Retrospectives, as applied in software development, have historical roots in Project Retrospectives described as:

"A ritual held at the end of a project to learn from the experience and plan changes for the next effort." [KER01]

While Retrospectives conducted at the end of a project remain valuable, the spirit of Retrospectives should be imbued across the project continuum, conducted at key project milestones: at the end of project iterations, releases, and immediately upon occurrences of key project incidents (significant unexpected events).

When the practice of Retrospectives is intimately intertwined with the processes of the project, the health of the team is constantly monitored, the heartbeat of project progress is readily measured, and the team hones an awareness of opportunities for improvement and increased productivity. A symbiotic relationship emerges between an evolutionary development process and a Retrospective that supports the various methods of inspection and adaptation.

The iteration, incident, and project Retrospectives are designed, in part, to calibrate the team's progress with the goals of the project. Several methods can be used to incite the Retrospective team to begin their collective investigative work, such as posing the following three driving questions to the team: "What worked well for us during the past iteration (or project, and so on)?", "What did not work well for us during the past iteration (or project, and so on)?", and "What should we do differently, or what improvements should we undertake during our next iteration (or project, and so on)".

The questions are expected to generate actions that will assist the team in prioritizing suggested improvements for the project, to be implemented during the subsequent cycle. In addition to the aforementioned investigative questions, a Retrospective should include steps that provide structure for the team's focus and resulting work.

An effectively facilitated Retrospective will create an environment that is conducive to various practices of inspection and adaptation. The methods of inspection and adaptation are project control mechanisms that assume, and respond to, the existence of complexity, unpredictability, and constant change. Practiced in the context of a Retrospective, the methods of inspection and adaptation produce a feedback loop from which flexibility, responsiveness, and reliability are realized.

The mere execution of Retrospectives is insufficient without an organizational commitment to a collaborative culture. The success of Retrospectives is directly proportional to, and necessarily contingent on, an environment that engenders highly motivated and performing teams (not the individual), nurtures open and frequent communication, and a thriving sense of dedication to the team community. Retrospectives embody the spirit of team collaboration and self-reflection by offering an environment in which teams are encouraged to provide feedback and identify lessons learned [DER06]. The compositional aspects of the team are crucial in supporting the highly collaborative nature of Retrospectives, enabling the team to produce insight(s) into improving the processes of the project.

The participants that gather in the context of a Retrospective constitute more than a "working group". The participants should be thought of as "a small number of people with complementary skills who are committed to a common purpose, performance goals, and approach for which they hold themselves mutually accountable." [KAT93]

The participants should consist of individuals representing cross-functional groups, having been involved in the project period or project incident for which the Retrospective will be conducted. The size of the team is important, for the rigorously participative environment of the Retrospective may be difficult to achieve with an overwhelmingly large group (25+ individuals), and a time-boxed period in which to conduct the Retrospective. Conversely, a small set of participants that is under-represented by the appropriate functional groups will limit the benefits and productivity of team collaboration and self-organization. Although a Retrospective achieves productive results by actualizing team responsibility, self-organization, and opposing traditional imposing authority, the work conducted in a Retrospective - involving the members of cross-functional groups - demands the presence of a designated facilitator.

The individual that is designated to assume the role of facilitator, or Retrospective leader, should possess fundamental skills of a facilitative management approach:

"A facilitator is an individual who enables groups and organizations to work more effectively; to collaborate and achieve synergy. She or he is a "content neutral" party who by not taking sides or expressing or advocating a point of view during the meeting, can advocate for fair, open, and inclusive procedures to accomplish the group's work. A facilitator can also be a learning or dialogue guide to assist a group in thinking deeply about its assumptions, beliefs and values and about its systemic processes and context." [KAN96]

The facilitator can be expected to allow the participants to exercise a sense of ownership in the operating mode of thought, act to remove impediments to the team's effort to reach targeted goals, foster an environment of trust and thriving collaboration, and support the team in a manner that allows the team to achieve its best thinking. Ultimately, the facilitator focuses on managing the format of the Retrospective, while the participants hone their skills in managing the Retrospective content and maintaining a high-performance, participatory group dynamic.