Think your recent gaffe was the most embarrassing sales moment ever?
We’re here to make you feel better. Show you that awkward sales moments happen to everyone. Even the best sales professionals.
In fact, the best salespeople might be the best because of their embarrassments. Awkward anecdotes, weird words and stressful situations build sales character.
Not to mention, a good laugh at yourself (in retrospect, at least) can be an elixir, getting you out of a slump or creating a great story to build rapport going forward.
We have eight brave sales leaders who shared embarrassing moments so you can laugh, learn and share:
‘Kicked’ this deal to the curb
During a sales team meeting years ago, I conducted a debriefing with a salesperson and the pre-sales engineer who had just been on a customer call together.
They told me the demo had descended into a numbingly detailed technical monologue. So my salesperson asked the pre-sales engineer “Why did you go into so much detail? Couldn’t you read my reaction? And why didn’t you stop when I kicked you under the table?”
The pre-sales engineer replied, “Whoever you were kicking, it wasn’t me.”
The end result of this embarrassing sales moment? An unproductive customer meeting, and a prospect with a bruised shin who had remained surprisingly mute throughout the demo!
∼ Bob Apollo, Founder, Inflexion-Point Strategy Partners
Celebration of Life = bad time to cold call
I showed up on a cold call, eager to get in with a manager who I had researched and was ready to start building a relationship with. When I saw no one was in the reception area, I stepped into a work area where a group of people were in a deep discussion.
It looked intense and I didn’t want to intrude, so I started to slowly back away. I’d make the call another day, I figured. The owner – who was at the center of the group – spotted me and asked if he could help me.
I gave the name of my contact and got quick glares from the entire group. The owner explained my contact had passed a week prior, and they were gathered for her Celebration of Life.
It got worse.
The deceased manager whose celebration I just interrupted was also the owner’s mother!
But not all was lost: Much time passed, and I got the nerve to call on the company again. The owner didn’t turn me away. Instead, he said my timing was terrible, but they all had a huge laugh at my embarrassing sales moment. I had provided great comic relief to a somber occasion.
∼ Bob Barrow, President, Barrow Group
1 to 100 wasn’t as easy as it seemed
Many years ago, a substantially more experienced colleague got sick. My boss asked our group if anyone would like to take over and deliver the presentation, which was to a group of 100+ people who were all potential paying customers.
I volunteered because I thought it would be a good learning experience. Plus, I understood the product and had presented it many times to individuals; so I thought I could also present it to a large group.
The presentation included about 20 slides and I planned to add anecdotes, testimonials and insights. I wasn’t prepared for the physiological response my body would have in front of so many people for the first time.
After I was introduced, I nervously walked to the front of the room – and immediately forgot my opening. I stood quietly for way too long and started sweating and mumbling. When I realized I was sweating, I only became more self-conscious – and sweat even more!
I could feel the sweat beading up on my forehead and stream down the side of my face. I forgot everything! My brain was in an extreme fight or flight response. I turned to the slide presentation and just read the slides, one by one, until it was finished.
When I left the stage my collar, dress shirt and hair were visibly soaked. I totally bombed the presentation and I am still embarrassed of this sales moment every time I think about it!
The upside, is that after a ton of practice, I now deliver 30-minute to two-hour presentations in front of 500+ people all over the world and I don’t sweat that much.
The lesson is that everyone starts somewhere, and nobody ever starts good at anything.
∼Michael Tracy, Founder, Sales Journey, Speaker, Trainer & Consultant
I flipped for the flip chart
I have to admit: I have more than one mishap! But this is one of the best.
Like all prepared salespeople I was ready with a handy flip chart when I was giving a presentation. When it was a good time to brainstorm with the C-suite on that handy flip chart my heel got caught in the hem of my dress.
What a scene when I fell over the flip chart … and it fell on top of me!
But I rebounded in more than one way. I got up, and I closed the sale.
∼ Joy Baldridge, Sales expert, keynote speaker and trainer
Not all meetings are meant to be
I was on track for a great meeting. I had a call with a client at 11 a.m. We finalized the agenda for the in-person sales meeting we were set to have at 1 p.m. that day.
I showed up at his office at 12:45 p.m., prepared to have a great meeting. After all, we’d already confirmed what we’d discuss.
But I soon found out that in the intervening one hour and 45 minutes, my client had been terminated. Even worse, he’d been escorted out of the building by security. He was not even given the opportunity to clean out his desk.
Talk about feeling weird!
While that meeting didn’t turn out as expected, I’m happy to say, a decade later, I still have a great relationship with the company, despite that one embarrassing sales moment.
∼ John Larson, Senior Partner, John Larson & Co.
Too much talk left me red-faced
I was a newly minted sales consultant, calling on a VP of Sales for a huge firm.
How fortunate was I? He was very interested to hear about our offering!
I was so excited to have an eager audience, I jumped right into my pitch describing how “great” our solution was. I went on and on about how sure I was we could help his people connect better with customers.
Almost at the end of my monologue, the VP says, “Oh, our people don’t meet customers in person. All our work is over the phone.”
Silence.
I had spent a solid 10 minutes describing the wrong solution – something they couldn’t even use. It was so embarrassing. I fumbled all over myself.
I hadn’t asked a single question. The irony is, I was trying to sell a solution to teach salespeople how to ask better questions and listen more!
It was a total head-smack moment. And I learned a hard, valuable lesson early.
∼ Lisa McLeod, Founder, McLeod and More
I should’ve stuck to sales talk
The meeting was going so well. It was early in my sales career, and I was excited I was able to get a meet with this prospect. I felt we were building some serious rapport.
She was totally interested in what I had to say and was seeing how our solution would be a good fit. I wanted to cement the bond we’d started to make and move on to securing another appointment. So I thought I’d try some more personal talk and flattery.
I said, “Oh, my gosh! When are you due? How exciting!”
The look in her eye told me immediately she wasn’t expecting a baby.
What I thought was flattery turned out to be an insult.
The conversation ended quickly and awkwardly.
It’s best to stick to business until prospects share something more personal.
∼ Keenan, CEO, President and Chief Antagonist at A Sales Guy
‘Writing on the wall’ was misspelled
I could practically see the writing on the wall – and the numbers were big. I was excited about this potential sale. And I grew more excited when the prospect met with our leadership team and they all hit it off.
We agreed this would be a good deal and great relationship. I wrote the contract – crossing every T and dotting every I – and sent it to the customer. Then I didn’t hear anything. For a few days. Then a week.
Finally my CEO called me to his office where he held the contract I had sent the prospect. My CEO quickly pointed out that I had misspelled an important name throughout the contract.
The prospect was reconsidering. He probably wondered that if I missed that detail, what else might I let fall through the cracks if he was a customer.
The embarrassment didn’t hold me down too long. I rewrote the contract, then hand delivered it and a sincere apology. I closed the sale and learned the valuable lesson to check and double-check contracts.
∼ Gabe Larsen, VP Growth, Kustomer
