My current boss is switching companies and has asked me to go with her. I really want to go, I love working for her, and wouldn't want to stay at my current company once she's gone, but I feel like I need to ask for some incentives and also a pay raise to make it worthwhile to switch. Also, I feel like this is a great opportunity to get a jump in pay and to get some additional benefits, like more vacation time, and maybe even to get a signing bonus. I feel like those are fair things to ask for, but I just have no idea how to go about it! I'm so bad about negotiating, every year at my review I just end up taking what they offer because they make it sound like they're doing me a favor, and then I end up regretting it! Any suggestions??? I would appreciate any advice you can give. I have been working for her for over 4 years and she is really high up in the company if that makes a difference. Also, I've been in my field for over 6 years, and have always gotten excellent reviews.
This is something I have a hard time with as well. It sounds as though you have every right -- and the great qualifications -- to ask for more if you make this switch. My suggestion is to sit down privately with your boss and ask her to outline what you'd be getting if you follow her -- the vacation time, the benefits, and of course the salary increase. Do some research on what people are making in your field at your level so you have some numbers to compare and use as evidence in your favor, if it turns out she's not offering you enough.
Scarlett's advice about doing some research is excellent, since it strikes me that you don't really know what you want. You aren't going into these reviews with an agenda or goals. So take pencil and paper and figure out what you want to earn, what health/retirement plans would be best for you, and the amount of vacation and bonuses you would like to have. You may not get all you desire, but you should be entitled to some.
And think about other benefits that improve your life, like working from home one or more days a week, getting better accounts or assignments, having a role in recruiting new hires, a key to the executive gym - whatever floats your boat. There are cultural and environmental factors that make a difference in how happy you are or aren't - and they aren't a matter of pay.
On the negative side, you are considering walking into a new company where you have very little understanding of the way they operate, and no history with them to show that you're worth what you're asking. Your current boss will have less authority to go to bat for you than she does now (and why hasn't she before?). They may be unable to even match what you're currently getting, so you need to deal with that before proceeding. Companies tend to assume you want them more than they want you. Also, as a new employee you may not be eligible for some benefits until a few months down the line. Often retirement contributions take three years to kick in.
To be honest, my first thought is to wonder why you aren't interested in your boss' job at your current company. Career-wise, that is clearly the best move. You have a history of loyalty there, so it makes sense to cash that in rather than jumping into an unknown.