Tricky Treats: Spooky Sales Short Stories

Tricky Treats: Spooky Sales Short Stories

On sunnier days, life in sales can feel like a fun ride in a beautiful park. But on some most days, it’s a never-ending, energy-sapping worry-go-round.

Since it’s Halloween week, I thought it would be fitting that we write some spooky sales stories that capture life in sales. 

Proceed with caution. You have been warned ?

The wait


#1. A prospect promised to put me in touch with their Head of Sales. It’s been 20 years since.

#2. One day before signing Prospect: Let’s reconnect in Q1 of 2022.

#3. “We just don’t have the budget for this at the moment”. It’s Q1 of the fiscal year and they’re a public company.

#4. “We loved the demo and your product seems fantastic. We’ll get back to you.”

#5. The buyer said they’ll have to talk to the VP of Sales to get the sign-off for the purchase. Their company has a one-person Sales Team.

The pain


#6. “Leave application cancelled.”

#7. There’s nothing like vacationing in Green Bank, West Virginia. Until your wifi connects.

#8. Facebook and Instagram faced a global outage. Zoom was still working.

#9. My boss approved my Christmas leave. I just had to be available on standby.

#10. I got yelled at despite hitting 2x my sales quota. I’d forgotten to update Salesforce.

#11. A prospect diligently took notes during the demo. Then they went ahead and replicated our platform.

#12. I’ve been diagnosed with hypertension, high cholesterol, and anxiety. Today’s my one-year anniversary as a sales professional.

#13. 250 MQLs. 2 SQLs.

#14. I attended my first ever international sales conference today. On Zoom.

#15. My manager said, “Let’s do a quick call”. It was a Sunday.

#16. Received an email with ‘Sales Incentives’ in the subject line. They’d decided to scrap them.

#17. One day before signing Prospect: Our budgets have taken a hit due to unforeseen reasons.

#18. I shared my screen with the prospect for a demo. Our dashboard took 4 minutes to load.

#19. My boss rewarded my performance with a staycation. The hotel promised 24×7 high-speed free wifi.

#20. A prospect thoroughly loved our product. They decided to proceed with our competitor.

The fear


#21. I lied to them saying I hadn’t seen their last email yet. Didn’t know that they used Mailtrack.

#22. Told my wife that my manager was just as mean as a snake. I wasn’t on mute.

#23. One day before signing Prospect: I resigned today. Do keep in touch! ?

#24. My manager congratulated me on closing a deal that I’d promised to close before Q3. I’d forgotten to mention Q3 of next year.

#25. I was assigned a new lead on the CRM. It was a temporary, disposable email ID.

#26. The prospect agreed to move forward (after I mistakenly attached our internal cost price sheet).

#27. I wrote “Bosses are annoying most of the time. LOL”, in a casual email to the prospect. I hit “Reply to all” by mistake.

But also, the fearlessness


#28. Had a productive business dinner with a prospect last night. His COVID test came positive this morning.

#29. My manager congratulated me on closing a tough, high-value deal. I already know they’re going to be a bad-fit customer.

#30. I closed a huge sales deal this morning. My wife took me to the doctor soon after that. My hallucinations are getting wilder.

#31. MQL >> Prospect >> Opportunity >> Closed lost >> Alcoholism.

#32. Yesterday, a colleague of mine asked me to “relax”. They just found his dead body in the parking lot.

#33. I’m the most responsible employee. I was responsible for everything that went wrong at my last job.

#34. My prospect asked to speak to someone higher than me. I added mom to the meeting.

#35. My manager asked me to “close the deal by hook or by crook”. I was apprehended by the police today for threatening to kill the prospect’s family.

Make sure you watch a Disney movie right after reading this. Happy Halloween! ?

Neha Mestry

Neha Mestry

Neha is a Content Marketer by day and an illustrator at night. With a profound interest in art and all things creative, Neha often indulges in creating content in various forms—blog posts, watercolor paintings, digital illustrations, and quick doodles. Oh, and she can survive an eternity on a deserted island as long as she has a good book (read: fiction only) by her side.

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