Everyone knows the loaded question that women supposedly ask their husband's about a dress making them look fat. The idea is that whatever the man answers, he loses. If he says she does, she will be angry that he is saying she's fat and doesn't look good. If he says she doesn't, she'll say he's lying to make her feel better. The equivalent of that in Japan is the oft-made assertion, "my English is not good." Everyone of every level says this and it puts the native speaker in an awkward position position. If you say nothing or agree, you deny the obviously desired reassurance. If you disagree and say they speak (or at least communicate) well, there is denial that that is so.
I'm tired of feeling like I'm lying*, patronizing, or patting people on the back about their English abilities and I won't miss it.
*I never lie to people about their English ability and level. However, I will often say that people are capable of communicating despite their limits when their level is low. This isn't a lie, because it is often true. Most Japanese people speak English enough for basic communication, and a great many more can do better than that if they believe they can.