I'd ask him what his dream project would be, and then what he would dislike it's a good way of finding out strengths and weaknesses without asking directly.
I would ask him about aspects of his work, how he deals with tight deadlines, examples of his work
ask useful questions rather than typical interview questions, maybe use knowledge of the job to construct questions that would give you a clue as to how he would do the job.
ask him why he thinks he's particularly suited to the job he's applying for? You probably need to know his strengths more than his weaknesses. You could ask him to suggest possible improvements to your publication/website (of whatever the job is).
I'd ask him what his dream project would be, and then what he would dislike it's a good way of finding out strengths and weaknesses without asking directly.
I would be quite interested in how he would answer... "So why is it you are finding yourself in a position to look for a new job... what is it about your current job that you feel it is the right time to change"
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