What I say when people ask me for more money

Brad Dunn
9 min readJun 30, 2021

Every now and then I’ll have a discussion with someone on the team who is looking for more money, a promotion, or just wants to talk about how they progress their player token on the financial scorecard of professional life. People want to progress. Sometimes it’s being called something different, sometimes it’s more money in the bank. Often it’s both.

Across various companies, both with myself and other managers, I have seen people ask for money well and get what they want and I have seen them ask terribly, and get nothing. I have also seen huge levels of incompetence rewarded beyond your wildest dreams, so in truth, there is often no logic to the madness. But for the most part, people still ask me how to do it.

When people ask, I give the same advice. Recently I realized this wasn’t exactly common knowledge so I figured I’d share the same advice here I give people all the time in case it helps you get that 💰

A few notes before we start….

This has nothing to do with being fairly compensated. If you’re being paid below market rates, my advice is the company should just correct that imbalance regardless of what I’m writing here.

If you’re being paid less than someone else who is doing the same job, then that should also be corrected.

If you’re being paid less than someone of a different gender, this too (all things being equal) should be corrected. I’m lucky enough to work in an organization that puts this kind of stuff front and center and we do corrections like this when we see them. But not all organizations are that lucky, but generally speaking, companies have an obligation to get their act together on this front and more people do talk about this than they used to — which is good.

Also it’s worth noting that while money is not a motivator for most people (Autonomy, Master and Purpose seem to be the leading causes), saying things like “money or titles don’t matter” is often spouted by those who have both. The more senior I get, the more I fundamentally acknoledge that while money might not make you happy, often people are trying to buy a home, plan for their kids futures, invest, pay for medical bills, and to just dismiss money as an irrelevance is a bit one dimensional. So when people ask for money, if you’re the kind of manager who thinks ‘this won’t make them happy’, maybe put that aside for a minute and realise it might help them — and they are within their rights to ask. Perhaps don’t judge the why so much.

Finally, I’m not really talking about who deserves to be promoted here. I’ll just assume for the purposes of this argument, both you and the company feel you deserve these rewards. My notes here are really to help make the conversations easier not to make you a better performer.

How to get a promotion or more money

This is the same advice I give everyone. So it's general and hopefully appropriate in most cases. Note that I have worked in tech since I was 17 years old so most of my experiences come from that world view too. If you’re looking for a raise as an anesthesiologist I cannot help you.

Step 1. Lower your expectations

Always go into this process with low expectations (I know, starting with a real downer — sorry). There are a lot of factors for salary reviews and when people get their hearts broken it can really damage your motivation. Nothing makes me sadder than to watch someone get their hopes up because a friend at brunch told them they should be getting twice as much money, and when it doesn’t land, your world feels like it’s falling apart and a job you liked 3 weeks ago suddenly seems like the worst place to work in the world. Just take a breath. It’s just a job, after all.

So when you are ready to talk about money, go in with an open mind, be objective, and try not to get your heart set on some number in your head too much. Take a stoic approach and just assume the world is full of suffering and misery and there is a chance you’ll be disappointed. You shouldn’t get attached to the outcome, instead only focus on what you can do — your actions, behaviors, and how you handle yourself. That’s what matters.

Also know not all companies pay at market rates. Some provide other value to employees beyond salary and this is referred to as the employee value proposition, which also includes what percentile people get paid. For instance, some people pay in the 90th percentile. Some don’t because they offer mad perks. Recognize that even though you can occasionally earn more elsewhere it still might not be worth it. What you value should influence if a job is worth it or not.

Now I don’t say lower your expectations to be uninspiring or clip your ambitious wings. By all means — you should go for it. If you want a million dollars a year, say so. Get after it. Get that paper yo — I’m just saying focus on what you can do — not the outcome. I firmly believe this is just good, stoic advice.

Always make sure you understand the process for salary reviews

If you ask for money ‘out of cycle’, which means asking for it outside of the standard review process, the probability of you getting it is much lower than when you’re in a cycle where it’s being reviewed. These cycles apply at certain sized companies and if you’re in a small startup, you can probably just ask anytime you want and it’ll be totally fine. My guess is over about 100 staff, you’ll start to see formal pay review cycles. Or maybe when you have your first HR person.

If you want money out of the cycle you either need lots of leverage or need to be performing at really astronomical levels or there is some other retention factor at play — like the company would be dead in the water if you left. Managers will find it really traumatic (and maybe, if you’re using leverage, resent you a little for it) to ask for salary reviews out of the cycle on your behalf if they have to get approvals from someone up the chain to make it work.

The odds of you getting what you need are low in out-of-cycle requests, the HR teams will also likely resist it as it creates lots of overhead for them. So just get that as it's more structural than you might be aware of and the headwinds will be stronger. If you’re unsure, just ask your people leader or manager about the cycles and how they work, they can probably tell you the criteria under which salaries go up.

Just by asking, “What would I have to do to be paid 20% more within 6 months is the single best question you could ask.” If you ask this and can get it on paper, the rest of this article is probably not worth your time :)

When you are ready to ask, you want to drive the conversation.

Set up a meeting to talk about the salary review process and come to that meeting with the following information.

  1. You want to show that you’ve completed all your stated goals and objectives (or at least, by whatever measure you actually talk about performance, you can credibly talk to doing a good job). This is why it’s important to have documented goals.
  1. You want to show you’ve done things beyond those objectives and show what they are and the impact those projects have had on broader business goals. This is just a list of projects that may have not been your responsibility but you did them anyway. Maybe you helped another team with a project late one weekend that really had a huge impact. If you did, point to it and highlight the value it generated.
  2. You also want to show market data and say “someone at my role, at my experience level, at a company like this, would be paid XYZ.” HR can help you with this, but also just asking around and Googling a bit and looking on LinkedIn or Glassdoor. Just make sure you’re comparing Apples with Apples here. If you’re looking at roles in New York but you live in Arizona, the numbers could be really different.
  3. You want to show how you’ve embodied the ways of working (or company values) and have some good examples. Talking to values is a great way to show you’re on board with the company culture. Some organizations (good ones usually) also use values as a way of measuring performance. Segment only uses values as their performance review process actually.

The 4 things that matter the most

Finally, just know there are usually 4 things that matter most when it comes to getting more money anywhere or being promoted. It boils down to this normally.

  1. Did you complete your objectives?
  2. Did you go above and beyond the call of duty and can you demonstrate that clearly
  3. Your working relationships with others. People don’t talk about this because frankly, they want to believe the world is fair and equitable, but it’s not. Your ability to build relationships with your team and the business as a whole is important and this is also why emotional intelligence and forming good patterns when you are young in how you deal with others pays huge dividends in your professional career later in life. Being able to work with others matters. To pretend this isn’t a factor is just ignoring the reality of working in an organization. It is why the phrase ‘high performing jerks’ exists. People love high performers, but only if you can stand being in the same room with them. The bigger the jerk, the higher the performance would have to be for you to tolerate them. And as companies' attitudes towards cultures evolve, this is fast becoming a thing organizations have zero tolerance for. There are professions where this matters less, but in cross-functional team structures and software companies — you need to work with people to get things done.
  4. How your work is viewed. You want to not just be doing good work, but you want to be seen as doing good work. (Note: you actually do need to do good work as well obviously) But much like number 3, you want to be seen in an organization. This isn’t about just going around shamelessly self-promoting work that sucks. There are plenty of quiet achievers who are recognized. Generally speaking, doing good work, keeping people informed, and sharing your work with others is enough here. But just know you can’t sit in a basement doing good work interacting with nobody and think someone will care enough to come to you to recognize your worth. Now and then, you gotta put yourself out there and share your awesome stuff with the world.

Now, there are some schools that believe in something called a 9 box — HR people love it. Kim Scott also has a different box which I tend to prefer popularised in her book Radical Candor as an alternative which talks about the difference between rockstars and superstars.

Growth trajectory performance box from Radical Candor

But the 9 box is where you rank things like potential and performance. Companies have a habit of wanting to pay people with high potential and performance and use money as a way to retain people. But in my experience, the above 4 things matter in practice more than the 9 box thing. But knowing where you are on a 9 box grid may help you understand why you did, or didn’t, get the money you thought you deserved.

That’s it. Now go get paid. Be a boss.



Brad Dunn

Product Management Executive 🖥 Writer 📚 Tea nerd 🍵 Machine Learning Enthusiast 🤖 Physics & Psychology student @ Swinburne