How to Negotiate With Your Jerk Boss: A Litigator’s Guide From the Trenches (Part I)

default author image09.20.2016

Every woman who strives for success, to attain the best for herself and her family if she has one, must negotiate at some point in her life. Negotiation is scary and unpleasant for many because it involves confrontation, and many people haven’t developed the skills yet to handle confrontation without stress. Negotiation with your boss is even worse: (A) you’re in the position of lesser power, and (B) you may feel like your ego is on the line.

Negotiating with your boss is hard for everyone, but especially for women. Women who correctly assess their own worth, and make demands accordingly, are harshly evaluated. It’s not our place; we should be nicer (quieter); we should demand less; we’re less important, less valuable, less deserving.

You know that is false, and so do I. But we also live in the real world and so, as savvy negotiators, we’re going to deftly incorporate navigating this bullshit to all the other stuff we have to do to achieve success. More money, more leave time, better benefits, more flexibility: it is there for you if you’ve done the preparation and you have the fortitude to demand it. To get the results you want, you need to engage your heart, your brain, your muscles, AND your steel ovaries.



Step one is the “heart” step. Whether you want more money, time off, or something else, don’t start with figuring out the details. Figure out why this is important to you. Do you feel undervalued and it’s negatively impacting your self-worth? Do you want and deserve certain things that cost money but you can’t afford them because you’re not getting fairly compensated for your hard work? Do you suspect there are less qualified people at your company making more than you, and the injustice makes you angry? Are you thinking ahead to your future career path and understanding that each increase you get has an upward increase on every increase you get for the rest of your life? Are you expecting a child and you know it is important to establish for yourself that your family comes first to you? Do you want to set a good example for your kids by standing up for yourself and valuing yourself so that your kids will do the same for themselves?

Whatever your reasons are, I suggest you start by exploring them. Once you can articulate why this negotiation is important to you, that importance will become more real. And ultimately, if you have prepared properly, you will succeed at any negotiation where your feelings are stronger than the other person’s.


Allot enough time to do your research outside the office. You simply cannot enter into a negotiation if you are not performing your best at work. Even if your employer doesn’t notice, YOU will know. You need to be ready to enter the conversation from an ass-kicking position of strength. This is the part where you engage your brain.

Here are the questions you need solid answers to. Solid answers.
1) What specifically are you demanding?
2) Why should they give it to you? Look at other companies in the market, other positions in your company, other comparably sized organizations in different markets, and other positions outside the company where you might conceivably be hired. Figure out which information helps your position. For information that doesn’t help your position, figure out how to distinguish your position.
3) What are you going to do if you don’t get what you want? Are you going to slink away and go back to your desk and cry? NO. YOU NEED A REAL PLAN FOR THIS. Think it through. Research other positions. Can you afford to take time off? Do you have a business idea of your own? Obviously, being able to walk away altogether puts you in the strongest position, but that’s not everyone’s reality.
4) Why are you worth it? What makes your performance awesome? Why does it benefit them to keep you in the position? Why is your proposal the best option for them? Remember that this is not about your worth as a human being. This is about your performance at work.

If you don’t actually believe you are worth it …. Then why not? Why aren’t you doing better? Go back to step one, figure out why you want more for yourself, do better, and come back in six months.