BigCheese
Notorious Answer
10
Agency Recruiter
Finally booked a call with a prospect I'd been hitting up for months. The call didn't go too well as they were kind of awkward but still set up another follow-up meeting.

After the initial call, I went to email my notes to my AE including notes of the prospect being a tad bit strange. Guess who I accidentally emailed the notes to instead :---)

Granted, a deal wasn't even on the horizon yet, but definitely one of the stupider, more embarrassing mistakes I've made.
Telehealth_2the_Moon
Notable Contributor
4
Director of Business Development
Ouch, I feel like that's a mistake that you have to make at least once, and then from there you'll probably be checking your attachments and email addresses 3x over!
BigCheese
Notorious Answer
2
Agency Recruiter
Oh trust me, I became paranoid after that one! I quadruple-check everything now. Still terrified of accidentally replying all lol.
Telehealth_2the_Moon
Notable Contributor
0
Director of Business Development
I have such a personal aversion to emails being reply all'ed to that I'm worried about that one. 

On the other hand, I certainly have not double check the full line of addresses on the email and dropped my customer facing façade when it came to language and opinions...
Spade
Arsonist
0
Global Business Development Manager
Oh dude I feel that pain through this screen. Cheers 🥃 
SalesSavage4Ever
Good Citizen
0
Account Executive
Sounds like you need Quip :) 
CorpSheep
Good Citizen
0
Sales Rep
Been there done that!
Saastastic
Executive
3
Account Executive
My prospect was trying to wait a month before buying our software. I texted him that "people get hit by buses every day, it makes sense to buy now to avoid potential blockers in the future?
Telehealth_2the_Moon
Notable Contributor
2
Director of Business Development
What happened after? I'm guessing it wasn't great if you're posting it on a mistakes thread?
Saastastic
Executive
1
Account Executive
They ended up kicking the can down the road for two quarters until they eventually signed :)
Telehealth_2the_Moon
Notable Contributor
0
Director of Business Development
Haha there you go! Maybe you got them thinking about the big picture, and in the big picture is it really that big of a deal to sign this contract or not?
CoorsKing
WR Officer
3
Retired King of the Coors Knights
Working with Fortune 2 company. They have strict security review policies, etc. In a cycle for a business unit, they asked if we had done the security review yet because if not there was not enough time and they would go with a competitor. 

We had actually completed the review a few months prior, but I completely blanked and said no. They went with a competitor, and I found the completed doc a few days later. 
Spade
Arsonist
0
Global Business Development Manager
What a heartbreak. 
#battlescars
StringerBell
Politicker
2
Account Executive
Later stage in a deal and I’m dealing with their infosec team. They sent over a questionnaire and asked I confirm it’s receipt. At the time, when I’d reply to an email with someone in the thread they’d automatically get added to our CRM. So I replied that I got it and we’d get it answered. As a result of being added to our CRM this person then got a marketing email they hadn’t signed up. The person was their chief data privacy officer for a European company and a real GDPR nut. He freaked the fuck out and basically cancelled the deal. It’s not a great practice what we were doing but it’s also not exactly the worst thing since we were doing business with them so getting marketing info isn’t necessarily a faux pas. It was supposed to be a done deal so it was a real kick in the nuts. Everyone actually blamed our marketing team so at least that.
Spade
Arsonist
0
Global Business Development Manager
Daaaaammn. Ouch!!
MMMGood
Celebrated Contributor
1
Senior Account Executive
Well...it wasn't entirely my fault. (Said everyone, lol)

But I was working for a SaaS provider that had both on-prem and cloud delivery features. A prospect I was working with had a use case that perfectly aligned with the on-prem delivery version (they had some different features in each). We tried to be up front when presenting the specific solution we were recommending and as far as we knew it was totally understood by the prospect.

Several calls and pricing discussions later we were kicking off a POC with them and began talking about the ports they needed to open and spinning up a sever, etc. And the call went silent...on-prem? What do you mean? Call over. Dead. 

Long story short, they couldn't accomplish what they wanted with the cloud version. 

So...while it was out of my control because of product constraints. It taught me to be VERY clear and gain agreement from the customer, the implications for the proposed solution before moving forward in the sales cycle. I wasted a lot of time with those guys...
Spade
Arsonist
0
Global Business Development Manager
What a painful process man, battle scars 🗡
Coffeesforclosers
Notable Contributor
1
Director Sales and Market Development
Attached a file for a different organization i did volunteer work for that did not go over well. Was harmless enough but killed the deal. I didnt accidentally send him a terrible pic like my family's first nanny did. Yes, she sent a nude accidentally to my wife, i asked to see it and she said she deleted it lol. 
bartonmyfrench
Fire Starter
1
Account Executive II
This deal had been ghosting me a bit and I had his cell. I'm decently big on not texting but this fucker had eaten up enough of our time where he owed a response and hadn't opened emails. I sent a text and instead of saying my upper management was looking to hear back on how pricing went over I texted pupper management hahaha. It fucking autocorrected after I finished the sentence for some reason and it just sent I was laughing bc I knew that shit was dead. 
Spade
Arsonist
0
Global Business Development Manager
😂 
UserNotFound
Politicker
1
Account Executive
Just yesterday I called a hospital prospect (on speakerphone with my boss in my office) who constantly flakes on me. We're only in the beginning stages but it should shape up to be a really nice sized deal once/if we ever get good traction. Anyway, I call the guy on the date/time I told him I would. He answers. 
"this is [bob]"
"Hey Bob! It's [me] from [my company], still up for a quick conversation today?"
"Sorry, it's not a good time. I'm in the hospital right now and don't have the time" 
"Well, Bob- I know you're busy because we've been in this position a few times now, but I also know this initiative is important to you. So, let's make a commitment to carve out the time for each other. When do you want to get together, and do you prefer we loosely set a date/time, or can I send you a calendar invite w/a link to a virtual meeting that you'll actually attend?" 
"I guess just call me Friday and we can set something up, I should be out by then... gotta go, bye"

My boss says [Mrs. Tech Sales] I don't think he was WORKING in the hospital. I think he's IN the hospital, and you were just really mean to him. 

#whoops
Spade
Arsonist
0
Global Business Development Manager
🤣🤦🏻‍♂️
JuicyKlay
Celebrated Contributor
0
AM
Hahahahaha that is painful 
Adslanger1
Opinionated
1
Senior Account Executive
Biz owner said he has to discuss with his wife. I replied “does she get you dressed in the morning too?”
Gentry
1
Sr. Manager
In my first few months on the sales floor years ago I came back slightly boozed up from a client lunch and left a voicemail for a top prospect. 

This guy owed me an answer and hadn't responded the week we were supposed to close. Aggressively said "Been trying to reach you and you're very clearly ducking my calls. (Sarcastically) Would appreciate a call back when you're not too busy to answer me".

Guy hit me back the next day reminding me he told me he was going to be out of the country on vacation that week and to never contact him again. Would have been a massive sale for me at the time, brutally stupid.
Chep
WR Officer
1
Bitcoin Adoption Specialist
Ouch that one hurt me just reading it 
JuicyKlay
Celebrated Contributor
1
AM
Booze and sales calls have not been my friend either 😂 
Blackwargreymon
Politicker
1
MDR
My prospect was trying to wait a month before buying our software. I texted him that "people get hit by buses every day, it makes sense to buy now to avoid potential blockers in the future?
Cyberjarre
Politicker
0
BDR
It can be a relief for a prospect to get an email from us that isn't clearly trying to move the sales process along (new developments, updates, blog post, whatever) and I think getting a conversation going with them at all does the same job.
Error32
Politicker
0
ISR
It can be a relief for a prospect to get an email from us that isn't clearly trying to move the sales process along (new developments, updates, blog post, whatever) and I think getting a conversation going with them at all does the same job.
6

What's the worst mistake you've made... that turned out to be a huge blessing / turning point?

Question
1
5

Biggest deal you have ever made?

Discussion
6
17

Funniest accident at work

Question
10