What I’ve Learned From My Failed And Successful Salary Negotiations

You can’t always guarantee success, but you can always put yourself in the best position to get what you want.

What I’ve Learned From My Failed And Successful Salary Negotiations
[Photo: Gary Waters/Getty Images]

I remember vividly the first time I asked a boss for a raise. I was 24 and had just finished my first week as the office manager and assistant to an executive producer for a music video company in L.A. I was holding a check for $500, my salary for that week of work and the foreseeable future. I had agreed to the rate out of desperation, when my internship (through which I was earning $50 a day labeling hard drives) opened a door to joining the company full-time.


The night before, it had suddenly dawned on me how little $500 a week was. Between rent, car insurance, gas, and food (not to mention forthcoming taxes), there was the high risk that I would actually end up in the red after covering my basic necessities.

So I did what I had never done before. I opened up my laptop, wrote a heart-pounding email to my boss, and asked for $650 a week. Via email. A week after starting the job. On a Friday night. Needless to say, I had a lot to learn about salary negotiation. And in case you were wondering, I wasn’t successful that time around.

My family immigrated to Canada from Malaysia when I was a baby. Growing up, my parents took on grueling blue-collar jobs around the Greater Toronto area, earning hourly wages doing shift work at odd hours. I’m the first generation in my family to graduate from university. I share this to convey that I didn’t grow up with people who could advise me as to how to negotiate a salary in a corporate setting. Everything I’ve learned about salaries and salary negotiation, I figured out for myself.

I’ve negotiated (or attempted to negotiate) my salary about five times, and I’ve been successful three times and rejected twice. I now negotiate anytime I start a new job, at every annual review, and every time I’m given a promotion or a significant increase in my job responsibilities. Why? Many jobs earmark a salary range, not a specific salary number, for new positions, and most companies should expect a salary-increase ask at annual performance reviews. Otherwise, thanks to inflation, employees are actually making less money every year. Think about that.

Financial considerations aside, I’ve also learned that negotiating earns you respect because you are setting a value for yourself and your work instead of letting someone else set it for you. It’s an important skill to master if you want to be taken seriously and climb the ladder in any industry.

Related: Exactly What (Not) To Say When Negotiating Your Salary 


So as learned through my own successes (and more importantly, my failures), here are my best practices for asking for–and getting–more money:

1. Pick An Appropriate Time To Ask

You already know that initial job offers, promotions, and annual reviews are key times to negotiate your salary. That being said, you can certainly ask for more money outside of those moments, so long as you choose your timing wisely and are sensitive to the events in your manager’s work life. Major upheaval in the company? Your manager just got a new manager herself? It’s a Friday night the first week into your new job? You might want to wait until your boss is less stressed or preoccupied.

Related: How To Negotiate Your Salary When You Have No Obvious Leverage

2. Have The Conversation In Person

I learned this the hard way in my $650 email ask. Negotiation should be a dialogue between you and your manager, and not come in a one-sided email that may go unread. A simple verbal declaration on your part that requires only a “yes” or “no” response from your manager isn’t your best bet either. Salary negotiations are a conversation–about your work, the future of your position, and where the company is overall. It’s more than okay to have notes and a loose script for your in-person meeting so you feel prepared to bring up all the relevant points as to why you should receive a raise.

3. Warn Your Manager Ahead Of Time

Don’t drop the salary-negotiation bomb at the end of a check-in meeting during which you were discussing other routine projects. Be clear that you want to set up a meeting specifically to discuss your compensation. (If it’s your annual review, your manager should be expecting as much.) This allows your manager to mentally prepare for the conversation and to investigate if there are salary caps for your position. (Oftentimes these are out of his or her control, and he or she will need to ask for information from HR or his or her manager). A fruitful conversation doesn’t start with making your boss feel blindsided.

4. Mention Tangible Results In Your Negotiation

Promptly take the word “deserving” out of your vocabulary. “Deserving” a salary increase because you feel like it’s time is unconvincing. Instead, make the numbers case for higher compensation. That means quantifying as many aspects of your job as possible. Your manager is less likely to rebut clear, hard evidence. For my most recent salary negotiation, I made a Powerpoint presentation that summed up all the work I’d done in the past year, along with the quantified results of that work and details of the additional projects and initiatives I’d taken on. I included information around the volume of content I’d worked on, other colleagues’ work I’d supported, presentations I’d made across the company, and a detailed list of new processes I’d proposed, organized, and templatized. My manager remarked afterward that she didn’t realize how much I had been doing, which signaled to me how important it was to regularly quantify and communicate your work to your manager.


Related: Here’s What You Need To Negotiate At Each Stage Of Your Career

5. Check Your Emotions At The Door

This one is hard, I know. It’s natural to feel like a rejection is a personal blow to your worth as a human being and as an employee. I’ve found myself in the cycle of soaring high when I got a compliment on my work and falling really low when something was called out as not up to par. But it wasn’t sustainable, and when I got better at separating my personal self from the work, I became a more effective professional and a happier person.

6. Whatever The Outcome, It’s Important To Pat Yourself On The Back

If you are unsuccessful negotiating, it’s still a win, because you most likely gained information on your position that you can leverage in the future. This might include the salary cap for your position, the financial situation of your team or company, what skill sets you might lack, and what you need to do before revisiting the salary conversation with your manager. Putting yourself out there will only help you.

A version of this article originally appeared on the Well, Jopwell’s digital magazine, and is reprinted with permission. Jopwell is the career advancement platform for black, Latino/Hispanic, and Native American students and professionals.