Since there are technically no "mistakes" in improvisation, it often becomes difficult to assess the quality of each jam session, and/or if what had transpired was "successful" or not. While some greatly appreciate the open-endedness and the endless possibilities that the process has to offer, others find themselves frustrated with the activity's lack of clear objectives and eventually turn to other ideas in order to find fresh inspiration.
Both mentalities each have their respective points, but the beauty of improvisation is that by approaching music in this way, the power of goal-setting is determined by the performer themselves. If the objective for a jam session between 3 people was to play something in the key of C major, then that can be established ahead of time and performed with that understanding in mind. If the goal was to play something in an ABA form, that could be attempted as well. If the intension was to simply play and explore the resultant sounds, or break the ice between the performers, that could also be time well spent.
In my experience, the sessions that I felt was the most productive were the ones where the musicians established simple but clear-cut structures played for relatively short durations (1-2 mins). This helps the musician to quickly internalize the concepts behind the exercise and also helps them to direct their ears toward what's happening around them. As with any improvised session, the music will sometimes take a different turn from what was originally conceived, but having a place to start from tends to give its departure a stronger sense of intentionality and significance. Many or most of the ideas listed on this site are designed for this purpose -- not as prescriptions of how or what to play, but as general guidelines for musicians to direct their ears toward what they might want to play next.
We now have access to cheap and easy to use recording technologies which makes the process of assessment a much easier task. It is recommended that, at least in the beginning, musicians record everything they play during these sessions and determine if the outcome matches what they originally intended. If they're performing with other musicians in a group, talking about what had transpired is also extremely helpful since it allows for the individual to gain additional perspectives of the same event.
It could be argued that the overall goal of improvisation is to eventually get to a point where musician's intensions (theory) are in complete correlation with their actions (performance). Outcomes will vary depending on background, experience, and skill level, but there is a certain integrity and "trueness" to a musician's output when their ideas are completely synchronized with their instrument. Regardless of style or medium, this is something that everybody can achieve if the will to do so is there, and it is this type of directness that tends to speak to audiences on an emotional level.