Sales Prospecting Nightmares (Based on True Events)

Sales Prospecting Nightmares

Sales prospecting makes the best of salespeople nervous. The pressure of approaching leads and prospects with the right criteria and asking all the right questions to steer the conversation in the right direction is always high. 

What nobody talks about though, are the instances when the prospect says something that’s so absurd that they’re borderline nightmarish. We’re talking about responses that leave salespeople in splits and those that are so weird that they haunt them for days after the conversation has been put to rest. 

Sadly, what happens on sales calls, stays on sales calls (JK. Marketing knows everything!). But, we coaxed our sales team into sharing with us some of the most “interesting” responses that their prospects startled them with. Some of these are ridiculous and some will leave you questioning human behavior at large. Let’s take a look at them.

#1 The one where the “little birdy” failed to land

The one where the "little birdy" failed to land
Photo by Hello I’m Nik on Unsplash

We found out that one of our prospects, let’s call him Mr. A, was looking to hire SDRs for their team. Now, hiring generally means that the team needs more resources to share the load of increased targets. One of our sales folks saw this as an opportunity to talk about how our product can help them solve the meeting-your-targets problem. After all, resources also include technology. So, he asked Mr. A if he’d be up for a quick call.

Mr. A wasn’t amused. Instead of refusing to engage in any further conversation straight up, he decided to grill our sales rep. What for, you ask? For doing his job.

Let’s just say that even though our sales rep didn’t get a call, Mr. A definitely got a lesson in politeness.

#2 The one where the prospect “literally” hung up

The one where the prospect "literally" hung up
Photo by Hello I’m Nik on Unsplash

A sales rep wrote to a prospect asking for a quick call to discuss a possible business deal. She opened her email with –

“Hey, can I have 30 seconds of your time?”

The prospect (Mr. B, this time?), evidently a lover of time and literal meanings, agreed for a call. As someone who had just bagged a meeting with a single email, our sales rep began preparing hard for the call. She had everything ready—a study of the prospect’s needs, a tailored pitch, a well-rehearsed demo, battle cards, and loads of patience. Cut to the call—our sales rep introduced herself and before she could begin with the pitch, exactly 30 seconds into the call, Mr. B hung up! 

Mr. B had agreed for a 30-second call and a 30-second call it was! Some hard lessons on patience and letting things go were learned on that day.

#3 The one with a little surprise in the end

The one with a little surprise in the end
Photo by Tengyart on Unsplash

You know how sales folks really look forward to prospecting calls, right? It’s their once chance to hit the nail on the head and convince the prospect to give your solution a shot.

On one such occasion, our salesperson had an important call scheduled with his prospect (obviously, Mr.C!). He made the call, right on time, and went in with conviction. After his exhaustive monologue ended, there finally came a voice from the other side of the phone—“are you calling for Mr.C? I’m his father.”

Could he have done this on purpose? We guess we’ll never know!

#4 The one where things got out of hand

The one where things got out of hand
Photo by Tengyart on Unsplash

One of our sales reps wrote a follow-up email to a prospect. As is the case with any sales professional, she was hoping for a positive response, but was also prepared for rejection.

This prospect (you know by now, it’s Mr.D!), a not-so-kind person, could have easily asked to drop the conversation. But he decided to drop the F-bomb instead. But our sales rep knows what it means to kill ‘em with kindness. Here’s how she responded –

“It takes 0 minutes and 0.5684 seconds to unsubscribe :).

In our world, it is acceptable to take a no for an answer but we won’t let anyone, let alone a CEO, swear at us. Anyway, good luck being nice, and if you celebrate Rosh Hashanah, Shana Tova u’metuka!”

Dignity = 1; Disrespect = 0.

#5 The one with a “beautiful” poem

The one with a "beautiful" poem
Photo by Nishaan ahmed on Unsplash

After all those tricky scenarios, we’ve sneaked in a treat for you! 

Sales folks are mavericks; no, really. One of our sales reps wrote a poem (yes, you read that right!) to get one of her prospects to listen to her pitch. Here’s how it went –

SDRs are brilliant

but your leads ain’t pure

Slintel’s an angel,

of that I’m sure

you call up your prospects

spoke to the wrong man

but you will lose no sleep no more

’cause I’ve got a plan

don’t be frustrated

when the pipe’s looking low

you book a meeting

it doesn’t close

I saw your space

it’s a crowded place

and it’s time to face the truth

our intent was meant for you.

*singing in James Blunt’s voice* 

PS: On a completely unrelated note, you’re beautiful 🙂

Can we just take a moment to appreciate the effort and the creativity that went into writing this? If this is not brilliance, we don’t know what is! 

But guess what happened? The prospect wrote back an angry response because he thought he was being “spammed”. *facepalm*

That’s all folks!

When we asked our sales folks to share some of their most memorable AKA ridiculous prospecting conversations, they were hesitant at first. Some of them recounted instances where the prospect had been unnecessarily rude to them, while some recalled times when the prospect crossed professional boundaries and went wild with hurling abuses. 

You can also check out Better Outreach for effective cold prospecting.

What this teaches us is that there’s no better answer than politeness to anything that’s otherwise. Also, shout-out to each one of these sales folks for putting up with all this predicament with a smile, day in and day out!

BTW, if you want to know when your prospects are actively buying, what are they discussing within their company, and other key news—install our Chrome Extension and get all this information in one place.

Neha Mestry

Neha Mestry

Neha is a Content Marketer by day and an illustrator at night. With a profound interest in art and all things creative, Neha often indulges in creating content in various forms—blog posts, watercolor paintings, digital illustrations, and quick doodles. Oh, and she can survive an eternity on a deserted island as long as she has a good book (read: fiction only) by her side.

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