How to Ask for a Raise, Bonus & Equity Refresh at Year-End

It's already October. Between now and the holidays you'll spend money on yourself, your family, and your friends — and everything costs more than it did a year ago. But here's the thing that should actually get your attention: your compensation for next year is being decided right now, in rooms you're not in, whether you ask or not.

I've been in those rooms. I manage a team, and every year I sit in calibration and help decide who gets a raise, who gets a refresh, and who gets a "strong year, we'll revisit." So let me tell you the most expensive myth in your career: that good work speaks for itself. It doesn't. Good work gets you considered. Making your case gets you paid. The people who get the raise aren't always the best performers — they're the ones whose manager walked into calibration already armed to fight for them. This is how you arm them.

Most people dread this conversation because it feels like begging. Flip it. Your company runs the numbers on your cost and your value constantly — compensation is just a business decision to them. So make it a business decision for you too. You're not asking for a favor; you're presenting evidence. That mindset shift changes everything about how you show up. Two tools build your evidence.

Nobody — including you — remembers what you did in February by the time December rolls around. So keep a running brag doc, and structure every entry three ways:

• Win — what you did
• Business impact — what it did for the company (ideally in dollars, %, or time)
• Example — the specific proof

One from my own file, as a model:

Win: Built out the team and doubled marketing spend while holding profitability. Impact: Accelerated revenue growth by expanding existing channels and opening new ones, without blowing up cost. Example: [specific channel, the numbers, the quarter].

The impact line is the one that matters. "I worked really hard on X" is invisible in calibration. "I drove $Y" or "I saved Z hours a week across the team" is the sentence your manager repeats to their boss. Write the sentence you want them to repeat.

Internal evidence tells them you deserve more. Market data tells them what "more" costs to replace you. Pull two to three live sources so you have a defensible range, not a single number:

• Tech: levels.fyi is the standard — just make sure you're comparing level-mapped roles, not titles.
• Cross-check with one or two others (Glassdoor, Blind, a recruiter you trust, or an offer a peer recently got).

Important nuance so you don't anchor wrong: company size, stage, profitability, and local cost-of-labor all shift the band. A pre-profit Series B startup and a cash-rich public company pay the "same" level very differently. Know which band you're actually in.

Lead with your internal evidence (Method 1), then support with market data (Method 2). Market data alone reads as "pay me because the internet says so." Impact first, market second, makes you sound like someone who earned it and knows their worth.

Comp decisions get locked in before they're announced. By the time raises are communicated, the budget is already spent. So you want to plant your flag 4–6 weeks ahead of year-end calibration. And request the meeting explicitly. Do not ambush your manager in a regular 1:1 — it puts them on the back foot and signals you didn't take it seriously. Put it on the calendar:

Hi [Name] — I'd like to grab 25 minutes before calibration to talk about my comp trajectory for next year. I've put together a summary of my impact this year and where I see my scope heading. Would [two specific times] work?

That message does three things: it's explicit, it's short, and it tells them you're bringing evidence — so they come prepared too.

Here's a trick from the manager's side: the people I find easiest to say yes to are the ones who ask how the process works instead of issuing an ultimatum. Curiosity gets your manager explaining the system — and once they're explaining it, they're on your side of the table. Open with questions:

• "How have raise and bonus decisions actually been made here so far?"
• "What's the timeline — when do comp decisions get made, and who's in the room?"
• "How should I be thinking about the mix — base vs. bonus vs. equity?"

Then state your case (impact, then market), and ask what it would take to get there.

Base and bonus, people remember to ask about. Equity, they leave on the table — and for anyone at a startup or tech company, that's usually where the real money is. The quiet trap is this: your initial grant vests down over four years, and if no one proactively grants you a refresh, your annual equity silently shrinks toward zero even as your base ticks up. The top performers aren't just negotiating base — they're keeping their equity topped up. So ask directly:

• "How do you think about equity refreshers — time-based as people vest, performance-based, or both?"
• "Is there anything I should know about my vesting schedule or cliff going into next year?"
• "For options: what's the current 409A valuation, and how should I think about the exercise window?"

A quick plain-English decoder so these land right:

• Refresh grant = new equity granted on top of your original, usually annually for strong performers. The thing that prevents your equity from decaying.
• 409A valuation = the independent valuation that sets the strike price on new option grants. It moves over time, so timing of a grant matters.
• Exercise window = how long you have to buy your vested options after you leave. A short (90-day) window vs. an extended one is a genuinely big deal — know yours before you ever need it.

(RSUs vs. options, public vs. private, change these answers a lot — so ask, don't assume.)

1. Leading with personal need. "Rent went up / the holidays are expensive" is why you care — it's not a reason they'll pay. Keep it to impact and market.
2. Ambushing the 1:1. Covered above. Book it.
3. The ultimatum (when you don't mean it). Only raise the market if you're prepared to act on it. Bluffs get called.
4. Anchoring low. Say the number first, grounded in data. Don't make them guess and then negotiate you down.

Your comp next year is a decision being made right now. You don't control the budget, but you absolutely control whether your manager walks into that room with a loaded case for you or a vague "good year." Build the brag doc, pull the market band, book the meeting 4–6 weeks out, lead with curiosity, and — whatever you do — ask about the equity refresh.

If you want the exact word-for-word scripts — the meeting request, how to state your number, how to counter the "there's no budget" line, and the equity questions laid out to copy-paste — I put them all in my Salary Negotiation Scripts pack. It's the thing I wish I'd had the first time I walked into one of these.