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Nightmare on Sales Street: 7 Nightmares That Keep Salespeople Up at Night (and How to Stop Them)

Table of contents

It’s late. You’re on your way home. You choose to take this out-of-the-way, dimly lit alley. Usually, you’d be more cautious and take the bigger roads, but, again, it’s late and you just want to get home. You hear a noise. You feel your hair standing on end and forget to breathe. Ah, it’s just a cat running out of a dumpster. Well, that made you jump. Silly. With a relieved smile, you continue on your merry way, certain that “it’s all in your head”….

Just to get jumped by an oh-so-murderous guy in a hockey mask. 

Or is it the creepy girl with an unhealthy TV habit, climbing out of a well? Or a cool hat guy with unfortunate skin problems and love for lullabies? Whatever your scare, the good thing about them is that all you need to do to make them go away is switch off the TV or close the book. 

In life, it’s a bit trickier than that. And double so if you’re a salesperson.

Where other people wake up in a cold sweat because of dreaming of forgetting to put on pants, salespeople are kept up at night by the visions of not hitting the targets, coming to a meeting unprepared, or being unable to answer a client’s simple question. The sad fact is — it’s scary because it’s true. Or it can be.  

So here’s our treat for you for this Halloween: the best resolutions for the worst sales nightmares. 

The “Misery” of a Bully Prospect

You’re chasing this colossal prospect and in the beginning, they are all rainbows and sunshine. But when it comes to negotiating the price (or other aspects of a deal), they turn full Annie Wilkes on you, start shouting, calling you names, and making (unreasonable) demands. 

What to do: 

What you don’t want to do is to cave in or meet aggression with aggression. The first one will only reinforce their feeling of control and make them a nightmare client, and the second will most likely cost you the sale and a big deal of nerves. There are, however, a couple of good ways to deal with a bully prospect.

Establish your expertise

You are a professional and you know what’s best for the client. Because you’ve seen and done it all hundreds of times before. So come from a position of calm strength, explain that you only want to help (and know-how), and let them know that your offer is final and based on rational estimates and your previous experience.

You are both already invested in the sale, it’s just your job to bring it home as quickly and efficiently as possible. It might be a good idea to decide ahead of time what you’re willing to negotiate on, so you don’t cave in under the bully’s pressure.

Give them the silent treatment

Bullies thrive on attention, so by meeting their accusations and demands with stone-cold silence or a stare makes them rethink their strategy and often even feel embarrassed for their behavior.

Run for the hills

Don’t get us wrong, it’s not an excuse for you to give up on difficult prospects. But when everything else fails, sometimes the smartest thing you can do is walk away. More often than not nightmare prospects make nightmare clients. So learn your lessons and think about it as dodging a bullet.

Being stalled by a Gatekeeper

We’ve all been there. You’re trying to get to an exec prospect but hit their assistant instead. They routinely inform you that Mr Venkman is in a meeting and no, they don’t know when he’ll be back. You call again in two hours but get the same response. 

What to do:

First, remember, it’s the gatekeeper’s job to sieve through all the incoming requests and determine which ones are worthy of the executive’s time. If they let someone ‘unworthy’ slip through, it will make them look bad. So don’t be too harsh on them. Start by establishing your credibility as a ‘key master’ — what are the prospect’s needs and how exactly can you address them.

Request the bare minimum of the exec’s time (5-15 minutes), enough to pique their interest or convey value. If you’re still given the runaround, politely call them out on that, and build your case.

Casper prospects

There’s nothing (or almost nothing) more frustrating than to invest in a prospect, prepare a presentation, and spend a day on the road to get to them…only to discover that they “completely forgot” about your meeting and made other plans. 

What to do: 

Ideally, make sure you confirm (and double, triple confirm) the time of the meeting with your prospect beforehand. Call or send an email or two, just to make sure it’s on their calendar. If you arrive and still find yourself in Ghostbuster shoes, turn it to your advantage.

When you call them to reschedule the meeting, add a drop of good auld guilt there to add an extra incentive. It’s a powerful thing though, so be careful not to overdo it.

And while you’re in the area, why not check out other prospects nearby? You came this far, right? Having a mobile CRM to do a quick search can come in really handy there. Make a list, ring them up, and don’t forget to bring some treats! 

Going full ‘Johnny’ on a client during an argument

Ok, so you’re actually a mild-tempered guy/gal. And you can usually go through dozens of iterations, answer the…not-so-challenging questions for the umpteenth time, and politely smile at quite crude/insensitive jokes. But this one is just pushing it too far.

It might be their attitude, a clash with your company’s culture, a remark about your product, or just about anything else. The fact is — you feel the anger rising and steadily reaching the Shining level.

What to do:

Take a deep breath. And listen. If it’s a disagreement about a particular subject, perhaps, you can try to understand where they are coming from and why they feel this way. It will give you a useful insight into the ways they think and the best way to deal with them or to close a sale.

This research found the golden ratio of talk-to-listen: it’s 43/57. Now guess which one you should be.  

The Slenderman of a question

You didn’t see it coming. In fact, you were just taking a stroll in the woods. But here he is, jumping right from around the corner, staring you in the face, and making you feel like you’re losing your mind. The question.

It’s the one you never prepared for or expected. There’s that awkward pause when you realize that your whole deal might depend on you handling this situation.

What to do: 

First of all, do your homework. Know your product from top to bottom, research the potential client, their competitors, and their needs, and try to prepare the answers to all the questions you can imagine.

However, that doesn’t always protect you from being blindsided by a question you’ve no idea how to answer. The worst thing you can do here is to make something up. The truth always comes out, and it will not only make you look unprofessional but will also come to bite your company in the soft spot.

So own up to your ignorance. Admit that it’s a great question, and to answer it correctly you need to consult with an appropriate expert in the company. Promise to get back to them as soon as you can (and do) or if you can, make the call there and then.

This way you don’t damage your company’s reputation but show your investment in the deal and your honesty, and that will help you build trust.

Rise of the machines

You had this brilliant presentation prepared, with beautiful graphs and quirky images. But when your prospects are sitting there ready to be amazed, the projector doesn’t turn on, the PowerPoint crashes, your laptop decides to take a break, and the whole thing just shuts down.

In an alternative scenario, you’re trying to run a teleconference, but half of your prospects can barely hear you and enjoy your robot impersonation on camera. 

What to do:

Stay cool. Like, Terminator I-need-your-clothes cool.

You never know when the machines finally decide they had enough, so just be alert.

Always have backups and be ready to run with a good auld whiteboard or just your charismatic self. In the second scenario, if you can’t fix the problem quickly, focus on those who are able to participate and offer to reschedule the call for those who can’t.

One solid presentation for some is better than one disastrous presentation for all.

Turning into a Yes Man

Alright, alright. It’s not a horror movie reference per se, but bear with us. You know how it happens. A valuable client is making a request, and you say, “yes, of course, we can do it”. Then comes another ‘request’, and another. Before you realize it, you’re losing money, the customer is walking all over you, and, worst of all, you built up all those expectations. Now, one sudden ‘no’ will feel like a slap. 

What to do:

Ideally, set a good precedent from the start. If what a customer wants is profitable to you and you can deliver, say yes. If the request is unreasonable, say no.

If you’ve already embarked on the ‘yes-man’ journey, it’s not too late to take a stand. Rationally explain to the client why you won’t do what they ask. Use numbers, references, charts, or whatever gets the message across. It might feel like a bucket of cold water to them now, but it will save you a lot of time, money, and nerves in the future. 

What nightmares keep you up at night? Or maybe you have a scary story to share? Let us know in the comments or tweet @OnePageCRM!

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