12 Most Embarrassing Moments in a Salesperson’s Career

12 Most Embarrassing Moments in a Salesperson’s Career

Most people don’t choose a career in sales, a sales career chooses them. No wonder it’s one of the most difficult career paths there is. It takes years of training, practicing, failing, and flailing to feel even slightly confident that you have a firm grasp of what it takes to be tops in sales in your industry.

It’s a bumpy road, and a road filled with rejection, dejection and some of the most embarrassing moments of a lifetime. For most of us, we learn from those moments, share them, laugh at them and then move on.

Here are the 12 most embarrassing lessons and laughs experienced by those of us lucky (unlucky?) enough to have been chosen by a sales career.

1. Not knowing exactly what you are selling

Every salesperson at one time or another has been let loose in the field a little too green and much too confident. Eventually they find themselves sitting in a prospect’s office, reciting their best version of their memorized sales pitch and suddenly the prospect asks a very simple question about the product.

It goes something like this:

Prospect: “Let me interrupt you for a minute. Does it have 4 or 7 perlunkas? I’m not crazy about the ones that have 7”.
Salesperson {Thinking}: What’s a perlunka?
Salesperson {actually says}: “Let me check on that for you”.
Prospect: “You don’t know that? That’s like selling a car and not knowing how many doors it has! Why don’t you have your boss send someone over who knows the product”.

Fortunately, for most of us, this only happens once in a career. And once is enough.

2.Getting caught making something up

Same situation as above, but the salesperson quickly says: “It comes with either 4 or 7, and I believe 6 as well!”

Prospect: “6! Never heard of that! Run down to where we keep our unit and count how many perlunkas it has for me will ya?”

Eventually there’s a halting, red-faced confession of not knowing where the unit is kept, not knowing how many perlunkas it has…and a quick blurt of having no idea what the heck a perlunka even is.

3. Assuming too much about a potential customer

This one has cost almost every salesperson a commission at least once in a career. We make a mental decision that someone can’t afford what we sell based on some visual cue that really has nothing to do with whether they actually can afford it or not.

“He wore a cheap suit.”
“Her website is cheesy.”
“He drives a mini-van.”
“She works out of her home.”

So we pass over the above, only to discover that the salesperson in the next cube closed the sale, and made quota for the month… a week early.

4. Trying to cross a burned out bridge

Regardless of career path, we are all told early on in our professional lives not to burn bridges. No matter how many times we are told this though, we don’t truly understand what it means until we burn one and then try to cross it at a later date.

A friend, I’ll call Tom, tells the story of quitting a sales job that he absolutely hated. On the day he quit, he left a letter of resignation that contained a detailed description of the reasons why he was quitting. The letter was basically a nicely formatted bulleted list of whiny pompous insults.

Four years later, while working for another company, Tom was thrilled to get a sales presentation appointment with a decision maker at a large company. Closing this sale would have guaranteed Tom a promotion and a raise. Unfortunately, his former boss, the recipient of infamous resignation letter, was the company’s CFO and also attended the sales presentation.

No sale for Tom. In fact, the CFO ushered him out the door after 15 minutes and on the way out, asked Tom if he “had been doing any more writing lately”.

5. Having the lowest numbers of your team

Someone has to be at the bottom and sometimes it’s you. Sitting in a sales meeting knowing that at any minute the manager is going to bring up the numbers is stressful. And it’s downright embarrassing when your numbers are the lowest.

The first time it happens, almost all salespeople will blurt out excuses in rapid fire fashion, one after the other. That’s when everyone in the room is also embarrassed… but embarrassed for you.

When it happens to you, fight the urge to come up with excuses, just suck it up and vow to work harder and smarter.

6. Getting fired

If you are in sales long enough, you will eventually get fired. And it will suck.

In sales, it’s all about the numbers. You need to make the company more money than you (and the non-revenue generating staff) cost them. When you don’t, out you go.

Getting fired is not the embarrassing part though. The embarrassing part is cleaning out your desk and walking by your former coworkers with a cardboard box with a plant sticking out the top. If you’re lucky, you only have one trip to make to the car.

I once saw a fired coworker take all afternoon to clean out her desk and office. She literally paraded past the rest of us 17 times with boxes of knickknacks and doodads. From that point on, at anywhere I worked, I never had more personal belongings on my desk than I could easily carry out in one trip.

Even now. And I work for myself.

7. Forgetting a potential client’s name

A sales person I know, whom I’ll call… hmm… oh… Jeannine Morber, once gave a perfect sales presentation to a roomful of executives. Every question was answered flawlessly. Every objection was addressed smoothly. Every word was perfect.

Except for one. The decision-maker’s name was Robert. I called him Kevin. Repeatedly.

8. Totally forgetting who a customer is

In many companies, once the sale is made, the salesperson is out of the picture. A good salesperson though will make an effort to keep in touch — that’s how great referrals happen.

I once saw a salesperson at a networking event talking with a woman he obviously had no clue as to who she was. From the gist of the conversation, it was easy to gather that she was a client of his company and he was the one who had sold her the contract. After a bit, she blurted out “You have no idea who I am, do you?”

He fessed up and they laughed a bit. But it was obvious that the client’s feelings were extremely hurt.

9. Getting caught in someone else’s lie

A salesperson I once knew, let’s call her Michelle, had the bad habit of trying to impress others by handing out referrals the way most of us hand out business cards. The problem was that these “referrals” were not actually referrals at all — meaning that these were not people who expressed an interest in purchasing a specific product or service. These were simply people whose names happen to pop into Michelle’s head at the same time she decided to impress someone by giving them a referral.

Calling one of these “referrals” often went like this:

Salesperson: “Hi Mr. Referral, Michelle told me to give you a call about our new widget machines. We have them with both 4 or 7 perlunkas…”
Mr. Referral {interrupting and shouting}: “Stop right there… I don’t want or need no freakin’ widget machines and so help me to god if that Michelle doesn’t stop giving out my name every…”

You get the drift.

10. Getting reamed by a gatekeeper

Every salesperson develops tricks, techniques and tactics for smooth talking their way past the gatekeeper. Eventually we get really, really good at it… and we get cocky.

That is, until we get reamed out, called out or totally used up and tossed out by a gatekeeper.

Here’s my favorite story:

Gatekeeper: “Thank you for calling Perlunka, Inc. This is Helen, how can I help you?”
Salesperson: “Hi Helen. This is Bill Jones with XYZ Company, can I please speak with Connie Smith, your Marketing Director. She’s expecting my call”.
Gatekeeper: “Our Marketing Director, CONRAD Smith is presently in a meeting. I sincerely doubt HE was expecting your call, but I’ll be sure to give him your name and let him know that you think he’s a woman”.


11. Realizing that you’re selling crap

At some point in every sales career, a salesperson will sell crap, i.e. a product that doesn’t really work, services that are sub-par or a product that’s just not right for the customer.

Usually we get out when we can no longer pretend that we’re selling something with any value. Unfortunately, it’s usually an embarrassing encounter with a ticked off customer who helps us make that decision.

A good friend once sold services for a company with the worst reputation of any similar company in the area. One of his clients had major problems as a result of this company’s weak technical skills and customer service.

He quit when he walked in on the staff planning how they were going to blame all of the problems on another vendor and on the customer. The salesperson is still so embarrassed that he worked for this company that he refuses to list it on a resume or on his LinkedIn profile, believing a gap is less damaging.

12. Getting sold

They say that great salespeople are also very easy marks and I believe it. You’d think the opposite would be true — that we’re immune to a pitch — but usually it isn’t.

In my early days in sales, I was sold a number of useless gadgets, knickknacks, doodads, thingamabobs and whatnots. There was always that twinge of embarrassment when the realization hit that yet again, I’d been sold.

A colleague once asked me, “When you were young, admit it, you bought a Pet Rock, didn’t you?” I of course answered “No! I’d never buy one of those!”

The truth is, I bought two.

There you have it — the worst moments in a sales career in a nice compact list. What about you? If you have an embarassing sales story to share, please do so. We could all learn a lesson from it. Or at least get a good laugh.

If you liked this article, please give it a thumbs up  in Stumbleupon. Thanks!

Featured image courtesy of PeraltaC775 via Creative Commons.

Jeannine Morber


Jeannine Morber is the owner and founder of Morber Marketing Group. She develops and conducts customized sales and marketing training sessions for companies all across the US. Morber is also a popular public speaker, an avid blogger, an amateur photographer and a reality TV addict.

468 ad
Steve Birkett
Steve Birkett

Great mix of fun, humor, and real world smarts here Jeannine, congrats and welcome! #11 is the reason I turned down several temp jobs during my University days. I'd simply rather wait tables or clean floors than sell someone complete crap! I am intrigued as to the origin of this much-vaunted Perlunka, however. Can't even find it defined on Urban Dictionary, raising its mystery and making me want one (perhaps seven) even more....let me know how to buy them from you ;-)


OK... my most embarrassing moment was realizing I had 2 different shoes on in the middle of a sales call... but that's a different story.Realizing you're selling crap is the worst; I just can't do it.


#12 is spot on. I know some fantastic "cold sales" sales people. From life insurance to gutter-toppers, the best sales people also tend to be easily talked into buying.

This is a fantastically fun post. I don't think I am the best salesperson, but I can recall a few of these in my past.


#10 might have been my favorite. Gotta watch it when you act familiar, and the name could be either female or male (Kelly...Madison...Ash). #3 is also an excellent case study. Gotta watch those purse-string controlling decision makers driving around in slick minivans!!


As a full time sales manager and working with sales and sales development I really liked your blog. It is informative, short and to the point. I can see that you have done your share of sales.

All 12 reasons are great. The main message I guess is to take responsibility and ownership. Once you realize that whatever happens it is thanks to you. You will gain a new insight.

Sales is really a fun and fulfilling job. Many people think it is difficult but it is not. It requires skill and sensitivity. Most of the things you can learn and this blog surely provides some really good points.

Peg Fitzpatrick
Peg Fitzpatrick

Great thoughts Jeannine! Sales is hard but being prepared is always important.

I love that you recommend not making excuses but suck it up — everyone needs to learn this!

Can't wait for more from you!


Thanks Paul! Building a business is about building relationships and that means we're ALL sales people nowadays. It's a tough job but those who learn to laugh at their goof ups are the ones that succeed. I still laugh at mine and in fact, include them in many of my training sessions. No fun laughing alone!

PaulBiedermann moderator

Love this post, @jeannine morber and a big welcome to 12 Most!

I have never been “in sales” per se, yet so much of what I do is sales (and probably some of the toughest sales there is, as selling creative ideas is never easy). You obviously speak from lots of experience and relayed the information in such an entertaining way that even this “non-sales” person enjoyed this post immensely!


@Steve Birkett Thanks Steve! Ahhhhh, the origins of the famed Perlunka! It's actually one of the many words my Dad made up when I was a kid - I figured if I used a made up word, it'd be easier to imagine the scenarios as related to any industry. Ive got a few other 12 Most ideas brewing....so hopefully you'll see me on here again!


@AmyMccTobin I actually did that too Amy! I totally forgot about that! It actually made for a pretty good ice breaker though. :) The crap one is a toughie and it has given me many sleepless nights. BTW, TX Amy for tweeting this...really made my day!


@dbvickery Thanks Brian! I've always been careful about #10 but I was nabbed by #3 back in my early days!


@100010001 Totally agree Shahram about sales requiring sensitivity - I've found that the best sales people are ones that have a true desire to solve people's problems and "make things better". It makes the job very fulfilling!


@MorberMarketing Well of course I'd tweet it. In my heart of hearts I have always been and will always be a Sales person.


@MorberMarketing Does that mean I am probably a sucker and didn't realize it, either? ;)

Just re-read the list, I like it more and more.