Try This When Your Boss Turns Down Your Request

Rejection at work can be discouraging.

Olga, a successful trial attorney in a small firm, shared the following story and strategies about overcoming an initial “no” from her boss.

1) Outline your goals without creating rigid expectations about what you want.

Here’s some helpful negotiation jargon to get us started. When preparing for a negotiation, consider both your position and your interest. A position is your desired outcome – the best way you can think of to resolve the negotiation. Alternatively, an interest is your underlying goal or motivation.

Because of a demanding caseload, Olga wanted to hire a paralegal. Her position was that she wanted her boss to hire a full-time support person. Olga’s interest was to improve her efficacy, increase firm revenue, and improve her quality of life.

2) Frame the request in terms of how it benefits your boss.

Olga approached the conversation with her boss focused on why hiring a paralegal was good for the firm. She shared how much a paralegal would cost and explained the specific ways having support staff would increase the overall revenue she could generate for the firm.

Unfortunately, Olga’s boss didn’t want to allocate the funds for a paralegal or to take on the responsibility of paying an additional salary on an ongoing basis.

3) Find a smaller request that is more likely to get approved.

While Olga was frustrated, she was also clear about her goals: she knew her quality of life and job satisfaction would improve if she had a paralegal.

Olga found a paralegal who agreed to work part-time for six months, the duration of a big case. Olga decided she was willing to use her own money and hire the paralegal to work directly for her, without creating any additional burden on the firm financially or in terms of staff management.

When she approached her boss with this proposal, he accepted.

Olga’s goal wasn’t to trick her boss into doing what she wanted or to go behind his back. Instead, she approached her boss with a new potential solution that addressed his concerns, while still meeting her goals.

4) Share new information with your boss, ideally showing how your request benefits them.

Within a year, Olga was able to demonstrate the tremendous value of having this paralegal at the firm.

Olga’s boss agreed to hire the paralegal full time and began invoicing clients for the paralegal’s billable hours, so the new position didn’t create an additional expense for the firm.

The new role served as a significant benefit to Olga, the firm, and the firm’s clients. Not only has Olga’s income increased by well over 50%, but the return for her clients has been substantial. Their cases are getting closed out nearly twice as fast, and her clients are seeing far larger financial returns from their cases.


While many of us aren’t in a position to pay out of pocket for additional staff, Olga’s approach is one that we can all replicate using the steps above.

Let’s review. Olga’s ideal negotiated agreement or position was for her law firm to hire a full-time paralegal. When her boss rejected her initial proposal, Olga could have sulked away in frustration, pushed her boss harder to hire someone, or started interviewing at other firms. Instead, because Olga got creative, she was able to get what she needed and walk out of the negotiation well positioned to have her boss listen to her in the future.

If Olga and her boss had gotten stuck in their positions, the conversation would have ended at the impasse of Olga’s position (I want my boss to hire a paralegal) and her boss’ position (I don't want to). Being focused on positions often prevents people from seeing alternative ways to have their underlying interests met.

By discussing interests and deeper goals, Olga and her boss were able to come up with a great alternative option that was beneficial for everyone involved.

A version of this piece was originally published by Forbes.