the street’s edge and the floats were soon passing by.  I heard a guest ask Michael, “How many lights are on that float?”  Without hesitation, Michael (who had apparently embraced his role of pseudo-Disney-Exec) answered, “40,000”.  And I am quite sure we heard him humming “It’s a Small World after all” on the way to the car.