Re: Continuing education
I think that MOOCs can make it easier for IT pros, but that still requires the IT pro to have the initiative and self-discipline to complete the course. The other thing I've long recommended for IT pros is an online library subscription. There are many other resources also available.
Stretch projects are definitely a great way to develop critical thinking skills, but also just wargaming a problem around a conference table that directly relates to the workplace and job can help. "If this <server> you're responsible for administering demonstrates <these symptoms>... what's your approach." Of necessity, however, this process requires three things:  a facilitator,  a mentor, and  a committment from the employer to invest the worktime on the task.
This could also be done on an individual basis. Offer a staff member a "homework assignment" that involves developing and exercising critical thinking skills. For some staff members, it may require some preliminary classroom education on the type of physical and mental tools that can be used in the process. I'm continually amazed at the number of IT pros who can find a public forum to ask a Level 100 question, but apparently were not aware or (worse, I fear sometimes) simply not willing to start with the basic resources: Like product documentation or a search engine.
But even more so than just continuing education to keep up with new skills, a notable number of first-year IT pros barely have the skills necessary to perform their assigned job duties. If it's the intent of the employer to hire a green candidate, that's great! Everybody needs someplace to start, and I applaud those employers willing to take the risk. But taking the risk also means committing to the investment in developing that staff member.
I'm reminded of a recent quote, which unfortunately I've lost the source for so cannot attribute as I'd like: Manager A: "What happens if we train 'em and they leave?" Manager B: "Worse, what happens if we don't and they stay?"