Nervous to ask your boss for a raise? Jenny Hoff shares advice for how to ask for what you’re really worth.

By Jenny Hoff

One of the best ways to get what you want is to ask for it. But it’s not as easy as it sounds. Asking for something opens up the possibility of rejection and discomfort. Many of us go to great lengths to avoid asking for anything, and while that can be a noble pursuit, more often than not, it results in leaving money on the table, money that could be enriching your life, bettering the lives of others and setting you up for retirement. Learning how to ask with finesse and confidence provides you a powerful tool to add to your skill set, and it’s a crucial element to successfully negotiating. Negotiation expert, speaker and author Linda Swindling suggests some strategies for mastering the art of asking so you can start taking control of what—and how much of it—you get in life.

1. SMART SMALL AND PRACTICE OFTEN. Asking can create adrenaline in the body, and it doesn’t really matter if it’s asking for something small or something much more significant; the effect on your body is the same. That’s why Swindling recommends starting small, so when you have a big ask, you’re physically and mentally prepared for the discomfort. In her book Ask Outrageously! The Secret to Getting What You Really Want, she recounts a survey that showed the No. 1 thing people were afraid to ask was whether they could cut in line. That’s a good place for you to start. The next time you’re at the grocery store, ask the person in front of you if you can check out first. She may say no, and Swindling says that’s the point. If you ask for things in low-risk scenarios, you’ll be more comfortable asking in a situation in which the outcome really matters. Garage sales also offer great opportunities to get practice. Stop by a sale and ask whether you can get a lower price on a toy or other small item. Practice as often as possible and soon, asking will become second nature.

2. DO YOUR RESEARCH. Now that you feel more comfortable asking or negotiating for smaller things, you’ll want to make sure you’re prepared for the big negotiations. Part of preparing is researching what is actually possible. For most job positions or deals, there is an upper limit people are willing to pay—even if they don’t tell you what that limit is. Your goal is to get as close to that upper limit as possible without suggesting an amount so out of the ballpark that the negotiation is halted before it can even begin. Searching an online resource like to determine an appropriate salary for your job or researching what your competition is charging when dealmaking can help guide you to the upper-limit neighborhood of what an employer or client is willing to pay.

3. RESPECT THE GATEKEEPER. If you’re applying for a job or trying to land a deal, it’s important to treat every person you encounter along the way with respect. Someone may seem like a less significant player in the company, but the gatekeepers can keep you from talking to the person who can make the decision. “The gatekeeper can’t say yes,” Swindling says, “but they can sure say no.”

4. NEGOTIATE FOR THE FUTURE, NOT THE PAST. If you’re looking to negotiate a higher salary at your current job, know the odds are in your favor. “A little more than half of people get a raise when they ask for it,” Swindling says. “And 8 percent get more than what they asked for.” However, it’s not just about saying you want or deserve more; you need to prove you’ll bring even greater value to the company or client going forward. You can discuss what you’ve accomplished thus far, but make sure you’re also prepared to talk about what you plan to accomplish in the future. The more concrete your plans are, the better. For instance, if your company has increased sales by a certain percentage, strategize how you plan to increase that percentage in the near future. If your job success isn’t as easy to quantify, you can still talk about the significance your strategy will have on the company’s brand, operations or whatever department you work with. But remember it’s about the future and not just what you’ve already accomplished.

5. ASK FOR THE GREATER GOOD. Many people, women especially, are better at asking on behalf of other people than for themselves. If that incentivizes you more, Swindling recommends mentally putting yourself in that position. When you’re asking for a raise or a better deal, tell yourself you are asking on behalf of your family or community. With more money, you’ll be able to give loved ones the things they need or donate more to a cause you believe in. As long as you are honest and have good intentions, you never need to fear asking for what you want. Your boss, potential employer or clients will likely appreciate the transparency. And if they don’t, it might save you from spending years in a dead-end job or with business partners that aren’t a good fit. People will better understand your worth if you tell them, and no one knows what you want better than you do, so don’t be afraid to ask for it!


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