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How to negotiate anything–from people who have done it

From asking for a raise to getting to a flexible work schedule or a sabbatical, we got advice from people who have successfully gotten what they asked for.

How to negotiate anything–from people who have done it
[Photo: Yagi Studio/iStock]

Part of business–no matter what type you’re in–is bargaining and asking for what you want, deserve, and need. From going after opportunities to making a case for a raise–or requesting the ability to work from Bali–in a fierce, competitive landscape, standing up for yourself is an often undermined soft skill. If there’s a part of your current gig that you want to change, consider these negotiation tips from people who have been there, won that:

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How to negotiate a job that doesn’t yet exist

It is always a bummer to find a company that captivates you with its mission but isn’t hiring. Instead of turning your attention to other pursuits and hoping an opening will will come up, why not pitch yourself? That’s exactly what Daniel Clark did when he discovered Brain.fm. The company didn’t have a budget for a developer, but he was convinced of the company’s potential, so he bargained to prove to them why his skills were needed. And the kicker? He did it for free: “I asked myself what was the ‘win-win’ I could find–what could I give up to eventually get what I want? I came to the conclusion the best way to do it was to give up my salary, and I did just that. I worked the first month for free and knew that if I showed what I could do they would keep me on, worst case, I lose a month salary,” he explained. Considering he’s now the CEO of the company, the risk was worth the wager.


Related: How To Pitch A Role That Doesn’t Exist (Yet)


Understandably not everyone can quit their current gig and lose out on a paycheck, but Clark says there is still a way to state your case and prove it. The first–and most important step–is to come prepared and open-minded. When you’re vying for a job opening that isn’t technically available, he says the worst case scenario is a “no”–so prove to them why you’re a “yes.” Negotiation simply is a process aimed at reaching an agreement between two parties. Usually it has to be successful for both people, and can’t be tipped in anyone’s favor.

How to negotiate remote work

As the freelancing population continues to increase, the requirement of an office space decreases. More solopreneurs are taking their gigs around the world, where only strong Wi-Fi is required to meet deadlines and maintain cash flow. Even so, it takes a shift in thinking for most managers. So when the director of administration and marketing at the Player Progression Academy (PPA), Annie Gavett, was offered the opportunity to globe-trot for a year, she had to figure out a way to make it work. Her former employer declined her request, but PPA was open, since Gavett was honest from the get-go about about her needs. After explaining the ins and outs of the program, sending them a proposal, a few phone calls and in-person interview, they agreed to let her work from anywhere. Though her contract initially featured a lower salary, after four months of hard work, she asked for–and received–a raise. These days, she has two employees who report to her, too.

The key to her success? Gavett says it’s all about self-advocating. “Stand up for yourself. Verbalize your wants and needs. But also have the facts to support why you’re asking for X, Y, and Z. Ask for more than you want and need, and be willing to negotiate down from a higher base,” she adds.

How to negotiate a leave of absence

You’ve heard of folks who take sabbaticals after the loss of a loved one, a tumultuous divorce, or another emotional or physically tasking experience. But what if you just want to take a break? After years of working as an attorney at a large law firm in Manhattan, Stacey Trimmer managed to negotiate a 10-month leave of absence to see the world. After expressing her need to have freedom, she spoke with a partner who–to her surprise–was fully supportive of her idea. “After our discussion, I walked immediately to the associate personnel director’s office to explain my request and was able to say I already had this partner’s backing,” she continued. “She asked for details on when I wanted to leave and return, and the next day I had confirmation that the firm had approved.”

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Related: How To Convince Your Boss To Let You Take A Sabbatical


If you’re bargaining for any period of “pause” from your job, Trimmer says it is important to demonstrate and prove your worth over time. That way, when you’re ready to ask for a short (or long) stint away from day-to-day responsibilities, they are willing to hold your position. “It wasn’t just luck that the firm allowed me to take the leave of absence. The reason was that I had produced excellent work for five years and built a lot of trust in several partners and senior associates that were willing to support me,” she added.

How to negotiate your rate

As a freelancer, you’re not only your own boss, but often your own accountant, client services executive, psychologist–and the list goes on. As new opportunities come across your inbox, you’re tasked with the sometimes grueling and tricky process of naming your rate. For Jonathan Rick, an entrepreneur and ghostwriter, earning what he is worth was less about negotiation and more about remaining steadfast. While considering taking on a digital-marketing project, he explained the value of the experience and expertise he would bring to the project, when they attempted to lower the rate. “I wasn’t defensive or curt, but I was respectfully firm this is the market rate for professional work,” he explained. “And as it turns out his reluctance wasn’t a negotiating ploy; he didn’t understand the scope of the services I was offering, and so after a few emails, I ended up getting my full fee.”

For those in similar situations, Rick suggests shying away from using ultimatum-like language, even if that’s basically what you’re presenting. “Couch your words in a way that communicates firmness but respect, and resist the temptation to get chatty. Succinctness here is a virtue; often it’s best just to bottom line it and say, ‘This is my rate,’ ” he says. End of story.

How to negotiate a deal with a potential partner

Regardless of whether you’re a two-person show or a full-service company with dozens of offices, effectively working with current and potential partnerships is essential to the growth of your company. And frankly, your career prospects. President of Enterprise Strategic Partnerships Glenda McNeal at American Express has worked on some of the credit card company’s largest deals, including Hilton, Marriott, PayPal, and others. To ensure they are receiving as much as they’re giving, they often use a creative approach to these negotiations, outlining in specific ways the value they’re bringing to the table–either through co-branded products, tech integration or access to customers. “By taking an enterprise view of a potential or existing partnership, we can develop more holistic and deeper relationships that derive mutual value for years to come,” she explains.

For smaller operations, McNeal recommends starting with the outcome and developing your strategy for execution from day one. “Engage your team early on to develop a game plan that is agile and takes into consideration compromise, concessions and trade-offs. Preparation and focus provide a shared vision for the team, clarity on the process and a clear roadmap to the end game,” she shared.

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How to negotiate with a difficult client

There are great people to work with–and not so easy-peasy. No matter your industry, you’re bound to come across personalities that don’t mesh with your own, or whose ethics aren’t up to the standard you require. For beauty expert Sara Drury, being taken seriously as a hair and makeup artist is an uphill battle, especially when agreed-to terms are broken. Once, a client agreed to pay a certain amount and then tried to pay less when an invoice was due. Instead of typing up the angry email she wanted to pen, she decided to pick up the phone and cut to the chase, stat. “I wanted her to hear my voice and know that I wasn’t angry, but I wasn’t going to let that stand,” she explained. “We discussed the situation and, while I knew she wasn’t happy about it, eventually she agreed to pay me the full amount.”

For those who are less comfortable with confrontation, this method can be intimidating, but Drury stresses the importances of leaning into it: “Regardless of the profession you are in, there will be times that you have to stand up for yourself,” she shares. “Believe it or not, you teach people how to treat you by the way you treat yourself. You can be kind while still standing your ground.”

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