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Four Reasons We’re Scared to Negotiate Salaries, Benefits and Flexible Schedules

Casandra Andrews  |  August 16, 2021

Afraid to ask for more money, time off or a hybrid work schedule? Our experts offer strategies for crushing fears, asserting yourself and asking for what you deserve.

For some, the idea of asking for more money (or more anything) at work makes our palms sweaty and our legs limp as a panicky-feeling settles deep inside our souls. Research shows that at least half of all workers NEVER ask for a raise because they are afraid of what might happen next. Career and negotiation experts say it’s time to face your fears.

“Generally speaking people are hesitant, particularly women, to ask for more or engage in negotiations because of fear – fear the offer or interest will be rescinded if we push,” says Carolyn Kleiman, Career Coach & Expert at ResumeBuilder.  “When preparing to negotiate, you need to be ready to be flexible and to have reasons for what you’re asking. Do research on similar jobs at similar companies, think about what you’re asking for and why. Asking for money is difficult, but if you are prepared and show your value it can be rewarding.” 

As in, yes, you can get a raise and a few more days off. And all you had to do was ask and give good reasons for the request. Here are more tips on why we fear negotiating for more and what we can do about it right now:

Fear of Seeming Greedy

Here’s a little mantra you should repeat to yourself as you prepare for your next job interview or when you get an offer of employment. This is so important you might want to write it on your bathroom mirror. The person hiring you expects you to negotiate. Stop and read that again, please. A negotiation is expected. The figure they start with is an opening offer. It’s almost never a final one. And unless you are going to work for a small business where the owner interviews you personally, it’s also not their money. You aren’t taking food off their table when you ask for $5,000 more and another week of vacation. You are showing confidence that you know your worth and aren’t afraid to ask for it. 

“Women in particular are hesitant to speak up and assert themselves,” Kleiman says, “but they should even more than men because that’s how to get what you want!”

Fear of the Unknown

Often in a negotiation we will be unsure of what the other person is thinking or what they will do or say. We can’t predict the outcome, of course, and so the uncertainty can be scary. “We naturally don’t like the unknown, and so we try to avoid it,” says Jeffrey Cochran, a partner with Shapiro Negotiations Institute. “Before heading into a negotiation, try to identify why you are fearful. This will help you better understand what part of the negotiation process makes you feel afraid so you can work on these insecurities to help gain confidence.”

Lack of Preparation (AKA The Underwear Dream)

Remember that dream where you are standing in nothing but your underwear in front of a crowded room and can’t remember your speech? Sometimes, our fears can creep up – even in our subconscious – because we aren’t prepared. This is likely the easiest situation to control  and one of the most common, Cochran says. We didn’t expect a negotiation to happen at that moment or we just simply didn’t prepare for it as much as we should have. This happens when we are caught off guard. It feels awful, so we fear it occurring again, even if we have some control over it. 

Once you have identified your fears, you can do your homework to find the necessary information and develop a plan to ensure your concerns don’t become a reality again.  That plan, says Cochran, is to create a written script of how you want your negotiation to go. Write down what you want to say, including how you will respond to someone’s expected objections or comments, and how you want to open and close the meeting. 

Then, show it to a friend who can give honest feedback, even play the role of devil’s advocate. Take some time away from the document, sleep on it, then take a fresh look, editing as needed. You can also ask a friend to role play the script with you, so you can practice saying the words out loud to get more comfortable. This can also help you mentally prepare so you can ask for what you need and negotiate with confidence.

Fear of Losing ( + Winning) 

Besides worrying you won’t get what you ask for, and you’ll be rejected, Cochran says, some people also suffer from the insecurity and fear of winning or of getting exactly what they ask for: “If I’m going in for $100,000 job, and if I go in and say ‘I’m worth $150,000’ I have to be able to deliver $50,000 more value… and now what do I do for that? What am I going to have to deliver?” Another concern for people who may play hardball in negotiations is that they will have to work for the person they pushed for as long as they stay in the job. It’s important not to burn bridges on the way into a new position. There is a way to be polite and firm instead of being a demanding jerk.     

Money Isn’t Everything: Have Options Ready to Discuss   

When you finally get up the nerve to negotiate only to have your boss or potential boss tell you the budget is tight, and they can’t afford to pay you more right now, it’s time to think beyond initial dollars, Kleiman says. Consider bonuses for making goals ahead of schedule, time off, a flexible schedule, waiving health coverage if you can be covered by a partner, or semi-annual review to reassess your compensation.  

“Twice in my own personal experience,” she says, “I’ve waived the health coverage the employer offered me and received a cash payout instead. My cousin recently negotiated and received a relocation stipend plus moving costs. You do not know unless you ask.” 

Cochran likes to tell clients that the person who comes to the table with the most options typically does better in the negotiation. “When you have more things to present,” he says, “you show the other person you have considered their needs as well and you don’t look unreasonable.” 


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