6 Ways to Overcome Your Discomfort and Ask for What You Want

As an entrepreneur, business builder and corporate ladder climber, I’ve had to get comfortable asking for what I want. It’s rarely given. The tough part is, as humans, we are typically uncomfortable not only in asking for what we want, but also how we ask for what we want. If I had a dime for every time I have been called aggressive, crazy, intense (or worse), I would have a lot of dimes. But I think about my personal motto:

• Always ask for what you want. Always. You will hands down never get what you don’t ask for. This is especially true for women and people of minority backgrounds. There is much research that proves that we don’t negotiate enough. If we look at salaries alone, it’s imperative. In Linda Babcock’s book, Women Don’t Ask, she found that about 7% of female MBAs attempted to negotiate, compared to 57% of men from the same program.
• Assume you might get it. When you remove the fear from your ask, you are more thoughtful, you consider how to make it a win-win, and you become less emotional.

Let’s discuss how you earn your seat at the table.

Practice Your Pitch

Nothing beats practice. Start small. A perfect example is my most recent trip to Belize: Every time I checked into a hotel, bought an excursion or paid for just about anything, I asked for a discount. What happened? Every single hotel (four over two weeks) upgraded us and gave us anywhere from a 10% to a 30% discount.

Don’t Come in Committed to an Outcome

Come with options, not outcomes. Instead of saying X amount, consider flex work, vacation, and/or a virtual assistant. Get creative with your asks.

Explain Why You Deserve It

Never say, “I want more money.” This rubs me (and many people) the wrong way. When an employee comes to me with this language, I immediately calculate the percentage change they are asking for and say, “What are you doing to earn 35% more money?” Rarely do they have an answer. Often, they didn’t even realize they were asking for such a big percentage increase. Back up your asks with facts and numbers. Say, “I did X, Y and Z and my plan for the coming months is to accomplish this and that. I think the work I am doing is worth more than I am currently making. So, I wanted to talk to you about a pay raise.” Then, don’t say anything. Your manager may be about to let you know you’re going to get a raise higher than your ask.

Put Yourself in Your Boss’ (Or Counterparty’s) Shoes

What are their goals, and how can you align yours with theirs? If you’ve ever been asked for a raise by an employee, you’d know that there is only so much you can do. How can you put yourself on the other side of the table? When I first negotiated to get time off for an MBA and had my first company out of school pay for it, I started with my small ask first and I aligned our goals.

I said, “I’m committed to having a long career here and believe I need to better my skills in international business for us to really succeed, so I want to go back to school while working. If I can find a way to do that won’t interfere with getting my job done, and I promise to beat out my goals every single quarter or I’ll quit school, would you be open to it?” He said yes. Then I came back once I got in and said, “If I can get Georgetown to cover X percentage of the cost and beat sales goals by X, would you sponsor me for the rest of my schooling?” He said yes. I was planning on offering a longer contract with the firm as well but I held back. He said “yes” to all my asks.

Don’t Make the First Move

Making your “opponent” like you is worth its weight in gold. Smile, cajole, and appeal to their better instincts. My go-to line is, “You can’t blame a girl for asking, can you?”

If you are negotiating a salary or package with a new gig and the person asks you what you make currently, you don’t need to answer. You can say, “’Well, I’m flexible depending on how you structure compensation for the growth potential and the right company fit long term. Would you be willing to share the rough salary range you have in mind for this position?” If they push you, say, “This is really not something I give out broadly. Kind of like a woman never tells her age. Why don’t you tell me what your range is and I’ll let you know if that fits my range.”

Confidence is everything.

Play Hard to Get

The one who wants it less wins. So even if you want a new job, client or raise so badly you would sell out your mother, pretend you don’t. Say you have a job offer you’re dying to take, and are about to quit your current job anyway. Reframe your mindset. They must negotiate to get the best deal for their company and you must negotiate the best deal for you. You can say, “I’m really happy in my current role and growing immensely. I’m always open to the right opportunity at the right company, but I’m not actively looking.” Remember playing hard to get? In my experience, this increases your perceived value, and makes them want you more.

Remember the commandments and you just might always get what you want.