Bad Sales Advice – What Not to Do/Say to Prospects

An image illustrating two men facing each other and a crack on the wall between them.

Hey there! It’s me, Jack. 

You may know me as the heartbroken SDR from the Valentine’s Day Spotify Playlist who lost his beloved prospect. If the playlist gave you the feels, let me tell you that that wasn’t the only time I had to deal with a closed-lost situation.

In fact, my most disastrous attempt at sales prospecting happened just last week with my prospect, Todd. In my desperation to impress him, I might have gone a *wee bit* too far. Emojis were sent. Neighbors were spammed. Restriction orders were filed.

Long story short—he said no.

Sales advice - Slintel | Blog

As I retrospect, there are several things I did that I regret. I’ve listed all of those things below so you won’t make the same mistakes I made.

Bad (worst is the word, actually) Sales Advice

#1 Send them ‘crappy’ gifts—like scented candle discount coupons

In order to impress him, my first idea was to send him the scented candle discount coupon I found in between my couch cushions.

I was sure he’d appreciate the 40% discount since I didn’t need it anyway. You see, I buy a scented candle to comfort myself every time I lose a prospect. So, I already have enough to last the year… and it’s only just February.

Unfortunately, it didn’t occur to me that sending your prospects “crappy gifts” (quoted as per his email response) was a bad idea. 

#2 Tell them all about your nephew’s peanut allergy

So what if the scented candle discount coupons were a bad idea? I brainstormed a dozen more ways I could make things better. The next day, I called him out of the blue and decided to start small talk with him.

And boy, did I get carried away! I ended up engaging him in a five-minute conversation about my nephew’s peanut allergy (five because he hung up on me). 


I knew that having a small valuable conversation with your prospect before you get to the pitch was a crucial part of sales prospecting. However, I made two teeny-tiny mistakes:

  1. The conversation wasn’t valuable, and 
  2. I totally forgot about the pitch.

#3 Spam them with memes over a decade old

They say – “If you get them to laugh, you get their attention”. 

And that’s precisely what I had in mind when I sent him those memes, making sure not to forget the pitch this time. Unfortunately, I might have come across as mildly creepy in the process(?).

Sales advice - Slintel | Blog

Needless to say, he asked me to stop. I thought maybe he just didn’t like the memes, but to be honest, the memes were not only old but also completely irrelevant to what I was pitching. So his displeasure sort of made sense.

That was a pity because I was so pumped about making him laugh that I had an entire album of memes from 2012 ready for dispatch. 

#4 Send them anonymous emails

By now, I was convinced that Todd was having a bit of trouble saying yes to me. So I thought it would be a good idea to send him some emails posing as a happy customer who benefited immensely from our product.

I got no reply. 

So I sent some emails from my own (real) email address, prompting him to reach a decision quickly before the (non-existent) deadline, after which there’s a price hike. 

The idea was to create FOMO by getting him to see how happy our customers are while also adding a sense of urgency. 

However, a bunch of emails from strangers, singing praises of our product, right when I’m prospecting might have seemed too fishy. And he saw right through my spurious deadline. 

#5 Promise the sky, the stars, and the seven seas

Since my previous plans didn’t work out, I thought I could pique his interest if I focused on the value our product could offer.

In my enthusiasm to get him on board, I may have exaggerated a little *clears throat* too much and over-promised on our platform’s value. 


It was nothing too much, really. Just a few multiples here and a few extra zeroes there on the numbers… for aesthetic purposes.

However, Todd was no match for me. Since he had already done his fair share of background research on us, he knew our customers were sort of happy with our product, but not to the point where they worshipped us. So I ended up having to do a lot more un-explaining than I had planned.

#6 Turn objection handling into a battlefield

After many tries, much to my dejection, I was convinced that Todd was here for nothing but business—not old memes, not scented candles, not fishy emails—just business.

So I finally decided to drop my antics and get to the point. I put on my salesman’s face, picked up my phone, and called him. I apologized for my immature behavior and for the first time, I got to the pitch without being hung up on.

Then came the objections.

“Why should I trust you? How can I be sure that your product would be of value to us?”

I blew my top. Here I was, prospecting him with all my heart and soul, and now he’s calling me a liar? It’s hard to not take something like that personally, so without missing a beat, I snapped –

“Why should I trust YOU?”

And that’s when he hung up. “There! I showed him who’s the boss, all right,” I told myself as I triumphantly sat back in my chair and added another scented candle to my virtual shopping cart.

Sales advice - Slintel | Blog

#7 Kidnap your prospects

I don’t like to talk about this one. But maybe I’ll share a story someday. Who knows?


To Todd: Todd, if you’re reading this, I hope you know now that I’ve changed—for real. If you’re willing to withdraw the restriction order, I’m still open to prospecting you the right way this time.

To my fellow salespeople: I hope you’re able to take home something from my story. Even though I might not be able to tell you what to do as a salesperson, I’ll always be able to tell you what NOT to do.

Roshan Nair

Roshan Nair

Content Marketing today, caffeine relapse tomorrow. Hopes to tell a great story one day. I consume satire and horror in the meantime... Say, would you watch it if I made a satirical horror movie one day?

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