(reading time: 4 minutes)

Other than sitting through sales meetings, there’s rarely a dull moment when you work in sales. Because the job is so fast-paced, and puts you in front of so many different people on a regular basis, you can encounter lots of interesting, exciting, and sometimes shocking situations. You’re unlikely to find a salesperson who doesn’t have at least a few stories to tell that would leave you with your mouth open.

However, some of these stories often don’t get told, because they’re either too shocking or could reflect badly on anyone involved. In an effort to get some true sales confessions, we polled a group of salespeople and asked them to tell us their most interesting secret confessions. Of course, we’ve kept everyone anonymous for their own protection. Here are eight secret confessions of salespeople:

Note: these answers have been edited for grammar and clarity. 

1. Competitive Advantage

“I think you always need an edge if you want to win, and I came up with one when I was working as an Account Executive at a software company. The company didn’t have any rigorous enforcement of lead management in place, so I would give our Business Development Reps cash if they would filter and send the most promising leads to me whenever possible. This worked and I became the top producing AE on the sales floor. No one ever found out and I made a bunch of money before moving on eventually.”


“I was selling cars a while back and we had a guy working for us who seemed like a nice enough guy. One day, a bunch of federal agents showed up at the dealership, along with a fully outfitted tactical team and arrested him (without any incident). It turns out that this guy was a wanted fugitive out of another state who had been involved in a major drug trafficking operation. He ended up going to prison for a very long time.”

3. Unnecessary Inflation

“I’m really not proud of doing this and it still bothers me to this day, but I was working for a business to consumer company years ago and had a very nice couple who came in to look at our services. My manager pressured me to raise the price on the product because he wanted to squeeze out more profit, and knew that these people were very nice and we had built a good rapport. I didn’t push back on him, and instead went out and sold them on the inflated price. They paid it and didn’t complain, but I know that I wasn’t acting in their best interest. I regret it and if I could go back and do it over, I never would have agreed.”

4. Cut and Paste

“I was working for a mortgage company in the mid 2000s, right at the height of the housing boom. I was new to the industry and really didn’t know the ropes yet. I walked into the printing and faxing room one time and caught a coworker cutting up a piece of paper and then taping it onto another piece. I asked what he was doing and he told me not to worry about it. But I saw that he was basically creating a fake W2, which was done to inflate the customer’s income so that they could qualify for a loan that they obviously didn’t qualify for. I never said anything about it, but my time in the industry didn’t last much longer after that.”

5. Special Delivery

“I once worked for this sales manager that I absolutely hated with every fiber of my being. I ended up leaving on really bad terms after we had a blowout. In any case, I wanted to get revenge so I ordered a few dozen pizzas to the sales manager’s office, and signed him up for an endless amount of online subscriptions to weight-loss websites so that his inbox would be completely inundated with them. I know it was petty and immature, but it did make me feel better at the time.”

6. Behind the Back

“I was working for a manager who was the biggest jerk you could possibly imagine. He treated everyone like crap and liked to publicly embarrass people when they made mistakes or didn’t follow his ridiculous rules to the absolute letter. I finally got sick of it and went behind his back and set up a meeting with his boss, who was the VP of the organization and was located at a different office so it was unlikely I’d get caught. I told him about the manager’s abuse and behavior, but he didn’t seem to have any response to it until I mentioned some of the manager’s policies, which were essentially causing us to burn through good leads because we had to focus so much on an arbitrary number of calls everyday instead. Three weeks later the manager was fired. It turns out that the VP had called him out on his backwards policies and they got into a shouting match. Everyone at my office was thankful, even though they never found out that it was me who did it.”

7. Fake Phone

“I once worked at a place that required a minimum of 100 calls a day. Needless to say, not everyone who worked there was completely above board with their calls, especially with everything else we had to get done throughout the day. Sometimes you had to cut corners because there weren’t enough hours in the day. We had one guy who worked for the company that got caught calling the local supermarket literally over and over again until he got to 100 calls. He got caught and fired on the spot. The sad part is that everyone else had little workarounds, we were just smart enough not to call the same number over and over again so we never got caught.”

8. Double Jeopardy

“I once worked with a guy who – I kid you not – literally had two full-time jobs at the same time. One was an outside sales role and the other was a half inside half outside role. He would juggle between the two and actually had salaries coming in from both. This went on for close to a year, but I don’t think he ever even got caught. The guy was super smooth, he would coordinate his office face time between the two companies and somehow no one was ever the wiser. Smoothest guy I’ve ever worked with.”

Here’s one more confession: You can close 47% more deals if you use a Proactive Relationship Management platform, like Spiro!

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About the Author Ken Kupchik

Ken Kupchik is the creator of Sales Humor and the author of the funniest sales book ever written, The Sales Survival Handbook, which you can order on Amazon.com. Connect with him on LinkedIn.

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