Since humans don't naturally think abstractly, it must be teachable since some of us have learned it. A linear argument to abstract instruction. The ability to do it is going to depend on the ability and motivation of both the student and the teacher. When you have someone who is set in their ways, unwilling to change or see things a different way, you're going to have a very difficult time teaching them anything.
The student must be receptive to a new way of examining problems and structures. They also must have an open mind with respect to cleansing themselves of assumptions and impossibilities. Abstract and lateral thought are practiced exercises, so it will require patience and diligence from both the instructor and the student.
On the same note, the greater burden is placed on the teacher. You have to be able to express not only the abstract idea/result you're looking for during the instruction process but how to arrive at it. You need to be able to explain the techniques you use to arrive at different thought results, and you must also be able to explain why you use them and why they work. You have to be encouraging of the student to find their own processes for achieving similar results. You have to establish a timeline for instruction, examination and success. It's too easy to give someone a book, hand them a written test and say "make it so".
This kind of re-learning thought will require daily diligence and practice on various exercises of increasing difficulty. I would recommend finding a text book or similar learning material from your past (presumably an updated version) that helped you begin to think abstractly and begin to teach directly from it through your own experiences. Then let the student's questions guide where you go.
Most important of all, don't interrupt the student's OODA loop. You can't force the light bulb to come on, you can only wait patiently for it to appear, and after enough practice it will come on more frequently and more quickly.