How to Avoid Landing the Sales Job from Hell


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Sometime in the next 12 months, you’re going to experience a back-you-into-the-corner-sign-the-contract-right-now appeal. A full-frontal sales pitch that homes right in on your jugular vein. I gaaaah-ron-teeeeeee it!

For what? Used cars? Home security systems? Timeshares in Aruba? No. The hiring speil from the VP of Sales who wants you to work for him, badly. He spews his company’s marketing fireballs with verve so powerful, it would make the most polished televangelist envious: “Our product sells itself! . . . We have no competitors! . . . The market on freaking fire! . . . Employees are our most valuable asset . . .”

Mmmmmmm. That sweet intoxicating aroma of money, with a hint of personnel love on the side. “You had me at ‘I just reviewed your profile, and . . .’ but let’s move on, and talk about comp, shall we?”

“Sure. At plan, you will earn . . .”

The numeral at the beginning has seductive curves, and it’s followed by the expected number of decimal places. The figure has mostly zeroes, with a smattering of 5’s cleverly embedded to break the monotony. “Talk to me. I’m listening . . .”

There’s further upbeat conversation. No smiling, though, but lots of direct eye contact. “At plan, you will earn . . .” I become giddy thinking about a second house, a boat, and a less-hungry, more-corpulent 401K.

Still, that subtle hedge, at plan, nags at me. At plan. Drat! Always a sour flavor that despoils the compensation stew. But I understand. Even though its taste cannot be masked, no right-minded company would dare remove that essential ingredient. Reality, biting again. Tacit admission that when it comes to making quota, [stuff] happens. Agreed – those risks must be shared. After all, I’m no socialist!

But here, let’s cut to the chase: No matter how compelling the income opportunity might be, at plan always carries a continuum of probabilities – from achievable to not-a-snowball’s-chance. The problem is, how can you tell? And how do you assess whether you will make the right decision by accepting the VP’s ardent appeal to join his team?

Before I answer those questions, please allow short digression to share something about the deleterious properties of quicksand. Hang in there with me. If you’re unclear about my reasons, they will become apparent shortly. Quicksand: “deep, wet sand into which heavy objects sink easily.” Or, the metaphorical meaning, “a situation that is dangerous and difficult to escape from.” Talk to anyone who has been selling for a while, and just by mentioning the word, you’ll hear a raw, emotional story about a past gig. A recounting rich in wisdom and saturated with insights. Take copious notes. They will help you avoid walking into a comparable trap.

OK. Where were we? Assessing. Right! Or, to be precise, assessing risk. Hard to do when comp – I mean, potential comp – obscures every important concern. But Gerry Cullen, author of The Coldest Call: Why Some Good Products Don’t Sell, provides a valuable risk-assessment framework for candidates seeking sales positions. His book, a straightforward counterpoint to the pervasive salesforce sucks tripe that infects the blogosphere, is an entertaining read, eloquently written. Had it been published twenty years ago, it would have saved me untold angst.

At plan, you will earn . . .” Before you initial Accept on the employment contract the VP has pushed toward you across his desk, before you prematurely trade in the six-year-old Scion you bought used, and replace it with a brand new German-built ride, take a moment to consider what Cullen examines when determining whether a salesperson can succeed at a company – or more ominously, whether a company can succeed for a salesperson:

1. Pain. If no one at the company can articulate anything coherent about the pain the company solves, you probably won’t have the patience to invest the time figuring it out. Cullen writes, “It’s a joy to work with companies that have a clear understanding of the pain their products eliminate. They understand the purpose of their efforts and understand why people like and buy their products. They know what they are good at, and may have a shot at being the best in their product category . . . On the other hand, it’s far harder to sell for companies that don’t use pain as part of their dogma. The salesperson has to create the pain statement on their own and bridge the gap between the company’s products and the prospect’s needs – a process that takes much longer and has a good chance for error.”

2. Promotion. Some companies dump the business development brick onto the shoulders of the sales force. Marketing, outbound lead generation, prospecting, qualification. Even content development. The whole kahuna. “Hey, we’re a lean company! Besides, if we just hand opportunities to sales, they’ll get lazy!” But, as Cullen writes, “Cold calling is terribly time consuming and generally it has a low rate of return. The task is finding out what your prospective company does to generate qualified leads for you and what sales support tools they have to help close the order.”

3. Price. Are the company’s prices and pricing policies clear and unambiguous? Can they be explained without your eyes glazing over? Equally important, are prices readily accessible, or are they squirreled away somewhere deep within the company’s document management system – or worse, just stuck inside someone’s head. “You can learn a lot about a company by examining how it prices products,” he writes. “It’s not what the actual price is, it’s getting the price to the prospect without confusion or hassle.”

4. Policy/culture. How does the company’s management regard its sales organization? As something valuable and necessary? Or, as a necessary evil? Does the company promote its star salespeople into new, challenging positions, or does it churn and burn? Does the company have star salespeople? Ask current employees, past employees, and people who have done business with the company. You’ll feel the vibe.

Deal breakers

Many sales veterans can relate a story about a job they accepted, or stayed in, even when their better judgment told them not to. A curious weakness that commonly plagues sales professionals, made poignantly funny through a dark joke in Cullen’s book:

A salesman meets a super model at a seminar, falls in love, and announces to his friends that he plans to marry her. His friends immediately advise him that she is an alcoholic and a drug user. They further counsel that, once married, she will bankrupt him, be unfaithful, and leave him despondent. “But still. . .” is his classic response.

Such delusional outlooks are often confused with positive thinking. “You can do anything you want if you have the right drive and motivation.” True. Just make sure to append “. . . but don’t be an idiot.” to that inspiring quote. If your assessment uncovers the following radiant-red flags, don’t sweep them under the rug, because they should be regarded as deal breakers, or at least give you reason to pause:

1. Commission or earnings caps.
2. A compensation plan that’s undocumented, unclear, or utterly indecipherable.
3. No compensation plan. “We’re working on it, and promise to have it you when you start.”
4. Less than 50% of the sales force makes quota.
5. Higher than normal sales force churn.
6. No resources committed to sales force development or skills training.
7. Racist, sexist, or obscene remarks made in the job interview.
8. Other comments or remarks made during the interview, or in other conversations, that are patently bizarre or inappropriate.
9. Employer contrives an annoyingly stressful situation to see how you will react.
10. Employer disrespects your time by being grossly late for the interviews and meetings, or by continually accepting phone calls and other interruptions during the interview.
11. Employer fails to disclose litigation history with salespeople, former employees, and/or customers.
12. Website content and corporate communications contain major factual inaccuracies, especially claiming marquis accounts as customers when they are not.
13. Sloppy corporate communications that include bad writing and poor grammar.
14. A CEO with a track record of running failed companies.
15. No significant new product introductions in previous 12 months (six months for IT companies).

Finally, in recruitment postings, be wary of the following phrases:

“Hunters wanted.”
What it means: “Our marketing and sales teams don’t work together, so lead gen is up to you.”

“Must be a self-starter.”
What it means: “Our work environment is stultifying.”

“Able to work independently.”
What it means: “Don’t expect anyone here to support or mentor you.”

“No limit on earnings.”
What it means: “You’ll get little or no base salary.”

“Must be comfortable multi-tasking in a fast-paced environment.”
What it means: “We operate in crisis mode, 24/7.”

As we know from Tarzan, quicksand can be deceptively camouflaged. The same for sales jobs from Hell. Everything looks great, until, flooooooossssshhhhhh! – you’re consumed in a swirl of passive aggression, confusion, leaderless meandering, finger-pointing, and overwhelming aggravation. Not to mention, you’ll realize that the at plan compensation discussed in your interview was only a mirage.

Even the best sales organizations have sales impediments, so seeking job perfection will lead to frustration. But knowing ahead of time what quicksand feels like under your feet will help you avoid sinking in it.


  1. Bravo! Great article, Andy. There are a huge group of companies out there who are fundamentally unprepared for the future. They’ve failed to adapt to the changing times.

    Worse yet, they expect salespeople to create opportunities out of thin air — with no support from the organization via marketing, sales tools, a decent website and more. The list is endless.

    In many cases, the leadership actually believes it’s possible to succeed–even though their turnover is astronomical and revenue growth is stagnant. Or, they’re too stupid to know there’s a better way.

    Salespeople should be wary of all the indicators you mentioned. If they take the job, they are virtually guaranteed to lose their confidence, feel like a failure and think they’re not cut out for sales.

  2. Thanks, Jill. So many of us put the onus for sales success directly on salespeople. I believe that’s where it belongs. But a less-common understanding is that sales success depends on avoiding the abundant situations that are, by anyone’s estimate, utterly wired for failure.

  3. I like your article, Andy. You did a very thorough analysis of the Sales job horror that often goes unmentioned in business settings. I especially relate to the point about managers contriving an uncomfortable meeting to see how the salesman reacts. There are sadists in sales environments and they can exploit even those who are least likely to be masochists.


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