The Application Process

What should i ask my recommenders to write in the LoR?

My boss isn't used to doing LoR for grad, so what should I have him write to help me the most?

Depends on your goals. He should be focusing on leadership qualities and things that make you a good leader (as opposed to a good worker) - things like leading teams & projects, good communication skills, people skills, etc. Depending on what your goals are, the focus of recs should probably be directed towards those goals. For example, one of my stated goals was working abroad around the world so my recommenders went into detail about how great I am with meeting new people & cultures and learning new languages.

In the end, it all has to tie in together - the last thing you want is for your recommender to write something incongruent with your goals and the rest of your application.

I'd recommend providing your recommender a list with bullet points of accomplishments to help him/her draft the LOR. One of the most important things of a good recommendation letter is good examples. So it doesn't suffice if your recommender just writes that you have strong analytical skills. The recommender needs to provide an example as proof (e.g. when you dealt with a complex business problem and were able to solve it). Good examples are key!