The Top 10 Scariest Things Facing Your Sales Team

From kids to adults, there is something exciting about fear. For many, it’s the unknown. For others, it’s the loss of control. Either way, the exhilaration of fear increases our heart rates, stimulates our senses, and tingles the tiny hairs on our necks and arms. No doubt, this accounts for the popularity of ghost stories, the proliferation of true-crime podcasts, and the endless sequels and remakes of classic horror films. It’s also why the anticipation of Halloween starts in late August. However, despite all this, a sales career can cause its own unique anxieties and things that go bump in the night. As you settle in with your kids’ stash of candy, here are the top-10 scariest things facing your sales team:

1. Change: While many people fear change, it can be especially difficult for sales professionals. Do you remember the look in your sales team’s eyes when your organization went full virtual? Of course, they were fine dipping the occasional toe in the cold, impersonal virtual water, but the idea of going all virtual induced actual panic attacks. For many, their skill sets were not adequately prepared. After a lifetime of warm, friendly, face-to-face meetings, shaking hands and patting shoulders, the idea of setting a virtual sales stage and building rapport over a computer violated every rule of engagement. However, as with ghosts, goblins, and masked killers, familiarity breeds comfort, and the idea of videoconferencing soon became their new normal.


2. Commission Only Compensation: If you like the security of a regular paycheck, the thought of a commission-only comp plan can be terrifying. However, for sellers who truly believe in themselves, there’s great potential, flexibility, and value in these plans. For this one, think about the things that are most important to you. It takes a special kind of self-assured seller to thrive with commission-only plans, so if that’s not you, heed some Halloween advice: Never flee up the stairs, never laugh off cryptic warnings from the toothless proprietors of delipidated gas stations, and always choose the comp plan that is best for you and your needs.


3. Not Meeting Quota: Like an incessantly beating heart, a sales quota can be the loudest bump in the night. While some can see it as an ever-fixed mark, a bright, shining North Star, lighting the way to our sales goals, for others, it’s an albatross that weighs a little heavier with each unsure prospect, stalled deal, and echoing tick of the spooky grandfather clock. In the words of the poet John Donne, “Ask not for whom the bell tolls. It tolls for thee”—if you don’t make your monthly quota. For sellers with mortgages, car payments, and kids who need braces, your quota is like a buzzing, crackling, flickering neon sign that’s halfway down a desolate street called Hope.


4. Cold Calling: Though it’s a staple of sales professionals everywhere, there’s something creepy about cold calling strangers. It’s like the anonymous crank caller in the film When a Stranger Calls who famously and terrifyingly asks, “Have you checked the children?” Today, with its association with spam, it’s like a recipe for a hang up, rebuke, or expletive-laced denunciation. Yet, despite all the advances in technology, cold calling is still in practice because it can be effective with the right strategy. Of course, as with everything in sales, the more you do it, the easier it gets, and after your first few hundred cold calls, you’ll be a fearless expert.


5. Not Knowing the Answer: Good salespeople help clients. To do so requires extensive research into their business and industry. When sellers enter a meeting, they’re riding the confidence of preparation. They know how many employees the client has. They know their distribution sites. They know the company’s revenue. That’s why the thought of an unexpected question can be the stuff of sales nightmares. Do not panic. Don’t fake it. In these tense and frightening situations, take a breath, tell them it’s a great question, and promise to investigate further. The best sellers don’t always have the right answer ready, but they know how to find it.  


6. Discussing Money: Many don’t like to discuss money. There can be something so uncomfortable, so unseemly, so grossly inappropriate about money conversations that even the best sellers bristle before bringing it up. Like an ancient evil whose name must not be spoken, we tiptoe around it and use euphemisms like “neighborhood” or “ballpark.” Of course, for many, money equals success. It’s something we can’t help but judge. Good sellers know to approach budgets with tact and empathy. They know a company’s ability to pay is not a reflection of the prospect, and the best sellers focus on value over cost and present solutions for every budget.


7. Multiple Decision Makers: It’s one thing to have a ghost in your basement. Or maybe you incurred the ire of a witch. Perhaps there’s a vampire set on your neck. No matter the challenge, it’s easiest to face them one at a time. Sellers, however, do not always have this luxury. Larger organizations can mean complex deals with so many decision makers, it’s like a party for ghosts, witches, vampires, werewolves, and creatures from the black lagoon. How can you get these disparate entities to agree on anything? Of course, the best sellers know to seek alliances, align needs, and present broad spectrum solutions that address multiple issues.


8. Saying No: You have the expertise and the experience. You’ve done the research, and you know the solution your client needs. This can be a great feeling. However, sometimes clients don’t see it that way. They’re sure they know their business better than anyone, and they want something that is not in their best interest. For many sellers, this is a fight or flight moment. We all know the adage about customers being right. But what if they aren’t? What if opening that ancient box unleashes a torrent of demons and spirts from which they will never recover? Top sellers know that it can be difficult to say no, but trusted advisors know sometimes the best deal is the one you don’t close.


9. Procurement Teams: In the pantheon of Halloween costumes, you have ghosts, goblins, witches, and other monsters. All are scary, but perhaps the most frightening for salespeople has no costume. Though no child will appear at your doorstep so dressed, all experienced sellers know procurement teams make formidable opponents. After all, these unfeeling, unsmiling, professional negotiators have no wants or needs of their own, no personal stake whatsoever. Their sole purpose is to secure the best deal they can. Though this may seem an advantage, underneath their cold exterior, they are a lot like salespeople, and the best sellers know to work with them to seek win-win outcomes.


10. Rejection: Of course, everyone wants to win. However, in addition to quotas, commissions, and bonuses, sellers have their pride and an innate desire to help people. This makes their stake in winning more than just financial, which makes rejection another fear that keeps sellers up. This fear is compounded the more they invest in the sales process. Did I just waste all this time researching, preparing, and even presenting, just to walk away empty handed? Even those who eventually fall asleep are besieged with nightmares of clients agreeing to terms and shaking hands—before laughing manically as they remove their pumpkin heads.

Of course, Halloween is rooted in fun. There’s nothing like a good scare to keep us in tune with our hopes and dreams. But, despite the fun, there must be something under the surface. After all, if fear wasn’t real, it wouldn’t be fun. Halloween lets us indulge these feelings. It’s a reminder that, though every profession has its unique fears, most deal with loss—the loss of limb, the loss of heads, the loss of life—and all the demons and monsters are metaphors for our own anxieties. For salespeople, most fears are centered on our ability to make money while keeping the interest of our clients as close as our own. It can be a tough tightrope to walk, but at the end of the day, it’s what makes selling so rewarding, even when it keeps us up at night, binging on candy.

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