💕You know what every girl is supposed to want for Valentine’s day? Chocolate, flowers, jewlery…I mean sure.

But personally? I would like DIRECT DEPOSIT, BABY!

I’m about to say something a slightly unromantic but highly useful: we have got to stop acting like money chats are taboo… asking for more of it, negotiating offers, sharing ranges so we know what to ask for…and pushing for raises when our scope grows.

So today, I’m walking you through a simple, practical formula for asking for a raise that you can actually use.

Sneak preview of step 1:

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I talk with a lot of EAs and Chiefs of Staff who are carrying far more scope than their original role: running projects, owning operations work, managing meaningful budgets…and still feeling unsure about asking for a raise.

It’s uncomfortable. That’s normal. Most people were never given a playbook for this.

Behind the scenes, though, raise decisions are usually handled as business cases, not personal favors. Your leader often needs to justify the increase upward and the clearer you make that case, the easier it is to approve.

There are two parts to getting this right: how you prepare, and how you ask.

Most people prepare for a raise conversation by thinking about how hard they’ve been working, or what the ~feel~ they’re worth. While this is totally understandable, it’s not particularly persuasive.

What usually works better, though, is preparing something more concrete. A scope-and-impact case your leader can actually take forward and defend internally.

Here’s what’s worth pulling together ahead of the conversation.

Start by writing down everything you’re responsible for now that was not in your original job description.

For EAs and Chiefs of Staff, this list usually gets long faster than expected. Conference ownership. Offsites. Project management. Operational work. Responsibilities you picked up after someone left. Systems you built. Decisions you’re now trusted to make on your own.

Put it side by side if you can. Original scope vs. current scope. It makes the growth easy to see at a glance.

Remember, you’re not complaining here, and you’re not venting. You’re documenting how your role evolved.

Save the feedback you’ve received over time. Emails, Slack messages, executive praise, quick thank-you notes after big deliverables.

It might feel minor when it happens, but in a raise conversation it becomes pattern evidence. It shows that your value isn’t just your opinion, it’s observed and repeated.

Think of it as supporting documentation, not bragging.

People often assume their work isn’t measurable, but a lot of it is once you trace the downstream effect.

Time saved for an executive. Vendor savings. Process improvements. Events executed. Projects delivered. Revenue-connected activities.

If you run events, ask sales or marketing what typically comes out of them. Pipeline created, average customer value, conversion rates, etc. Even directional numbers help anchor the conversation in outcomes instead of effort.

Market data helps keep the conversation grounded and less personal.

Pull a few current job descriptions from local companies, of a similar size and stage as yours, at the compensation level you’re targeting that match your scope. Highlight the overlap.

You’re not saying “pay me more because I want more.” You’re saying “this is where the market prices this level of responsibility.”

That framing travels better internally.

Compensation adjustments are usually easier to approve when paired with a title that reflects expanded scope.

Senior EA. Senior EA to the CEO. Lead EA. Expanded operations title. Chief of Staff track.

Titles give HR a structure to attach the pay change to. It helps more than most people realize.

The phrasing of the ask is where most raise conversations just simply fall apart.

If you walk in and say, “Can I get a raise?”, you’ve created a game show buzzer round (I ❤ you Steve Harvey!). Yes or No, fast!!!! That puts your leader in verdict mode instead of planning mode. Change the frame.

The key is to approach this as a COLLABORATION!

You might say something like:

That last line, how can we get there together, changes the temperature of the entire conversation. Now you’ve solving a problem jointly instead of asking for a prize. You’re not asking for a prize, you’re aligning on a plan…and plans get approved far more often than prizes get granted!!!

And listen, if the answer isn’t yes on the spot, don’t panic! This is where we can start to get creative.

One of my old bosses used to say, “The sale starts when the prospect says no.” Same energy applies here. A thoughtful “not yet” is often an opening to design the path, not a closed door.

Your job now is to turn the no into a plan.

Instead of pushing harder in the moment, shift into build-mode with them.

You can say:

That question is doing a lot of work for you. It moves the conversation from emotion to criteria. Now you’re talking about targets, scope, outcomes, and timing, not just budget.

From there, you can suggest structures like:

Now you have visibility. You have a scoreboard. You have something you and your manager both agreed to..which is very different from “we’ll revisit later,” which usually means never.

Quick recruiter PSA from someone who has watched this go badly more than once:

Please do not walk in waving another job offer and use it to force a raise or counteroffer…unless you are genuinely prepared to leave.

When you do that and then stay, you’ve labeled yourself a flight risk and strained trust at the same time. In future reorganizations or budget cuts, that label tends to get remembered.

If you want to leave…leave.

If you want to grow here…negotiate here.

Mixing the two strategies usually backfires.

Stuck in your job search? Not sure how to handle a tricky interview question or navigate the hiring process? Submit your question anonymously, and I’ll answer it in an upcoming newsletter.

Was any of this helpful?! Hit reply and let me know :)