Be sure to things you think (lies, whatever, etc) are presented as maybes, possible, very possibles and things you know for sure are presented as facts. What are his feelings about the company? Can he look for another job while still there? Are there more opportunities while still employed. He sounds like a good employee but the company does not sound like a good place to invest too much time. I am 53 (age and wisdom?) and have worked at cruddy places and then good places, and oh what a difference. The other person doesn't sound like a very good or reliable friend. I once made a decision as I grew older (and wiser 8-) to lose toxic people from my life. Easy to say, harder to do.