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Guide to Conducting Effective Project Retrospectives

Many project managers are familiar with the concept of “lessons learned” meetings conducted at the conclusion of a project. But lately, project retrospectives have overtaken "lessons learned" as the preferred term. While the two phrases may sound similar, project retrospectives have a more positive connotation that spawns from the agile principles of teamwork, collaboration, and celebrating successes.

Many project managers are familiar with the concept of “lessons learned” meetings conducted at the conclusion of a project. But lately, project retrospectives have overtaken "lessons learned" as the preferred term. While the two phrases may sound similar, project retrospectives have a more positive connotation that spawns from the agile principles of teamwork, collaboration, and celebrating successes.

When teams accustomed to participating in projects hear the phrase “lessons learned”, they immediately picture a meeting where the objective is to discuss what went wrong during the project. This biased meeting does not lend itself to productive, actionable plans.

Project retrospectives, however, stem from the agile project management culture of failing fast and learning from mistakes in order to quickly focus on satisfying your customer’s needs. This forward-looking mentality provides a strong foundation for producing actionable results from retrospectives, in order to help the team execute more effectively on future projects.

Why are project retrospectives important?

Any team striving to improve their ways of working should make retrospectives standard operating procedure for their teams. You'll realize the best results when the team conducts retrospectives two or three times throughout the course of a project, in order to catch potential issues early on in the project, rather than waiting until the project's completion.

The value in retrospectives, which are traditionally conducted at the end of every agile sprint, is that they occur frequently during the development process and allow team members to pivot direction quickly. By conducting a retrospective regularly, the team harvests more value out of the reflective process, especially as retrospectives typically include action items to make the team better. Team members walk out of the room with assigned tasks to research and address the “what could we have done better” question, rather than simply venting about the issues that arose during the project, and forgetting about them after the meeting ends.

How To complete a successful project retrospective

Retrospectives typically answer 4 key questions:

  • What did we do well that we should keep doing?
  • What could we have done better?
  • What shout outs would you like to give to your team members?
  • What action items need to be taken to improve in the future?

Notice that the questions use the word "we", rather than "I" or other singular phrases. The goal of a retrospective is to reflect on the team’s ability to collaborate. Therefore, when an issue arises, it isn't the fault of a specific team member, but of the team as a whole. This avoids the finger pointing game, and puts the onus on all team members to call out concerns before they become problems.

Because it may be difficult for team members to answer these questions on the spot, some retrospective facilitators conduct pre-work for these sessions. By anonymously surveying team members prior to the live retrospective meeting, the facilitator can get a general sense of the themes that should be addressed, and that are of the utmost concern to the team. This is commonly done by using anonymous online survey tools, such as Google Forms) to ensure the anonymity of the participants.

Given the results of the survey, the team can focus on a more in-depth analysis of specific themes, fleshing out the details of why particular areas were successful and how other areas could be improved. For instance, knowing that documentation was a problem area for the team, instead of simply calling out the problem, the team can focus on discussing the root cause of missing documentation, which feeds into an action plan for the future. Root causes might include miscommunication where two team members each thought the other was writing the documentation. In this scenario, one possible action plan could be to provide clearer owners for each task.

Retrospectives should be about collaborating to solve problems so that the entire team can be successful; that’s why celebrating successes is also a key component of retrospectives. When a task is done well, the team should also ask why it went well, so that repeatable steps can also be incorporated into your standard operating procedure.

Referring back to previous retrospectives

It is disheartening when a team sees the same themes repeated at each retrospective, without any improvements. This happens when the team is more concerned with their next deliverables than they are with confirming that old issues have been properly addressed in a sustainable way.

This is why it's the project manager’s responsibility to track the action plans from retrospectives and raise any risks associated with repeated issues before they become problems subsequent projects. Unfortunately, like ever busy project teams, project managers are also always moving on to the next project. In order to avoid this, it's helpful to enforce that the project closing phase includes the proper creation and filing of project artifacts and the results of retrospectives.

Making retrospectives actionable

In larger organizations, the process of filing the results of retrospectives is key to ensuring that other project managers can leverage the learnings from other project teams. Intel, for example, addresses this challenge by ensuring that project managers hold a retrospective readout with upper management and other project managers within a month of completing the retrospective. This direct communication gives leadership a heads-up that certain preventative actions should be taken, and highlights risks that other project managers should look out for in the future. Even if this readout happens months before the next relevant project, it helps other project managers know to go back into the retrospective archives to find the specific mitigation plans that should be used for future projects.

Of course, if the retrospective data isn’t stored properly in a searchable manner, the documented results are of little use. Document repositories that are well-organized with searchable categories, labels, or tags helps larger organizations leverage best practices from projects even after the original project leader has moved on or left the organization. Project managers should be trained to file their retrospectives away in a standardized format, and make a habit of referring to previous retrospectives as part of the project initiation phase. In doing so, issues that arose during previous projects can be added to the risk mitigation plan, and teams can get ahead of potential issues without having to learn the hard way.

In summary

Retrospectives are a key component to the long-term success of an organization. The motivational aspects of celebrating wins, recognizing individuals, and encouraging growth takes the concept of “lessons learned” from a negative review of the past to a forward-looking meeting to improve the team's execution. By integrating the practice of retrospectives into the project management life cycle, teams are empowered to own their growth and leverage the organizational knowledge of their predecessors.

Bruce Hogan

Bruce Hogan is Co-founder & CEO of SoftwarePundit. He leads the team's research and publishes content about software products and trends. Bruce has experience investing at multi-billion dollar private equity firms, leading teams at venture-backed technology companies, and launching new businesses. You can connect with Bruce on LinkedIn.

Bruce is an expert in several software categories including:

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