Sales Horror Stories

To close out the month of Halloween on the Maestro Mastery blog, we’re sharing some of the most frightening tales we’ve heard—yours.

October 27, 2021

By Rachel Smith

We asked for your scariest, most cringe-worthy sales moments, and you did not disappoint. Read on…if you dare.

SCREAM SHARING

You would think by now we would be accustomed to Zoom and know better than to ever assume we’re really on mute, or at least maybe the mishaps wouldn’t be so painful. Sadly, no. Just ask the dad of two young kids who muted himself to let them know to FOR THE LOVE OF GOD STOP DOING THAT!!!! We never found out what “that” was, but we do know it was enough to push a stressed-out parent to use some colorful language. And we know this because he had never actually muted himself.

GETTING THE AXE

Sometimes the scariest things that happen on Zoom are not what you hear, but what you see. A CEO we heard from thought he was sharing a slide deck with a prospective client and some other members of his team. Unfortunately, the screen he actually shared was of an Excel file that listed which of his employees were about to be let go. The list included one of the staff members on the call. He quit on the spot in front of the prospect.

DOPPELGÄNGERS

When you are putting together a proposal for a large government contract, it’s important to have all of your t’s crossed and i’s dotted. Your proposal should make you look professional, competent, and polished. Notice we said “proposal” and not “proposals.” Because nothing says “we are disorganized, uncoordinated, and lacking in internal communication” quite like sending in two proposals from the same company. That’s what happened to an engineering firm we heard from. Needless to say, they did not get the contract.

GHOST COMPANIES

One of Maestro’s clients was approached by a former mentor with a great opportunity—a major home-improvement chain was adding a bedding and furniture department. The mentor wanted our client’s company to be one of the vendors. We helped our client prepare with decks, role plays, and strategy sessions. Our client flew down to the store’s headquarters only to learn that they were not, in fact, starting a bed and furniture division, had never heard of our client’s mentor, and were baffled when shown the (evidently fake) bath and bedding section of their website.

MITIGATE RISK—NO SUSHI BEFORE SIGNING

One sales professional we heard from was closing a seven-figure deal in Tokyo. He had just had a great meeting with the CEO of his soon-to-be client company. Everything was agreed upon, but the CEO wanted to wait and sign the contract in the morning with the rest of the staff. The two businessmen went out to celebrate with sake and sushi. Bad sushi, as it turned out. The CEO died that night from eating improperly-prepared fugu (a kind of blowfish that is a delicacy in Japan, but also highly toxic).

HOTEL HORRORS

When a company is widely known to put customer service above all else, the sales professionals can be forced to deal with some frightening customer behavior. This was definitely the case for a former business-travel sales professional at the Ritz-Carlton. “I helped Jerry Lewis, and he yelled at me constantly,” she says. “He would call me up to his suite, be standing in his underwear, and he and his wife would yell at me about the furniture. We had to take all of it out of their room and replace it.” This same individual also worked for Nordstrom, another company known for its customer service—lots of being yelled out by customers there as well.

ALIENS!

Glen Hellman says that a long career in sales means you have a lot of stories. He told us that back in the 80’s he sold secure computer equipment to the Marine Corps Intelligence Headquarters near the Pentagon. While Glen was showing a young Marine how to operate the system he had just installed, a woman walked into the lobby.

She claimed that she was an alien and had been instrumental in putting down revolutions around the world. She had recently overheard a plot to overthrow the U.S. government, but the radio she used that used to pick up foreign agents was broken and would now only play radio stations. Without cracking a smile or batting an eye, the young Marine told her, “I’m very sorry, but if foreign agents are involved, you don’t want Marine Corps Intelligence. You want Counter Intelligence. They’re down the hall.”

HOT SANTA

It may be Halloween, but just like Macy’s, it seems like it’s never too early for Christmas. One sales leader got an unexpected “gift” in his inbox from a job applicant shortly before the scheduled Zoom interview. Seems as though the applicant, in an ill-advised attempt at a tech-check, logged into the Zoom link about 15 minutes early. The only problem was, this generated an email notification from Zoom to the sales leader that “Hot Santa” had logged into the meeting. By the time the actual interview started, the applicant had changed the screen name, but as you can imagine, the damage was done and there was nothing but coal in the stocking for that applicant.

If you’re looking for tips and training to avoid finding yourself in a sales horror story, get in touch with us at mastery@maestrogroup.co.