In her first years as an entrepreneur, Merri Mai Williamson followed the Glengarry Glen Ross dictum: "Always be closing." A refugee from corporate HR, Williamson packed 90-hour workweeks with countless sales calls after starting Application Researchers, an employee background-check service in Chattanooga, Tennessee. She was great at it, too, landing her fish about half of the time.

Too bad she couldn't stand sales. "Just presenting my business plan to my friends for practice was painful to me," says Williamson, who manages a staff of 300 (most of them contractors) at her 12-year-old business. "It's not that I wasn't confident or that I thought I wasn't capable," she says. "Some people feel comfortable with sales. I'm not one of them."

Leadership and innovation are the glam aspects of entrepreneurship. But the job description of many founders also includes a whole lot of selling. Entrepreneurs must sell investors on their ideas, employees on their workplaces, and customers on their products, value, and reputation. Perpetual pitching is dandy for happy extroverts who salivate at the scent of each new lead. Others, though, rate the process somewhere between distasteful and ulcer inducing.

Part of that aversion is cultural. The term salesman has long been shorthand for "slick," "obnoxious," and "integrity-challenged." An analysis of movies and television shows from 1903 to 2005 found that "the salesperson character personifies some of society's most despised characteristics--greed, deception, distrust, and selfishness," according to Katherine B. Hartman, a marketing professor at the University of North Carolina at Wilmington. That's an unfair generalization, to be sure. But it's tough to shrug off a century's worth of stereotyping and view sales as a noble pursuit.

Aversion to sales is a type of social anxiety, explains Larina Kase, a Philadelphia psychologist who often counsels the sales phobic. "Almost everyone has normal amounts of social anxiety from time to time: speaking jitters when giving presentations, the worry they won't look their best when talking with key business partners, or feeling nervous about making cold calls," Kase says. "The anxiety may be uncomfortable, but it doesn't necessarily stop people from doing important things." One of the best ways to get over such anxiety, she suggests, is simply to sell more often. (Social anxiety should not be confused with social anxiety disorder, a condition that affects roughly 7 percent of the population and greatly interferes with a normal social and work life.)

Selling frequently may help people for whom sales aversion reflects a temporary anxiety. It will not help when the obstacle is something more fixed--specifically, the entrepreneur's personality. Introversion is rarely the problem; true shrinking violets rarely start and lead their own companies. But entrepreneurs are used to calling the shots, and selling transfers decision-making powers to someone else: the buyer. Also, good salespeople are good listeners. Some entrepreneurs don't like that role. They would much rather talk about their favorite subjects, such as themselves and their companies.

Selling also requires facing two universal undesirables: uncertainty and rejection. CEOs, arguably, are pretty comfortable with uncertainty. Still, "the nature of sales is that you're always doing something different, and you don't know what the outcome is going to be," says Lou Schachter, an executive at the Real Learning Co., a sales training company in Scottsdale, Arizona.

Furthermore, when it comes to rejection, entrepreneurs are especially vulnerable. They take those inevitable losses hard because the product or service in question is their own. "When you're selling something that's really important to you, that makes it feel more risky," says Kase. "When you're selling someone else's product, you can detach from it."

In coping with rejection, professional salespeople have another advantage over entrepreneurs besides emotional distance: seasoned support. Good sales managers motivate their teams and suggest explanations for rejection that teach a lesson. (For example: Spend more time making sure that the customer has the sales volume to support your services.) That helps salespeople isolate the problem and raises their confidence in future success. Entrepreneurs, by contrast, may have no source of bucking up, advice, or perspective. "When I was cut from the first round of a request for proposals, when I wasn't even given an opportunity to give an in-person presentation…it really cut me off at the knees," says Williamson of her early days. "And since I was the chief cook and bottle washer, I didn't have anyone else to cheer me up, to tell me we're great, or good, or even fine."

Fortunately, one needn't enjoy selling to be able to sell. "There's no reason to assume you'd be bad at sales, even if you hate, hate, hate it," says Kenneth Evans, a dean at the business school of the University of Oklahoma. And those entrepreneurs who aren't much good can become better. Kase says she has seen clients overcome their anxieties and become stellar salespeople.

Like leadership, salesmanship was long considered innate. Academics and others spent decades trying to isolate the traits that make the difference between a Ron Popeil and a Willy Loman. They came up empty. "There is no such thing as a natural born salesperson," says Evans, who is also the editor of the Journal of Personal Selling and Sales Management. Instead, studies from the 1990s associated strong sales performance with thorough preparation, extensive knowledge of customers, and other things that can be taught.

Of course, learning to sell and learning to like to sell are two different things. An aversion to selling may not affect the bottom line, but nothing sucks the joy from life like doing every day the thing one disdains. To some extent, that hatred can be overcome by cognitive therapy, says Bo Forbes, a psychologist and management consultant in Boston. In cognitive therapy, people identify negative thoughts--those they perceive as limiting their performance--and reframe them. So, for example, if the problem is fear that a sales call won't result in a sale, the entrepreneur would learn to treat each individual call as an interesting exercise and ultimately to bolster his confidence for the next round. He would try to see any individual rejection as part of the routine: a discrete, inevitable setback that can improve the chances of ultimate triumph.

You don't need professional assistance to try this technique. Beth Zimmerman is one entrepreneur who did it on her own. As principal of Cerebellas, a Long Beach, New York, strategic planning consultancy that has worked with companies such as Motorola (NYSE:MOT) and Western Union (NYSE:WU), Zimmerman was less worried about rejection than put off by the reputation of sales. "It conjured up all kinds of negative associations for me, with ugly types of selling," she says.

So Zimmerman mentally reframed the process. She tells herself that she's "not pushing used cars, not selling things that are unseemly." In fact, she no longer considers what she does as sales at all. "Instead of selling, I think of it as listening to the challenges that my customers face and providing them with a way to help solve them," she says.

Another proponent of the rose-by-any-other-name-smells-sweeter approach is H. David Hennessey, professor of marketing at Babson College in Wellesley, Massachusetts. Hennessey, who teaches a sales skills class to M.B.A. students, counsels them to think of selling as helping people, "just like a doctor, a fireman, or an EMT."

Of course, the decision to tackle a boss's sales demons should be considered in light of the company's real needs. "Most entrepreneurs have the sense that they need to be independent and do it all on their own, and if the objective is to get over the sales fear, that's great," says Kase. "But if the objective is to expand the business, then it could make sense to consider hiring people to make the sales calls."

Unfortunately, not all entrepreneurs have the resources to hire salespeople--especially early in the life of their companies. Others shy away from mental reconditioning as a solution. For those who doubt they can change themselves, the challenge is to modify the sales process to make it more palatable.

Williamson, for example, attended seminars and workshops to address her anxiety, but they didn't help. So four years into her company's life she completely changed strategies. Why should she have to sell, Williamson mused, when she had a product that was compelling enough to sell itself? Out went the sweaty-palm cold calls and fruitless responses to RFPs. Instead, Williamson sent out 1,000 letters to prospective clients offering a free trial of her background-checking service. "It was a gamble," she says. "Quite a few of my mentors warned me that I would lose more than I'd gain."

The gamble paid off astonishingly well. Every single company that took Williamson up on that first offer signed on as a client. The free trial became Williamson's primary strategy; word of mouth grew and the need for cold calls dropped significantly. Still, she does have to sell occasionally. "Although I have gotten more comfortable over the years, I still get nervous when I have to stand up and sell to an individual," she says.

Though the natural born salesperson may not exist, hatred of sales may be bred in the bone.


How is sales evolving? Richard Hodge, co-author with Lou Schachter of The Mind of the Customer, assesses the most pivotal changes in the sales process in a series of podcasts at