I asked for a raise three times before I got one right. The first time, I waited for my annual review and said "I think I deserve more." My manager said "let me see what I can do" and nothing happened. The second time, I compared myself to a coworker and said "Sarah makes more than me." My manager said "that's confidential" and nothing happened. The third time, I prepared for two weeks, practiced the conversation, and got a 15% raise. Here's what I learned.

When to ask

Timing matters more than you think. The best times to ask:

• After a win. You just shipped a big project, landed a major client, or solved a problem no one else could. Your value is fresh in your manager's mind.
• During budget season. Most companies set budgets in Q4 for the next year. If you ask in September or October, your manager can include your raise in the budget. If you wait until January, the money is already allocated.
• At your annual review. This is the obvious time, but don't just say "I want more." Come prepared with your case (see below).
• When your role has changed. You're doing work that's above your title or pay grade. You've taken on responsibilities that weren't in your job description.

The worst times to ask: when the company just announced layoffs, when your team missed a big target, or when your manager is stressed about their own performance review.

Do the research first

Before you ask, you need to know what you're worth. Don't guess — research.

• Glassdoor and Levels.fyi: search for your title, company, and location. You'll get a range. Note the median.
• Payscale and Salary.com: similar to Glassdoor but with different data sources. Cross-reference.
• Your network: ask people in similar roles at similar companies what they make. This is awkward, but it's the most accurate data. You don't need to ask directly — "what's the range for your role?" is enough.
• Recruiters: if you've talked to recruiters, they often share salary ranges. Even if you're not looking to leave, this data is useful.

Write down three numbers: your current salary, the market median for your role, and your target (a realistic number between the two). If you're already at the market median, you'll need a stronger case (you're performing above your role, you've taken on new responsibilities). If you're below the median, the market data is your case.

Prepare your case

Your manager needs to justify your raise to their manager and to HR. Make it easy for them. Write down:

1. What you've accomplished in the last 6–12 months. Be specific. "I shipped the X project, which increased revenue by Y%" or "I reduced support tickets by Z%." Numbers matter.
2. What you've done beyond your job description. Mentoring new hires? Leading a project? Taking over a task when someone left? This shows you're operating above your level.
3. What you'll do in the next 6–12 months. Your manager is investing in your future, not just rewarding your past. Show them you have plans.
4. Market data. "Based on Glassdoor and Levels.fyi, the median for this role in [city] is $X." This isn't a threat — it's information.

Keep it to one page. Your manager doesn't need a novel — they need bullet points they can forward to HR.

Practice the conversation

Don't wing it. Practice out loud. I practiced with my partner, and I practiced by myself in the car. It feels awkward, but it makes the real conversation easier.

Here's the structure I used:

"I'd like to talk about my compensation. I've been here for [time], and in that time I've [accomplishments]. Based on my research, the market rate for this role in [city] is [range]. I'd like to discuss adjusting my salary to [target]."

Practice until it sounds natural. You don't want to sound like you're reading a script, but you also don't want to freeze up.

The actual conversation

Schedule a meeting with your manager. Don't ambush them in the hallway or bring it up in a team meeting. Send a calendar invite: "Compensation discussion" or "Career growth conversation." Keep it private.

During the meeting:

1. Start with your accomplishments. "Over the past year, I've [accomplishments]."
2. Share the market data. "Based on my research, the market rate for this role is [range]."
3. State your ask. "I'd like to discuss adjusting my salary to [target]."
4. Be quiet. Don't fill the silence. Let your manager respond. The first person to speak after the ask loses leverage.

Don't apologize. Don't say "I know this is awkward" or "I don't want to be difficult." You're having a professional conversation about your value. Own it.

How to handle the response

If they say yes: great. Ask when it takes effect and get it in writing. Don't leave the room without a timeline.

If they say "let me check": ask when you'll hear back. "Can we follow up next week?" Don't let it drift.

If they say no: ask why. "Is it a budget issue, or is there something I need to improve?" If it's budget, ask when you can revisit. If it's performance, ask what you need to do to earn the raise. Get specific: "What would I need to accomplish in the next 6 months to be considered for a raise?"

If they lowball you: don't accept immediately. "I appreciate the offer, but I was hoping for something closer to [target]. Can we meet in the middle?" Or "Can I take a day to think about it?"

The mistakes I made

• Waiting for the annual review. By the time reviews happen, budgets are set. Ask before budget season.
• Comparing myself to coworkers. "Sarah makes more than me" is a losing argument. Your case should be about your value, not someone else's salary.
• Not preparing. "I think I deserve more" isn't a case. Accomplishments and market data are a case.
• Accepting the first offer. If they lowball you, counter. "Can we meet in the middle?" is a perfectly reasonable response.
• Not getting it in writing. A verbal promise means nothing. Get the raise confirmed in an email or updated offer letter.

Negotiating a raise is uncomfortable, but it's one of the highest-leverage conversations you can have. A 10% raise on a $70,000 salary is $7,000 per year — that's $7,000 you'll get every year for doing the same work. If you're preparing your finances, my compound interest calculator shows how much that extra money could grow over time. And if you're not sure where your money is going each month, my savings goal calculator helps you build a budget that actually works.

I've negotiated salaries at three companies over ten years. This site is one person writing about money — not a financial advisor, just what actually worked.