Have you had success working for or with someone despite a substantial difference in work culture, values, or communication style?

I’m trying to decide whether to agree to work with a prospective client. The project is interesting, and I have a great deal of respect for the client’s experience and ideas about the project. I also think I have a great deal of value to offer the client. The client wants to work with me, but I’m not sure I’m comfortable with the client’s communication style. The client is substantially older than I am, and I’m worried that my feelings of discomfort might be “ageist.” However, I also know that projects fail all the time because of communication problems, and I don’t want to set up myself or my client for failure because we can’t communicate well with each other.

Have any of you had a similar experience? What did you decide to do? If you succeeded, what helped to bridge the cultural gap? If you failed, what do you think might have prevented failure?