If it's "learn to use a VM or lose your job", coupled with a good computer basics course, I'm pretty sure he/she will be properly motivated.
I work at a megacorp that recently switched the local branch to terminal servers + virtual machines, not one has had any difficulty with the retraining, and the previous megacorp I worked for had a 70 year old using a pretty complex environment.
My grandmother went from being afraid of clicking a button to being a decent internet user, using both IE and Firefox (since her hospital's website didn't work in IE).
There are two reasons why most places don't use this: they've been skimping on RAM or their IT people don't want to learn something new. Neither reflect well on their IT management.
It might be hard to believe, but there are plenty of people in the world whos job has nothing to do with being tech-savvy.
In this specific case the persons job is to manage HR process, not to keep their IT infrastructure up to date. The computer and browser are just tools.
The above comment still holds. If your job is to use the tool all day, every day, one would expect that you would learn how it works.
I see the same issues as well where I work in education. Teachers, whose job is literally all about learning, are terrified to learn about technology tools for their classroom.
I'm not saying they have to be tech-savvy, where did I say that? And keeping the IT-infrastructure up to date? What has that got to do with anything? Did you reply to the wrong comment?
If part of your work depends on using a computer (to manage HR or whatever), you can't be afraid of doing basic tasks like maximizing a window, turning it on, etc.
Just like a carpenter can't be afraid of picking up a hammer.
You would think, but there are plenty of barely competent tradesmen around. Why should it be any different here?
There use to be a phrase referring to wood workers [edit, my mistake - boat caulkers], 'His mallet rings.' Meant as a complement. When you've got the skill to do it, the beats of your mallet create a particular pattern of sound. It's a different mindset to just picking up a hammer ... or a nail gun as the case may be ... and smashing something in. It's, pride in your effectiveness, a dedication to get better at a task.
It's pretty rare to find someone these days whose hammer rings.
This is what virtual machines are for...