Hindsight is 20/20 — the future can be too

  • Project teams may be physically disrupted by COVID-19 but that doesn’t mean business goals should be.
  • Using ‘retrospective sessions’ to engender a culture of continuous improvement will help projects and personnel stay on track for happy outcomes.
  • Deceptively simple, retrospectives allow teams to talk about issues they face and create constructive actions to overcome them.

Most businesses have found themselves in the situation where they’ve let a deadline lapse, missed an opportunity or had a return on investment that didn’t quite meet expectations. The difference between good companies and great companies is how they learn from those failures, and how they avoid them in the first place. 

Retrospectives, to borrow a term from Agile, are meetings where project teams focus on how they work together and address things that aren’t working. The intent is to set up a cycle of continuous improvement, focusing on actions and outcomes that the team can take to engage differently or improve the flow of work.

In the current pandemic, there is plenty of opportunity to look back on what’s worked and what hasn’t — not least virtual working itself. Where remote working has become the norm and workforces are in various stages of returning to the office, retrospectives need to go virtual.

Retrospectives: The basics of a backward glance

It’s important to note that the focus of a retrospective is not the work itself — even if it has veered off course — but on how the team is working. Talking about what’s not occurred in the project will only bog the meeting down in minutiae and encourage a blame game, rant or scapegoating. Given that most people don’t like talking about failure, it’s critical that psychological safety underlines these meetings.

People who feel exposed are unlikely to open up about what isn’t working for fear of reprisal, and being able to discuss the elephant in the room is the only way that the team can then successfully get around it. For this reason, the general rule-of-thumb is that “What gets brought up at retro, stays in retro.” Communicating a list of agreed actions on what the team has agreed to, and are happy to share, will help, even if it feels awkward to be so blunt.

Running a (virtual) retrospective

While all retrospectives are different, as are the ways that teams work together, there is a basic format that can be followed to drive to actionable outcomes and improved working. Here are six steps to start crafting your own:

1. Run the right session

A quick web search will bring up hundreds of different types of retrospective sessions that you can use to suit the particular dysfunctions of your team. Choosing the right one will go a long way towards creating effective outcomes.

Some easy ones to start with are: ‘start, stop, continue’ where the team focuses on those three points in relation to the way they work;1 ‘plus, minus, interesting’2 which is great for new teams who might not be comfortable calling out ‘negatives’ and can frame them as ‘interesting’; and ‘sailboat’ sessions for teams beginning or midway through a project which will challenge them to project forward as well as look back.3

2. Prepare beforehand and open strong

In person is of course the best way to run a retro, but if virtual, you’ll want to use the right channels. There are a variety of tools (often free) that offer virtual whiteboards or murals that allow participants to use digital sticky notes — for example, Mural, Ideaboardz or Reetro. Paired with a video meeting, you can get a surprisingly good approximation of a co-located experience. 

Make sure you share the link to the board before the session so that participants can familiarise themselves. In your opening session, explain how the tool works and give a couple of minutes over to practicing. 

3. Prime the session with the prime directive

Particularly if this is the first retro that the team has done, or a new team, it’s a good idea to start by explaining the structure as it will help with conversation flow. Include how the session will work, and go over the ‘retro prime directive’: “Regardless of what we discover, we understand and truly believe that everyone did the best job they could, given what they knew at the time, their skills and abilities, the resources available, and the situation at hand.” This will help frame the session and keep it outcome focused.

4. Idea time

Give the team two to five minutes to add ideas to the virtual sticky notes on the session template you chose in point 1, such as what they should start, stop or continue. There should only be one idea per note. If it’s the first time the team has done this, a little extra time is fine, if you’re retrospectively meeting often then less time should suffice. If people need more time, explain that they can keep adding things as the discussion progresses. Additionally, If the team is super ambitious (or large) and there are a lot of ideas listed, you may need to cluster similar ideas and themes to allow for easier discussion.

5. Circle through the idea

The next step is to go through all the ideas. Start with the positive notes and read each out (or groups if they are clustered) and ask if anyone would like to expand on the point. The anonymous author of the note doesn’t need to explain it and everyone should be encouraged to comment. Continue through all the positives and if there are any actions that come from them (for example, continuing to have weekly check-ins) then capture them as an action on a separate note.

Next up, the negatives. Once again, circle through the negative ideas and ask the team to expand on them — they may build on or even disagree with them. Does the team think there is an obvious remedy to the situation? If yes, get agreement from the group and capture the action on a sticky note. All the negatives must have an associated action or group agreement. 

6. Action!

Finally it’s time to address the actions. Generally actions come in two different flavours: those that require effort and have clear outcomes, and those that are values or behaviours that the team should implement. For the first kind, ask for volunteers to own and check-in on their implementation, or if you are an Agile team, add them to your backlog. For behaviours and values, once the team agrees to do them it’s a good idea to circulate them via email or other comms channel (perhaps even a team channel). If there’s a team charter, it’s a great place to add these. 

If there are a lot of actions you may want to prioritise them by giving each person two votes to allocate to those they feel are the most important (by adding a mark to the ‘action’ sticky notes).

Finally, it’s important to make retros work for you. If your teams are already performing or used to regular sessions, your retros could be much shorter but still held to maintain good practices. If the team is time-poor, any improvement may be better than none — a 15 minute session sharing highlights, lowlights and shoutouts can go a long way. That said, if you get to the point that the team is too busy to ever do retrospective sessions? It usually means you need one!

Good old conversation

Retrospectives are a great way to get teams aligned and projects back on track without assigning blame or causing rifts. While simple, they are nicely structured towards outcomes and actions. 

That said, while the actions are important, often it is the discussion as much as anything else that proves beneficial to the team and project. Team members value the opportunity to be heard and air any grievances they might be harbouring, and if they can see that progress is being made to overcome obstacles it can be all the more inspirational. 

With practice, transparency and a commitment to well-functioning teams, hindsight and ‘if only’ wishes will turn into natural, continuous improvement — no rose coloured glasses needed.


  1. https://www.groupmap.com/map-templates/start-stop-continue-retrospective/
  2. http://www.funretrospectives.com/pmi-plus-minus-interesting/
  3. https://luis-goncalves.com/sailboat-exercise-sailboat-retrospective/