My Top Embarrassing Career Moments

Mistakes and embarrassing career moments come with the territory. They are a part of life and happen to everyone. These moments need to be viewed as valuable learning experiences. In the business world, I see them as a rite of passage.

The goal is not to work so carefully or perfectly to avoid these moments. Instead, accept the inevitability of blunders and focus on developing resiliency and a good sense of humor.

“Don’t place your mistakes on your head; their weight may crush you. Instead, place them under your feet and use them as a platform to view your horizons.”

If you think you have some classic embarrassing career moments, wait until you read about these!

- During my first-ever sales presentation, as a rookie right out of college, the prospect, the owner of the company, nodded off about 15 minutes into the meeting. Needless to say, I was stunned and was convinced I had an out-of-body experience. I kept coughing loudly and knocking on the table to stir him and keep him awake. I thought Candid Camera was secretly filming me!

‍- While sitting opposite a client behind a large desk, my pants completely split along the seam from the knee to the crotch! Dear lord! I held my briefcase on my lap with the top open to cover this up so only my head was visible. The client kept straining his neck to look over the top of the briefcase lid. I didn’t have the nerve to let on what happened. He looked at me with this puzzled expression as if he was thinking, “What the hell is wrong with you?!”

- After signing a big order one afternoon, I invited a few clients for a nice lunch to celebrate. While paying the bill, still feeling giddy from the success of the meeting, I realized I had locked my keys inside my car. My expression gave away the fact that I was in a panic. So, what does any person do when faced with this dilemma? You dash around to locate a payphone (this was 1980!), call your mother, plead with her to leave her job, go home, get the extra set of keys, and bail you out. She arrived when my clients left the restaurant and saw the exchange. They never let me forget this classic moment.

- At Eastman Kodak, I sold large coper-duplicators. One morning, I had scheduled a prospective client to visit the office headquarters for a demo of the equipment they were considering buying. At one point, when I tried to make sample copies to show her the efficiency and reliability of the equipment, the machine kept jamming over and over again. Nothing I did could make that damn copier cooperate. So, halfway through the demo, the woman politely excused herself and left our office. My colleagues thought this was hysterical. I never heard from her again.

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- One day, after driving my new company car off the lot, a van from out of the blue ran a red light and plowed into me. Fortunately, I wasn’t hurt, but my pride was when I had to tell my boss. One month later, while driving a loaner and waiting for the repairs of the new car to be finished, the same thing happened. Again, I was not hurt but mortified when I knew the whole office would find out. Management politely cautioned me after a few days, “One more strike, Bill, and we’re putting you in a walking territory.” That was the beginning of the nickname “Crash,” which I could never live down.

- I was excited one day because I brought a client in the Legal space a beautiful mini replica of one of the newest copiers we marketed that I had just sold him. This replica would serve as an excellent desk paperweight and remind him of our company and brand. However, the excitement quickly waned when I learned the sales rep for my main competition had offered this client the keys to his Hamptons summer house for the weekend. Talk about apples and oranges!

- I felt confident during my final interview to secure my first sales job at Kodak. At one point in the discussion, I crossed my leg, perhaps a little too enthusiastically, and my shoe tassel flew off and landed close to the foot of the District Sales Manager. It was as if I was watching the flight of that tassel in slow motion. He didn’t notice, but I became fixated on it and prayed he wouldn’t see. For about 5 minutes, I did not hear a word he said. Fortunately, we were interrupted by a call he had to take. While he was occupied, I quickly retrieved the tassel and put it in my pocket. Class act all the way!

- During an American Express sales presentation, my colleague turned to me and asked me to share a research deck we had prepared for the sales pitch. The spotlight was now shining brightly on me. There was only one problem. My briefcase, which contained the deck, was locked, and I could not open it for some reason. After 5 minutes of getting strange looks from my colleague and the client, and after trying to pry the lock open and appear calm and focused, I decided to excuse myself from the meeting. I scurried around to find an empty office with a briefcase in hand and beads of sweat forming all over my face. What a bizarre moment that was! I quickly found what I thought was a vacant one, rushed in, opened the desk drawer, and found a pair of scissors. I went to work trying to pry the case open. When the office occupant returned, witnessed what was happening, and asked, “Can I help with something?” there were no words to explain the predicament adequately. On the flight home, my colleague laughed the entire trip.

- During my first week in the field at Eastman Kodak, I shadowed a more senior sales rep before I was given my territory. My first official assignment was to cold call NYC office buildings in his territory to see how many new leads I could generate. After a full day of canvassing the designated area, when I returned to the office, I was excited to announce that I had uncovered three new leads! I was pumped and sure I would receive high marks from this guy. Upon hearing the results of my efforts, the senior sales rep told me he had good and bad news. “The good news is that you put in a great day of effort with three new prospects to show for your efforts…the bad news is not one of them is in my territory. Your navigation was off by several blocks!” Oh well.

Remember that life’s greatest lessons are usually learned at the worst times and from the worst mistakes.