1) Encourage whoever you're teaching to stop you immediately if they don't feel like they understand something you're saying, even if it's a single word that's throwing them off, and especially if they're not rock-solid about a simple concept they "should already know". Modern school teaches people that "returning to the basics" is a waste of time; but as Feynman says, you should return to the basics often, as masters do. Pianists don't stop playing scales once they're famous. This means that if your student want to review what an "expression" is, or a what a "string" is, or what "returning" means, you've got to encourage them to do it. If a 10-minute explanation of RegEx turns into a 45-minute review of how the string variable type was invented, that will be more useful for the student in their pursuit of RegEx mastery than will a technically accurate but shallow regurgitation of your 10-minute spiel about what RegEx is. This is because they need to lay the mental framework of how they're going to think about RegEx; you are able to explain it in 10 minutes because you already have that built in your head, but they need to build those background pathways and connections themselves before analogies and summarizations make sense.
2) Try to figure out how you can make them experience the problem that led to the invention of RegEx. A student will never truly understand why a solution is valuable until they really, deeply understand the problem that the solution is solving. Note that I'm not saying that you need to teach the problem before the solution--not every student needs them in that order--just that they won't master the solution until they understand the problem.
3) In lieu of "testing" a student, have them take many breaks to re-explain what they've learned to you, even if you haven't reached a real conclusion about anything and are just checking that they understand a sentence you said. Many students, especially if they have a good teacher, will experience the sensation of comprehension even if it's not actually there. This is the "it makes sense when he says it, but when I try to explain it I can't find the words" phenomena. Taking frequent breaks to have them explain things back to you in their own words will reveal their conceptual weaknesses, and those are what you focus on.
4) Don't try to get it all done in a single session. Learning requires both forgetting and sleep. First, you should tell them to expect to forget, and that they will need to come back over and over again to topics that seem basic or simple; forgetting is part of the process of learning, like painting multiple layers on a wall. Second, they need to sleep in between sessions, which means that you can't teach everything in one day and you can't learn everything in one day, and multiple days may need to be spent reviewing the same material.
This all makes a lot more sense when you treat learning like sports. Learning <programming topic> is like learning a slice serve in tennis. You don't need to serve slice, especially if you can hit flat serves at 115 mph, but serving slice is an invaluable technique when you're playing someone who can't return slice serves at all--that's a near-guaranteed 3/6 games out of every set. But in order to learn it, you need to focus on your tennis fundamentals (stay loose, eye on the ball, toss correctly), practice the same basic movements over and over again, get lots of sleep, and understand why you're learning the skill in the first place.
