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What the Best Salespeople Know About the Art of the Sale

August 14, 2014

By: Crystal Spraggins

I used to know a salesperson (let’s call him “Al”) whom customers either loved or hated.

Al’s beat was college campuses, and rumor had it that when professors knew he was coming to town, they’d either bring out the welcoming committee or suddenly decide it was time to run an errand.

Overall, though, Al was pretty darn good at this job, consistently performing better than most of his peers.

How did he do it? How does anyone do it? Read on to find out.

A word with a pro

Bill Kaiser is the Area Vice President, Sales & Marketing, for Arthur J. Gallagher & Company, an international insurance brokerage, and risk management services firm. Gallagher is headquartered in Illinois but has operations in 25 countries and clients in more than 140 countries worldwide through a network of partner brokers and consultants.

Bill, a well-established and experienced sales pro, serves the Mid Atlantic region of the business, including training and mentoring sales staff. He should know a thing or two about closing a deal.

Well, that’s what I thought when I asked to interview him.

It turns out I wasn’t wrong.

Here’s what Bill shared with me about the art of the sale:

Aggression isn’t all bad.

Al’s aggressiveness is what made some faculty members run for the hills whenever they thought he’d be around. Aggression (and other forms of incivility) costs companies millions annually. That’s costs, not earns.

Still, the idea of an aggressive salesperson is very much alive and well. According to Kaiser, that’s because when it comes to effective salesmanship, “aggressive” is not so much away to relate interpersonally as it is a way to view goal setting.

“An aggressive employee is one who is ‘militant and diligent’ about hitting goals,” says Kaiser. “Aggressive salespeople are comfortable with the energy and activity required to get the job done, and they’re willing to ‘out hustle’ the competition. They always have their foot on the gas and wake up wondering, ‘Where is my next sale coming from?’ They understand that a good salesperson needs more than one sale.”

Motivation matters

When Kaiser trains sales folks, he focuses on the “personal why” popularized by Simon Sinek.

Sinek says, “People don’t buy what you do; they buy why you do it.” For Kaiser, this means each of us has a different story to tell. Before speaking one word to a prospective client, then, a good salesperson will know the answers to these questions—why am I doing this and what can I bring to the client that will distinguish me from another salesperson?

Sales is about driving to the “no.” 

Too often, Kaiser says, salespeople fail because they don’t ask for the business, which keeps them going back and forth with the prospect instead of being able to hear and act on a “no.” A real no means it’s time to move on.

That said, a good salesperson can tell when “no” is more of what Kaiser calls a “smokescreen,” or a refusal based on the prospect’s lack of trust or interest in the seller, rather than the absence of a problem that needs solving.

“If I’m listening, if I’m asking clarifying questions, if I’m paying attention to body language, then I’ll know when no really means no,” Kaiser told me. Kaiser says that good salespeople need to take their cues from the prospective client rather than assuming interest.

Could we be talking about emotional intelligence here? Yes, indeed. And that brings me to …

Also Popular: How to Become a Successful Negotiator in 10 StepsEmotional intelligence is key.

Briefly, EI is the ability to perceive how your actions and words are affecting others accurately. It’s also the ability to understand and manage your own emotions. In Kaiser’s experience, EI is what differentiates the best salespeople from everyone else. Fortunately, experts agree that it's entirely possible to increase your EI quotient if that’s what you want. 

Better questions yield better answers.

Kaiser says that exceptional salespeople know how to ask good questions, understanding that “the quality of the answer is related to the quality of the question.” In fact, Kaiser trains the salespeople at Gallagher to ask good questions.

It’s okay to backpedal

Sometimes, despite a salesperson's best efforts, a conversation will start to go South. That’s when emotional intelligence really comes in handy. Kaiser says that the best salesperson can tell when a prospect is bored or not quite “getting” him (the seller). At times like these, Kaiser says it’s best to be honest, and regroup.

Statements like “It seems this isn’t a good time to talk, can we reschedule?” and “It seems like you have some reservations about my company’s ability to solve your problem, can you help me understand why that might be the case?” can help to re-establish a connection with the customer.

Crystal Spraggins

Freelance Writer, Editor, and HR Consultant in Philly. You can find more of Crystal's work at:

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