Before I transitioned into personal finance as a Financial Planning Resident here at Tessara Wealth, I held a unique role that gave me rare insight into how salaries and raises are decided. I worked for a small, local staffing firm whose biggest client was Google. Google provided a list of roles they needed us to fill with our contractors, and we chose who to interview, select, and hire. Many of those contractors spent their days onsite at Google - riding the shuttle, eating the free food, and reporting to a Googler—but ultimately they worked for us. They were paid by us. We were the company that placed them at the client site. That meant that if they wanted a raise, they had to talk to me, the sales representative who negotiated the contracts with Google.

This setup made my role unusual. When a contractor asked for a raise, their first step was to talk to me. I told them I’d be happy to go to bat for them, but I needed their help. I asked for a list of compelling reasons to justify an increase to their comp. Together, we prepared a self-assessment, I built their case, and I scheduled a meeting with the client manager to request a higher bill rate. Most of the time, the contractor got more money. They couldn’t ask their on-site manager directly (if they tried, they were sent back to me), so I became the gatekeeper. Here’s what I noticed from that vantage point.

I observed that men typically booked time on my calendar six months before their performance review to understand what I needed to present their case. They reached out unprompted and followed up by email, phone, and chat until the raise was written into their new contract. Six months later, they were back on my calendar to discuss next year’s increase.

Out of roughly 100 contractors I supported, about 40 regularly asked me to negotiate for them; in my three years at the company, only three women ever did.

Lessons from those conversations:
1. Know what you’re good at, document it, and share it.
Because I wasn’t their manager - and often worked with teams in fields I didn’t understand (engineering, innovation) - I needed them to educate me on what they did and why they deserved more money. The best communicators, who could clearly outline their contributions, earned the biggest raises. Their explanations usually followed the pattern: “Here was the challenge, here are the steps I took, and here’s the impact on my team/the company/my manager, which in turn allowed us to do X.”

2. You don’t always have to be the best - sometimes you just have to be the loudest.
My job was placement, not people management. I didn’t have time to check in with everyone. Those who found me, booked time, and helped me promote their work to the client were the ones who got raises.

3. If you’re not advocating for yourself, no one else is.
I’ve seen this in every organization I’ve worked with. Most people are buried in their own responsibilities. Even great bosses aren’t constantly thinking about your career trajectory. Be your own biggest cheerleader. Don’t leave your growth entirely in someone else’s hands - those who get ahead have a plan and think about it daily.

Your next raise starts with the next conversation you initiate, not the one you wait to be invited to. Advocate early, advocate often, and watch your value get recognized.