We’ve all been there – that awkward moment when you’re hoping to connect with a prospect on a call, but things go horribly, and sometimes hilariously, wrong. Whether it’s a cringeworthy personal gaffe or an angry prospect who wants to watch the world burn, the sales world is full of stories as hilarious as they […]

We’ve all been there – that awkward moment when you’re hoping to connect with a prospect on a call, but things go horribly, and sometimes hilariously, wrong. Whether it’s a cringeworthy personal gaffe or an angry prospect who wants to watch the world burn, the sales world is full of stories as hilarious as they are painful. 92% of customer interactions happen over the phone, which means there are a whole lot of opportunities for things to end up sideways.

We’re pulling back the curtain on the worst sales call experiences that real sales pros have lived through. We’ll also share tips for gracefully handling those “sales call from hell” moments so you can turn your next awkward encounter into a chance to impress your prospect. After all, the ability to think on your feet and maintain composure under pressure is a hallmark of sales success.

Grab a cup of coffee (or something stronger) and get ready to commiserate.  

1. When you assume, you make an as– well, you know how the saying goes.

The story

“On a call the prospect said, ‘My manager is running two minutes late; they’ll be here soon.’
I replied, ‘We could introduce ourselves before he arrives.’

Crickets. Then the prospect pointedly said ‘She is joining us now.’”

How to handle it

Making assumptions about prospects and their teams can lead to an objection early into the call. If you mess up like this (making assumptions rooted in stereotypes or that you’re unaware of due to cultural differences), don’t ignore it and hope it blows over. Leaving it unacknowledged is likely to make the prospect even more upset with your rudeness. But don’t make it into a huge deal, either. Simply say something like, “oh, excuse me,” and then continue with a polite but genuine conversation. If you acknowledge the slip-up and handle the rest of the conversation well, you can still recover the relationship. 

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2. Thawing out a voicemail brain freeze

The story

“Recently I started leaving a voicemail for a prospect when all intelligent life left my body. I don’t know what happened but I just could not string together a coherent sentence. The guy probably thought I couldn’t rub two brain cells together. I struggled through and ended the VM but it was so embarrassing.

I ended up following up with an email and asked for a chance to prove I do in fact know how to use words. He booked a meeting based on that email, probably to see if I was actually a human and not some strange alien lifeform.”

How to handle it

The best way to recover? Call it out and laugh it off. Blame Monday brain or insomnia or something similar – most people can relate. If you experience a similar situation and freeze up while leaving a voicemail, follow up with an email to help clarify what your voicemail could not (multithreading, anyone?). Plus, “Per my awkward voicemail” is a pretty compelling subject line that humanizes the sales conversation. And if your brain freeze happens live on a call, saying something simple like “Sorry, I haven’t had my coffee yet” can do a lot to help smooth the situation. 

3. Never trust the mute button

The story

“This was back when I was young and brand new to selling. I thought I was hot stuff. I put him on mute to ‘talk to my manager’ about the ridiculous discount he wanted. What I really did is call him something that was, well, let’s just say non-work-appropriate.

Spoiler alert: he wasn’t on mute. It was a bad time.”

How to handle it

Unless the prospect has a good sense of humor, this one’s pretty hard to bounce back from – especially if they were already disgruntled. The best approach: apologize sincerely and take ownership without making excuses. You’ll have a lot of work to do to rebuild the customer’s trust, so offer reasonable ways to make amends like a discount or credit. In this case, you’ll have to go above and beyond if there’s going to be a chance at salvaging the relationship. 

But even with all that, be ready to call it a loss and move on. Use it as a learning experience and ask mentors for advice on how to handle challenging customer interactions. 

And for the future, remember: the mute button is never actually on. Don’t blow off steam and gossip about the prospect before the call is over… and always triple-check the mute button. 

The bright side of nightmare phone conversations

What makes sales calls tricky is you’re “doing it live.” There’s no chance to go back and edit like with email. But what makes cold calling challenging is also its greatest strength. Because it’s all unfolding in real time, you get to build direct, instantaneous connections with your prospects. 

When you make a mistake you can laugh off, it reminds them that you’re a real person, not just a sales robot. And the goal of a cold call isn’t to get them to buy your product right away, anyway – it’s to make sure they remember you. 

Another benefit of messing up badly on a call? It gets it out of the way. 48% of sales reps are afraid of cold calling, partially because of the risk of a bad interaction. After you’ve already fumbled a call or two, you realize it’s not a huge deal. 

Hopefully, after you’ve messed up a few calls and learned you can bounce back from them, you’ll get that extra boost of confidence you need to continue picking up the phone again and again. As far as we’re concerned, getting some funny stories out of it is an added bonus.

Have your own stories about sales calls from hell you’d like to get off your chest? Share them with us!

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