Many Hats: The Ins and Outs of Cross Training

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When your organization only has so many positions at the top, how do you keep your top performers? It’s a question many employers wrestle with, especially those running small and medium-sized businesses. By nature, top performers thrive on developing themselves, and if they can’t evolve their skills with you, logic dictates that eventually they’re going to seek opportunities elsewhere.

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Hence, one argument for cross training: If that model employee can’t climb any higher in their own department, perhaps they can develop new skills in another area, right under your own roof, thus remaining engaged with your company rather than heading for greener pastures. Another benefit of cross training employees—one that is equally important—is that it offers an organization flexibility and a safety net when the chief expert in a certain area is suddenly (or not so suddenly) unavailable. The more well rounded the team members are, the stronger the team is.

Everybody Should Do It

Chris Cansialosi, partner and founder of gothamCulture, a management consultancy focused on organizational culture, believes that companies should make cross training mandatory. Having served as a commissioned officer in the U.S. Army in combat operations in Iraq, Cancialosi’s viewpoint is this: If only one team member possesses the skills to do a job and suddenly they’re gone, you’re in deep trouble, whether you’re executing a military operation or trying to keep clients happy.

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Chris Cansialosi, gothamCulture

Cancialosi also points out that cross training is a great way to introduce various aspects of an industry to younger employees. “What I find in most organizations—especially in organizations with more millennial workforces—is that if you’re not doing this, you’re missing out on a huge opportunity to attract and retain talent because millennials want opportunities to continue to learn, to continue to be pushed,” he said. “And what better way than to use a resource that every organization has at their disposal—these other jobs, these other tasks—to help people understand an industry?”

Program Vs. an Informal Approach

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Brenda Murphy, Diversified

If you’re sold on the benefits of cross training, the question becomes: Do you make it a formalized program, or do you roll it out on an informal basis? Brenda Murphy, senior vice president of human resources at Diversified, an AV, IT, and media technology design and integration firm, prefers to see initiatives like this grow organically. “If you promote that you have a certain type of program or a training path for folks, then you really have to do it because you either hired people or promoted it within the organization that this will occur, and that takes a lot of ongoing management support,” she said. One headache an employer doesn’t want is a new hire inquiring about a cross-training program that, on a practical level, doesn’t really exist.

Murphy also believes that formalizing certain activities isn’t the best way to fulfill whatever goal they’re designed to achieve. She uses formalized mentoring programs, something she is not a fan of, as an example: “The people who want to be mentors are mentors. And to try to pair people up, personally I haven’t seen great success with that, so I don’t happen to be somebody who advocates that on a program level,” she said. What she does advocate, however, is when these efforts develop out of conversations: An employee expresses interest in learning a new skill from a more senior employee, for instance, and then another employee hears about it, and requests something similar, which gets the ball rolling, “and then all of a sudden at the end, you realized you’ve baked the cake that somebody might put a label of ‘mentor’ on.”

Don’t Make Promises

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Phyllis Hartman, SPHR

Another potential pitfall is that employees equate cross training with promotion and/or an increase in pay. Phyllis Hartman, SPHR, an HR consultant, urges employers to let those being cross trained know that this isn’t necessarily the case. “You need to make it very clear to the employees from the get-go that this is an opportunity; it may help them in the future, but there is absolutely no guarantee,” she said. While she agrees that cross training as an initiative should be flexible, she said that this is an area where making it a formal program for everyone has its advantages. “If you can have a program where everybody gets involved, [employees having that impression] is less likely to happen because everybody is learning a little bit about everybody else’s job anyway, and so it’s more about ‘We’re all in this together,’ rather than, ‘I’m picking you to learn new things,’ and that means, ‘Oh, I’m going to be the next boss.’”

Regardless of the errors a company may make in structuring (or not structuring) its cross-training efforts, Cancialosi emphasizes that the biggest mistake an organization can make is not cross training at all. “You can’t have one point of failure,” he said. “How on earth can you sleep at night knowing there’s one person who holds the key to the kingdom? [If that’s the case,] that’s something that needs to be corrected immediately.”

Carolyn Heinze ( is a freelance writer/editor.

“I Would Prefer Not To”

While providing opportunities to learn and grow is a common strategy applied to employee retention, there are those individuals who prefer to stay right where they are rather than receiving cross training on a different skillset.

“Some people want nothing to do with this,” said Brenda Murphy, senior vice president of human resources at Diversified. “Then a company needs to decide: what’s the balance of folks who are not going to express interest in doing something else—learning more, or learning a different side of the business—whatever the case may be? They need to understand what their threshold is for how many people like that can be in the organization. Because you do need some people who are just good at what they do today.”

HR consultant Phyllis Hartman said that in her experience these cases are rare, “particularly if you have a good workplace environment and employees trust their management and want to learn more.” That said, there are still those who balk at being cross trained, and this is where employers must decide how important an issue that is. “If somebody refuses to learn a new skill that’s going to be a regular part of their job, that could be insubordination, and that may mean you don’t want to keep that person,” she said. “If it’s cross training to enhance everybody, then how important is that? You have to decide: Is it voluntary or mandatory?”


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It is critical to have a plan for first training your team, and second, knowledge retention to ensure that you do not waste your training investment.

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