Submitted by Jared Chimovitz:

Background info:  My office line rings to my cell phone. 

One evening, I get a call and only notice the last name. 

Assuming it was a good friend of mine, I answer: "I'm naked and about to do terrible things to my wife".  

The voice on the other end is much deeper than my friends.   As he clears his throat I realize my mistake. A big mistake.  The voice on the other end asked if he could speak to the owner of the company. While I am my own boss, I was concerned that I may have lost business before I even started.

Luckily, It turned out it was said friends father. I profusely apologized and restarted the conversation in a much more professional manner. He did hire me and continues to do so to this day.

We laugh about it all the time, but I learned a valuable lesson...Always assume that any caller is a business caller.

Submitted by Jeff Katz:

I cant believe i wore a sombrero to a sales call! 

Roughly 15 years ago, I was the Sales Manager for a company that provided services (translation, language training, Cultural awareness training) to companies to assist them in communicating, reaching, conducting and expanding business with their international counterparts. 

Being based in Detroit, Several of my accounts and sales targets were within the automotive sector, Tier 1, OEM's, fortune 500 companies. By this time, I was already 5 years experienced in this industry, and had developed a solid "stable" of clients. I had been chasing a sales lead for at least 3 years at one major OEM, to no avail. as time went by, a college friend was employed there. My friend got me a meeting with the decision maker (V.P. of HR). before the meeting, I did my usual needs analysis on the phone so i could be prepared for my sales call. I was told that they were opening an office in Mexico, and they were looking to train the American employees, Spanish. 

Easy enough. 

We did that countless times before. I was also told, that there is no way im getting the business, because they have had a long lasting relationship with a competitor, they were meeting with me, to fulfill a vendor quota. Thinking that we werent EVER going to get this business (or future biz), we wanted to make a lasting impression. My meeting was set for November 1. (i know this because it was the day after halloween, part of my fall back plan) My co-worker dared me to wear a sombrero to the sales call. As im waiting in the lobby to be called into my meeting, I was gaining attention by several people walking by. 

I finally get called into my sales call, my heavy sombrero and all. As I walk in wearing my suit, tie and sombrero, the VP of HR is just staring at me, The jaw of my college friend who arranged the meeting, dropped. horror in her eyes. We start the meeting, and 2 minutes into it, The VP of HR says " will you take that damn thing off"? 

We finish the meeting and say our good byes. As previously warned by my friend, Im confident that im not going to get the business, but that i made a lasting impression. I get back to my office, and my friend left me a msg on my VM saying that i embarrassed her tremendously. 2 weeks later, we were awarded that business opportunity, at a higher rate than our competitor that had a long lasting relationship, all because the decision maker, laughed and saw us thinking out of the box. 

That account grew exponentially over the next 4 years. To this day, i cant believe i did that, and no, ive never done anything remotely similar to this, since. 

This was not only my most embarrassing sales call, but most memorable.  Ole!