What are everyone's thoughts on 'prewarning' your boss that you would like a wage discussion? Background - I work at a start up, I started 6 months ago as the sales and customer service manager, I am now the project and operations manager, I've yet to receive any increase. I am currently working for way below market range (15k) my research shows the average is between 37-45k per year. I would not ever ask for this much as I respect that I am at a start up. I adore my job, I am second in command to the CEO, who is a fantastic boss and I don't think I will ever leave because I know what a bad job is like and I know when my bread is buttered, but I would like to earn my worth. How would you go about this conversation and what price tag would you be looking at?