Life in a Day as An Executive Assistant

Post-it Note Moments

Having been an executive assistant for over 30 years, I have encountered some unbelievable moments in my career that left me scratching my head, wondering, “Did that just really happen?” I thought, “You want me to do what?” or “You’ve got to be kidding me!” I soon discovered that many other administrative professionals and executive assistants have similar funny, unbelievable, or crazy stories that need to be shared.  

I have collected those stories, but they sat in my folder (maybe for a possible book) for years until now.

Now I want to open that folder and share some of those true stories with you in the months ahead, hoping that they will make you laugh, resonate with you, or even validate our shared human moments in this demanding and challenging role.

Miracle Found In a Dumpster

Kay’s day was going quite well. The double-shot caramel macchiato she had bought from Starbucks had finally kicked in, and everything was running smoothly. With the caffeine boosting her energy, she was getting things done! Her mantra of “I’m calm, collected, and way cool” was working perfectly. Kay was the office Executive Assistant, beloved by her peers and management. She was a dynamo! Her ability to keep her executive happy and productive was unmatched.

One morning, her executive arrived at the office looking harried and stressed; she immediately sensed he was ‘off’ and not his typical self. Before she could even ask, he began to share his dilemma with her. "Kay, I stopped by the coffee shop to get my latte this morning. Once I arrived and parked my new car, I took the empty cup and threw it into the big trash dumpster behind the building. Suddenly, I realized that the silver “ring-thing” from my car cup-holder was attached to it! It is a new car, and I do not want to have to replace it. Can you please get it for me?”  Then he was gone in a flash. 

She needed a moment to process what had just happened. “He wants me to do what?” As an efficient executive assistant, she knew that making her executive happy was a priority; she had to retrieve her executive's silver "ring thing" cup holder, or else their day would not be a good one. 

Off she went to the back of the building and the monstrous dumpster. When she arrived at the dumpster, it became very clear that the bin was huge relative to its depth. But worse for her, standing at 5 feet 2 inches in her high heels, it was higher than her short frame, and to make matters worse, it was full!

Not to be deterred, she found a ladder in the warehouse and dragged it towards the dumpster and firmly propped it up against the side. Her heels came off, she rolled up her pants and climbed right in! It can be said that it was not an easy task given there were a weeks’ worth of trash she had to sift through; however, the silver cup “ring thing” and the discarded coffee cup appeared, and with a massive sigh of relief, she grabbed it,  climbed down from the bin, brushed herself off, thoroughly washed her hands (and the silver cup “ring thing”) and hurried back to her desk to await her executive’s return.  

When her executive finally returned from his meeting, she wore a huge smile and proudly stated, “Mission Accomplished,” while showing him the silver cup “ring thing” holder. He looked at her and then at the silver cup holder “ring-thing" and exclaimed, "Awesome job! I hope you don’t mind but here are the keys to my car – you can’t miss it, it is the new one parked right outside; so, if you can just put it back for me, that would be great!" "I’m going to be late for my next meeting, so can you call and apologize for me and let them know I’ll be there in 10 minutes?" A definite signal that it was time for her to get back to her day. 

Although her executive did not outwardly acknowledge it, she was aware that she had gone above and beyond (and literally dumpster dived) to perform a miracle that day!