Some people take a while to warm up to a conversation. Some people are cagey. Some just don't know how to dance the phone interview minuet.
The conversation didn't follow the script in the interviewer's head. Maybe that's because he wasn't interested in the topics at the start of the interview, maybe it's because the interviewee wasn't comfortable until the interviewer expressed an interest at a less impersonal level.
Think about it this way, what really interested the interviewer was the website, and until that came up the topics were from a checklist. Many people can tell the difference between going through the motions and seeking information.
The icebreaker was the website and then the conversation ended. To keep things moving, it's often better to put the icebreaker in front of the convoy.
I used to be terrible at interviewing. I know when I see other people going through similar problems, and make every attempt I can to work around them. There is only so much you can do though, and you have to accept that you will miss out out on some good candidates.
The phone screens I performed were just a quick first round check to see if a candidate would be a valuable employee for us. They weren't supposed to be super in-depth or time consuming for either party. The whole thing is basically one big ice breaker. Hoping that I can hit on some topic that will cause a candidate to expose some skill, knowledge or enthusiasm that would move the company forward. There was very little structure. It was all about finding skill overlap, and then trying to decide if they would pass an in-person round of interviewing. If I hit on an ice-breaker at the end of a conversation, it means I had already exhausted all of the others.
Oh yeah, I know it's business and I'm not suggesting someone missed out on an ideal candidate. I was really just thinking it through and thinking about how people at the fringe see the world and how hard it is to cross that barrier.
Part of that is mediated by my experience when I first discovered his site. I was learning about Emacs when I found it, I'm pretty sure. Anyway, there was something I thought was pretty interesting - might or might not have been Emacs related - so I submitted it to HN. Showed up dead, immediately. Apparently his site was banned. It no longer is, of course.
But that's the way his relationship with the tech world was structured - banned by HN. Now maybe he had been spamming submissions or trolling, but it's possible his site was just blocked because it was Xah Lee: I mean there are people in this thread who are still judging him based on his behavior a decade or two ago.
A person who has spent a lifetime as an outsider is likely to have a different set of defense mechanisms - a different set of survival skills. What I was getting at is that the thing you both were interested in on a personal rather than a business level was his website. Unlike his 'professional career' it's something he can take full credit for and which is objectively worth being proud of - it's full of useful content.
My sense is that creating content is what he could be exceptionally productive. Maybe what's called for is an agent and an editor.
The conversation didn't follow the script in the interviewer's head. Maybe that's because he wasn't interested in the topics at the start of the interview, maybe it's because the interviewee wasn't comfortable until the interviewer expressed an interest at a less impersonal level.
Think about it this way, what really interested the interviewer was the website, and until that came up the topics were from a checklist. Many people can tell the difference between going through the motions and seeking information.
The icebreaker was the website and then the conversation ended. To keep things moving, it's often better to put the icebreaker in front of the convoy.