Retrospective redesign challenge — shift from on-site to remote | Part 1/2

Yu Phoebe
Yu Phoebe
Apr 11 · 5 min read


As a UX/UI Designer, I am always interested in projects or tasks that are thinking beyond just the products and services I am working on. What if I can help with designing better workspace experience for the team.

Few months ago, I was given a challenge to redesign the sprint retrospective format so that it is suitable for a remote work environment for a team of 6.

It has been a very iterative, collaborative and fun design process working closely with the team (See the collaboration). We have tried several different formats and so far we really like the following format.

What is sprint retrospective?

  • As part of the SCRUM process, an hour session will be scheduled after every two sprints (In other words once a month)
  • It’s an opportunity for the team to we sit down together and to reflect what we have done well and not so well in the last two sprints .
  • For better team communication, good hour spend together to discuss future development. We have tried several methods

After joining the first couple of retrospective (original format), I noticed that there are some problems. I thought what if I start a self-initiated project to develop a better retrospective format for our team:

Major challenges

  • How might we apply design thinking to design better retrospective experience for the team?

In addition to the major challenge I will also cover:
- Shift from on-site to remote friendly retrospective
- Discuss the Pros and Cons of the formats we have tried

3 formats we have tried:

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Google doc retrospective example

Design approach | The original retrospective format suggested by a team member

How it works?

  • A google document is available in the following above where team members can write down their thoughts before the retrospective
  • Go through the thoughts in the document one by one during retrospective

Pros and Cons

  • Mobility — team members can edit the doc anytime anywhere

From my observation

  • Team members are forgetful — it is necessary to send a quick reminder to the team before the retrospective to remind them to write down their thoughts before the retrospective session
  • Problems remains as problems — there’s a gap between thoughts written and action plans
  • Quiet members — some team members may be too shy or too quiet to share their own thoughts


  • How might we encourage the team to write down their thoughts and speak freely/ comfortably during the retrospective sessions?
  • How might we turn the thoughts collected during retrospective to actionable plans?
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Retrospective poster in the office

Design approach | Inspired by the design thinking workshops

How it works?

  • Have a retrospective poster visible to the team at all time, to remind the team about the retrospective goals ( 📗 Achieved, 📕Stop and 📒Next)
  • Schedule an hour long session and have a facilitator as a time keeper
  • Spend 5 minutes to think and write down what they have 📗 Achieved in the last two sprints ( It could be personal, workflow/ tasks and team related )
  • Use 1 minute to share their thoughts
  • Repeat the process for 📕Stop and 📒Next
  • Rewrite 📒Next thoughts (into something tangible and actionable) and add 📒Next to the sprint board
  • Don’t forget to pick the next facilitator

Pros and Cons

  • Introducing a positive word — like “achieved” in the retrospective as a warming up question which makes it more encouraging (sense of achievement) for the team to speak.
  • Colourful and interactive
  • Time box — members can focus on thinking one topic at a time i.e. spending 5 minutes on 📗 Achieved, 📕Stop and 📒Next. Also everybody get a chance to speak and hear others’ concerns/challenges.


  • Time consuming — the facilitator needs to type up the notes afterwards which makes it a time consuming and painful process
  • On-site only — it’s not suitable for remote work members


  • How might we reduce the workload for the facilitator after the retrospective?
  • How might we redesign the retrospective that’s suitable for remote work?
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Slack retrospective example

Design approach | Keep the post-it format, instead of write down their thoughts on post-its the team will write down their thoughts on Slack.

How it works? (See step by step guide)

  • Schedule a time for (video) call an hour long session, have a facilitator as a time keeper
  • Quick recap of the last retrospective, to check whether we have achieved the goal as a team or as an individual
  • Team will type out their thoughts ( start with 📗 Achieved, 📕Stop and 📒Next)
  • Send their thoughts via slack starting with achieve
  • Each member will have 1 minute share their thoughts
  • Repeat the process for stop and next

Pros and Cons

  • Thoughts centralised in one place — It becomes natural habit to start each retrospective sessions by a quick recap from the last retrospective and members can always revisit their thoughts.
  • Remote friendly retrospective — As long as wifi is available you can run your retrospective in this format


  • Scalability — I can foresee scalability will be the next challenge. But let’s redesign when this problem pops up again.


  • How might we design a scalable retrospective?


It was a fun process to apply design thinking method to tailor a user friendly workflow/ tool for your team. Here’s what have learnt from the process:

  • Trial and error — Designing work flow just like designing any other process and workshops. It’s an iterative process and you got to listen to your users’ and business requirements.
  • Pitch your idea to the team is never an easy task. From my experience the best way to convince your team is to state the problem with an idea that you want to test.

Design thinking methods are not limited to solving products or services related problems. It can also help to solve day to day office challenges as long as you know what your challenges are.

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