Negotiating a Raise Takes Time, Not Just One Conversation, Says Compensation Expert

Asking for a raise may feel like a high-stakes, one-and-done conversation, but experts say the reality is far more drawn out — and strategic. According to Kathryn Valentine, CEO of Worthmore Strategies, the process of negotiating a better compensation package is not a single meeting but a multi-week effort requiring patience, preparation, and persistence.

Valentine, whose firm has helped hundreds of clients negotiate their salaries successfully, emphasizes that securing the raise you want is rarely achieved in just one discussion. “Some people think of this as this one-time conversation I have to have, and it’s so stressful, like buying a house,” she says. “It’s not buying a house.” Instead, she frames negotiation as an ongoing career skill that improves over time.

Two people shaking hands | Source: Pexels

A Strategic Approach to Timing

One of the key elements to a successful negotiation is choosing the right moment to begin the conversation. While annual performance reviews might seem like the natural time to raise the issue, Valentine notes that by then, most organizations have already finalized their budgets for the year. That makes it significantly harder to secure additional resources.

Instead, Valentine recommends initiating the conversation during a mid-year review or check-in. This timing allows managers to consider the request as part of future planning. “Your annual review can feel more like a celebration if it doesn’t include serious salary talk,” she adds.

However, the company calendar is not the only consideration. Valentine stresses the importance of picking a time when the manager is most likely to be open and attentive, not during a personal or professional crisis. Ideally, employees should request the meeting after taking on new responsibilities or achieving a significant win for the company. Setting up the meeting like a regular check-in and giving advance notice that compensation will be a topic of discussion can help set the right tone.

Two people shaking hands | Source: Pexels

Preparing for a Multi-Step Process

Valentine is clear that the first meeting is only the beginning. “In the first meeting to negotiate a raise or other changes to your compensation, your goal should just be ‘to set yourself up to be successful’ — not to reach an agreement,” she says.

Managers will often need to consult with senior leadership or assess financial viability before approving any adjustments. This delay doesn’t signal rejection, according to Valentine. Rather, it’s a standard part of the process that should be anticipated and planned for.

To keep momentum, Valentine advises employees to secure a follow-up meeting before the initial one concludes. Setting a specific date ensures accountability on both sides.

Following the meeting, employees should also send a summary email to confirm the next steps and include notes from the discussion. “A lack of documentation doesn’t delay the process even further,” she explains.

Two women talking | Source: Pexels

Collaboration and Patience Are Essential

The bottom line, according to Valentine, is that patience and persistence are critical to achieving compensation goals. While the process may take several weeks and involve multiple discussions and follow-ups, approaching it as an evolving dialogue — not a one-time pitch — ultimately leads to better outcomes.