The War Room

[MEGATHREAD] - What was the worst sales meeting you've ever had?

Sales is all about battle scars. Which one cuts the deepest? That one client you will never, ever, ever forget?


For me, it was Plantronics. I had worked SO hard to convince the VP Global Recruiting to take a small bet on us. He had the authority to swipe his card for <$10K purchases, so we did a $9,999 trial for 3 months. Worked my ass off to get him some high quality candidates from his job ads, and also educated their entire executive team on the importance of employment branding.

There was one last meeting with the Global CMO. I prepped so hard for that one. Walked in, delivered an A+ pitch, and got her sold in 45 mins. We were on the way to a $108K renewal on that $9,999 trial. 💥

Only Plantronics, as a MASSIVE global company, requires all paperwork to go through Indonesia or some random country like that for tax purposes. And they will only sign on their own paper (T's and C's), so it took us MONTHS of negotiations between our legal counsel (this in-house guy who was a jackass) to get all the contract stuff sorted. I had to spend many 11-1am nights on the phone in Asia hunting down their lawyer... but finally got us there.

Everything is ready for signature. I get a call from my contact asking if I can come see him. I assume it's for getting everything set up, so I agree and show up excited to FINALLY celebrate this puppy.

When I walk in, he's sitting there with 2 guys I've never met before. And they do not look happy. Uh oh?

He goes "Sahil I have some bad news. We are never doing business with your company again. Your legal counsel cursed out our lawyer, calling him an asshole and a dickwad during the legal process. I'm sorry, because I know you're a good guy and I really enjoyed working with you. But your company has been blacklisted and we will never do business with someone who treats our team this way."



10 years later, I'm still furious. 😡

On the bright side, it got our in house attorney fired when I told the CEO what happened. But I lost $25K because of his unprofessionalism that day, and even worse, lost a relationship with a MASSIVE org that I'd spent years building.


Whats yours?

🏰 War Stories
📈 Closing
Chief Revenue Officer
its amazing that most of us can remember the big losses as clear as day like they were yesterday, but all of the big wins kind of become a blur.    Here's my story. 

Every have the big whale client, with the biggest internal BLOCKER in the history of internal blockers sitting right smack dab in the middle of the org your trying to sell into.  Not only was this blocker not a fan of my company, but she was still holding a grudge on something I had sold her that "didn't" work in the early stages of my career more than 10 years ago.  (side note, "working" in my industry is very much a team effort between us and client - she was not a "team" player). 

So after a solid 3 months of getting destroyed by said BLOCKER, who (who was the middle management DM) - I decided to go over her head to the budget creator in her org, and it was an amazing perfect storm.  The top level DM and I had instant rapport (kids, sports) he appreciated my transparent and direct selling style, and expressed the interest in moving away from their current vendor (my biggest competition) in the coming months.   I put together a "perfect storm" proposal, which would have dropped as the biggest deal in my company's history and the DM requested the IO. It was Beautiful. 

Two weeks went buy and I got a call.  One of the crappiest calls in my career.  Turn out "New DM" got an offer from a sexy new startup to run marketing, and was leaving.  He assured me the IO was "in process" and as much as I tried to get him to expedite its signature before his departure he wasn't able to. 

I'll give you ONE GUESS who was promoted to replace him in his exploded. 
Big Shot
Associate Account Director
My heart breaks for that. Sorry dude.

Notable Contributor
Deepak Chopra of Sales
Ugh that is the WORST. Def been there (old foe returns to crush another hope/dream)
Notable Contributor
Deepak Chopra of Sales
Would love to hear from @GeneralCorp @CuriousFox @CadenceCombat - know you've got some good ones!
WR Officer
Needer of Life Alert
Sahil - condolences. I am pissed off for you. I have stories, but yours is...yikes. 
WR Officer
Needer of Life Alert
I spent a year researching,  studying, contacting every exec at a big hospital an hour away. I lost a bid before, and this time I was determined to have a meeting on why they shouldn't go to bid again. I scored a meeting with the CIO and his IT director. 

I worked on the presentation for a month.  Flew in our Healthcare IT specialist and the Regional Sales Director, then drove to the hospital an hour south. We were prepared from every pre-meeting, late night edits, weekend practices, and honestly I could still recite it to this day. 

We were escorted into a cold conference room near the morgue.  Unphased, I set up the laptop and projector and was ready to go. Nothing was stopping me. This was happening.

Or so I thought.

A meeting of 5 people total turned into 15. The IT Director brought in his entire team and they threw everything they could at us to derail the presentation.  I kept everyone cool and on track. This guy was a complete asshole. When I closed the meeting, I shook everyone's hand but this jerk. This jerk snubbed me. He didn't break me (I'm competitive damn it) and he was in a melt down hissy fit.

My RSM drove to a gas station and came back to the car with 3 40oz bottles in brown bags. We drank our way back home in utter silence. Not even the radio was on. 

We didn't recap or speak of it for a week.

Notable Contributor
Deepak Chopra of Sales
Wow that's brutal! Why do you think he acted that way?
WR Officer
Needer of Life Alert

To this day that's all I can come up with. Very puzzling situation to say the least.
Good Citizen
process development specialist
Logistics sales here. Happened three years ago. It’s a meeting with the customer & showing them example operations; and somehow they decided sales support (us) should join at the very last minute. BD Chief comes to pick me & my senior from the HQ, as BD Manager is with the customers. 

We miss the whole meeting, and accidentally enter the example operation field from a very different entrance. It’s a mess. Like nobody in their right mind would show that place as an example to any customer. Bd Chief calls the manager, gets the location and we go there. We don’t say anything to them yet, just answering a few technical questions. 

Then comes the time for the example operation field visit. 

Everyone gets in the cars, and BD Chief calls BD Manager on the way, telling him why it’s a bad idea. Manager dismisses. 

In the operation field, the operation chiefs start bitching about their customer, in front of the prospect, how awful they coordinate everything, how often they have backlogs because of it. They don’t mention their capabilities etc, no straight up customer bashing. We try to change the subject, even the Manager joins us but the damage is already done. 

It’s still a horror story for me. 
WR Officer
Master of Disaster
So I was a complete noob to my industry, and somehow I had convinced the company to hire me for a decent level role, selling insurance to an industry I have zero knowledge in. However, I’ve got that golden Rolodex and all the sassy charm you can handle (plus a stupid high work ethic). 

People in the company realize that I am ridiculously inexperienced, and everyone and their dog tries to sabotage and/or use my advantages for their own gain at my expense. This is during the height of the pandemic, where NO ONE is selling shit. 

Through my connections, I happen to know of a particular very wealthy contractor who happens to be paying out the ass for insurance and isn’t very happy. Not a big firm, but he’s in a high risk industry (within nyc construction - pricey enough without the added extra exposures). I’m in the middle of their “training academy “ and I manage to land an appointment, take the owner and his wife for lunch, get BORs on the spot (meaning, they fired their broker and hired myself and my colleague who helped set everything up. Needed the help because I was being sabotaged so badly). This was August, the client renewed in November. This was *2 MILLION* in premium. 

biggest deal of the year.

as soon as I hit “win” in CRM, my inbox exploded with congratulations- but “good job team!”. ONE person happened to mention me, but it was “good job at picking the right colleague!” 

so, because of internal bullshit, I’m never allowed to speak with the client. Also, I was assigned a service team who had absolutely no idea how to service a $20 account, let alone one this size. 

I tried to raise the alarm.

24567889 times.

kept getting told to “stay in my lane” and how insignificant I am as a new employee (I landed this after being there 5 months). 

So we go through the renewal in November and all hell breaks loose. Team fucks up so badly that the client is informed that their insurance policies are canceled and they will not be receiving payment from the Department of Transportation - their biggest client. We managed to somehow save this, get them insured and get them paid but NOTHING Was done to rectify the gross incompetence of the service staff. 

I sound the alarm again.

There was a bit of internal maneuvering, but again, I am not given the team an account of this size is entitled to. Their response was to “see if they’re going to leave. If not, then we will move it to the right people”. 

like fuck that, so I finally stopped caring if my firm was going to fire me and just sent the client an email introducing their new team (with the people who SHOULD Be doing it) without their approval. 

everyone internally is mad as hell but I really don’t care.

now shopping for an ADDITIONAL 3 MILLION for a project specific and the service team fucks up AGAIN. 

a few weeks later, the client fires us and cancels all remaining policies. Do you know what the top brass said the reason was? That I didn’t do enough research on the client and convince them that our company is the best thing in the universe. I will literally never forgive or forget that last meeting. And the fuckers wouldn’t even tell me that to my face. They had someone else do it. 

Big Shot
Associate Account Director
Im so sorry to hear that man. Nurturing a relationship and getting stuffed at the end sucks. My shitty stories are usually legal related too, but on the customer side.
Valued Contributor
Business Development Manager
I was a young buck, at my first "real" sales job. I was an Inside Sales rep but eager to get out and meet my customers, as those in that position at that company sometimes did. I decided to try to raise a dead account that we hadn't heard from in a few years, that on paper looked like it could be a good Lazerus type. I wanted to show everyone that the new guy could bring in accounts, and that I had a bright future outside of my cubicle. 

I talked to my VP of Sales who was a nice older guy but a little new to the org, and he told me he would come along with me and that it would be good practice (I don't remember what the Outside guy was doing at the time).

Well I reached out to the Purchasing Manager at this dead account, Warren. I stumbled through my introduction and he pretty much cut to the chase with "be here tomorrow at 8am".

I told my boss, and set it up to meet him at the company to see Warren first thing in the morning. I arrive in the lobby at 7:45, looking as sharp as I could with my cheap chinos and button-down shirt. My VP walks in a few minutes after and we are told to wait and that Warren would be out soon.

10 minutes go by. 15. 20. My boss asks the Receptionist how it is going, and she says he's coming. 25 minutes go by now and my boss gets a call from the office. He looks at me with regret and says he has to get back, and that I can either come with him and reschedule or stay and wait. I'm not one to back down, so I stay even though this is a big potential account and I'm still wet behind the ears.

Bossman bounces and a few minutes later the receptionist tells me Warren is ready. I walk into his office and I shit you not he has a phone on each ear, yelling, red-faced, into both of them like a damn cartoon. He's chewing out a different supplier and also has someone internal (his report or something) on the other end. I sit down awkwardly at his desk and examine my shoes for what seems like half an hour. Soon, I can smell red wine just fuming off of the guy.

He hangs up, puffs, and begins to tear into me about how shitty my company is, how I am going nowhere if I stay there, and grills me on details I wouldn't know if I had been there for 5 years let alone 1. His eyes are bloodshot. He tells me he buys more than anyone else I call on and how much better my competition treats him. Says my competitor would have him set up at the strip club or at the steakhouse instead of daring to come and try to meet with him first thing in the morning.

I don't know how long this beratement goes on, but it felt like hours. I tried to defend myself but I was so fresh I didn't have any weapons. I know now at this point in my career the only move is to thank him for his time, drop a card, and tell him to call if he ever needs something that I can help with, but Young Me just absorbed it in the chest.

I limped out of there with a whimper, Warren told me he'll never buy from me or my company, and to shut the door and take my card with me as I left. I was shaking when I got to my car from the dump of shame, anger, and frustration. I failed miserably, and left insulted. Thankfully my boss was cool, and when Warren inevitably pissed off everyone else and came calling a few years later, we told him we weren't interested in his business. By then I had generated enough business elsewhere!

A simple no thank you when I called would have worked too, I think.  All over something I had no control of. 

I'll never forget that meeting and I'll never treat anyone like that, let alone a young person trying to make it in this world.
Director of Sales
Small angry engineering manager threw a stack of AutoCAD drawings at me (literally) in a packed meeting and told me to try to bring this into “my fancy bullshit software” … so I took that as a no, for now…😆..literally left me with PTSD Every  time I see drawings. *shivers*
Who's your worst Sales colleague ever?
Worst Qualified Meeting You Ever Had?
Most EMBARASSING sales meeting you ever had?