Are You Daring Enough To Share Your Worst Sales Moment?


With sales, there are  a lot of maddening, patience-testing, and rage-inducing moments. Take a poll or just have a chat with someone from the field of sales and they will tell you all about it. All about their worst sales moment or probably 2 or even 100. (Now is that sad or funny? you be the judge of that).

We, as humans, can be cruel and let’s not even debate on that. Because we (not all but quite a few) find humor in other’s misery and misery loves company. So, don’t worry you are not alone to have your worst sales moment or even moments.

Here are 8 champs who were willing to share their worst sales moment

worst sales moment
Source: Imgflip

1. Nowhere to be found

How awkward is it to go all the way to the agreed meeting place and find them nowhere to be found? Did they fall off the face of the Earth? No one will ever know.

My worst moment so far is probably traveling to a meeting I had set up and the guy was nowhere to be found and we were asked to leave the building.
– Anonymous

2. The resounding no

How infuriating is it when they know it’s a good deal but they say no anyway, just because… just because they can. That’s not just bad but very annoying too. Now, I speak for everyone when I say that no one likes that but the drive you have after that to get where you want to be is reassuring.

There have been many over the years, sales is like being on a roller coaster so many up’s and downs it’s hard to pinpoint 1 as being the worse moment the real hard times are when you spend hours on the phone to someone and you know you can benefit their company and they can see this but still say NO it can be very disappointing, you then have to pick yourself up quickly for the next call its hard sometimes but I love it.
Ross Angell

3. Wrong Timing

Nothing will ever be as easy as wrong timing when you have to think of your worst sales moment. Wrong timing is never nice in any situation and it sure as hell isn’t when it comes to sales. It can be anything from calling a client when they are having dinner or when they are a middle of a break-up. Awkward Awkward. Would you count this as the worst sales moment if you were in his place?

With regards to my worst moment so far It would be calling a prospect while they were at their Dad’s funeral – Absolute disaster and left me feeling terrible for interrupting (But why would they answer in the first place?!)
Alexander Smith

4. Pool of Illness

If you are all about the cleanliness and hygiene, then hotel stay can be more of a nightmare than a vacation for you. Even worse if the whole family caught an illness right after having some good ol’ family time in the pool. And if we are talking about the real estate business let’s agree it’s not an easy path to go on.

I haven’t been in real estate too long and hearing about some of the moments some others have had, I have been pretty lucky. I was a travel agent previously (again sales) and experienced credit card fraud, helping people stranded after 911 and one client who’s family picked up very serious illnesses from the pool at a hotel.


In real estate, the more common frustrations are, unfortunately, dealing with other real estate salespeople who are sloppy or not trained properly. There’s a lot at stake and mistakes can be costly.

Lisa Davey

5. Awkward meetings and the CEO

Sometimes just sometimes it’s not easy to match up to the targets that are set for countless reasons. But what’s worse is the impossible targets that sadly don’t generate any revenue and are very demoralizing and then to have meetings daily about how to fix the unfixable. What do you call that?

Worst moment? That’s a hard one, it was probably a period with Cellarmasters, targets were impossible and the new CEO at the time was making promises we couldn’t match from a revenue angle.


We then had daily morning meetings that were very awkward talking about the numbers and why we were not hitting the impossible numbers and kept having to come up with “plans” to do so.

Greg Gravalas

6. God says…

What according to you is an awkward situation? Clients are usually reluctant about doing business with someone who’s in their training period. That’s a tricky place to be in but hey the best of the best have been trainees at some point in their life. What do you have to say about that?

A customer heard us coaching the rep. – We had something called “God Voice” where a Manager could put a headset on and listen to the call in order to coach the sales rep on what to say.


At one point we got a little too loud and the person on the other side of the phone asked if the sales rep was getting coached on the call. It was so embarrassing! It felt like we got our hands caught in the cookie jar.


We quickly told them the rep was new and got back to the conversation at hand – but boy was it an uncomfortable moment!
–  Gabriel Moncayo

7.  Press 1 to listen to the voicemail

Have you ever had to hear any sort of news good or bad over voicemail and didn’t know how to go about it right after? Did you call back immediately? Went to the kitchen and ate your feelings out or just curled up in a corner and cried your eyeballs out? How about when you are not on the receiving end of it but on the other side? How do you go about the dreadful deed?

I once had to my fire, my friend. He just invited me to his 40th birthday even though I fired him 5 years ago. I was a junior manager working for the first company that would go through an acquisition of sorts and asked me to move across the country to build a sales office. We had a top performer. I mean TOP TOP performer. 200%+ to target. We wanted 1 sale a day, he would get 2-4. Ridiculous numbers.


The problem? He still complained about lead flow and quality. He wanted 100% control over his schedule, 100%. And it seemed like it was hurting the team. So a couple things happened and we let him go. I could not reach him for a couple days so it happened over VOICEMAIL.


I FIRED MY FRIEND OVER VOICEMAIL. Overall the sales team improved to the point where numbers validated the decision, but omg when I meet his friends he always makes me share this story and let me tell you it is still a bit awkward 🙂
Gabriel Moncayo

8. It’s a rat race wait no it’s a race to the car

There are those annoying coworkers( who you’d gladly punch in the face) who are all cheerful on a Monday morning while you are sleep deprived(probably hungover?) reaching out for your morning coffee and then there are coworkers like these. Now that chatterbox coworker doesn’t seem that bad, right?

I was working at a car dealership, and the idea was that if anybody came into the dealership, and if you went and talked to them first, they were your client. So, anybody who just drove into the dealership…everybody walked briskly over to them to shake their hand and grab them as a client.  There was this one guy who always ran towards the people coming in and essentially scared them. He would push people out of the way and shake their hand and be really shady.


One day, he tried to do that with me and started sprinting towards the car. I started running too since I knew what he was going to do. I got into an angle so I would say Hi to the people coming out of the car before him, and when he tried to sneak in, I didn’t let him. The person opened up the car door, startled that two men were running at her, but I smiled and said, nice to meet you.” Haha. It was pretty crazy but from them on he realized I would out-do him and he stopped trying to take customers from my area.


Eventually, people started back-stabbing each other for deals and lying and cheating each other, and realized I had to quit and do something else.


The field of sales is an ever-evolving and just as interesting. There are good days and then there are days you want to kill everyone in the 500m radius. Either way, you’ll love your sales job and wouldn’t want to be anywhere else. Not just the bad moments that people in sales have to face there are challenges as well and they are no joke.

It’s not easy to tell your worst sales moment, so a big shoutout to all of the people who were sportive enough to share their stories with me.

Do share your worst sales moment in the comments!

About the author

Afshan Fatima

Afshan incorporates her knowledge of psychology and literature into sales and marketing through writing. While she is not blogging she reads books ,counsels people and bakes brownies.

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