How to Ask for a Raise: Say This to Your Boss

This week, Jeff and I are tackling an awkward conversation: asking for a raise. We know how terrifying it can feel to sit down and tell your boss you deserve more money, especially when you’re worried about being a "bother" or, worse, putting a target on your back. But you shouldn’t have to do the work of three people while only being paid for one. We’re here to help you navigate these high-stakes conversations with confidence and a clear plan.

This week, we are talking about:

•   The psychology of why asking for more is so scary
•   How to know if you’re actually ready and deserving
•   The "long game" roadmap for securing a raise
•   Setting concrete milestones with your manager
•   How to determine the right dollar amount or percentage
•   The best (and worst) times to have the conversation
•   What to do if your request gets shut down
•   Leveraging outside offers without burning bridges

Listen in to help us, help you give yourself the best chance of landing your Next Job… NOW :)

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Transcript

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SPEAKER_01 0:00

Welcome to the podcast. I'm Greg Langstaff. I'm a certified resume strategist. I've written over 2,000 resumes, and I love helping people get new jobs.

SPEAKER_00 0:10

And I'm Jeff, and I have a lot of questions about job searching. Together, we're going to talk about everything you need to know about landing your next role. Let's do it, Jeff. Let's do it. In this episode, we're going to talk about how to ask for a raise, how to know when you are ready for that raise, how much to ask for, what's a good time to ask, and what to say. This topic makes me so uncomfortable. I'll say it up front, going into this, asking for a raise, sitting down and saying, hey, I think I deserve more money, is probably the most terrifying topic I could come up with.

SPEAKER_01 1:04

Most people will never do this.

SPEAKER_00 1:07

Why is it so scary?

SPEAKER_01 1:09

Because because we don't we don't feel very highly of ourselves typically, and like we don't want to be a burden, a bother. It's the same reason you feel weird asking someone to drive you to the airport at 4 a.m. You know, and and like also there's this fear that like maybe if we think we're we're entitled to too much, they'll just get rid of us for some reason.

SPEAKER_00 1:31

Yeah, I I feel like asking for it can like hurt your reputation of like, well, now they're ambitious, now they want too much.

SPEAKER_01 1:40

Yeah.

SPEAKER_00 1:41

And if you don't continue to perform better, so like now they pay you what you're worth. Well, now they want more out of that because we're paying you more.

SPEAKER_01 1:50

Perhaps. Yeah.

SPEAKER_00 1:52

And then I feel like you're the first on the chopping block. Like, I'm so scared to ask for a raise because I don't want to bring attention to myself as a high-valued asset with low output.

SPEAKER_01 2:03

Yeah. And and like in the climate we're in now, and I don't want people to to I don't want to discount like the value of asking for a raise, because a lot of times we are in a position where like we are only asking for a raise to catch up to the level we're at. Like, how often, how often are we sitting there like, I'm doing two, three people's jobs, and I'm getting paid for one, and I'm not asking for three salaries, but maybe one and a quarter of what I'm making now would be nice.

SPEAKER_00 2:38

I mean, I guess if you're framing it in that way, you can see like, hey, I realize that the organization isn't able to hire a second person.

SPEAKER_01 2:46

Yeah.

SPEAKER_00 2:47

I am doing these jobs, I would value from having more money, and I would that would make me a lot happier.

SPEAKER_01 2:53

Yeah.

SPEAKER_00 2:54

And I would feel it's like a retention strategy to like make your staff happier.

SPEAKER_01 2:58

Yes.

SPEAKER_00 2:59

At the end of the day, buying more pizza, as fun as it is, doesn't get people want to stay. They really want money.

SPEAKER_01 3:05

Yes.

SPEAKER_00 3:06

Right?

SPEAKER_01 3:06

Yeah, and respect.

SPEAKER_00 3:08

Tell me more about the respect.

SPEAKER_01 3:09

Well, go listen to our toxic, uh, toxic workplace episode from last week.

SPEAKER_00 3:14

I think that we need to reframe asking for it as like this shows ambition, this shows, hey, don't hire a secondary person.

SPEAKER_01 3:21

Yeah.

SPEAKER_00 3:22

I'm happy to do this work and I will do it well, and I have been outperforming where I was, and now it's it's time. I I would love to stay here because you talked in this other episode, the fastest way to get a raise is to leave. So you're gonna leave. You have a LinkedIn poll out right now, and it's like skyrocket of people are gonna go to a company, another company, because they're gonna pay 20% more versus staying where they are.

SPEAKER_01 3:49

Yeah. Yeah, and like if even if you are like comfortable where you are, you don't want to leave, like but you need more money, the most effective way to get a raise is leveraging an outside offer. To like, it's it's time consuming, but to go like while you're working, also apply to some jobs, even do some interviews, and because if you show up in your boss's office and you say, boss, I like working here, but economically I need more, so I do have this offer for 20% more from this other company. I don't want to leave, but I need this money. Are you able to match? And I will gladly stay if you can match this salary. I I had a friend who who did that, and his company offered him forty thousand dollars a year more to stay.

SPEAKER_00 4:44

And did he stay?

SPEAKER_01 4:45

No. Because he also wanted to go work a 35 to 40 hour work week.

SPEAKER_00 4:53

Right. So there is more to it than just money, right? There's a lot more to consider than just, oh, you'll pay me more money, but that's not the same.

SPEAKER_01 5:02

Yeah, and if you want something like something else for yourself or something more stable, then that's also a consideration. But like in this situation, I guess when folks are asking for a raise, I think we're assuming like they either want to stay where they are or like it's gonna be a little tough to leave, so they're pursuing that option first for like uh more income.

SPEAKER_00 5:23

How do you know if you're actually ready and deserving of a raise?

SPEAKER_01 5:27

Well, I mean, my like my go-to kind of roadmap for getting a raise is something that would happen over the course of a few months.

SPEAKER_00 5:37

So, like play the long game.

SPEAKER_01 5:40

A little bit, yeah. Like it's not effective to just march into your boss's office out of the blue and say, I need 10% more, I don't have enough money to live my life. Like, the structure to do this properly is to like tell your boss in a in a controlled setting that you're looking to get a raise in the future. In the next, let's say, three months. And and you might ask, like, what would I need to do in the next three months to be like qua to like deserve a raise? To to provide enough value that I would be able to be paid more, 10% more, 15% more. What are some milestones you'd need me to hit? And they might lay those out for you. And they might say, Well, three months isn't really possible, let's set some six-month goals. Sure, at least the conversations moving forward. Because they will try to weasel out of this, and they will try to kick it down the line.

SPEAKER_00 6:34

Yeah. That's my fear of approaching it with such a long term. It's like, if you don't have those facts and you're just like, What can I do? What happens when they're like, hey, set these milestones, and just like, I've actually done all this.

SPEAKER_01 6:46

Well, then you can tell them you're ready for a raise now.

SPEAKER_00 6:50

Yeah.

SPEAKER_01 6:50

But but like realistically, like there's so many processes, right? Like, they're gonna have to talk to HR probably, they're gonna have to look at the overall compensation packages within the team. They might have to talk about like fair, you know, leveling for everyone in the team, people are doing similar jobs to you. So, like, there are a lot of factors. We can't just say like they're gonna say no because they're greedy. Like, it's it's time consuming, there's a lot to consider, but like making it more of a conversation and a goal to work towards, and like as best as you can to get some concrete milestones. Like, if you wanted to, like if they said, Well, if you want a 10% raise, your sales need to go up 20%.

SPEAKER_00 7:32

Right.

SPEAKER_01 7:33

And then you know, and then you you can document that. I would always email them back, like after that conversation, a summary of what was said, and then work towards those goals, update them with your progress. Like if they said in the next six months, if you raise your sales 20%, we'll give you a 10% raise.

SPEAKER_00 7:50

When do you check in? When how often are you bringing this up?

SPEAKER_01 7:53

Frequently.

SPEAKER_00 7:54

It's not annoying.

SPEAKER_01 7:56

It's your raise. Like it's yeah, you have to advocate if you want a raise.

SPEAKER_00 8:00

Okay.

SPEAKER_01 8:01

No one's gonna be like, man, you are killing it. Here's a raise. Right. Um, well, that I mean that's very rare. But then, yeah, like I would say if it's a six-month timeline, we want to be checking in every one to two months. Like, hey, sales are up eight percent, just tracking towards that 20 we talked about for my 10% raise. And then, like, when you get there, you can say, you can, you know, copy the old email. As we discussed on March 30th, if I achieved a 20% increase in my sales, I would qualify for a 10% raise. I'm excited to tell you I have achieved that 20% increase in sales, and I am looking forward to discussing when and how that salary increase will be implemented.

SPEAKER_00 8:42

I like that. How do you know uh how much? So, is that something that you kind of co-set with your manager in that like like you approach them ahead of time to say, you know, and I'm looking for a raise, I'm thinking X number. What do we need to get me to that point? Or is it I'm looking for a raise, and then there's a negotiation back and forth with your boss.

SPEAKER_01 9:04

I mean, I would always come in with some sort of number in mind, whether that's a percentage or a dollar figure, because like they might say, sure, yeah, you definitely deserve a raise. Here's three percent, two percent milk. Like that could be it. It could be all that, you know, if you ask for a raise, you go through this thing and you get this little piddly bump.

SPEAKER_00 9:26

Yeah.

SPEAKER_01 9:27

What are we talking about?

SPEAKER_00 9:28

So, how how do you determine what is an appropriate raise? And is there like a standard that like you should be getting a bump every year, five years?

SPEAKER_01 9:38

No, I feel like I feel like in the 80s there would have been like an answer to that. But you know how it goes now. It's like they're trying to pay you less and less, and they're trying to have less and less people and have you do more and more jobs. Like, we are up against it right now, in that like corporate greed is pretty prominent. Like, that's why all these efficiency layoffs are happening, all these AI layoffs, it's like cost savings, cost savings, cost savings. But like the cost you're saving is paying your employees and having employees, so yeah, it's tough. And like you gotta know when it's okay too. Like, don't go in and ask for a raise two weeks after a mass layoff. Because guess what? Like, you could be on the chopping block. That's the other thing. It's like the person who gets paid the most at their level would then generate the most cost savings if they were laid off. So, like, right now there's a little target on your head if you're getting paid too much.

SPEAKER_00 10:36

Okay, let's play a minigame. The weekly mini game. We want to find out when a good time to ask for a raise. So we're gonna list, we're gonna go back and forth and we're gonna list some times, and on three, two, one, we will say if that is a good time or a bad time. Annual review cycle. Three, two, one. Good time. Nice.

SPEAKER_01 10:59

That is definitely a good time to ask for a raise. It's part of it. Okay. One of your colleagues just got a raise.

SPEAKER_00 11:06

Three, two, one. Bad time. Good time. Good time. Oh, because like they did it. I want now?

SPEAKER_01 11:13

Yeah, it's it's like pay equity is definitely a good lever.

SPEAKER_00 11:17

I feel like just because they got a raise, now it's like now everyone has to get a raise, and like that's a bad time. Like you just got that person just got a raise for a reason.

SPEAKER_01 11:26

Alright, Jeff, it's lunch. I'm handing out sandwiches. I give Ariana a sandwich. What are you gonna do? Am I hungry? Yes. I'm always hungry. Ask for a sandwich.

SPEAKER_00 11:36

Ask for a sandwich.

SPEAKER_01 11:37

All right. They're handing them out.

SPEAKER_00 11:39

They're handing them out. Okay. After a huge project win. That went well.

SPEAKER_01 11:45

Oh, yeah.

SPEAKER_00 11:46

Three, two, two, one. Good time. Good time.

SPEAKER_01 11:48

Yeah. Any any if you're like, if you're if you're like on top of the world at work, it's a good time to ask for a raise. Yeah. Okay. After, let's say two months after a layoff, and you've been doing the job of yourself and someone else who was laid off.

SPEAKER_00 12:06

Three, two, one, one. Bad time. Medium. I feel like I'm picking up. It's like you want to.

SPEAKER_01 12:13

You deserve it.

SPEAKER_00 12:14

You deserve it, but there's layoffs, and you ask for it, and guess what? That's attention.

SPEAKER_01 12:20

Yeah. I mean, maybe that, like if the company is struggling, but you're struggling more. It just depends if you're willing to risk it, right?

SPEAKER_00 12:27

Yeah.

SPEAKER_01 12:28

You ask for a tiny raise.

SPEAKER_00 12:30

Ooh, tiny raise. Yeah.

SPEAKER_01 12:31

You get a little more.

SPEAKER_00 12:32

Whole milk.

SPEAKER_01 12:33

Yeah. Whole milk. 3.25%.

SPEAKER_00 12:36

Love that. The end of the fiscal year. Three, two, one. Good time. Okay. Yeah. I was worried you were going to say bad time because it's like money's tight at the end of the year.

SPEAKER_01 12:46

Well, they're making they're making decisions about the next year. Spending.

SPEAKER_00 12:50

So you gotta get you're getting ahead.

SPEAKER_01 12:52

Yeah.

SPEAKER_00 12:52

Would it be would your answer change if it was the start of the new fiscal?

SPEAKER_01 12:56

That might give them an excuse to be like, we can't talk about that right now. We already set our budget. So yeah. But realistically, I don't want like I don't want you to delay it a year if you want to ask for a raise. So yeah. Oh, it's my turn. Yeah. Okay. Right after you got hired. Three. Three, two, one, bad time. I don't think we gotta talk that one through.

SPEAKER_00 13:18

No, we don't gotta talk that one through.

SPEAKER_01 13:20

Your five-year work anniversary.

SPEAKER_00 13:23

Three, two, one, time. Medium time.

SPEAKER_01 13:28

Yeah. I don't know. If you've been doing a good job, yes. If you haven't been doing a good job, no. Like years should not indicate necessarily race. I think it should be like performance-based.

SPEAKER_00 13:40

Interesting.

SPEAKER_01 13:40

And leverage-based as well. Just like I've been here five years. You don't have any leverage there.

SPEAKER_00 13:45

Or except for you have to leverage that you hire a knowledge keeper and that you can do this job effectively.

SPEAKER_01 13:53

I would I would rather see you demonstrate that through successes, not years.

SPEAKER_00 13:59

I feel like the longer you work at a place, the safer you feel. Sure, especially if you're in a union. Definitely if you're definitely in your environment. So talk to me about what do you do if they say no. Oh, like if you get shut down.

SPEAKER_01 14:14

If you ask for a raise and they just say, sorry, we can't do that right now.

SPEAKER_00 14:18

Yeah.

SPEAKER_01 14:18

Uh I think I think you probably would like best you can do is say, well, this is really important to me, so like, do you have an idea of a timeline when that might come up? And and if they if they can't give you something concrete or they're like, oh, let's talk again in six months. It's time to job search.

SPEAKER_00 14:38

Yeah. If they're kicking the can down the road and they're not willing to have a conversation about it, yeah. You've asked for a roadmap, you've asked, is it now or never? Like not now, but never.

SPEAKER_01 14:50

Yeah.

SPEAKER_00 14:51

And there's no negotiation.

SPEAKER_01 14:52

Yeah. Like they they know they're risking leaving you when they say no.

SPEAKER_00 14:57

Well, any last advice for anyone asking for a raise?

SPEAKER_01 15:01

Just like there's never gonna be any harm in politely asking for a little bit more. It might not work, and you have to be okay with that. But as long as you like remain that pro keep their your professional decorum, prioritize the relationship, and ask politely, like there's no harm.

SPEAKER_00 15:20

Alright. It's now time for unusual interviews where we ask each other questions that we hope you never get asked in an interview. Greg, what is a non-work related vibe that you bring to the office?

SPEAKER_01 15:32

Non-work-related vibe? Yeah, what's your vibe? At the office? Yeah. Like the room next to my bedroom? No, no, no.

SPEAKER_00 15:41

An an office environment.

SPEAKER_01 15:43

Oh, okay. Um I would I think I'm kind of the like let's go for lunch guy. I think I think I'm the like let's go out for let's go out for a little little dinner once once every couple of months as a team guy. I like when everyone's kind of friends.

SPEAKER_00 16:00

Oh, so you'll you'll drive the like post-work social as well. Oh yeah. Yeah. Dinner usually? Dinner and dancing, even.

SPEAKER_01 16:08

Dancing with your colleagues? I mean, like, we built to that over many years, but yeah. Right. Or like, or it's like ping pong at a bar or whatever.

SPEAKER_00 16:21

I feel like you are someone that's comfortable being friends with colleagues.

SPEAKER_01 16:24

Yes.

SPEAKER_00 16:25

Yeah.

SPEAKER_01 16:26

But I would never work somewhere where I didn't consider most of the people there my friends.

SPEAKER_00 16:30

That's so interesting. Yeah, couldn't do it. I I'm the same. I recently had a friend talk to me about how they don't want to be friends with their colleagues. It's like that's work and like friendly and great, but like I don't want to hang out.

SPEAKER_01 16:43

I think that's an indication of, I don't know, just classic introvert, maybe? Or just like no new friends, go Drake. I don't love it. You don't want to work with that person. I guess I respect it, but and especially because like if you've worked if you've worked at places where people are mean to you, like I would a hundred percent come in with that vibe. But like, if you've worked with me, I'm gonna be pretty nice to you. We should be friends. We're gonna be seeing each other all day, every day. Yeah. What would you say is like something in your life that you've raised up to become a more a part of your life recently?

SPEAKER_00 17:22

Something I've raised up to be more a part of my life.

SPEAKER_01 17:25

Yeah, what activity in your life have you given a raise to?

SPEAKER_00 17:29

Oh. I honestly I'm pretty dialed in right now. This is a reference to coffee. On my little side gig of coffee.

SPEAKER_02 17:36

Yeah.

SPEAKER_00 17:37

I've had multiple meetings post in the evening this week to sell coffee, launch coffee, branding, long-term visioning. I'm like, oh yeah.

SPEAKER_01 17:47

Yeah.

SPEAKER_00 17:48

Yeah. That that's been my main focus.

SPEAKER_01 17:51

That is fantastic.

SPEAKER_00 17:53

Yeah, it's nice.

SPEAKER_01 17:54

A little pitch, a little commercial for your.

SPEAKER_00 17:56

Oh yeah. Please follow Colorway Coffee. Colorway with a you.

SPEAKER_01 18:03

We're Canadian.

SPEAKER_00 18:04

Yeah. Colorway Coffee Roasters, follow us on Instagram. We uh do some like cool micro lot roasting. It's it's been a lot of fun.

SPEAKER_01 18:13

Yeah.

SPEAKER_00 18:14

Yeah.

SPEAKER_01 18:14

I'm I it's fun to watch.

SPEAKER_00 18:16

It's the business side of it that's like the most fun for me. The roasting has been a hobby, but like it's fun to learn.

SPEAKER_01 18:21

Yeah.

SPEAKER_00 18:22

How to start a business.

SPEAKER_01 18:23

Well, I assume the coffee's delicious. I've never had a coffee.

SPEAKER_00 18:28

So disappointing.

SPEAKER_01 18:29

That's it.

SPEAKER_00 18:29

Talk about a toxic workplace. Won't even drink my coffee. We get you coffee. Oh, yeah, that's true. That's a great workplace. All right, thank you so much. Tune in next week where we talk about getting a promotion, not just a raise. What's the next level in your career?

SPEAKER_01 18:46

Oh, yeah. That is an easier way to get a raise.

SPEAKER_00 18:49

Oh, can't wait to find out.

SPEAKER_01 18:50

Yeah.