6 Embarrassing Sales Stories (and Sales Readiness Lessons Learned)

June 22, 2018 | Alec Shirkey
6 Embarrassing Sales Stories (and Sales Readiness Lessons Learned)

Learn from embarrassing sales stories shared by several sales experts.

The goal of any salesperson is to project confidence, expertise and business savvy when engaging buyers. Unfortunately, sales reps’ interactions with customers and prospects don’t always play out as smoothly as they hope. Even the best have had to endure awkward and humbling situations, whether because of overlooked details, eagerness or a lack of sales readiness.

We asked 6 sales experts to recount an embarrassing story from their days in the field and, more importantly, share what they learned from these uncomfortable experiences. Here’s what they had to say:

Jim Ninivaggi, Chief Readiness Officer, Brainshark (@JNinivaggi)

“Looks like they sent the wrong man for the job”

I was sent to Houston, Texas, to do a critical software demo to help close a very sizeable deal. The problem was, it was on a software application that I did not have a lot of experience with – I was a specialist on another product – and dealt with complex account processes, which I had no familiarity with. Our head of product and CFO tried giving me a crash course on both the product and account principals the day before I was to head for Texas.  

It’s the day of the big demo, and I bomb.  There were 15 finance people sitting around the conference table with their arms crossed and frowns upon their faces. I stumbled through the demo and could not answer a single question that was asked of me. About half-way through this painful demo, the CFO, who happened to be wearing a cowboy hat and boots with his suit, stood up and said, “Looks like they sent the wrong man for the job.” Beyond embarrassed, I was mortified.  

The lessons:

1) There is no shortcut to sales readiness.

2) Putting an unprepared rep in front of a buyer is not fair to either party.

3) I vowed this would never happen to me or one of my direct reports ever again. The experience definitely started me on my path to a career in sales readiness and fueled the passion I have for it today.

Barbara Giamanco, Founder and CEO, Social Centered Selling (@barbaragiamanco)

“Boring the executives to death”

I remember a sales meeting with a number of executives from a major credit card company who was a very important client of ours. I’m talking senior director level and above in that room. It was a meeting that took me weeks to put together. Joining me on that sales call was a sales engineer who was to help me brief these executives on some new technology our company had developed.

Though I had specifically prepped the sales engineer on their role and how/what to do during their portion of the meeting, they ignored everything we had discussed. Instead, this engineer did what he always did and rolled into a complicated, jargon filled presentation that I could tell was boring the executives to death. Moreover, I could tell they had no clue what the engineer was talking about but they were certainly not going to admit it.

I stopped the presentation the engineer was delivering. I summarized what he was talking about in less complicated lingo and got everything back on track.

What that experience confirmed for me was that buyers don’t want to hear us talk at them. They are also rarely impressed with overly technical presentations and jargon that makes no sense to anyone but the person delivering the presentation. Buyers, especially at the executive level, want to know about business results. Though the sales engineer was unhappy that I interrupted him, I was the account owner and owed it to the decision-makers to not waste their time. If you have to team up with someone else on a sales call and they don’t follow the plan, you must be willing to take control to keep things on track.

Dave Brock, President and CEO, Partners in Excellence (@davidabrock)

“Don’t trust Google Maps”

I've had many embarrassing moments in sales. One that both the customer and I found hilarious was my problem with Google Maps. It was the first meeting with a CEO of a small company.  I'm always paranoid about being late, so I planned to arrive about 20 minutes early.

I programmed the location into my iPhone – the intersection of two major roads. I made it to my "destination" with time to spare but struggled to find the office. I called the CEO’s executive assistant, asking, "Where is your office? I'm at the office park at the intersection of...”

Turns out these two major roads were a giant arc, and actually intersected each other twice – 50 miles apart. Google Maps had directed me to the wrong intersection and I didn't know it. The CEO and I had a good laugh, and rescheduled. I made it to the right intersection for the next meeting.

Colleen Francis, Owner, Engage Selling Solutions (@EngageColleen)

“Vice mail”

I am an atrocious speller and often autocorrect can figure out what I am trying to say. In one email to an important prospect I thanked him for his “Vice mail” and then apologized for “kissing him.” I learned the hard way that spell check doesn’t fix the wrong words – just the wrong spelling! The buyer had a good laugh about it in his response to me, and I learned to always read my important emails out loud before sending them to buyers.

Deb Calvert, President, People First Productivity Solutions (@PeopleFirstPS)

“Do you have my address?”

It was my first outside sales call. As an outbound tele-seller, I called inactive accounts. I needed prior approval to meet prospects in person. To prepare, I got my hair cut and styled, washed my car, and bought a new suit (with huge shoulder pads – it was the 80’s). I'd done my homework on the account at the library, poring through articles (on microfilm – it was the 80’s).

I rehearsed my presentation during the hour-long drive and the 45 minutes in the parking lot because I arrived so early. Then I went in, announced myself to the receptionist, and learned that my prospect worked in another office two hours away. It had never occurred to me that there might be a second location. He'd asked me when we scheduled "do you have my address?" and I'd said "yes."

Calling the prospect (from a payphone – it was the 80's) was terribly embarrassing. He invited me to stop by the next day. Calling my boss for permission to leave the office again meant confessing my blunder. But it was a great lesson to never assume anything in sales and to get the essential information first.

Matt Heinz, President, Heinz Marketing (@HeinzMarketing)

“You don’t need to push”

My most embarrassing and awkward sales situations have come when I either pushed a prospect to close too fast, or assumed they were ready to close when they were not. Prospects rarely work on the same schedule and timeline you have. Just because you want (or need) them to close this month or quarter doesn’t mean they will, or that they’re ready.  And pushing them too fast is only going to 1) make them uncomfortable, 2) make you uncomfortable, and/or 3) push them into a decision they aren’t ready for or might regret later. 

The answer of course is to have a bigger pipeline. Put more qualified opportunities in front of you so that, when some of those deals inevitably slip or go away, you have plenty more active to hit your number. If you have a healthy pipeline, you don’t need to push any prospect to close when they’re not ready. You can go into every sales call (even what feels like a closing call) allowing the prospect to maintain control of their decisions and timeline.

Download our exclusive eBook, "The 4 Pillars of Sales Readiness," to learn more about how to prepare your reps for any selling situation.

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