Except in emergency mediations, the clients are asked to fill out a confidential mediation form, so that Bob has a good idea of what each party is seeking.
For the first mediation session, Bob meets with all of the parties, and the parties' attorneys if they attend the mediation (that is decided before the first session). In high conflict cases, at the first meeting, the mediation process and Ground Rules for Mediation may be discussed; and the parties may be asked what their goals are for the mediation, In cases where the parties are able to agree more and have less conflict, the first session may begin immediately with a discussion of the issues.
In mediation, Bob asks questions to get the parties talking to one another. If they can't talk civilly to one another, then they carry on a dialogue by speaking only to him. While one is talking the other can take notes, bite his/her lip, or whatever, but he/she should not interrupt. In mediation, listening is as important as speaking.
Usually, the parties start together around a table, with the discussion guided by the mediator. Although a separate "break out" room is available for the mediator to meet separately with the parties, usually family mediation is conducted with everyone together. Particularly if there has to be future communication between the parties (e.g. they have children) it is important for them to work through the issues together. However, each case is different, and Bob uses his considerable experience to tailor each case so that each session will be most productive.