Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration,

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I was selling HR software as my first gig out of college. I had been prospecting a VP for about two months with no response. I'd check her LinkedIn profile every week or so to see if there were any updates I could use as a conversation starter. After my fifth or sixth email, she finally replied: "I can see you've been viewing my profile every Tuesday for the past few months. It's honestly kind of creepy. I'm not interested."

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I stared at my screen in horror. I had no idea LinkedIn showed who viewed your profile (I know, I know). I'd been essentially stalking this person on a weekly schedule, and she'd been watching me do it the entire time.

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The worst part: I'd been doing this same "research strategy" with at least 15 other prospects. How many of them had noticed? How many were creeped out but never said anything?

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I immediately went to my LinkedIn settings and turned on private browsing, but the damage was done. I started wondering if that's why my response rates had been so terrible. I still check LinkedIn for research, but now I'm paranoid.

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Anonymous       Location Withheld

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I sell logistics software to mid-size businesses. There was a key target account I was trying to book a meeting with. I decided to launch a two-pronged outreach: one email to a junior contact I hoped could become a champion, and another to the decision maker. It was a strategy that had worked for me before. I thought it was clever. I sent them emails expecting to maybe get a reply within a day or two.

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Twenty minutes later the backfire hit. The decision maker replied curtly that there was no way they’d do business with someone who couldn't be bothered to do personalized outreach. The junior person had apparently forwarded my version of the email to his boss telling him it might be an interesting opportunity. But the decision maker felt that him getting a similar message the same day was a spam campaign.

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I tried the polite reset: owning the mistake, apologizing, promising to do better. Nobody replied. I still do this strategy (and it still works) but I now make sure to stagger the outreach between contacts at the same company.

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Anonymous       Location Withheld

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I sell consulting services to deep-tech companies, meaning some of the prospects we deal with are absolute experts in all manner of electronics, software, chemicals, and so on. We have to carefully filter them to make sure we can actually help with their industry, and we also get our fair share of crazies reaching out to us.

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One time, I was training a new guy and my boss told me to pick an inbound lead with irrelevant technology, and have the new guy schedule a Zoom call, and watch quietly from the sidelines to provide feedback after. I arbitrarily picked a company called "Advanced Fashion LLC" and took a very brief scroll through their website to confirm they were not in our ICP (they design and manufacture luxury clothing. Definitely not our ICP). I instructed New Guy to go through the typical discovery questions and then politely let the prospect know it wouldn't be a good fit due to lack of technology. Not the best way to actually do discovery, obviously, but the point of the exercise was to really get New Guy comfortable on camera.

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We got on the call and started going through some of the standard questions, and before I knew it, the prospect was telling us all about how he invented an advanced sensor for industrial environments, and that he's already had major success selling it to the military. Obviously, this has just turned into a very relevant call, and New Guy is nowhere near equipped to handle it. I was about to jump in when New Guy said something like "We won't be able to help with fashion design, so I'm not sure this will be a good fit." (Again, totally not his fault. I told him to do that. There was no way he could have known and it was definitely me who dropped the ball here.)

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The prospect looked straight into the camera, visibly angry, and asked, "Did you guys do even an ounce of due diligence before this call? All you had to do was Google my name and you would have seen all the press releases about my new sensor. Or better yet, maybe actually read the lead-intake form I filled out to get on this call. Seriously, I've never seen such a lack of professionalism in my life. Have a nice day, gentlemen."

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After he hung up, I apologized profusely to New Guy and felt like an absolute moron for the rest of the day. Moral of the story: Don't judge a company by its name, and do a bit more research beyond just scrolling through the website.

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Anonymous       Location Withheld