Happy Thursday, and welcome back! This week, I wanted to share my thoughts about one of my favorite topics: compensation. It's also the topic I’m most frequently asked about by family and friends.

Many organizations are approaching compensation planning in Q1, and I’m sure you or someone in your network thinks they deserve more money. If they want some inside advice on what to do, look no further than the six recommendations below. And don’t forget to forward this to any family or friends who may benefit from this advice.

(6 minute read)

How and When To Ask For More Money

You want more money but are afraid to ask.

You may be thinking of the worst-case scenario: you’ll be fired, your boss will no longer like working with you, or you’ll be seen as greedy.

In my 12+ years in HR, I’ve never seen any of these fears materialize.

But there are plenty of things you can do wrong that will lead to a no.

After reviewing hundreds of comp requests, I’ve seen what leads to a “yes.” And as a hip-hop fan, I thought I’d include lyrical wisdom from some of the greatest hip-hop artists to help explain.

Are you ready?

Time for some “real talk, true story” - TI

1. “Numbers don’t lie, check the scoreboard “- Jay-Z

To accurately assess if you deserve a raise, you need to do your research. Simply assuming you’re underpaid because you want more money isn’t going to cut it. 

Would you buy a $100,000 car without researching how much it’s being sold for elsewhere?

To craft a data-driven narrative, work to understand what other people who do what you do are paid. Don’t trust a singular source. If you do, your data will be easily refuted.

Instead, triangulate using a few different sources, which helps you make a stronger argument and gives you more confidence in your answer. The best sources, in order of validity:

• People in your network who work in similar roles

• Job postings for similar roles at competitors (similar size and industry), especially now that many states require a salary range on JDs.

• Websites like Glassdoor, Salary.com, and other salary aggregators

People often rely solely on salary websites. Honestly, they aren’t great data points. Why?

• They are self-reported without thorough vetting.

• It’s based on the title only and often misses the nuance of industry, company size, and revenue.

• It poorly captures non-base compensation, which becomes critical as you become more senior.

Finding multiple data points helps you get closer to the company's data and can even make the company question its own data's validity.

2. “You only get one shot; do not miss your chance to blow” - Eminem

A friend recently came to me wanting help asking for a raise. As we started talking about the situation, he casually said that the company had a massive round of layoffs a few weeks ago, which is putting stress on everyone.

Sorry to burst your bubble, but the last thing your manager is thinking about during a stressful period is how to give you a 5% raise. And they sure aren’t going to go to Finance or ask their manager for more money.

You must read the room, or your request will backfire.

The timing of your request could be everything, especially because your manager will need to advocate on your behalf.

When are the three best times to request a raise?

• Right after you complete a massive project

• A month or so before org-wide compensation or promotion planning kicks off

• When you know that the company is overperforming and budget is plentiful

You should only ask for a raise once every two years. Don’t waste your shot.

3. “This is my canvas, I’m going to paint it how I want to” - J.Cole

What would you do in this scenario?

Unfortunately, this conversation is more common than you think. Someone asks for a raise but doesn’t have a valid narrative, leading to an unreasonable ask.

This will undoubtedly lead to a failed outcome. Someone close to you may tell you to get what you deserve. The motivation is helpful, but the logic may not be sound.

You can’t bring emotions into the conversation.

To be successful, you need a bulletproof narrative with two key features:

1. It has to be reasonable, and 

2. It has to be rooted in as many facts as possible (i.e. the research outlined earlier)

What’s an example of a great narrative?:  

4. “Last name Ever, first name Greatest” - Drake

If you are not outperforming expectations, you may not be in the best spot to ask for a raise. Just like you prioritize your money for the most important things, a company will do the same. If the same features of that $100,000 car can be found in a $75,000 car, you’ll buy the cheaper one instead.

Whether through a unique skill, deep knowledge, or hard work, you need a feature that makes you invaluable.

The best and highest-paid employees are the ones the company can’t live without.

If this isn’t you or you haven’t had enough time to demonstrate this, then wait. You will get your chance. 

Please don’t read this and immediately jump to the conclusion you aren’t worth it. This is a common response, especially for underrepresented talent. Instead, lean on my next point, which is depending on others for validation…

5. Look into my eyes and tell me what it is you see in me - Bone Thugs-N-Harmony

Are you sure your view of your performance matches your manager’s view? If not, understand your manager’s perspective on your performance before asking for a raise.

Asking for a raise when your manager doesn’t think you’re overperforming can backfire, and your manager will view you as lacking self-awareness (assuming they have attempted to communicate any performance concerns).

Unsure how you’re performing? Consider asking your manager a few weeks before you request a raise or wait until during or after a performance review conversation. This way, you can incorporate your manager’s opinions into your narrative.

For example, if they say you’ve done a great job collaborating and meeting your goals in record time, you can play their words back to them as part of your story for why you deserve a raise.

It’s hard for your manager to argue against their own words.

6. “Whether it's a check, a job, a loan, a dream, a goal, it all takes patience” -  Big Sean

Don’t expect an answer right away. The most common answer will be, “Not now, but I’ll look into it.”

Odds are, your manager has very little control over their salary budget. They can’t magically decide to give you more money, even if they think you deserve it.

Instead, they may have to go to their manager, who may have to go to their manager, and so on. The budget owner may need HR to propose and approve a compensation increase. HR will request rationale to show that the increase makes sense and doesn’t create internal inequities.

All of this takes time.

Think of the ask as the seed being planted. From there, the roots need to take hold, and over time, you’ll see the “fruits of your labor.”

Be patient and persistent. Follow up once a month to check in on progress and ensure your manager continues to prioritize your needs.

Asking for a raise isn’t about luck; it’s about preparation, timing, and owning your story. Do your research, understand your manager's perspective, and craft a narrative that’s impossible to ignore. You’re not just asking for money—you’re making a case for the value you bring. 

As Nas said, “The world is yours” if you’re prepared to ask for it. So take the shot, and make it count. You’ve got this.

Until next time,

Winston

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