What your boss doesn’t want you to know about asking for a raise
Asking for a raise is one of those career moments that can feel incredibly intimidating, especially in your early 20s when everything still feels new. You know you’re working hard, showing up, and trying to make an impact but the actual act of going into somebody’s office and asking for money is a different level of intimidating.
And then if you’re the eldest daughter, people pleaser type, you also have this whole other level of worry about not being perceived as greedy, wanting too much or potentially ruining the relationship for asking for something.
If you’ve been putting off the raise conversation because it feels awkward, scary, or you're just not sure what to say, you're not alone. If you’re even thinking about asking for a raise, there’s probably a good reason. While we all want to make more money, because of all the initiative required to make a pay change happen, you’ll generally only feel called to do it if you have a feeling deep down that you could be making more.
So in today’s post, we’re going to talk about the basics of asking for a raise so that you’re actually setting yourself up for success. It’s time to, as they say, “get that bag.”
Why you should trust me on this topic
You may or may not know that I work for myself now, so I’m not having to negotiate raises anymore. But back in my days in corporate america, I negotiated three promotions that came with raises over 20%. These happened across four years, at two different companies and each raise required a different leader to buy in because of changes at the executive suite. Because I saw my tactics were not exclusively effective with one person, I’m even more confident sharing them with you.
But before we jump into how to ask, let’s chat about why many people don’t…
Why most people never ask for the raise they deserve
If you’ve been scared to ask for more money, the first thing you should know is that you’re in good company. The fear is real and there are a few reasons why it runs so deep.
For one, many of us grew up being told to be “grateful” for what we have. That messaging sticks. We start to believe that asking for more is selfish, greedy, or might make us look ungrateful at work. And if you're a people pleaser or recovering perfectionist? Yeah, that fear of “rocking the boat” can be especially strong.
Then there's the issue of social conditioning. We’ve long heard stories about women making less, negotiating less, or risking backlash for asking for more. In combination with the above messaging, these warnings can easily scare an eldest daughter type away from making the risk.
Thankfully, there is evidence that the rate of negotiation has leveled out. While there’s still progress to be made in the outcomes of the negotiations and the overall realities of the gender pay gap, as an individual, the key is to not let all this fearmongering keep you from moving forward.
We have to be aware of the social realities of negotiating, but you can’t let it stop you from going after what you want. Because here's the truth: not asking is already costing you. Raises are rarely handed out without some form of advocacy, and you have every right to be compensated fairly for the value you bring.
How to tell if you’re ready to ask for a raise
Not sure if it’s the right time? Here are some signs you’re absolutely within your right to start the conversation:
It’s been over 18–24 months since your last raise. In many industries, that’s already considered overdue.
You’ve taken on significantly more responsibility. Whether you’re managing new projects, mentoring junior teammates, or just solving higher-level problems than you used to, that’s value your company should acknowledge.
You’ve grown in your role. If you’re consistently delivering above expectations or going beyond your original job description, your compensation should reflect that.
You’ve done your homework and realized you're underpaid. If your market research says your role typically pays more, it’s more than fair to bring that to the table.
Let’s be very clear, my friend, only one of these needs to be true. The first promotion/raise I negotiated, I hadn’t even been at the company a year, but I had taken on more responsibility and was stepping into new challenges and felt that I was ready to level up my official role.
Being “ready” doesn’t mean that it needs to be a slam dunk. The reality is that every ask may not be successful, but even if you end up getting told no, you can actually better set yourself up for the next ask because you’ve laid the groundwork in being interested in more.
“Ready” isn’t a set of facts, it’s a choice to take action.
Reasons that shouldn’t stop you from asking for a raise
Just like our companies would probably prefer that we just sit back and stay “grateful” to even have a job in “this economy,” we often have our own stories that we use to hold ourselves back from taking the scary step to ask for more pay, responsibility or title. These are the things that your boss really doesn’t want you to know because it might mean that you’re going to make an ask of them that’s going to push them! But you can be shooting yourself in the foot if you let these stop you:
Company numbers are down. It’s a common misconception that if the company isn’t doing well that there’s no chance they give anybody raises. In fact, if you can communicate how crucial you are in plugging the leaks (or even better, how your role can contribute to turning things around), there’s absolutely opportunity for a raise. For example, a previous client was going to be affected by downsizing but by applying some of this advice, turned the situation to get a 10% raise!
Your boss left or there was a recent leadership change. You may feel that all that history of your hard work and contribution was wiped clean if your direct boss has left but remember that it’s very expensive to replace good talent and any new leadership has a vested interest in keeping you. I started the negotiation for what would become a 20% raise and title bump a few weeks after I got an entirely new manager but because I was able to communicate how valuable I was, he was willing to argue on my behalf even with little personal experience with me.
You haven’t been at the company very long. Your contribution matters far more than any length of time. Generally, I’d say at least 6 months in is the earliest when you could reasonably start thinking about a negotiation, but it certainly doesn’t need to be a year. That being said, in a rare situation, like the actual role has turned out to be far different in scope than what you were hired for, there could even be situations where under the 6 month mark could be permissible.
You’re nervous to ruin your reputation. In any version. We’ve covered this above slightly but please do not let fears about other people’s opinion stop you from being paid what you deserve.
The one reason you might not be ready to negotiate
As you can tell, I’m a huge advocate for asking for what you want. But if you want to be successful in asking for and receiving a raise, you have to be very self-aware about this next piece. In order to explain, I need to be rather blunt for a second, okay?
You needing more money to afford your life doesn’t mean you’re ready for a raise.
Wanting to get paid for doesn’t mean you’re ready for a raise.
Feeling underpaid doesn’t even necessarily mean you’re ready for a raise.
Wanting more opportunity doesn’t mean you’re ready for a promotion.
Feeling disrespected doesn’t mean you’re ready for a promotion.
How much we are paid at work or our title and responsibilities are a reflection of our value to the company, not as a human. This is especially important to remember if you are being underpaid (more on that in a second), because it doesn’t mean that that’s all you can expect. If you feel undervalued in title, it doesn’t mean that you’re not worth more. But I find that young professionals often come at the conversation around raises all wrong in that they think about it in terms of what the more money or role can do for them. And frankly, your company doesn’t care if you’re behind on rent, if your outspending on lifestyle or anything else about your life.
To get a raise, you’re going to need to stop thinking about what the money or new role will do for you and more how giving you this additional money or title is good for the company.
In order to do that, you have to get very very honest about your actual value to the company. It’s time for you to get real honest to evaluate:
Are you delivering on every element of the job description? Even the areas or projects that you don’t like?
Does leadership depend on you? Are you consistently delivering on what they ask of you?
Are you finding opportunities to anticipate needs or deliver above average quality work? (If you are, you’ve probably gotten complimented and thanked for this.)
Could you be trusted as a spokesperson for the company? You don’t have to have a perfectly PR approved life but does your team trust you to interacting with customers or other partners unsupervised that would indicate they trust your decorum?
Are you consistently getting high marks on your quality of work? No major mistakes and dropped balls?
If any of these set off alarm bells, your job is to become the quality employee that would deserve a bump before you go ask for it. Ultimately, a raise isn’t something that anybody just gets - it has to be based on a reflection of your contribution to the company. Especially in uncertain economic times, making sure that you can firmly stand behind your contribution and ask for the raise with your whole chest is important to increase your chances of success.
How to figure out if you're underpaid (and by how much)
Assuming you do feel like you’re ready for additional recognition in your company, the first step is to get a sense of where you stand. One of the most helpful things you can do ahead of a raise conversation is figure out where your current compensation stands in relation to your market and/or the value that you offer the company. Here’s how to get started:
Use salary benchmarks. Sites like Glassdoor, Levels.fyi, and Payscale can only go so far, but they can be a starting point to begin to collect data. Open job listings at similar seniority (at your company or competitors) can also be great data points. You might even go so far as taking calls from recruiters in order to gather this info
Talk to people in your field. Yes, salary transparency can feel taboo, but it’s also one of the best ways to learn what’s fair. Trusted coworkers can be the best place to go here and often the best way to start is to share the data vulnerably yourself. Discussing salary is a legally protected right but if your company has any policies around this (they shouldn’t but always better to be aware), then make sure to have the convo offline and outside the office.
Remember total compensation. Pay is not just in your salary. Consider bonuses, equity (if applicable), and benefits. Sometimes a job with slightly lower base pay might make up for it with generous perks or flexible work policies — but sometimes, it doesn’t.
If your research shows you're underpaid, that gives you a data-driven foundation for the reason you need to have a raise conversation. You’re not just asking because you feel like you deserve more — you’re asking because the numbers support it.
BUT its’s market rates are not always the best argument to make for actually getting the raise. So let’s talk about how to best prepare so that you can set yourself up for success.
How to prepare for a raise negotiation (step-by-step)
If you want your raise conversation to go well, preparation is key. The biggest mistake I see people make is thinking about this process and thus, laying the groundwork for a raise too late. Ideally, you should be laying the groundwork 6–9 months in advance, not scrambling to make your case two days before your performance review.
The reason why this matters so much is because in order to successfully negotiate a raise, you need your boss or the decision maker on your side. They will have to do something for you, on your behalf, and even if she values and appreciates you, it’s still going to require incremental effort on her part. So in order to increase the probability that she’s bought in, we want to set up her agreement as early as possible.
Here’s how to set yourself up:
1. Start planting seeds early.
Begin casually bringing up your goals in one-on-ones. Something like:
"I’ve really been focused on growing in this role and want to make sure I’m on track to eventually step into the next level. What are some things I should be focusing on over the next few months?"
For all three of my successful negotiations, I had gotten some indication of what it would take to be ready for the next level at least 6 months before I made the ask.
2. Track your wins.
Keep a running doc of things you’ve contributed to: projects, launches, metrics you’ve improved, ways you’ve supported the team. If you saved your team 5 hours a week or brought in new clients, write it down. These are receipts you’ll bring to the conversation.
You should be tracking these for responsibilities within your role but especially in relation to any indication you got from leadership in your early conversations. For example, in my first negotiation, my boss had indicated that to be ready to go to the next level, I needed to show proficiency in a certain type of report that was outside the scope of my current role. In the 6 months between that convo and when I officially asked, I sought out any opportunity to get practice on those reports so that when the time came, I had already proved that proficiency.
3. Get clarity on roadblocks.
Find low pressure times to ask your manager: “What do you think might get in my way of getting to the next level when review cycles come around - are there areas I need to be focusing on to make a stronger case for myself?” Their answer becomes your roadmap on what holes you might need to stop up or, if the feedback is more about the economy or company performance, gives you key insight in how you’re going to need to make your argument to overcome those objections.
4. Choose your timing wisely.
Aim for a conversation early in performance review cycles or at the start of budget planning, not after raises have already been decided. If your company does reviews once a year, start prepping months before that.
That said, my most successful negotiation ever was off cycle. My boss was about to go on vacation and had delegated significant responsibility for me to cover for him when gone. I knew it painted a picture of how much the organization trusted me at a senior level, far beyond the technical scope of my role. By having the conversation then, there was implicit support for that perception of me that I knew would help strengthen my case. (And it did.)
What to say when asking for a raise (and what to avoid)
Now let’s talk about the actual conversation. This part can feel like the scariest and is often the hardest to advise on because it’s so personal. You need to make the specific case of why you are ready for the next level, or how your work translates to value for the company (in terms of dollars, saved time or strategic value) in a way that is most important to the company then.
For this reason, there’s only so specific I can get in an article like this. But I hope these will begin to give you some guidance as to how to approach the conversation.
Start with gratitude, then shift into value.
You want to come across as appreciative and confident in your contributions. Something like:
"I’ve really enjoyed taking on more leadership this year, especially with [specific example]. Based on the responsibilities I’ve taken on and the value I’ve brought to the team, I’d like to talk about adjusting my compensation to reflect that."
Avoid apologizing or downplaying.
No more “Sorry to ask this” or “I don’t know if this is the right time…” You are not a burden for advocating for yourself.
Be specific.
If you’ve done market research or know what you’re aiming for, name your number (or a range). Don’t immediately explain how you came to the number (save that for once they’ve reacted) but you can offer to explain further.Let them respond from there. Something like: “Based on the [insert number] value I’ve created for the company, I’d like to discuss a salary adjustment to the [number-number] range. Of course, I’m happy to explain how I got to that number if that’d be helpful but want to get your feedback first. How do you think we could make that work?”
Expect pushback.
Almost every leader will naturally have reasons why they can’t make it happen. This is generally just a part of the process and doesn’t actually mean the answer will be no. In fact, when you can withstand this pushback and calmly explain or substantiate your ask, you can even earn more respect with leaders.
Have a follow-up plan.
If your manager says they’ll “look into it,” ask when you can follow up. Put a reminder on your calendar. Keep the conversation active.
Final thoughts
If you’re nervous about asking for a raise, I get it. But you have no idea what money might be available to you if you ask, potentially more than you even hoped.
This skill is one of the key levers you have to increase the wealth available to you over your lifetime so the sooner you learn it the better. And on a confidence level, your ability to face an unknown situation and stand strong with the value you believe you have provided will rocket you to a new level of your sense of self.
The first conversation is always the hardest, but it gets easier. You build the muscle. You realize you can do hard things and that asking for fair compensation is not only okay, it’s necessary.
You’ve got this!
