Challenging your IT staff with growth-oriented assignments can be a win for everyone -- if you do it right.

A "stretch assignment" is one that requires a worker to take a leap beyond his comfort zone and, in the process, pick up new skills. Long used in business as a career development tool, stretch assignments are gaining popularity among corporate IT managers.

The idea is to help promising staffers round out their resumes by, for example, exposing them to a hot technology or placing them on a team of high-profile end users. In theory, both the organization and the employees win—the latter through enhanced career prospects, the former through the development of more capable workers.

In practice, though, stretch assignments are "fraught with peril," says Ron Jeffries, a veteran programmer and consultant based in Ann Arbor, Mich., who is also editor of XProgramming.com, an online resource for programmers. Jeffries adds that while the concept is sound, IT managers too often slap the label on impossible projects—only to blame the staffer when the assignment fails. "Telling a programmer, 'I bet you can't implement this compiler by Thursday,' is not a legitimate stretch goal," Jeffries says.

So what is? IT managers say stretch assignments, when handled properly, can be a valuable management tool. Their experience has taught them some valuable do's and don'ts.

The first key to a successful stretch assignment is to decide who can handle one. According to Murray Horwitz, CIO at Uline Shipping Supplies, likely candidates are "people who've done the same thing for a while and are getting bored."

Horwitz says Uline actively pursues stretch assignments for workers, with several notable successes. For example, the company's lead Web programmer began as a second-shift AS/400 operator. Managers marked him as a worker with talent and ambition, and he was challenged to learn HTML and Visual Basic.

A Gentle Push

For IT staffers, the payoff for a successful stretch is a richer resume, which could lead to higher-paying jobs. While it might seem that any employee would leap at such an opportunity, some workers need prodding, and some are simply not able or willing to tackle new, possibly uncomfortable assignments.

Horwitz recalls another stretch candidate who needed a gentle shove. "We had an extremely smart PC tech. He could fix any hardware problem," Horwitz says. But in order to better leverage the technician's time, managers wanted him to learn to write scripts for remote PC management tools such as PatchLink's Update.

"He didn't want to do it," Horwitz says. The tech's comfort zone was one-at-a-time PC fixes, and he balked at the stretch assignment. Horwitz persuaded him by pointing out the logical advantage of updating dozens of PCs at once. Implication: Uline needed more productivity in that area. "I told him he should do it for his career," Horwitz says. The employee saw the light and successfully learned the necessary script-writing skills.

Making It Work

Once you've chosen a likely stretch candidate, you need a legitimate stretch assignment—not, as is often the case, an impossible task with an optimistic label. "If I were coaching a [programmer or developer], I would try to sense a gap in their skill set—something they'd benefit from learning," Jeffries says. "Then I'd try to challenge them with a project that would sound interesting to them and be difficult but doable."

Stretchers should be provided tools and support to increase their chances of success. Otherwise, you're not helping them stretch, but rather practicing sink-or-swim management, an age-old but inglorious tradition in IT.

That support sometimes comes from peers. An IT manager who works in a division of General Electric Co. says that when he was offered a stretch assignment to spearhead the drive to comply with the Sarbanes-Oxley Act, he leaned on more than two dozen peers from other GE divisions. "We had all these other 'SOX' managers with more experience, and contacting them was encouraged," says the manager, who requested anonymity. One vehicle for this peer support was an internal portal called Support Central, where "you can have a community about anything," he adds.

Stretchers should also be assigned a mentor, says Diane Morello, an analyst at Gartner Inc. "The mentor should be outside the person's normal reporting structure," Morello says, because the mentor may need to discuss the stretcher's weaknesses—such as a lack of interpersonal skills—in a way that would be difficult for a direct manager to do.

Failure Is an Option

The GE manager says that in his division, every IT employee is expected to stretch; indeed, the company has long been known as a pioneer and leading practitioner of the stretch. "They call it a stretch goal," the manager says, "but you're expected to complete them." He says his stretch projects, while difficult, have been a vital way to learn new skills, make contacts outside his immediate group and boost his career prospects.

Nevertheless, some believe that GE's stretch-or-stagnate approach is a mistake. They argue that IT workers must understand that failing in a stretch project is not a career-breaker. "We've had failures," says Uline's Horwitz. When that happens, he says, "you've got to assess whether he failed because he's not capable, or because he didn't want to extend beyond his comfort zone." In Horwitz's experience, the latter is usually the reason, and it's important to let the worker know he's still a valued contributor.

That way, he retains elasticity—and may someday stretch again.

Ulfelder is a Computerworld contributing writer in Southboro, Mass. Contact him at sulfelder@charter.net.