The Big Retrospective

I hate to break it to you, but the end of the year is almost here. Of the many activities we undertake during this season, my favourite, by far, has to be the year end retrospective; and if there was ever a year to do one, it has to be this. 2020 has been a year of surprises, lessons and accommodation. More has happened over the last nine months as compared to the last nine years. Hence, irrespective of whether you are excited that the year is coming to a close or disappointed, ear mark time on your calendar to take your team through a retrospective exercise.

 What is a retrospective?

In order to excel, it is often important to step away from the endless loop of delivery to reflect on the events gone by and learn from them. Retrospectives help us do exactly that. Derived from the world of technology and the agile methodology, retros are a safe space for the team to discuss what went well, what didn’t, learnings from the time period and action items/ improvements for the next iteration. It keeps the team nimble and continuously improves delivery.

Technology teams do retro exercises at the end of every sprint, or a deeper exercise while analysing a process. I do one for projects and milestones that I am a part of. However, the year-end retro is the mother of all retrospectives. It is the perfect opportunity to take a look at everything that has happened in the past year, break it down into buckets and take the many learnings into the goal planning exercise that follows.

Organizing & delivering a retrospective

Start with a classic retro board. There are endless online tools available today to help conduct retrospectives. Most organizations also have their own build in tools to help with the exercise. While choosing a retro board, pick one that allows the option to vote and gravitate towards simplicity. I have used ideaboardz in the past and found it highly effective. Most boards allow you to customize the labels. So get creative or use the basic four (went well, need to improve, stop and actions). For my current retro board, I have included two additional columns–one for random thoughts and one for ambitious ideas. Even though you could create endless sections, try keeping it to not more than six.

Once you have created the board, invite participants to add their thoughts. Each thought goes in as a separate entry, allowing other to add their votes to the idea. I keep the board active for a week, encouraging everyone to keep it open on their browser and return to it at least once a day or whenever an idea strikes.

At the close of the week, get the team together to go over the entries and derive action items based on what they’ve read. In better days this used to be a high-energy, two hour in-person meeting involving a lot of whiteboard scrawling and pacing. In our virtual world, it is yet another video call but an exciting one nevertheless.

At the end of the exercise, what you uncover is a bounty of wealth to take into your goal planning exercise.

Some tips

1. Break the ice: Get everyone to say at least one word in the first five minutes. Those who speak early on are likely to pitch in throughout. Set the stage to help people get out of their everyday work mode, switch context, and sink into the exercise. Once you’ve set the stage ask a simple question. My favourite is ‘If you could go anywhere in the world, where would you go?’ and then once you’ve done a few retros, maybe ask which one is the best they’ve ever attended.

2. Don’t lose sight of what went well. Even though the conversation tends to gravitate towards what didn’t go well and needs improvement, it is important to discuss what went well in order to further strengthen it.

3. Follow through: It is often tempting to create an ambitious list of wants only to have them disappear into the vast digital landscape, never to be seen again. Like most other things, without diligent follow through, retrospectives do not work. Port the action list into the goal planning exercise and track on a regular basis.

4. Circle of influence: The other pitfall of retros is the temptation to blame everything that has gone wrong on characters not present in the room. Remind your team to separate out what they can control, what they can influence, and what they cannot. Use this distinction to help frame the action plan.

5. Do them often: While the end of the year is a great time to reflect and learn. Retros are not a once a year activity. It takes time to get used to the rhythm and derive maximum benefit. Find ways to incorporate retrospectives into each milestone achievement, end of projects or even once a quarter. The more you do them, the better you get.

6. The lack of dissent: if everyone is agreeing to everything, know that something is wrong. Retros often take people to uncomfortable spaces, one where they’d have to admit that they made mistakes. Doing so in a public setting makes it that much harder. As much as the person running the retro needs to bring people together, they also need to get to the truth. The best retros come with equal part disagreement, equal part laughter.

However, sometime retros don’t work. A successful retro needs two key ingredients—a safe environment and belief in the process. Without either or both, the exercise will never yield the results it can. So as you plan the big 2020 retrospective, keep this in mind and whether you are doing it for the first time or the 10th, I hope you enjoy it as much as I do.

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