This may be part of the issue...this type of individual is usually very good at organizing and manipulating people. The most important factor in their success is that people THINK they are doing the right things, and they are very adept at giving that impression. It is not so important that they actually DO the right things, as long as everyone thinks they did.

Placed into our world, they can have a hard transition...they cannot manipulate or bluff the laws of physics although they may try to fool you (and ATC and whoever else) into thinking they know what they are doing.

Also, those who were at the top rungs of the real-world ladder have difficulty accepting their natural newbie inadequacies in aviation. This makes it that much harder for them to approach flying with the proper attitude.

That fact that he is older doesn't help either, your capacity for learning to fly starts dropping off around age 30 and is very noticeable (for most people) by age 50. Multi-tasking is the biggest challenge, especially for those who did not grow up in the digital age.

First off maybe have a conversation with him to make it clear that any confusion, uncertainty, or lack of knowledge should be addressed with you and not glossed over. He needs to understand that asking questions and admitting weakness is not only encouraged but necessary for a flight student.

Also due to the multi-tasking challenge, definitely approach learning tasks one at a time. Only combine them when they are very solid. With a guy like this you will be doing most of the radios for a long time.

The guy should be made aware that his training is going to take more time and money than average...probably a lot more. It's also possible that he might not make it...there are certainly people who cannot learn to fly. As was mentioned you should also send him up with another CFI just to make sure that the problem is not you, or some communication barrier between you and the student.