How Do You Ask For A Raise? This Silicon Valley Veteran Tells All

Before Lean In was a global nonprofit organization, the name of Facebook COO Sheryl Sandberg's best-selling book, and a defining movement for women's empowerment in the workplace, it was just a seed of an idea.

Joanne Bradford, the COO at personal finance company SoFi, says she first heard Sandberg talking about the concept after one of her regular dinners. Bradford, who has held positions at Pinterest, Yahoo!, and Microsoft, is no stranger to working in the male-dominated tech industry. She knew she had to take part in Sandberg's initiative, so she volunteered along with other like-minded women who wanted to get the movement off the ground. You could say they succeeded — and then some.

Although Bradford is no longer affiliated with Lean In, she's carried the movement's principles with her from one Silicon Valley job to the next. "For so long, Lean In was about speaking up and getting a seat at the table, Bradford says. "For me, it's really evolved into not only leaning in, but to really standing up."

If there's one time at work when you've got to stand up, it's when you're asking for a raise — something that Bradford has had many experiences with on both sides of the table (as the one who's asking and the one being asked). This week, she's kicking off SoFi's Raise Week, an effort to educate and empower consumers with the tools they need to get the salary they deserve. Refinery29 sat down with Bradford to hear about her best and worst experiences asking for a raise — and to learn what works, and what falls flat.

Settle On The Salary First
Whether you're moving to a new role at your current company or starting a job elsewhere, deciding on compensation should come before anything else. "The sequencing is important, because once people are financially committed, then they're willing to be flexible on other issues," Bradford says.

Sometimes, this means taking a risk. The biggest raise that Bradford ever earned was when she was asked to move into a role that had recently been vacated. Although she wanted the position, she was told that the salary increase would come at a later point. This was unacceptable. "I knew that the job was a significant level increase at the company," Bradford says. "So I held fast and said, 'Look, unless I get that raise, I'll just keep my current job.' It was nerve-racking, but I did get the raise."

Timing Is Everything
Asking your boss for a raise is not something you should do spur-of-the-moment, or even within a day. It takes planning and is all about timing. "If you're delivering results, I think it's completely appropriate to ask for additional compensation," Bradford says. "If the business is not doing well, or you're not doing well in your specific area, you shouldn't do it."

Another time when you should not ask for a raise: When you get a new boss. Bradford says those requests are always a worst-case scenario. "It's because the person is trying to circumvent the new boss." Instead, let your new boss learn how valuable you are on their own; then, they'll want to give you a raise.

Don't Compare Yourself To Coworkers
No one person is the same, and even if you know how much one of your colleagues is making, you don't know all the circumstances around their contract and position. Trying to make a comparison and use it as a reason that you should get a raise can backfire.

"The times when I asked for a raise and didn't get it were when I based it solely on what I knew about other people in the organization," Bradford says. "I think that's always a poor strategy."

Instead, Bradford advises tying your reasoning to the work that you have done at the company and the impact your work has had.

Assess The Job Landscape
In the past, Bradford has regularly looked around at other opportunities and the salaries offered, regardless of how happy she was in her current role. "I don't want to waste anybody's time, but I think it's important to recommit to a company," she says. "Sometimes I found out that hey, look, I'm being paid really well [in my current role], and then I've been able to recommit to that company in a big way. Sometimes I've found out that I wasn't being paid that well." In the latter case, she could start preparing to ask for a raise.

Weigh Salary Versus Opportunity
Bradford advises against leaving a position just because you aren't given a raise. "I think the most important things to consider are: Is the company growing? And can it give you an opportunity to move forward?" she says.

If both of those factors are true, it might be worth sticking with a lower salary and understanding that you're putting yourself in a good position for future, higher-salaried positions. Bradford says that because start-ups don't pay as well as large, established companies, her salary from one role to the next has varied by as much as 50%.

"But the upside was way greater at some of those [start-up] companies, which is something that you have to weigh depending on where you are in your life and what kind of change you can afford to make," she says.

Know Your Value
Bradford says she would often be willing to give employees more money than they requested. But because they don't ask for it, she doesn't offer it. "I think that most people ask for a raise and then leave too much of the decision to the manager," Bradford says. "If you ask me for between $5,000 and $15,000, and I came back and gave you $5,000, that's one message. If I came back and gave you $15,000, that's an entirely different message."

The outcome of asking for a raise can give you a sense of how much you're valued at a company and how happy your boss is with your performance. But in the same way that you put together reasons why you should get a raise, you should also be able to explain how you got to the number that you're requesting.

Don't Be Afraid To Ask
If you prep for your conversation with your boss, there's nothing to be concerned about. "I really haven't turned down that many people who ask me for a raise," Bradford says. "If you're asking me for a raise and you have a very good plan, it probably means that the rest of your work is pretty good."

On the flip side, Bradford says that she has withheld raises from people until they ask for them.

So do your prep, find your range, and set up a meeting. That raise could just be waiting for you to ask for it.