Conquer Your Fear Around Asking For a Raise

It's all about WHEN + HOW (directly from a founder with 50 ppl on my payroll)

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Ah, the age-old question: when to ask for a raise? And HOW? Because I understand it can be intimidating. If I want a raise I have to go to my board of directors, and that scares me too.

However, with the right timing (critical) and approach, it doesn’t have to feel like walking into a lion’s den. Let me give you TheLoDown (HA) on when and how to have the “money talk” with your boss, so you’ll leave the meeting with confidence (and maybe a fatter paycheck). As the founder of a 9 year old brand with a significant number of employees, this is my personal advice on how to get that $$$ (I hope my investors aren't reading this):

Timing Is Everything

First things first: Timing isn’t just important in comedy; it’s critical when asking for a raise. Here’s when you should and shouldn’t bring up the topic:

1. Mid-Year or Annual Reviews

This is prime time! Companies often tie raises to performance reviews, so if your boss is already in the mindset of evaluating your work, you’re halfway there. Use this opportunity to bring receipts (we’ll get to that) and make your case.

2. When the Budget Is Set

Businesses typically plan their budgets before the start or at the middle of the fiscal year. Asking for a raise before or during this time increases your chances of success because money is still on the table. It's important to let your manager (or their manager - whoever is responsible for building the budget in your department) that you are hoping for upward mobility to happen in the coming year. This convo can be casual and happen in your weekly 1:1, and is NOT the actual "I want a raise" conversation. It's to float what you hope will happen in advance so the budget builder keeps you in mind.

Ask someone in the finance department the timing for budget building in the business — it’s like knowing when happy hour starts.

3. After a Major Win

Did you just land a big client, crush a project, or single-handedly save the company from disaster? Strike while the iron is hot! When your value is fresh in everyone’s minds, it’s the perfect time to ask for more.

4. When Business Is Thriving

Asking for a raise when the company is growing, hitting revenue targets, or celebrating big wins is a smart move. But avoid the “I know we’re rolling in cash” tone—it’s not professional.

Times to Avoid:

• Right after layoffs or during financial uncertainty.

• When your boss is visibly stressed or swamped.

• Monday mornings or Friday afternoons (mood matters!).

How to Ask for a Raise (Without Feeling Awkward)

Once you’ve nailed the timing, it’s all about the execution. Here’s your step-by-step guide to making the ask:

1. Do Your Homework

Research your market value based on your role, industry, and location. Websites like Glassdoor or Payscale are your besties here. Come prepared with numbers that show what’s fair—this isn’t about “I need more money for my avocado toast habit.”

2. Bring the Receipts

Create a list of your accomplishments, quantifiable results, and ways you’ve gone above and beyond. Show how you’ve made the company better, faster, or richer. This will take you farther than industry comps, because if you don't have another job lined up you are immediately ready to jump to at that higher salary, the comps alone may not get you there. Your achievements in your current position will.

3. Practice Your Pitch

Keep it professional and concise. Try something like this:

"I’ve really enjoyed taking on [specific project/responsibility], and I’m proud of the results we achieved, like [insert metric]. Based on my contributions and market research, I’d like to discuss adjusting my compensation to reflect my value to the team."

4. Be Ready for Questions

Your boss might ask for time to think it over or need more details. Be prepared to answer questions about your work and provide additional examples. Don't expect an answer in the meeting, and accept politely (and verbally) that your boss may need to think about it. They do actually need to go back to the drawing board and look at budgets/how they could be adjusted, and that takes time.

5. Stay Positive and Gracious

If they say yes, fantastic! If they say no, thank them for their time and ask for feedback on what you can work on to revisit the conversation in the future.

Off-Cycle Raises: When Is It Appropriate?

While mid-year or annual reviews are ideal, sometimes you need to break the cycle. Here are scenarios when asking for an off-cycle raise is fair game:

1. Significant Job Changes
   If your role has expanded or you’ve taken on extra responsibilities that weren’t part of the original job description, it’s reasonable to ask for your pay to reflect your new workload.

2. Outstanding Performance
   If you’ve consistently exceeded expectations and made significant contributions, don’t wait for review season to ask for recognition.

3. External Offers
   If you’ve been offered a role elsewhere with a higher salary but would prefer to stay, you can use this as leverage. But tread carefully—it’s not a bluffing game.

4. Cost-of-Living Changes
   Inflation, increased living expenses, or a move to a more expensive area could justify a conversation about compensation.

Final Thoughts

Asking for a raise is about knowing your worth and advocating for yourself in a way that’s professional, strategic, and respectful. Pick the right time, come prepared, and make your case confidently. And remember, the worst they can say is no—but at least you tried. Good luck!