A successful raise talk with your boss hinges as much on how you ask as it does on the validity of the ask itself. As such, taking a misguided approach or angle during the conversation can leave your boss on the defensive and you, empty-handed—even if you’ve very much earned the boost in pay you’re seeking. To avoid that counterproductive scenario, it’s worth considering not only what career experts suggest you do say, but also what not to say when asking for a raise.

First, though, remember that you are your own best advocate when it comes to getting the pay you deserve, so if the notion of awkwardness is what’s stopping you from broaching the subject of a raise from the jump, work to abandon that thought. As pay-parity advocate Claire Wassermanpreviously told Well+Good, if you feel as though you’ve earned it, it’s worth asking: “What I remind everybody is, if you do not ask, it’s 100-percent guaranteed that you will not get more money.”

Deservedness aside, coming to the conversation armed with evidence of why you’ve earned a raise will only help bolster your case. “Have clear records of the results you’ve achieved, positive internal or external feedback, and anything else demonstrating progress,” says Ashley Stahl, resident career expert at finance company SoFi.

“Have clear records of the results you’ve achieved, positive internal or external feedback, and anything else demonstrating progress.” —career expert Ashley Stahl

It’s also helpful to write out your accomplishments from the past six to 12 months, so you can relay them in an organized fashion during the talk, says Colleen McCreary, Chief People Officer at Credit Karma. “When describing your individual successes, focus on how they’ve helped the company achieve its goals versus your own,” she says.

To make sure you avoid common pitfalls during the conversation and keep the chat on a positive trajectory, consider these five expert tips for what not to say when asking for a raise, and why.

5 of the worst ways to ask for a raise, according to career experts:

1. Acting as though you’re entitled to the raise, based on tenure

It’s fair to want a raise for the substantial time, energy, and effort you’ve poured into a role, but the basis for that decision correlates with the responsibilities you carry and the results you achieve—not just your presence at the company for any particular amount of time.

“The duration play is a weak argument,” says Lily Valentin, head of operations for North America at job-search engine Adzuna. “Employee retention is important, but it’s far more effective to ask why you’ve been looked over for raises throughout your time as an employee rather than to push for one based solely on how long you’ve been at the company.”

2. Comparing yourself to colleagues

While salary transparency among employees can help you ensure you’re being paid within the industry-standard range for your role (and can shine a spotlight on unfounded wage gaps), basing your ask for a pay bump solely on the salary of a co-worker is tricky territory. That’s because you may be lacking some important information that renders the comparison void: “There are many reasons why a co-worker could be making more than you for a similar job, like their experience, results, education, background, language skills, and more,” says Stahl.

In fact, steering clear of any co-worker comparison is your best bet—and that includes comparisons surrounding performance, particularly if you’re attempting to show how much better your performance is over someone else’s (or, worse, criticizing a colleague to bolster your own case). “As more companies continue to focus on building unified teams, there’s nothing more unsportsmanlike than bad-mouthing your team in an effort to make yourself look better,” says Valentin.

3. Getting too personal

While your take-home pay likely supports your non-work goals and your manager may also be (and hopefully is) invested in your personal well-being, a raise still reflects a transaction made to support a business, not your individual life.

“The business has a need, and a raise is money paid for results satisfying that need,” says Stahl. “Your promotion in pay or responsibilities has nothing to do with the cost of your rent, the stress of your debt, or anything related to your personal needs.” And trying to leverage such matters as rationale for extra compensation simply wedges your manager in the awkward space between their concerns for you as a person and their responsibilities to the company.

4. Timing your ask poorly

Simply bringing up the conversation at the wrong time can be enough to put the kibosh on your raise prospects entirely. With that in mind, Stahl offers a few times that should be totally off the table when it comes to asking: Anytime outside work hours (including weekends), whenever your team is incredibly busy, or whenever your company is in the midst of a period of layoffs. “You should also avoid asking in passing or during a meeting focused on something else,” she says. “If you treat the request casually, your boss is likely to treat it casually as well.”

It’s also important to consider the timing of your company’s performance-review cycle (if applicable) and align your ask accordingly—which actually means not waiting until your annual review to do it. “Your boss will likely come into that conversation with a set budget in mind that’s perhaps already been approved by HR,” Stahl says. In fact, the money for raises may have been allocated several months prior, so it’s helpful to start the conversation three to six months ahead of your review to get the ball rolling while there’s still budget flexibility.

5. Offering an ultimatum

Threatening to quit if you don’t receive a raise is a very risky gamble, says McCreary: “Some companies may negotiate or offer you something new, but they also may not and could even ask you to leave sooner.” While it’s certainly inconvenient for your boss to have to replace you, it may be just as dissatisfactory for them to keep someone onboard who they know isn’t happy to be there, adds Stahl.

Not to mention, your boss’s hands could very well be tied by budget restrictions, so coming to them with an inflexible threat may push them into an impossible position. Instead, be open to negotiation, says McCreary: “Your manager may not have the power to approve a change to the budget on their own, but perhaps they can offer additional time off, shift your projects, or cover the cost of some professional development courses.” This way, you’ve both surfaced your ask (so that it’s on their mind whenever budget flexibility returns) and shown that you’re adaptable to the current needs of the company, while potentially securing an additional perk in the process.

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