A Chief Of Staff's Career & Salary Journey In Education

Illustrated by Jessie Wong.

In our series Salary Stories, women with long-term career experience open up about the most intimate details of their jobs: compensation. It’s an honest look at how real people navigate the complicated world of negotiating, raises, promotions and job loss, with the hope it will give young people more insight into how to advocate for themselves — and maybe take a few risks along the way.

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Age: 34
Location: Chicago, IL
Current industry and job title: Chief of staff, education
Current salary: $146,000
Number of years employed since school or university: 12
Starting salary: $12,300/year

Biggest salary jump: $50,000 to $90,000 from an internal promotion. I disclosed to my boss that I was going to be departing from my organization after two years (I started at $40,000 and earned $50,000 in my second year). There was some leadership structural changes happening, and they built a position for me within that structure. I didn't ask for the salary bump, but I knew it was more than I would earn if I exited.

Biggest salary drop: I haven't experienced a salary drop. I have had a lot of internal promotions and role changes, as well as some positions that have been built for me as a result of my growth within an organization. I know that is both lucky and strategic: I don't think I would stay at an organization that dropped my salary internally, and when I have considered an organization shift, an anticipated drop in salary is something I take into consideration with a shift.

Biggest negotiation regret: Recently, I earned a $16,000 raise that I was not expecting. My job is shifting to remote and I was anticipating a lower salary, given that it will eventually result in a move to a less expensive geographical location. I was really grateful for the unexpected raise, but my close relationship with my supervisor meant I wore my surprise on my face. I wasn't in a position to negotiate more or differently, and while I don't regret not asking for more, per se, I do consider what levers would have been available to me if I had approached it differently or if I wasn't as close with my supervisor.

Best salary advice: The book Difficult Conversations: How To Discuss What Matters Most was a hugely helpful book for me when it comes to negotiation. Salary negotiations are difficult conversations, and this book does a really good job of understanding how to grow more comfortable in uncomfortable conversations. I think it's a particularly useful tool for people who identify as women who have been conditioned to be more deferential!

Another bit of advice: Stay true to yourself. Knowing your worth is obviously important, but the ways you approach salary conversations need to be true to your own values. I express myself best in writing, so I always ask for time during a negotiation so I can articulate my thoughts in a values-aligned way — usually in writing first, and then followed by a phone call or other face-to-face point of connection.