Michelle Benjamin, owner of Benjamin Enterprises, an integrated facility support services company headquartered in Middletown, New York, was always a very hands-on entrepreneur and was involved in every aspect of her business, which began as a commercial cleaning service. But when a client asked her to take over maintenance of his factory's heating and ventilation mechanical work (something unfamiliar to Benjamin), she was at a crossroads: She could either turn down the new business or hire employees and let them handle the work. She opted for the latter and began delegating tasks to the 12 new employees she hired to tackle the project. They worked on-site, while Benjamin supervised. Rolling down her sleeves and switching to a managerial role was difficult at first, according to Benjamin, who says hiring the right people was the key to feeling comfortable about delegating responsibilities. "It was a matter of recognizing that [by] working alone, I couldn't realize my vision for the company," she says. Today, Benjamin heads up a company that provides mechanical maintenance, cafeteria management, security guard services, janitorial services, and construction flagging services for utility and large construction companies. While Benjamin says she's made peace with the fact that she's not as hands-on as she once was, many small business owners have not. Instead, they work on the "if you want a job done right, you have to do it yourself" philosophy or micromanage every aspect of their business. So how do you know when it's time to start delegating? According to Geri Stengel, co-founder of the New York-based Women's Leadership Exchange, if you're putting in 80 hours a week, chances are you could stand to hire another head. Profitability and cash flow are two other key signs to watch for. If your revenue stream can support one or more staff members, it's probably time to pass off tasks to someone else. A fatal mistake that entrepreneurs make when delegating, says Denise O'Berry, president of The Small Business Edge Corp., in Tampa, Florida, is handing off tasks, then looking over the employee's shoulder to make sure it's done right. "Small business owners have specific ideas about how they want things done, but that can also work against them," says O'Berry. "At some point, you must decide what is 'good enough,' or risk a very painful delegation experience." O'Berry says successful delegation comes when the "letting go" process is undertaken slowly, starting with routine activities like research, envelope stuffing, and photocopying. Be sure to communicate the results you're after, she adds, and not the procedure itself by focusing on the "what" and not the "how." Provide a scope and boundary for a draft report that should contain, for example, five key areas, but don't try to tell someone "how" to do it. Also, don't forget to identify the person's authority level and responsibilities, O'Berry adds, because delegating without authority (be it decision-making authority, or the authority to contact a client directly) is a waste of time. "The key is to give employees the capability to acquire the information or resources they need to accomplish the task without your help," she says. Although it's difficult for entrepreneurs to hand over the reins of certain operations after they've built a business and trust others to do the job, not doing so can result in health issues -- for the entrepreneur and the business.