While it’s certainly possible to teach people how to sell, it’s also possible to learn how to make sales from those who do it every day and do it successfully. Although they are so busy practicing their profession they’ve probably not thought of themselves as teachers, yet, they are the true experts and it’s their real world experiences as practitioners of the art of making sales that makes them so valuable.

Here are four salespeople whose stories clarify what selling is all about, and make it easy to see why they are successful.

Seeing Through the Eyes of the Customer

Preston Diamond is managing director of the Asheville, North Carolina-based Institute of WorkComp Professionals that trains and certifies insurance professionals.

He began his insurance career as a student at Cal Berkley in the 1950s when he started selling life insurance. Later, when he had his own agency, he prospected an auto dealer. The dealer was known for his TV ads, which closed with the dealer standing on his head saying, “I’ll stand on my head to make you a deal.” After several meetings with the dealer regarding his insurance, Diamond showed up to get the order.

“Where’s the proposal?” asked the dealer, noting that Diamond was empty-handed. “You’ve seen what your current agent proposes and you’ve seen mine,” Diamond said. And with that he walked over to an office wall and did his best to stand on his head, saying, “I’m standing on my head to get your business.”

A little dramatic? Perhaps. But he got the order. “That taught me to always see through the customer’s eyes if I wanted to close a sale.”

Another one of Pres Diamond’s prospects drove the point home. Diamond had two meetings with the owner of a successful surplus store operation and expected to walk away with his insurance account at the third meeting, but the retailer came up with several rather lame excuses. Even so, the meeting ended with Diamond getting an invitation to try again the next year.

It wasn’t until three years later that he landed the account and asked why he didn’t get it before. “I don’t trust people with facial hair,” the man stated. It took that long to earn the owner’s trust.

Not only is “beauty in the mind of the beholder,” so are sales.

Persistence Pays Off

Richard B. Lockwood, III, is a marketing and sales pro who welcomes challenges, even when the odds are stacked against him.

He took a position with a new company that was unknown to Lockwood’s prospects. In fact, they were using tried and tested services that he was asking them to replace from his limited menu.

If that wasn’t a high enough hurdle, the prospects were ultra-conservative and remarkably slow to accept change. And well they should be. They were New England community bankers and that was part of their DNA.

Over the next decade, Lockwood distinguished himself by bringing on board more than 100 community banks in Massachusetts, Rhode Island and New Hampshire. His work involved bringing on community banks as clients of Bankers’ Bank Northeast, a newly chartered wholesale financial institution providing correspondent banking services to community banks throughout New England and New York.

But that remarkable track record was just a first step for Lockwood. The hard work was marketing, preparing and presenting proposals for products and services for these banks. Even after focusing on the benefits of a particular service, success came painfully slowly. It took, on average, 21.5 months to go from the first contact to getting the final commitment for each service proposal.

Given such a sales environment, the magnitude of Richard Lockwood’s accomplishment is apparent. “Even though I knew almost all the bankers before I started with Bankers’ Bank Northeast, it was an uphill climb,” he reports. “Most had been working with well-established correspondent banks for decades.”

In such a situation, less persistent salespeople would have bailed out, but Lockwood made it work. Although he was a known quantity, the bankers were prudent and risk averse, which didn’t make it easy to close sales.

Unlike so many in sales, Lockwood is a detail person. He kept copious notes of each meeting and then sent follow-up letters, e-mails and other information, as well as a schedule of future meetings.

Ironically, the bankers rarely said no to him; but they were very slow to say yes. Because he understood them, he was persistent, and it was this quality that gained the advantage and won the day. Over a period 10 years, he accounted for a more than 50 percent of the bank’s sales. Today, he is an executive vice president of Bankers’ Bank Northeast, based in Glastonbury, Connecticut.

Be There When the Prospect is Ready to Buy

John M. Greene, president of ETS International, a ground transportation company serving Boston and Providence, is the quintessential entrepreneur and the consummate salesperson. He thinks, lives and breathes sales. Over the years, Greene has built, merged and sold more than a handful of companies.

He established CTS International in Boston and then sold it to Carey Limousine, where he became a vice president, and applied his sales magic more broadly. But working for someone else did not provide sufficient motivation for getting up in the morning. It wasn’t long before he and his brother, Peter, scraped a few coins together and started ETS International. Yes, Johnny Greene is gutsy. One car was all it took. He put on his black cap, picked up customers and drove them to Logan International. In between customer trips, he made calls and built a customer base.

And, as you might guess, he was just getting going when the recession hit. But that didn’t bother him. He knew the livery business so well, including its weak spots: no one cares as much as the owner of the business. He called on his old CTS customers and they remembered how he delivered for them. So, one-by-one they came over to ETS. Right through the recession, ETS showed month-over-month revenue growth.

His success becomes clear with what he calls his most memorable sale. “I tell it to every new employee,” he says, “because it’s what we’re all about.”

It happened in the early 1990s. He called on the travel manager of what was then the engineering division of GTE in Needham, Massachusetts, which later became part of Verizon. Potentially, it was a big account. Since engineers travel a lot, he wanted the business. A meeting was arranged and the travel manager welcomed his information. Nothing happened. He stayed in touch with her every six months like clockwork. In the third year of this “courtship,” she announced that they were ready to make a change. He had a proposal in her hand almost before they finished their telephone conversation. The next call from her wasn’t so good. “Management says that you’re too small and the deal’s off,” she reported.

Disappointed but undaunted, he kept contacting her every six months. By the sixth year, ETS International had grown to a fleet of 25 cars. Now he was big enough and she asked again for a contract. This time they decided to stay with the current provider.

On Valentine’s Day in year eight, Greene delivered a dozen roses to the travel manager and she handed him the contract. And this time it stuck.

It was $200,000 a year, a very big piece of business at that time.

The secret is out. Johnny Greene says, “If you really want the business, then you’d better be there when the customer is ready to buy.”

Find Out What the
Customer Wants

Edward A. Testa, the principal of Boston-based Champion Capital, an equipment leasing firm, understands that customers have their own ways of “evaluating” salespeople and he also knows how to use it to his advantage.

When he was invited to make an equipment leasing proposal for the dealers of a major manufacturer, he was told there would be three others making proposals, all national companies and all much larger than Champion Capital. He had only one question about the meeting. “Could we be last to make a presentation?” They agreed.

Prior to the meeting the coordinator asked about Testa’s A/V requirements. “I don’t need anything,” he replied. While each of his competitors brought along entourages of up to 12 people, it was just Testa and an associate who walked into the meeting. As an astute salesperson, he sensed that the other three companies had used their time to impress the committee why they should be selected, focusing on what they could offer rather than what the customer needed. Later, he found out that this is what occurred.

“Let me ask you a question,” were Testa’s opening words to the proposal evaluation group. “What do you need?” He reports that there was “stunned silence.” Not one of the first three competitors had asked that question.

“What followed was an exciting two-hour dialogue on what the company would like to see in a program,” he notes. “We answered a bunch of ‘can you do this?’ questions and evidently our answers made sense. They gave us the contract.”