How to Ask for a Raise, and Love It

For some people, asking for a raise is as simple as opening their mouths and letting some sassy words fly out. For others, they would rather rinse their nose with fermented bile than ask for more money.

I used to be firmly in the latter camp.

I remember 15 years ago when I started my career at a fast-growing startup. I felt I had finally established myself at the firm through hard work and deserved a raise. However, to get a raise, I had to ask. And I dreaded the necessary conversation with my boss, Mason, the company’s VP. So I googled every possible article about how to ask for a raise, but still didn’t have the guts to ask him.

Things were running wild in my mind:

“What if he thought I was a greedy jerk?
What if he didn’t think I deserved it?
What if he says NO?
What if he says YES, but hates me for it, and gets back at me in the future?
What if he fires me on the spot?
What if he starts laughing hysterically, sings a rap song, sprays me with a water gun, then calls immigration to get me deported?” (If you were an immigrant, you would understand the added stress of preserving your job and thus legal status in this country.)

With fear, your mind can go to weird places

I couldn’t sleep the night before. I wanted to vomit just thinking about it. When the day came, I full-on panicked. To avoid the conversation, I ­let my crocodile brain take over and made an in-the-moment decision – something no one should ever do.

I went to my boss’ boss, the company’s CEO, asking for a raise. I hated asking my boss for a raise so much I went around him.

The CEO said he’ll consider it, then went to my boss Mason asking what the hell was going on. Why was his employee not feeling secure enough to ask him for a raise directly, and had to go to the CEO? The CEO questioned Mason’s leadership, the stability of his department, and my maturity.

Mason was mortified. With a single action I took due to my own fear, I undermined him, made a fool of myself, and put my job in jeopardy.

But I was also lucky. Mason was a good, good man. He came to me telling me he was offering me a raise, but also implored me not to go over his head to the CEO anymore. And he asked me what he did to cause my action. I didn’t know what to say, because the only reason was that I was afraid of the conversation and possible rejection. 

My story had a happy ending. After all these years, Mason and I are somehow still friends. But until today, I still let out occasional yelps just thinking about how much I embarrassed him and myself. Moreover, I have continued to ponder why I avoided the conversation so radically to make that terrible decision and get both of us into that situation.

Me thinking about that moment today

I found two main reasons:
 
1. I didn’t want to be judged. I didn’t want to be seen as greedy or disloyal, someone who, instead of focusing on the work, being a good soldier and serving the customer, all he cared about was making more money.
 
2. I didn’t want to face the discomfort and the potential rejection. If Mason said NO, I had no idea how to handle it other than being upset and embarrassed.
 
Does this sound like you? Do you have similar experiences of dreading asking for a raise so much, that you avoided it at all costs, even to your detriment? (Feel free to share with me)
 
Now almost two decades later, things have changed. Through Rejection Therapy, I went from someone deadly afraid of rejection to a rejection expert. Over the years, as an employer myself, I have personally been asked for many raises. I have researched this type of scenario from many angles, and have studied the psychology of all parties involved. Moreover, I have also received countless similar stories from my readers. I have coached many of them on how to ask for a raise the Rejection Proof way.

Can you ask for a raise, get what you want, and not hurt your relationship with your boss in the long term? Instead of dreading the conversation so much, can you actually enjoy the negotiation process? Can you handle it and turn it into a positive if you get a NO?

Yes, you can!

How you should ask for a raise

Today, I want to share some of the tips with you in three main principles:
 
1. Turn the asking-for-a-raise question into a relationship builder.
 
One of the main reasons people hate this conversation so much is because they don’t want to ruin their relationship. Most people feel they have to choose either loyalty or disloyalty. It’s one way or the other. And asking for a raise make them look like the latter.
 
But the truth is, asking the right way can show your loyalty.
 
Position your ask like this: “Mason, over the past year and a half, I have really enjoyed working at the company. I have learned so much about the business and grown a lot personally. Now, recruiters are constantly bombarding me on LinkedIn, and I’ve known a few friends who have switched jobs to make more money and higher titles. That’s not what I want. I want to be here and continue to accomplish our goals. That said, I believe I’ve done a good job and do deserve a raise, and I would like to ask for one. I want to feel well-compensated, so I can focus on my work and not be distracted.”
 
This way, you ask for a raise while demonstrating your loyalty and love for the work. As someone who has hired (and fired) many people, I would rather chew on a kidney stone than lose a capable and loyal employee over a bit of money. The cost of lost productivity and hiring and training a new person could be devastating. If I can pay my employees a little more so they can stay happy for the long term, it’s a no-brainer.
 
Moreover, you have just demonstrated your character. Your company would feel safe about developing and promoting you long-term because you are not an immediate flight threat… at least not over money without telling them first.
 
2. Advocate for your family and your cause instead of yourself.

Another reason people don’t ask for money is the fear of being seen as a selfish and greedy person who only cares about money.
 
You can solve this fear. One of the most effective positionings I’ve researched is advocating for another person or a cause. It gives you an immense amount of power in negotiating. It’s called the Mama Bear Effect – think about an otherwise gentle mama bear fighting like a lethal beast, all to protect her cubs.
 
Position your request like this: “Mason, I have been very happy with my work and growth, and I believe the feeling goes both ways. That said, I would like to ask for a raise because my family has been under a lot of stress lately due to inflation. The added cost of everyday living has made it hard for us to budget daycare for my kids. As a dad, I want to make sure my wife and kids know that I am doing a good job at work means they are better taken care of at home. If my family is happy, I’m happy.”
 
You see, you can completely change the power dynamics with this position. Now you are like a lawyer advocating for your client, in this case, your family, not a greedy bastard. (Picture yourself shouting with force, “objection, your honor! My client deserves better treatment!”)

This raise is for my family!

3. If rejected, ask “how”.

Now, what do you do when everything you’ve tried has failed? Your boss didn’t budge. Instead, he gave you very reasonable and logical responses, as a trained manager would. Something like:

“I wish I could say yes. Trust me, I do. But we are entering a recession, our budget was cut, and the entire company has been put on hiring freeze.” 

“Jia, I am on your side and really hope to give you the raise. But you need to demonstrate more capability. Your sales number was good, but it could be better!”

“I, as the manager, would need to balance the wellness and happiness of everyone on the team. Just between you and me, you are already paid more than most of your teammates.”

Now, what do you do? You just got rejected after your best effort. Do you storm off now? Do you pull out your own water gun and aim at your boss’ eyes? Call immigration on him? (For heaven’s sake, please don’t do that.)

When your boss says you are already among the highest paid

One of the most magical words I teach people after rejection is to use the word “how.”

“Well, Mason… that’s disappointing, but I understand your difficult position. OK, how can I get the raise then? It is and will be very important to me to feel well compensated. So what can we do to make it happen?”

You see. You just put the ball in his court. There is no logical way for him to say, “you are never getting it, man. Dream on!” In this case, Mason is responsible for laying out the steps for this to happen. You listen intently. Write down what he says, and send him an email recap as a reminder. 

If the proposed course of action is reasonable and within your control, do your best to fulfill that requirement, and talk to your boss again. But if that proposal is some insane BS designed to be unreachable, then you have a bad boss on your hand, and you should talk to those LinkedIn recruiters. 

Very few people enjoy rejection and confrontation. Most would rather stew in anger for years before making a move to ask for a raise. But research has shown that you have a 70% chance of getting something just by asking. 

But with the power of rejection, you can request a raise with confidence and get the maximum result. You will also have a plan if things don’t go your way. This power applies to many more situations than just asking for a raise or promotion. Want to make a sale? Ask for funding for your company? Get someone to be your mentor or business partner? Give yourself a shot at the man/woman of your dream? If you can master the power of rejection, it’s truly a superpower.

Start your Rejection journey today!

Jia