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When to Ask for a Pay Raise & When Not

The professional world can be tricky to navigate. This is especially true if you’re just entering the workplace for the first time. Or, even if you’re a long established pro coming off a bit of a hiatus. No matter the case, it’s important to understand when and how to ask for a pay-raise, and when not. The exact timing of this can come down to a situational basis, however, there are some easy benchmarks and milestones to know when the opportune time to ask for a pay raise might be. Recognizing these opportunities isn’t only good for you as an employee, but also keeps employers honest, and keeps them aware of employee value.

“Deciding when to ask your boss for a raise is stressful. It involves a certain level of risk—what happens if they say no?—not to mention, money is a difficult subject to talk about in any situation, let alone with a superior at work. So you need to be sure you’ve got a solid case before you make the request. It’s especially tricky because asking for more money depends on factors within your control, like performance, but also outside factors, like how well the company is doing.”

-Nell Wulfhart, Decision Coach

During Negotiations

During negotiations is one of the best times to ask for a pay raise. This is because you’re brand new to the company. Establishing an understanding of the value that you bring to the table, and not compromising on that value earns respect in many offices. Take the time to do some industry research and to check up on a company before the interview. You don’t necessarily want to shoot for unreasonable figures, but don’t be afraid to ask for what you deserve, either.

“Good employees often know what they’re worth. Whether they’re coming from another organization or if they’re entering the industry fresh. It helps too, to know that your employees know their value. It shows a level of self-awareness and I think that’s why it can be so impactful. If you don’t know your worth, how will I?”

-Trey Ferro, CEO, Spot Pet Insurance

Negotiations are also a good time to ask for a pay raise because it sets expectations from the start. When both parties come to an agreement on an offer, it increases the chances of a long-standing employer-employee relationship. This is more valuable than it might seem at first glance. As many business owners, entrepreneurs, and hiring managers know, employee turnover is one of the most expensive costs a company can incur.

When to Ask for a Pay Raise & When Not
businessman in office room begging gesture raise

“Good employees are hard to come by, it’s very true. I think the quality of most organizations comes down to the people. How they work as individuals, how they work together, what motivates and drives them. Money, a lot of the time, but also not money a lot of the time. Extra vacation days, or good benefits for their entire family. These things matter to employees too, and they play a significant role in reducing turnover.”

-Chris Gadek, Head of Growth, AdQuick

After The First Year

This is a classic time to ask for a raise as an employee. Partially because it will most likely align with some sort of review period around the same tenure. With that in mind, and a year under your belt, this makes for an excellent opportunity to make your value and your worth known. While some jobs can take a while to get used to, most employees have a solid grasp of their role after the first six months or so. With a strong performance over the first year, asking for a raise is certainly within grasp.

“A year is a great benchmark for most employees, I think. It gives them enough time to settle into the role without feeling rushed, but it’s still new enough that they have a lot of thoughts and energy about what could be improved and how. This is all really potent fuel for the right organizational leader. Of course, it can be easy to become stagnant and complacent, but the influx of new ideas from a fresh pair of eyes can sometimes be a total game-changer.”

-Michael Hennessy, Founder and CEO, Diathrive

While the end of your first full year in a new position can be an opportune time to ask for a raise, it does depend slightly on your role, your performance, and the company’s overall standings as well. Understanding where you fit into the greater context of the organization as a whole can help in deciding when to take the leap of faith and ask for a raise.

“I respect employees who can see the bigger picture of things. In a dream world, we’re all millionaires, but that’s just not really feasible. It can be refreshing to hear someone ask for a raise when they’ve been putting in the hours and their work is paying off. On the other hand, it’s nice to know that my employees have a sense of when the business is in a position to actually deliver those raises.”

-Amanda E. Johnson, Chief Marketing Officer, Nailboo

Following an Impressive Quarter or Accomplishment

This pertains to jobs that have easily trackable performance metrics. Sales is a great example of this. In the world of sales, professionals have to be willing to ride the roller coaster, so to speak. There will be down months, and slow quarters, but there will also be hot-streaks and wild peaks. Moving beyond strictly sales, though, it makes sense to ask for a raise after a particularly impressive performance over a period of a whole quarter.

“Performance is always helpful when asking for a raise. If you can say ‘look this is where I added value, here are the numbers.’ That makes for a pretty compelling case in most instances.”

-Jorge Vivar, Creative Director, Mode

There are other key performance indicators to mind as well, though. One such case is leadership. Some employees are charged with leadership tasks, or heading a large-scale project for the organization. In these instances, it can be appropriate to ask for a raise after successfully bringing a project to fruition.

“When someone takes on their first big project it’s a huge professional milestone. It can open a lot of doors within the organization, too. Then, raises are certainly warranted if it’s successful and the employee charged with the project does well.”

-Jae Pak, Founder, Jae Pak MD Medical

In the Wake of Continued or Extended Education/Training

After completing a course, a training program, or adding a new degree to your resume, it’s absolutely worthwhile asking for a raise. Employees that stay up to date on the latest trends and industry tools, often soar above the rest and stand out. Knowing the value of continual education is vital in the pursuit of fair compensation.

“Education and training is huge. There are a lot of positions that pay simply based on the level of education and training. Nursing is a great example. The more nursing school one has, the higher the pay-rate scales. Industries that offer a lot of continual training make for a lot of potential raises.”

-Michael Ayjian, Co-Founder & Executive Producer, 7 Wonders

One caveat to note about continual training and education is that it needs to be relevant to the job or career at hand. If the courses aren’t pertinent to the role or function of the position, it may not warrant a raise.

“Employees are at the core of any and every organization. There’s a certain level of trust that goes into a hiring decision, and maintaining that throughout an employee’s tenure relies on the company’s ability to really take care of that person and provide them a space in which they can succeed and feel successful.”

-Jaymee Messler, CEO, Gaming Society

Know When to Ask and How

Time and time again, employees leave money on the table by missing opportune moments to ask for a raise. This is the most important thing to take away from all of this: recognizing when it’s a good time to ask for a raise, and being confident in expressing your worth at that time, are key ingredients to reaching a fair and competitive compensation package.

“I’m constantly alarmed by how many people tell me they’ve never asked for a raise. They feel awkward about initiating the conversation, or feel like they never get an opening to do it, or they’re worried they’ll sound greedy, or they just have no idea how one would ask for a raise at all.”

-Alison Green, Columnist, The Cut

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