Yikes. Guy probably is doing black hat stuff. Not signing a contract and using a suspect tool for backlink building are red flags to me. The conversational style of asking leading questions is a very old, very common sales technique. Manipulative? Absolutely. Black hat? Not necessarily. Just means the guy has sales experience.
I’d be more concerned about your boss. I’ve worked for multiple people that acted exactly like that over the years. It never ended well. Asking you to do shit way outside your job description, refusing to listen to advice from qualified sources, complete assurance in their own opinions instead of throwing out ideas once they’ve been proven not to work. That’s a nightmare.