I know I shouldn't add another answer, but I think my other answer went off on a tangent that didn't really address your question. I did not initially read it carefully enough to realize you were tutoring students, not teaching a class. I really don't think the label of "Teaching Critical Thinking Skills" is either relevant or pertinent--teaching is teaching, if we want to label "teaching" as "teaching critical thinking skills" then I think we are defining want teaching is--if you actually want to "teach" critical thinking, then this is a far more broad question which is not at all specific to mathematical instruction.
When tutoring students, you have a very good opportunity to give them deep and meaningful instruction (much more so than in a classroom setting). It's easy to just give them the solution, but obviously not very helpful (and unlikely to further the students learning). Having said that, the end goal must be to have the student leave with a solution, preferably one they arrive at as close to on their own as possible. Different students will come to you with different abilities and for some students, you may have to end up explaining the entire solution (but this should be a last resort).
Asking questions is vital. You need to nudge the student but not push them over a cliff (i.e. give them the entire solution). I will use your problem as an example:
Step 1: Ask the student whether or not they drew a picture. If no, then tell them to draw one, if yes, have them show you their picture.
Step 2: Analyze their picture. Is the picture correct? Perhaps they drew the cars going in the same direction (as opposed to driving towards each other). You want to avoid cuing the student; so do not automatically accept a correct picture (assume it's wrong no matter what they draw). Ask them to explain their picture. Does the picture agree with the setup of the question? Why did they draw car $A$ on the left and car $B$ on the right (or vice versa)? Is that correct? Does the problem specify this? Does it matter?
Step 3: Label the picture. What is given in the question? Can we introduce variables (unknowns) that we may or may not be able to solve for? Assuming the picture is now correct, hopefully the student will, at a minimum, label the initial distance between the cars as $88$ m. If this is all they label, then point out the distance between the starting point of one of the cars and the collision point. Ask them if they can find this distance. No? Then let's just label it was an unknown. If you do that for one car, hopefully they will see you can do that for both cars. If not, you will have to point that one out too.
Step 4: Point out relationships we can deduce from the picture. Is there anything we can say about the two distances? Do we know anything about them? If they are baffled, ask does the initial distance of $88$ m change? They may say yes, it changes as the cars get closer together. If they go this route, then let them continue. Explain that they now need a second picture with the cars closer together. Do we have more or less information in this second picture? Do we know how far apart cars are now? Can we figure it out? How much time as elapsed from the first picture to the second?
Step 5: Start solving the problem. With any luck, you stopped around the 2nd or 3rd step and the student did the rest, but you may still have to go this far. If the student is still confused, you will need to start asking about time. OK, we have the two distances labeled, how long did this take? Can we come up with a relationship between the distance and time? If that doesn't work, you may have to ask what if I told you that car A traveled its distance in 2 seconds? Could you find the distance then? If car A traveled its distance in 2 seconds, then how long should it take car B to travel its distance? Hopefully the student will answer 2 seconds. So what can we say about the times it takes car A to travel its distance and the time it takes car B to travel its distance?
If the student is still baffled, you may have to just tell them the two times must be the same. Now ask, what if the time was 2 seconds? What would the two distances be? Is that correct? How do you know it's not correct? Hopefully the student will realize that the two distances (using $t = 2$ seconds) do not add up to the full $88$ meters or they add up to more (and hopefully $t = 2$ seconds is not coincidentally the correct time--if so choose a time you know won't be correct). Can we find the correct time?
If they are still unsure, ask them again, how you knew $t = 2$ seconds was incorrect. Have them write out the equations without evaluating (i.e. $d_A = \frac{1}{2}A_a(2)^2$ and $d_B = \frac{1}{2}B_a(2)^2$). Ask why these two distances are incorrect (hopefully they already answered and thus have the answer ready). Because they do not add up to the full distance. So if $2$ seconds was the correct time, what equation would you expect to be true. If they are unsure, tell them to write it out in full, you may have to simply tell them to write down $\frac{1}{2}A_a(2)^2 + \frac{1}{2}B_a(2)^2$. Ask them what this equation should equal. They now should essentially have the equation. Can you find the time now? If they are still baffled, ask them what do we do when we have an unknown? We create a variable for it. At this point, if they are still confused, you may have to flat out tell them to substitute $t$ where they placed $2$ (remind them that $2$ was the time we guessed).
Now you have two problems: 1) we need to solve for time, so you are now no longer a physics tutor, but an Algebra I tutor and 2) you need to ask them, after all of this work, what was the question asking for? Did it ask for the time? No? It asked for the distance car A traveled? If we know the time, can we find this value? Hopefully they realize they can, but if not, remind them that we have an expression for $d_A$ already, we just need to plug in our value of $t$ into it.
Conclusion
I know that this explanation was very specific to your example problem, but the strategy is essentially the same: 1) Draw a picture, 2) analyze the picture, 3) label the picture, 4) find relationships, and 5) solve the problem. The absolute hardest part is trying to avoid cuing the students' responses. For instance, don't ask: "does [insert kinematic equation] help us?" If you do have to resort to this, then you should go through them all and have the student explain why each is either useful or not applicable. Don't automatically accept correct answers and don't automatically reject incorrect answers. Let them continue with the wrong way until you hit a point where you can no longer solve, then help the student backtrack to find where the mistake is. Your goal as a tutor, should be to do as little as possible. The more time you spend with a particular student, the more you will learn what they need from you (duh).