Start with a sheet of paper. Write down the top 3 things that are most important for you to get from the trucking company that you choose.
For example.... Is it....
Being able to come home every weekend
Getting the best family insurance coverage
Being able to transition to owner operator
Seeing the country
Getting the most pay as company driver so you can stack
ETC
After you have the top 3 things that are important to you. Now you rate each company that you talk to based on which provides the most of what you want from the trucking company.