It/that

The second refers to some specific instance of 'not listening' earlier in the context.

You mean 'that' in the second example refers to some specific instance earlier in the context? Or the entire sentence refers to it?

That

If so, then 'That is not reasonable for him not to listen to what others say.' would be the same as 'His not listening (to his friends etc.) is not reasonable for him not to listen to what others say', which doesn't seem to make sense, or does it?

TakaIt is not reasonable for him not to listen to what others say.That is not reasonable for him not to listen to what others say.What kind of difference do you native speakers detect between the two above?

For some reason I can't even make sense of the second one, try as I might to contextualize it. Maybe if the ending was left off:

That is not reas

You don't think these below make any sense, Jim?

·That's not reasonable for the company not to have adapted to the changed workforce.
·That's not an answer to reduce the opportunities for the players.

TakaYou don't think these below make any sense, Jim?·That's not reasonable for the company not to have adapted to the changed workforce.·That's not an answer to reduce the opportunities for the players.

They make sense in that an English speaker can understand what is meant, but they don't make grammatical sense. I see two solutions for the first one. Either

Then aren't there some cases where you feel you have something in mind that you don't think is reasonable/an answer and you use 'that' as a 'pointer' which points to what you have in mind (I think in such cases, you point somewhere up in the air saying 'That's not reasonable/an answer...), and after saying 'That's not reasonable/an answer', you clarify what is not reasonable/an answer using infin

Takaafter saying 'That's not reasonable/an answer', you clarify what is not reasonable/an answer using infinitives?

You could do that. I just preferred the -ing form in the example you presented.

TakaI think in such cases, you point somewhere up in the air saying ...

Hmm. I've never seen anyone do that.

CJ

CalifJim I've never seen anyone do that.CJ

Even if you haven't seen anyone do it or you haven't done it physically, I bet you mentally point to something that exists within, unless it exists outside yourself, when you use 'that'.