How to: run a team retrospective day

Some of the PledgeMe team after our retro day.

PledgeMe is a small team of seven, based across four locations. Our company mission is to help people fund the things they care about. We do that through a crowdfunding platform and education. Once a year we do an annual retrospective, where we try to fly everyone together (unless they decide to abandon us for Berlin, too far Babe!). Here’s a bit more about what I’ve learned in the past few years running annual retrospective & planning days.

As a team, we check in every week on how we’re doing. We do a good / bad / change session at our weekly team meeting where all sorts of gems get raised — both to celebrate and improve. But, an hour isn’t enough to get deep into the work of how we improve our company — both for our customers and for ourselves.

So, we try to take time every year to check in. The format has varied a bit over the years, but I thought it might be useful to share a bit about how we run the day, and what we’ve learned:

Book a date!

Try to get two week days (because, we shouldn’t expect folk to give up their weekend for work — you are welcome to work then, but we shouldn’t require our team to give up that time unless we give them time off at other points). Also, try to book this a few weeks in advance so there’s time for people to get childcare if you have a flexible work environment.

Get a draft agenda out so your team knows the basic flow and can add their thoughts to it.

Here’s what we had on our draft agenda:

Day One

9am: Context setting as a group: What have we achieved in the last year? Good / Bad / Change.

10am: Half hour quiet time with A3 paper: where do you want to be in 5 years? Where do you want PledgeMe to be?

10:30am: Come back and present. Each person has 5 minutes

Noon: Lunch

1pm: Check in on buddy system — how’s it going? Group Discussion.

1.30pm: Feedback pairs — good & constructive. How it’ll roll: everyone spend some time prior to Monday working out what you’d like to say, and then we have five minutes per pair (timed). You should cover:

  • What’s one thing this person does that really contributes to the team and our ability to be effective?
  • What’s their biggest learning edge? What skill could they work on that would help us achieve the goals of PledgeMe. (eg. modelling self care, time management, communication skills)? This is about working out how we can do better together.

2.30pm: Theme setting session: what do we want to focus on?

3.30pm: Afternoon tea

4.00pm: Dive into a working bee session, or loose ends.

Day Two

9:30am: Session Setting

10am - 4pm: topics from Day 1.

If there’s anything new to the format, touch base with your team individually to make sure they’re ok and answer any questions.

If you’re running teams across multiple timezones that will be video conferencing in, you’ll need to be clear when different folk are calling into the day (and what they need to do if they aren’t present for parts of the day).

Here are four sessions I’d really recommend touching on during your retrospective:

1) A “good / bad / change” session on the previous year

Everyone gets post it notes, and has 5–10 minutes to individually write down all the good things that have happened in the last year, all the bad things, and all the changes. They should write one item per post it note, make sure the sticky bit is at the top, and for all that’s good in the world use a dark marker / vivid.

The content of the goods / bad / changes can be personal, or for the company. We don’t expect or require people to talk about their personal lives, but we do let it become part of the discussion if people want to. Because, what’s happening in all parts of our lives are important and should be valued.

Once everyone has written up their post it notes, each team member goes up to the board, and adds their goods. The team should discuss / celebrate / cluster similar goods.

Then you repeat the process for bads & changes. You do these together, because often the bads will be linked to a change the team member wants. Again, discuss, and note any actions down.

In previous years, we’ve also had a “leave” pile. Things we want to leave behind in that year (sort of like a karmic cleansing). Big thanks to Silvia for helping inspire this format, and the Rabid team who taught me about Agile.

2) A “where do we want to be in five years” session

Everyone gets an A3 bit of paper, and has a half hour to write about where they want to be in five years. Again, this will probably cover the personal and the professional, but it doesn’t have to.

After 30 minutes, each member of the team gets 5 minutes to share where they want to be. The team can offer up insights / ideas.

This helps set the goal of where you want to go, but not how you’ll get there. This will be drafted up in the plan for the year.

3) A “theme setting” session

From the first two sessions, you should have a pretty clear idea of some themes of work that you can spend the planning day on. Spend 15–20 minutes drafting up the themes on the board.

Working bees on specific themes

The next day we took the specific themes, and prioritised them as a group. Some of the working bees involved the whole group, and others were only relevant to a few folk in our team. We then spent 30–45 minutes on each theme, deep diving, rolling around in our insight, and then planning out next steps. Instead of deciding everything needed to be done, we started framing up the questions we need to ask to make a decision.

In the end, make sure everyone is clear on their actions (and has the time / space to complete them). In your next weekly meeting, check where things have gotten to.

4) A “Feedback Pair” session

This is probably the scariest session we did. But, my very wise friend Lani showed me the way and said if it was well framed it could be pretty powerful.

The focus of this is to give everyone a chance to celebrate their colleagues, and give developmental feedback. It’s not a space for airing grievances, but a chance for the group to learn from each other and get reflected back their super powers, as well as where there learning edge is.

As a leader, I tried to call every team member before the session to prep them. I asked them to frame the feedback in a work context, and make it constructive — what is the stuff we want to see each individual keep on doing to help our company sustain / grow? And, where could that person get feedback on where they might want to develop to help the company as a whole? I asked them to spend a few minutes before the day, thinking up what they wanted to say.

In the session, I framed the pair work again, and then gave everyone 10 minutes to finish drafting up their feedback notes. Then, everyone got into pairs, and had five minutes (so roughly 2.5 minutes on each person). In hindsight, we should have given them five minutes each so they could ask more questions on the feedback.

After the time allotted, we swapped partners, until each team member had given and gotten feedback from everyone.

We did a debrief afterwards, and everyone admitted how scared they were. That they might learn something they didn’t know about themselves, or that it would be mean.

What we found, was the feedback given was often something the person knew about themselves. Also, often the good was tied to the learning edge. For example, one of my team told me that I care deeply, and try to help everyone I meet. But his feedback was, sometimes I need to take time out for myself, and maybe be a bit more strict on how much I try to help.

Here’s my full feedback from the team. You won’t be surprised to see, they all basically told me to take a holiday:

Try to leave some space in the day for fun stuff

We didn’t do as well on this as we’ve done in the past, but we did manage to make Kelsey in Berlin run outside in the middle of the night and throw a snowball at us (on the laptop, being held by her friend, two levels up). We did eat donuts (and a lot of good food) together. We also sampled some Bundaberg rum, to celebrate my new home region of Queensland, Australia.

I want to want to end this by saying: I am no expert on the agile methodology, planning, or team psychology. If you have any thoughts or feedback on how we could improve our process, I would love to hear ’em in the comments or via social media. I’d also love to hear how you do this at your organisation. Let’s all be better, together, hey?