I'm on the board of a non-profit volunteer lawyer organization that has been surveying its volunteer lawyers and their clients. Among the questions are questions about whether the outcome was good or bad, or whether the result of the case improved the client's life. The answers of the attorneys and the clients don't correlate well.
It's clear that the context is different. The lawyer looks at the case in isolation. A dismissal or a favorable settlement is a win. To the client, the legal problem is often just one checkbox on a long list of problems. It may be an obstacle cleared, but it may not make a measurable difference in their life.
Private clients may not usually be in the same kind of dire straits as impoverished clients often find themselves, but there is often a similar disconnect. An expensive win may be a barely-preferable alternative to losing. A settlement may feel like capitulation.
Setting expectations is always a challenge, but it's equally important to agree with your client on what "success" means. That's the only way to assess the end result of the representation. Maybe an expensive win is the best you can hope for, but that should be something your client signs off on from the beginning of the representation.
How do you make sure you and your clients view success the same way?