Sales Calls from the Crypt: 5 Experts Share Their Worst Sales Horror Story

We asked five of the industry’s top sales pros to share their most nightmarish sales experiences. They didn’t disappoint.

If you’ve worked in sales, you’ve undoubtedly made a mistake or had an experience you wish you could forget. Whether it’s accidentally (and permanently) deleting a presentation deck just before a big meeting, or realizing you called a prospect by the wrong name after hanging up the phone — sales snafus can be haunting.
Can’t relate to the five bone-chilling tales below? Count yourself lucky. But the truth is you’re bound to experience something similar before the final bell tolls on your career, and having these key takeaways and lessons-learned to fall back on may just help you avoid the same grisly fate.
From accidentally using a prospect’s competitor in a very obvious way, to being ushered out of a CIO’s office by a flurry of f-bombs — at the very least these tales from the sales crypt should make you feel better about walking into that big sales meeting with an enormous coffee stain on your white shirt.

Mike Weinberg, The New Sales Coach

Deferring is Deadly

I remember I flew to Newark, New Jersey, from St. Louis to meet with a huge prospective client. Our channel partner’s salesperson, who was supposedly a star, not only got the appointment with this giant company, but even managed to have the president of the division sit in on the meeting along with the committee evaluating the potential vendors. Because it was the partner’s client and because he secured the meeting, I deferred to his sales process.
That was a mistake.
I’ll call this guy “Frank” to protect the guilty. Frank stood up in the front of the boardroom to (his exact words) “tee-up our demo with a brief presentation.” And in front of the president of this giant company and the committee, Frank put up self-focused slide after self-focused slide. Multiple slides with pictures of his company’s buildings. Then slides with his company’s clients’ logos. Then flow charts of his company’s performance improvement processes. It was some of the worst sales malpractice I’ve ever seen. After 22 minutes the president banged on the table and demanded to see the demo. We complied, but it was too far gone at this point.
The lesson: A first meeting should never be deemed a presentation — ever. And never let some joker tee-up your meeting without knowing what that means. For the record, that was the last time I have ever deferred on a matter of sales process. And that day I coined the phrase, “no one cares how great you think your company or solution is, they want to know what’s in it for them.” For more on this horror story, check out the fully-documented, uncensored version in chapter 13 of my book.

Jeff Hoffman, MJHoffman

Return to Shipper
I once had sales call at a major shipping company. It was a tech call to walk through the use of our hardware, which the prospect was evaluating for 90 days. We sat there for over an hour waiting for the hardware to arrive from their receiving dock.
Then we realized that the dock rejected our shipment because we used a different shipping service — a direct competitor of the prospect. Needless to say, we never closed that deal…

Dave Brock, Partners in EXCELLENCE

The Case of the Blankety Blank Screen
I was a very young sales rep and I’d been working for some time to get a meeting with the CIO at a major bank. Finally, I got the meeting, but it wasn’t going well and I noticed the CIO was distracted — he kept tapping a few keys on his PC. Apparently, he had a dashboard display that showed how the bank’s systems were operating in real time.
At some point, he tapped a few keys, and the display showed nothing. He asked to pause the meeting, focused on his PC, and tapped a few more keys, but again the screen was completely blank. Immediately, he yelled to his assistant, “What’s wrong? Are all the systems down?” He demanded his operations VPs show up in his office immediately.
They came running in and he was yelling at them, “What’s wrong, why wasn’t I told…” They were confused and said things were working on their end, but he wouldn’t listen — repeating that his computer display was blank and the critical systems were down.
While they were talking (or screaming), I wandered around to look at his PC. I noticed the problem: Somehow the display intensity had been turned down all the way. So, I tapped on the display button a couple of times and the display returned to life. The dashboard displayed that all systems were normal.
While you might think everyone was relieved, the CIO was pissed. He didn’t say anything, but I realized that I’d embarrassed him in front of a few of his key subordinates. For several months, our relationship was “icy.” But at least the ops managers had a good laugh and bought me a couple of beers that evening.

Steve Richard, Co-founder of Vorsight

How C-Suite It’s Not
When I was selling for the Corporate Executive Board in 2004 there was a $1 billion insurance company in the Chicagoland area that no one was able to arrange a meeting with over an eight year period. We tried everything to get in with any of the C-level executives.
Eventually, I was able to get the direct line of the CIO from a random employee in the company and the CIO answered. He was polite and agreed to a meeting. Two weeks later, I walked into his extremely large office, which was adorned with lots of leather chairs and an expensive looking rug. Mind you, I was 23-years-old and conducting this appointment solo.
We sat down and I started in typical fashion — confirming time, asking what he wanted to accomplish, etc. Then, the CIO interrupted and said, “Why the **** are you here? We’ve told your company multiple times we are not interested. I brought you here to tell you ‘no’ to your face so that your company will leave us alone.”
I was shocked. Yes, we had persisted for over eight years to get this meeting, but nothing about the CIO’s temperament on the phone led me to believe that he was upset, or that the Corporate Executive Board (or I) had been overly persistent. I opened my mouth to respond but no words came out. At that point, he said, “Get the **** out of my office now or I’ll call security.” WOAH. My adrenaline was rushing as I carefully walked out over a rug that, in the executive’s eyes, was probably worth more than my life.
If it ended there, that story might seem like a cautionary tale of over-persistence. But that’s not where it ended. About a month later, I was doing some more digging on Chicagoland companies and stumbled upon an article talking about how that same insurance company had been indicted for fraudulent activity. The article also stated that the top C-level executives were likely all going to prison — and that jerk CIO was one of those bad guys.
When the next wave of C-level executives entered the company, they ended up working with the Corporate Executive Board and derived great value from their memberships over the years.
The point is, you have no idea about the inner workings of the company you are selling to. They may hate each other. They may be great people who are completely aligned. Or they may all be criminals.
In short, companies are made up of people. The lesson is that persistence does win the day. In this case, the cost was being reamed out with f-bombs by a CIO who ended up in jail. But the reward was eventually getting to the good guy C-level executive replacements who ended up buying. There is no substitute for persistence and knowing you are in the right. For this reason, ethical and persistent salespeople should hold their heads high.

John Barrow, J.Barrows LLC – John is a sales trainer to some of the world’s leading tech companies. As Owner of J.Barrows LLC, he provides sales training and consulting for clients like and Box. He is also the Founder of SalesFromTheStreets, an online video library of insights from successful sales professionals. Connect with him on Twitter @johnmbarrows.

Great (Mis)Expectations
I had an in-person meeting with the CEO of a prospect that went so poorly it lasted less than 15 minutes. A good friend of mine had joined the company as VP of Sales and wanted to bring me in to train the team on prospecting skills. It was a small and diverse team, with some field reps who had been in sales for 20-plus years and some who were newbees.
The VP had been through the training before, so he knew exactly what it was about and believed in it 100 percent. He was actually one of my biggest advocates. Needless to say, the CEO, who had never invested in outside training before but believed in investing in the team, wanted to meet with me to review what I was going to go through with the team.
I prepped for the meeting as usual — I did my homework, looked on LinkedIn, reviewed the website, came up with some specific questions, set my goals, etc. The one thing I didn’t do was send a “shared agenda” before the meeting and ask the CEO what he wanted us to make sure we covered. Had I done that, I may have saved myself the embarrassment.
I started the meeting as I usually do, reviewing what I knew and then asking some specifics about him, his business, and where he wanted to take things. He immediately hit me back with, “I could talk about that for an hour and we don’t have that much time. I was under the impression you were going to show me what you were going to go over with the team, so why don’t you just tell me what you got.”
It was very abrupt and direct and usually the response I expect when someone asks a stupid question like, “tell me about your business.” I thought my question was a little better than that, but I guess not. The meeting went downhill from there since it now had somewhat of a negative tone to it. I tried to get it back on track, but nothing worked. He kept interrupting me and picking apart what I was saying even though a lot of what he threw at me was the information I was trying to gain from my initial questions. Needless to say, the meeting lasted less than 15 minutes and we walked away agreeing to disagree.
So what’s the takeaway from this?
First, regardless of how strong the referral you have into a prospective client, make sure you don’t take anything for granted. I may have been a little too comfortable walking into this meeting based on my relationship with the VP. Second, ALWAYS ensure you align expectations before you walk into a meeting on what you are there to talk about. Again, if I had sent a shared agenda to this guy and asked what he wanted to review during the meeting, I probably would have known walking in that all he wanted to do was see what I had. From there, I could have either addressed it sooner or changed my approach.
All in all, I was actually fairly happy about the whole experience. It had been a long time since I got punched in the face during a meeting with a prospect and this woke me up a bit. It reminded me that you always need to bring your A-game, you can’t skip steps, and you must focus on getting better every day.

Have a horror story that tops these experiences? Share your own sales call from the crypt in the comments below (if you dare).
Image courtesy of Powerhouse Museum
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