When it comes to money and your career, plain old negotiating will get you far—but that doesn't mean it's easy. Cara Friedman, now the director of community at ClassPass, was one of Likeable Media's first employees. Over the years, I've watched Cara become the consummate career woman, and I wanted to check in and see what she'd learned during that time. It turns out, she'd learned a whole lot.

Cara told me the number one thing that she's learned to do when talking about money with people in positions of power? "Own the awkward."

Cara takes her awkward feelings around conversations about money and uses them to her advantage. Take the topic of salary negotiations. "I remember that someone once told me that when you're on a phone interview, ask the salary of the job, and put yourself on mute." Cara tried it on the first interview she had after hearing that advice, and it worked. She might ordinarily have interrupted, making excuses for why she wanted more, or commenting. Instead, she let the hiring manager do all the talking. And when she went for her next interview, which was in person, she did the same exact thing, except this time, she just hit the mental mute button versus the physical one on the phone. It worked like a charm.

"There's power in making the other person have to deal with the awkward part of the conversation," Cara says. "That's how I learned: watching how others reacted when I put it on them."

Turns out, Cara took that knowledge, and used it to her advantage in negotiating raises and promotions. She found that the people who communicated best around money were direct and clear, and metrics oriented. So Cara decided to practice that type of communication with her boss, every single week. "I started by asking what specifically it takes to grow into a new role, and earn more money here. I hit my mental mute button and let her talk. Every week, I would follow up with a simple 'How am I doing? Am I working towards these goals?' question." Cara says that while at first this might feel awkward, eventually you get used to it and your boss does, too. And, best of all, it eliminates any surprises.

Finally, Cara feels it's very important to know your worth. For Cara, that means lots of research. She doesn't, however, look at salary bands of positions at her own level. She looks at positions one level up. "That's what I aspire to be, so why not?" says Cara. "I want to know what I'm working towards, and I want to stretch myself to get there."

Judging from Cara's career path, it looks like her strategy is working. Promoted multiple times, she currently heads up social media for all of ClassPass, a fitness startup that has disrupted the fitness industry.

Sum It Up by Pat Summitt

Excerpted from WORK IT: Secrets for Success From the Boldest Women in Business by Carrie Kerpen. © 2017 by Carrie Kerpen. Published by TarcherPerigee, an imprint of Penguin Random House LLC.


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