You could try suggesting to him that he sits down with pen and paper and writes down all the options he can think of. Then to write down all the really way out options that seem daft, but write them down anyway.
Then think hard and imagine having made each option in turn, and what it would be like. Visualise each situation. Write down how each one feels.
Then eliminate most, right down to a small number of optiuons that seem the best.
Repeat the process.
That's a method I evolved many years ago if I was in a dilemma or faced with unpalatable choices...and if they're all truly unpalatable sometimes there's another choice out there that would be better. So creative thinking comes into it.
Another method, or to use towards the end of the process, is to tell yourself this is really, really urgent, and give a time limit (like 5 minutes) and stick to it.
PS:
Another method, totally different, is to think about it very hard, maybe all day, and then decide to sleep on it. I find I often wake up in the morning knowing exactly what to do. Good old subconscious mind! (Or is that the unconscious mind? I never know!)
Or he could ask Jehovah. Only joking!