The biggest thing I've learned when being in (loose) teacher or mentor relationships is NOT to push someone to do what I think makes the most sense or that I think strongly is the easiest way to go. Instead the best thing to truly help someone out is to encourage them to do what they WANT to do.

The reason is because even if there truly is a simpler way, it isn't always simpler for someone in their current position based on their current biases/experience/knowledge/etc. But what you WANT to do is a really powerful motivator and the most important thing is that you keep trying things and get better eventually.