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Tell Me Your Horrible Boss Stories


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20
InQ5WeTrust
Arsonist
+8
Sales Savages, what is our profession? Trauma!
OK - let's get into it. 

We'll refer to my former boss as John Doe. 

So John joins highly recommended - former savage at a big enterprise corp. Monster quarters both as a solo contributor and managing a team.  

Highlights from the first month of John being there. 

- Kept asking me if I was Jewish (I'm not) and then if I was sure.
- Would tickle me whenever he walked past me to I quote 'cheer me up.' 
- Told me one of the female co-founders was pretty hot for being a co-founder.
-Said he loves having people work for him who are on visa's as they'll do anything to keep the job. 
-shit talked the CEO's ability to sell whenever he wasn't around. 
- asked me for advice on his sex life with his girlfriend in semi-graphic detail. 
-said I was underperforming with lead gen and yet spent all his day booking holidays/looking at restaurants to go to. I sat next to him. 
-He made me listen to revving supercar engines during our Monday stand-up to 'hype me up. I was distinctly not hyped. 

He lasted 5 months. By the end, he was a running joke across the 20 man startup - 'Thankfully we have the big dog John - to do all that closing' etc.

He put me on PIP the day before he was fired. I survived. 

Thank you for coming to my TED talk/therapy session. 
InQ5WeTrust
Arsonist
+8
Sales Savages, what is our profession? Trauma!
He also had the audacity to ask for a Linkedin recommendation. 
SiliconBBQ
Politicker
+3
The Metal Rooster
sure, "Don't ever work for big dog john...he's a scapegoating empty suit."
Show 1 more replies
justsomegirl
Acclaimed Answer
+9
Senior AE
Boss:  "You've got great boobs.  Are they real?"
Me: 😐
HR:  "Uh, what do you want me to do about it?"
Me:  😐
Me: "Hello, Labor Commission?  I'd like to file a complaint."
Me: Sues boss
Me: Wins lawsuit
Me: Keeps working there for six more months AFTER winning said lawsuit - in the office every day like a walking, talking middle finger 🖕🏼!  😏
Donutpanda
Good Citizen
Enterprise Account Executive
This is amazing 
InQ5WeTrust
Arsonist
+8
Sales Savages, what is our profession? Trauma!
Yeah, I'm sure your lawyer was happy with this case. 


InQ5WeTrust
Arsonist
+8
Sales Savages, what is our profession? Trauma!
but also like that's awful. 
Wanna.Be.Rick.Spielman
Opinionated
+3
Account Executive
I don't know you, but all I can do is respect you.
Hudsonsmom
Opinionated
+2
Area Sales Manager
Had a boss tell me in my yearly review if I “acted more like a lady and didn’t cuss” I would move up quicker and be respected more. I work in automotive....everyone cusses like a sailor. Not to mention I don’t talk to clients like that, it was office talk. 
teachertotech
Old School Bravo
Account Executive- Mid Market
f*&k that lol 
Hudsonsmom
Opinionated
+2
Area Sales Manager
Had a Director as me if I was a lesbian because I didn’t have a boyfriend (to his knowledge....I just kept work and personal separate). 

Same Director was hammered at a client event, grabbed my ass in front of people, was hinting at going back to the office together. I was told at that event I was switching teams and my new boss tried to “save me” by walking me back to my car. Only to text me how terrible the situation was and apologizing for it...”but great ass though. Ok delete this text”

Same Director forced me (was in diff job at the time not sales) to give his mistress company cars to drive whenever she pleased. His wife and kids were still in another state waiting to move where our office were. 
BamPeesly
Good Citizen
Sales Director
Same story here, different city! Asked HR to work for the other manager but their response was to tell my same manager and then he proceeded to make my life hell. Recently found out he was fired for harassment though so glad to see what goes around comes around! 
CaneWolf
Politicker
+12
Call me what you want, just sign the damn contract
JFC. PLEASE tell me this dude got fired.
Salespreuner
Big Shot
+11
Regional Sales Director
Yes, indeed!!
Show 12 more replies
Hudsonsmom
Opinionated
+2
Area Sales Manager
Also reported a horrific boss to HR. Legit the guy was a monster. Called and screamed at me for no reason all the time, just straight up rude to me. I think he just didn’t like me, but REALLY took it out on me. 

would send me emails to do things with no context/no info. If I asked for the info needed would scold me and told me I should know it. Finally just stopped talking TO me and told another coworker what to ask me to do for him and I lost it and went to HR. 

he got promoted to be a director and I got scolded and not believed. 
Chep
WR Officer
+10
Business Development Team Lead
Have not had one personally, but had a buddy who got fired because he was taking too long on his bathroom breaks. Beautiful thing is the company did not last long after my friend left and he loves his new job!
pi
pief
Politicker
+3
Account Executive
He was just sticking to the ABC’s of sales: Always Be Crapping
InQ5WeTrust
Arsonist
+8
Sales Savages, what is our profession? Trauma!
Boss earns a nickel, and I earn a dime. That's why I poop on company time. 
CoorsKing
WR Officer
+11
King of the Coors Knights
My boss actively sabotaged me interviewing twice for an internal promotion on a new team because I have too much tribal knowledge and would be too difficult to backfill. 
ATrueCloser
Account Executive
This happened to me early on in my career during business development. What a twisted way of thinking! 
alwayzbizzie
Catalyst
+2
Commercial Sales Manager
About 10 years ago, I was in a terrible car accident and I had to go on medical leave for about 4 months to recover. While I was out, my boss didn't have my voicemails or emails forwarded to him, so prospects and customers that I had been working with were confused, frustrated, assumed I had just dropped the ball, etc. He pulls me into a conference room on my first day back and basically tells me how my accident was a huge inconvenience for him. Although I wasn't the driver in the accident (and that shouldn't even matter), I was a passenger, you'd think he might have been able to scrape together an ounce of sympathy for circumstances that were completely out of my control.       
JuicyKlay
Politicker
+9
AM
That is so messed up!
Dig
Valued Contributor
+6
Head Prospector
My last boss worked as a manager for 2 companies simultaneously during his whole stint. This is during Covid btw.

He ignored people, was obviously over worked, and generally shitty at his job. It all made sense in the end, after he left. 

However, he knew how to con just enough to get by for over a year. 
AZ
AZ_Seller
Good Citizen
Director
My sales team was #1 in the world with the #1,2,4 sellers company-wide.  The brand new Sales Director comes in and proceeds to tell the entire team that they are incompetent, undisciplined, and incapable of doing the job.  Proceeds to absolutely berate/destroy/dress-down/etc... a perennial Club member in front of the sales team + marketing, support, SE's etc...  The entire sales team sends an anonymous letter to HR regarding hostile workplace/harassment.  SD gets a firmly worded letter from VP of Sales to be nicer and half the sales team quits in <90 days.  



Shitty culture exists everywhere but shitty managers perpetuate it.   
InQ5WeTrust
Arsonist
+8
Sales Savages, what is our profession? Trauma!
Challenge with sales hires imho - if they're good, they're also really good at masking who they are. 
MXB
CEO
Every overly educated and privileged CEO with an MBA and no clue about the front lines of Sales who I had to stop from running the company in the ground 😎oh and still pull off the IPO or Exit
InQ5WeTrust
Arsonist
+8
Sales Savages, what is our profession? Trauma!
I feel this + the Head of Ops who's an ex-strategy consultant and has read 2 sales books and thinks he's cracked outbound. 
TheHypnotist
Opinionated
+2
Sales Manager
I was 23 at the time, the only male in a staff of 5. Out for staff Xmas dinner, afterwards my boss had a few drinks in her, decided to "simulate stuff" using her hand and my little finger in full view of the rest of the staff whilst saying I should leave with her (they could also hear what she was saying). She was married and I didn't fancy getting into that kind of shit. I politely told her "you're married" to which she responded "yeah, but my husband and I understand each other and have our little friends".
I escaped that night, but the work atmosphere was never quite the same after that.
InQ5WeTrust
Arsonist
+8
Sales Savages, what is our profession? Trauma!
That's a big yikes. 
GrindingSales
Opinionated
+5
Account Executive
My Assistant Manager at a sports store hated me since Day 1.  No clue why, we literally liked the same exact sports teams too.  He would spend an hour on the phone with his wife everyday from 8a-9a during our opening hour.  One day, my girlfriend got tripped up by our dogs on a metal chain and wrapped around her leg and ripped through the skin sending her to the ER.  She called to tell me she was on her way to the ER.  I told my Asst. Mgr. that I needed to leave and he spent the next several minutes scolding me on not taking personal calls at work.  

Another day he blamed me for stealing things because I never purchased anything at the store.  I owned a house and was working for minimum wage, of course I didn't buy anything.  


SammySandbags
Politicker
+6
Account Executive
I started a war with my Food and Beverage director as a server. He used to torment me, yelling screaming in front of customers. He was a sociopath, would sleep with staff and was a con artist. I stayed patient and knew he would slip. Finally, he got the can and me and the other servers started running the place, nice bonus and raise for dealing with him. 
InQ5WeTrust
Arsonist
+8
Sales Savages, what is our profession? Trauma!
I feel like hospitality always has bosses from hell - unsure if it's the lack of sleep, chronic alcoholism or the cocaine that causes it. 
SammySandbags
Politicker
+6
Account Executive
id say all of the above

Show 1 more replies
MaoMao
Fire Starter
+2
SDR
My boss literally told me that I'm not a good fit for the company because I am uncomfortable with the people I work with. These people make very unprofessional comments that are misogynistic, sexiest, and straight-up disrespectful and I don't let those comments slide by. Also, I have very bad anxiety from this pandemic ( I know a lot of people that died) and am not ready to come back to the office and work with people who refuse to get the vaccine. Somehow he made all that a problem with how I fit.
SiliconBBQ
Politicker
+3
The Metal Rooster
seems like a shit culture, but there's a reason for the term happy as a pig in shit. 

you would probably enjoy your time more elsewhere, so despite your disdain for him he might be right. but it's a double win because you'd be done with him.
Tapati0
Opinionated
+3
Business Development Manager
At my old company I had a boss who was overall an unhelpful dick. Dress code was pretty strict (dress pants and button up shirts) except on Friday’s we could wear a dress shirt and jeans. He would constantly be bringing people into his office to yell at them if they didn’t have their dress shirt tucked into their jeans. 
fast forward a couple months and this guy gets a DUI. His name’s all over the news for it and being a small town the HQ is in everyone knows about it. He ends up getting promoted to president of one of our smaller sister companies and then comes back as the VP of sales for a while. Needless to say it was a pretty toxic culture at that company and I’m grateful they laid me off during COVID. 
caS2ie
Good Citizen
+1
All things people
The day I joined the company, my manager said "I didn't want to hire you"... then kicked his feet on his desk and continued to grill me like we were interviewing. Surprisingly lasted a year at the company and bounced. Throughout the year, his 1:1s with me were comprised of him telling me that my direct peers were talking shit about me behind my back. I surpassed quota the entirety of my year there, so who the hell knows what was wrong with him.

Mind you, this man was 50+ years old. Drama has no age, eh?
LostAngeleno33
Old School Bravo
VP Sales
At a 10 person startup.....CEO showed up coked up once (at least) and drunk more than once to investor and customer calls. Had to mute mic, cut him off, apologize, etc.  Missed multiple in person meetings when we would fly in the night before because he was hungover or just literally missing and not responding. Got drunk and left his briefcase and laptop at a bar and lost it. Would try and hide massive tabs on the company card. Would also text me belligerent pages long messages late at night that were about how great he was and inferior me and the team were. Chased away our largest customer when he showed up at their corporate offices demanding money in advance. The most toxic human being I've ever met. 
InQ5WeTrust
Arsonist
+8
Sales Savages, what is our profession? Trauma!
So this was Charlie Sheen? 
Worf
Politicker
+5
SDR
The worst/best boss I've ever had was the United States Military.
The worst/best boss stories are confidential lol.
Salespreuner
Big Shot
+11
Regional Sales Director
Knowledge shaming and non competence & I showed what it takes to close 6 accounts in 8 months 🔥
sales7
Politicker
+5
Sales Enablement Manager
My old boss went on the Apprentice... she nearly got voted off ep1 because she forgot to hide her true colours, figured it out to fake it quick though and made it pretty far.
Wanna.Be.Rick.Spielman
Opinionated
+3
Account Executive
One of my old sales managers (like 3 years ago) would have us stand against the wall and he would take a shot at us with a hockey stick and a rubber ball if he felt we were "being too negative" that day.  Believe it or not, this guy has since been promoted even though his entire team ended up quitting and telling HR/C-Suite about his anticts.

He claims his goal was to "teach us to be positive no matter what in sales" but I think the goal was really to fuel his own ego. Also dude was totally a sexist scumbag.  He also called me a "pussy" about 3 times a day, everyday, because I was "too sensitive" when in reality I was the only one who would stand up to him and talk back about him being inappropriate. 
SpamFolder
Good Citizen
Business Development Representative
I had a boss once that reminded me of high school bullies. He was a father in his 40s... 

-Used to come knock on the private room door when i was making dials and make funny faces to distract me. Used to have other AE’s come with him and make a spectacle. 

-Would get uncomfortably close to you and try to make you laugh or lose concentration while on a call. 

-Would tease me when i would ask for the corporate card to expense flights and hotels etc. Acted like he wouldn’t let me use it and then throw it on my desk. 

-Continually told me i was not ready for “the big leagues”

I was laid off from that company due to covid and it was the best thing that could have happened. I make more in my base salary now at my new company now than i did under his “management”
NY
NYsalesguy
Old School Bravo
Sales Development Manager
My favorite comment from previous CEO referring to who we should let go "Who is this months sacrificial lamb?"
privateryan
Politicker
+5
Director of Sales
I am the director for our location, and only report to the owners. Kind of nice...but the owners are divorced and don't align on the business vision so I am trying to lead a team in 2 different directions to appeal to two different personalities and visions. One is super lazy, wants to be out of the business and collecting his checks. Trusts me....but kind of an idiot. The other is a clinically diagnosed bipolar (no jokes. its sad...) and she works in the business at all hours, never pleased with anyones performance. No crazy stories....just one living hell. 

I remember one year when I was selling "full time" with zero other responsibilities...I ended as a top 2% performer for our industry. She gave me a review she felt I could have helped her more on the marketing side with her team, as they need more strategy in marketing from the sales side. I nearly got fired.....what a time to be alive. 
Who
BDR/SDR
My manager: 
“I know we’re changing the comp plan because your conversion ratio is double the team. Kudos, but don’t want to give you a big head. Now that we have a baseline this new hire class will blow you out of the water.” 

“Good job” wasn’t in his vocabulary unless you were a male. Even then it was a hard concept for him. 

Being questionably good at sales doesn’t = management. 
JuicyKlay
Politicker
+9
AM
Our CEO told everyone in the company that "they sucked and should do their jobs better" word for word in an all hands meeting.
Novaredneck
Valued Contributor
+3
IoT Sales Specialist
Found this thread because my boss is terrible and was looking for advice. Got vacation approved by him and the system. He just sent out an event and said it was mandatory to go to. I told him I would miss due to being on vacation. Everything is fully booked and non refundable at this point. He told me to make other plans and that this is mandatory. Not sure what to do but definitely going to HR about it.
CCP
Opinionated
+6
VP, Business Development
I once had Kevin Spacey as a boss. He touched me. I didn't hate it. 
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Sales Manager Horror Stories?
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11
Does anyone have any great “I quit.” stories?
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