As a rule of thumb, the more aligned incentives are, the better. When you're dealing with someone whose incentives are aligned with yours, you can usually trust that they'll do you good.
Imagine you are a guest in a TV game show. The host, a certain Mr. Monty Hall, shows you three large doors and tells you that behind one of the doors there is a car while behind the other two there are goats. You want to win the car. He asks you to choose a door. After you have made your choice, he opens another door, revealing a goat. He then asks you whether you want to stay with your initial choice, or switch to the remaining closed door. Would you switch or stay?
This is a fascinating paradox. For a good explanation of the solution, see montyhallproblem.com.
On the 14th of April 2019, the Jordan B. Peterson Podcast starred Akira the Don. It's a fascinating conversation that covers a range of topics.
I've found Akira the Don's music very helpful, especially his album The Path with Jocko Willink. (Willink is a man you don't want to let down.)