Sales Fails: "I got an OOO responder from a prospect, but I texted him anyway. He was at his mother's funeral"

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

I managed to sign a deal on several buildings with the Head of Asset Management for one of Europe's biggest owners on the private investment side. He put me in touch with his colleague, “John Doe,” Head of Asset Management on the institutional investment side. We had a smooth on-site initial meeting with his team. Then, John suddenly cancelled our next meeting.

I wrote an email to propose a time to reschedule the meeting, and one guy from his team told me that John was on holiday and invited me to call him another day. I sent him a text message asking if he'd like to call me back. He called me back.... and said he was attending his mother's funeral :/

Obviously, he wasn't happy. Fortunately, the internal champions took over and I was able to make his teams an offer for 2 buildings.

Anonymous       France

I started at a mid-sized software company last October with about twenty people on the sales team. During my second week, our weekly team meeting was wrapping up when the sales manager casually mentioned the annual Halloween costume contest was coming up and the best costume would win a $250 gift card to this really nice restaurant in the area.

I decided to go all out. I dressed up as The Wolf of Wall Street the year before so I had the double-breasted pinstripe suit, and styled my hair to match Leonardo DiCaprio's slicked-back look. Halloween morning, I strutted into the office feeling confident. I walked through the bullpen expecting to see creative costumes.

Instead, I found everyone was in regular business attire, all staring at me with barely contained grins. The silence was deafening until someone finally broke: "Dude, there's no costume contest." Turns out the entire team had been in on it—a little hazing ritual for the new guy. They felt so bad watching me stand there in my full Wall Street costume that they actually chipped in and bought me the gift card anyway. But the damage was done. For the rest of the year, everyone called me "The Wolf." At least I got to take my girlfriend out to a nice dinner.

Anonymous       Location Withheld

I sell commercial real estate and was invited to a high-end charity fundraiser at an outdoor country club last August. It was one of those networking events where half the city's business elite would be there, and I'd been trying to get face time with several potential clients for months.

The event was brutal—95 degrees with humidity that felt like a sauna. Within thirty minutes, I was sweating through my cotton shirt like I'd just finished a marathon. All the other men smartly took off their suit jackets, rolling up their sleeves and looking comfortable in their breathable fabrics.

I desperately wanted to remove my jacket too, but I could feel the back of my shirt was completely soaked through. The cotton had become see-through, clinging to me like plastic wrap. I could feel sweat pooling at my waistband. I kept my suit jacket buttoned just to try and cover it up, which only made me even hotter. For three hours, I suffered in that blazer, trying to network while looking like I was slowly melting. I could tell some people I was talking to were not listening to what I was saying, more focused on the sweaty mess of a man in front of them. I managed to exchange business cards with a few people, but follow-up calls went nowhere. I can't blame em. I bought a linen suit the next week.

Anonymous       Location Withheld

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