5 'What If' Questions That Are Holding Your Negotiation Back


Negotiating can be intimidating, especially if you’ve never been taught how to do it. It’s not something we learn in school. Even folks with MBAs and law degrees have shared with me that they learned how to negotiate for their company or client, but they never learned how to translate those skills to benefit their own careers. 

In my experience, many people will look for an excuse to wiggle out of negotiating, even if they know they should. The uncertainty they feel can be crippling. 

In the last few years, I’ve taught workshops and coached well over a thousand people in negotiation, most of them women. Here are some of the questions I hear over and over again, and my guidance on how to move forward.

What if the company I work for isn’t doing well financially? Should I still ask for a raise?

I would ask a few follow up questions: can you provide rock solid evidence that you deserve a raise based on your recent performance? You’ll need to justify your request, so be ready to show how you’ve earned it.

How big is the company you work for? Large companies can often still hand out raises and bonuses even if their stock is down or they’ve had a rough quarter. A brand new start-up might not be in the same position.

Finally, is anyone else getting a raise? Ask around. If no one else has received one, you’ll need to be able to articulate why you deserve it given the current climate.

What if I work for a non-profit?

The culture at non-profits can discourage asking for more. You knew going in that you were serving a mission and that wasn’t necessarily going to come with a big paycheck. Still, that doesn’t mean your expertise isn’t valuable.

Let’s say you work at a small organization with limited budgets. Over time, you realize that you can’t save enough on your current salary, but you’re reluctant to ask for a raise. Eventually you decide to change jobs and go work somewhere bigger that pays more. You’d be taking all your expertise and institutional knowledge out the door with you. If there’s no one in your role to execute the mission, the mission ultimately suffers.

What if my clients push back against my rate?

 First, you need to be confident in the rate you’ve set. You need to know with certainty that you deliver value to your clients and that you’re worth it. Benchmarking others in your industry is a great place to start, but nothing can substitute for your own inner sense of peace with what you charge. 

If you find over time that your clients are constantly pushing back against your rate, revisit both your rate — and your target clients.

What if I find out that I’m making more than my colleagues?

Good for you! What’s the problem? 

Kidding aside, you can only control your own actions, not those of your colleagues. Maybe they didn’t come in with the same level of experience as you, or they don’t perform as well. Or they don’t ask, and you do. If you’re a high performer and your manager agrees to a raise, you’re in a good position. 

What if I’m switching industries? Is my old salary relevant?

No. You want to be paid for the job you’re about to do, not the job you did before. Soon, employers in New York City won’t be allowed to ask you for your salary history. This is already true for employers in Massachusetts. If you live somewhere without this protection, you can reframe the conversation by telling a short story about your background. For example, “I studied economics in college and went on to work in finance for the first five years of my career. Then I decided I wanted a fresh start. I invested in a two-month coding bootcamp, and now I’m excited to transition into a career in tech.” 

What ‘what if’ questions do you have about asking for more? Leave a comment below and let me know.

This post originally appeared in Women@Forbes, where Alexandra Dickinson is a contributor. She writes about how to use a negotiation mindset to achieve your goals.


Alexandra Dickinson

Alexandra Dickinson is the CEO and founder of Ask For It, a boutique consulting company working to close the gender wage gap by effecting change at both the institutional and individual level. We work with companies, schools, organizations and individuals through a combination of trainings, workshops and consulting. Our goal is for women and men to be paid based on their talents and skills, regardless of gender, and for our company to have been an important part of that change.