@DavidK You can be rough, if you warn, and set it up as a game. You'r the "devils advocate". He must see it's in his interest, and agree. I once mentored two persons planing to open a business. One a good friend, the other unknown to me. They explained their business, I started to explain what I think. When we somewhat knew each other, I explained that I now want to pose critical questions in a direct, rough way. Ok, I was very rough. It was effective, tiring, and it worked. Later I found out that the unknown was very hurt by roughness personally - even she had no problem. And thanked. — Volker Siegel 1 min ago