How to Spot Sales Job Quicksand Before You’re Knee Deep


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Collette, a former sales colleague, has a problem. She’s tenacious, poised, and highly motivated, but when she asks questions, she goes right for the jugular—and that’s where she gets into trouble. Collette doesn’t tiptoe around topics.

Collette recently interviewed for a technology sales position. “Their CEO said that they were going to grow their market share by 40% in three years,” she told me over lunch, one week after her meeting. “I asked him ‘How are you going to do that?’ and do you know what—he couldn’t answer my question!”

Oops. Collette chose not to pursue the opportunity. I’ll add that she did not get called back for a follow-on interview, either. I suspect the CEO was put off by the disarming simplicity of Collette’s question, or he was embarrassed by his own lack of preparedness. Maybe he just didn’t like Collette.

Regardless, had she received an offer, Collette saved herself at least six months of solid frustration. Her chances of making her number were as likely as Jonathan Sanchez winning this year’s Cy Young Award. Why? Companies that lack a plan for achieving challenging goals have little recourse other than to simply shovel quota onto the sales force. “Here you go—and don’t forget that quarterly bonus waiting for you, if you make your number.” Faux strategy, supported with weak tactics. If only their bankers knew.

That situation often means lower-than-expected compensation, no bonuses, and moving the Achiever’s Club venue from St. Thomas to Daytona Beach. Nobody’s disappointed, because nobody made Club. I’ve seen it happen more than once. And by using just one bang-on question, Collette smoked out the problem from a mile away.

Whether or not you admire Collette’s style, she did manage to quickly cut through shaky facts and piles of assumptions built on flimsy predictions. Go Collette! What else might she and other sales candidates need to listen for to uncover hidden risks? Here’s a short list:

“At plan, here are your expected earnings . . .” The operative words, at plan, need close examination, because not all plans are created equal. Some plans are achievable. Others, after you peel away the covers, are not. Find out what are the key assumptions, and ask historically, what percent of the sales force achieves plan. If it’s 50% or less, figure out whether that risk comports with what you can accept–even if you think you’re really, really good. On the other hand, a company that can substantiate that 75% or more of its sales force consistently makes goal can probably tell a positive story about what they’re doing to achieve it. That might include using sound methods to formulate quotas, making good hiring decisions, equipping salespeople with useful resources, using effective processes, and providing effective professional training and development.

“As Sales VP, I’ve led multiple teams.” True, VP titles carry a certain gravitas, but it’s not always well placed. Being tasked with leading a team doesn’t make one a leader. An effective sales leader will be able to share how, more than once, he or she has created a winning environment for people to reach goals and to achieve an equitable financial reward. A confident leader will share names of direct reports—present and past. Contact those references, and ask the questions that come naturally: “Would you work for her again?” “How does he resolve issues when they occur?” “Was she an effective coach?” “Do you think he is/was fair?” “Is/was she well-regarded by her peers in the company, and by customers?”

If the Sales VP or manager has a LinkedIn profile, look for recommendations from direct reports. If there are few or none, that’s cause for concern. One Senior VP of Sales I know has held similar titles for multiple companies over 21 years, but only one of his nine recommendations was written by a person he managed.

“We really need the person in this territory to hit their number.” That’s good. But your curiosity should drive you to learn whether the predecessor salesperson in the territory was promoted out of the position, quit, or was canned. Ask “how have people performed to quota in this territory in the past?” It’s great when positions open through promotions or growth. But if the predecessor—or predecessors—”just didn’t work out,” find out why.

A recent survey from Baseline Magazine (Talented Workers in Demand) indicated that 43% of hiring managers are concerned that top workers will leave their organization this year. Ironically, 71% of job candidates seek longevity in considering a future employer. For recruiters, this discord portends a robust sales year. For salespeople, it’s a reminder why it’s important to know what quicksand looks like, before you step into it.

Republished with author's permission from original post.


  1. Great points, Andrew, and quicksand is the right metaphor. The sad thing with these ‘jobs’ is that you can struggle to do them well but in these environments, all that happens is you sink deeper and deeper into the murk.


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