As a tutor, how should I handle anxious/avoidant adult math student? I'm a private math tutor, and I have an adult student right now (age 28), who is enrolled in algebra II in a community college. He is both very bright and has a kind of inferiority complex about academics because his siblings were much more successful than him in school and employment. This is his third attempt to pass algebra II.

He seems to struggle with math not because he can't do it, but for two reasons: because that's where he feels most inferior to his siblings, and because he has a hard time concentrating (perhaps has ADD). 

The trouble is that when math gets hard for him, or when he's disappointed by a test result, he spends the sessions with me talking about anything but math, changing the topic when I try to bring it back to math. Or if I do manage to get in a couple minutes on math, he starts asking questions on peripheral topics that superficially seem like they are about math, but I think are really another way of avoiding the task at hand. 

I've tried different ways of bringing him back to math, starting with using my body language (I'll, say, start writing with my pencil), then verbally suggesting we come back to math, then gently pointing out the pattern so he sees that he has to make a choice, etc. 

One thing I don't do is criticize him. He's so vulnerable to shame, and so anxious (his voice trembles sometimes when we do math), that I have a feeling if I'm strict or demanding with him, that will be the end of all tutoring. He'll fire me or become even more intractable. 

I've also tried supporting him by pointing out his strengths, and I do it honestly and with integrity : I genuinely see strengths in him and I can point to specific examples, so he knows I'm not flattering him.

As of now, he spends about 50% of our lessons avoiding math entirely like this. There are always other periods in which he learns, and the situation is not completely stuck. 

I would like suggestions for how to handle this. Everything from how to more directly suggest or control our session activities, to how to support him in feeling less anxious and inferior so that he would more spontaneously choose himself to put in the effort.
Let me make a suggestion that may or may not target the real reason. I don't have a way to evaluate its relevance. 

I've almost never had to give up on a student, but it has happened. The reason wasn't them or me, but just time. I've had students in math who were really terrible at it and didn't really know why. Nothing seemed to work for them. 

But in exploring things, I learned that somewhere in their background some teacher (or several) just failed to do their job and let them slide by. In order to help them learn (I think it was) statistics, I would have had to take them back through elementary school math from the beginning. They had never learned to add or multiply properly.

Even worse, no one ever gave them any incentive to learn math, nor any insight into why it might be important. They never had any experience with figuring out how to translate a problem into symbolic form, much less equations. 

I had to give up, just because I didn't have the time to teach them ten or more years of things they'd missed. 

It is possible, I suppose, that someone has figured out how to short-circuit that process and bring a student up to speed relatively quickly, but at the time, I had no real idea how to do it. 

My action suggestion is to give your student a diagnostic test of some sort, even quite informal, to find out if they are just missing so many basics that the new material has no foundation on which to build. 

I'll note that in my personal case, I was neglected by one teacher and didn't learn my multiplication tables. I managed to overcome the problem and finally forced myself to learn them - just after I completed my doctorate in mathematics. Now, I can faithfully recite seven times eight = .........