5 innovative retrospective meeting ideas to energise your team

When your team finishes a quarter of hard work, it's important to take a break and reflect on their achievements. This is where retrospectives come in. By celebrating successes, identifying improvement areas, and creating a shared understanding of progress, teams can set more effective and realistic goals for their next Objectives and Key Results (OKRs) cycle. 

OKR Retrospectives involve team members getting together to grade their objectives, discuss what went well and what didn't go as planned, and brainstorm what to start, stop, and continue. This lays the foundation for setting better goal-setting the next quarter. 

While the OKR Retrospective meeting is tried and true, sometimes it’s good to mix things up and try out new formats. By stepping away from traditional retrospective meeting structures, teams can discover new ways of thinking and problem-solving. Fresh formats encourage team members to tackle challenges from different perspectives, leading to innovative solutions that might have been missed in a traditional setting. 

5 innovative retrospective meeting format alternatives

1. Sailboat Retrospective

The Sailboat Retrospective is a visual and metaphorical format that helps teams reflect on their progress, identify enablers and obstacles, and set a course for future improvements. This format uses the analogy of a sailboat navigating through the challenges and successes of a project or quarter. Teams can look at what's helping them (the wind), what's slowing them down (the anchor), and what could get in their way (the rocks). By doing this, they can get a good idea of where they're at and come up with plans to use their strengths, overcome obstacles, and get to where they want to be.

How to facilitate the Sailboat Retrospective meeting format

1. Preparation

• Schedule a dedicated time and space for the retrospective.
• Draw a sailboat on a whiteboard or digital collaboration tool, including the following elements:
  • Boat: Represents the team.
  • Wind: Indicates the things propelling the team forward.
  • Anchor: Represents the things holding the team back or slowing progress.
  • Rocks: Shows potential risks or obstacles ahead.
  • Island: Represents the team's goals or desired destination.
• Provide the team with sticky notes or digital equivalents.

2. Set the context (5 minutes)

• Explain the Sailboat Retrospective format and how it works.
• Clarify the focus on reviewing the team's OKRs and progress.

3. Individual reflection (10-15 minutes)

• Ask team members to reflect on the OKR cycle and write their thoughts on sticky notes for each sailboat element:
  • Wind
  • Anchor
  • Rocks
  • Island
• Encourage specific and actionable observations by guiding team members to focus on concrete examples, behaviours and outcomes related to their OKRS. 
  • Example question: "What specific actions or initiatives did we undertake that directly contributed to the increase in our NPS?"

4. Populating the sailboat (10-15 minutes)

• Invite team members to place their sticky notes on the corresponding elements of the sailboat - Wind, Anchor, Rocks, and Island. 
• Encourage brief explanations or clarifications as needed.

5. Discussion and analysis (30-45 minutes)

• Review each element of the sailboat, starting with the Wind and moving on to the Anchor, Rocks, and Island.
• Facilitate a discussion around the following questions:
  • What are the common themes or patterns in each element?
  • How did the Wind factors contribute to our progress? How can we sustain or amplify them?
  • What Anchor factors impeded progress? How can we address or mitigate them?
  • What Rocks or potential challenges do we foresee? How can we prepare for or navigate them?
  • Are we on course to reach our Island (Objectives)? What adjustments or course corrections are needed?
• Encourage open dialogue.

6. Action planning (15-20 minutes)

• Based on the discussion, identify key actions to capitalise on the Wind, address the Anchor, mitigate the Rocks, and steer towards the Island.
• Prioritise actions based on impact and feasibility.
• Assign responsibilities and timelines for each action item.

The Sailboat Retrospective provides a visually engaging way for teams to reflect on their OKR journey, identify enablers and obstacles, and chart a course for future success. 

2. Postcard Retrospective

The Postcard Retrospective helps teams to think about their future success and potential challenges by writing postcards from a future point in time. This way, teams can look at their work from a different perspective and evaluate its long-term impact.

How to facilitate the Postcard Retrospective meeting format

1. Preparation

• Schedule a dedicated time and space for the retrospective.
• Provide each team member with a postcard-sized piece of paper or sticky note.

2. Set the context (5 minutes)

• Explain the purpose of the Postcard Retrospective.
• Encourage honest reflection and constructive feedback.

3. Individual reflection (10-15 minutes)

• Ask each team member to imagine they are writing a postcard to a friend or family member about their experience working on OKRs.
• Prompt them to reflect on the following:
  • Key accomplishments and successes related to the OKRs
  • Challenges or obstacles encountered
  • Lessons learned, and insights gained
  • Suggestions for improvement in the next OKR cycle
• Encourage them to write concisely, capturing the essence of their thoughts on the postcard.

4. Sharing and discussion (30-45 minutes)

• Invite each team member to share their postcard with the group.
• Facilitate a discussion after each postcard is shared, allowing team members to ask questions, provide feedback, or offer support.
• Capture key points, insights, and action items from the discussion.

5. Identify themes and patterns (10-15 minutes)

• As a group, review the postcards and discussion notes to identify common themes, patterns, or areas for improvement.
• Look for recurring successes, challenges, or lessons learned across the team.

6. Action planning (15-20 minutes)

• Based on the identified themes and patterns, facilitate a discussion to generate actionable next steps.
• Encourage the team to propose improvements, solutions, or experiments to address the challenges and build on the successes.
• Prioritise the action items and assign responsibilities and timelines.

The Postcard Retrospective enables teams to look back on what they've accomplished, figure out what they can do better, and decide on the next steps together. By pooling everyone's ideas and perspectives, this method encourages everyone to take part and agree on the same goals. 

3. Timeline Retrospective

Teams can use the Timeline Retrospective to visualise their journey through a project or quarter by mapping out key events, milestones, and challenges on a timeline. It helps everyone see the bigger picture and identify patterns or trends that might not be visible when dealing with individual experiences.

How to facilitate the Timeline Retrospective meeting format

1. Preparation

• Schedule a dedicated time and space for the retrospective.
• Set up a large timeline on a whiteboard (or digital collaboration tool).
• Divide the timeline into relevant intervals (e.g., weeks or months) based on the OKR cycle duration.
• Provide the team with sticky notes (or digital equivalent).

2. Set the context (5 minutes)

• Explain the purpose of the Timeline Retrospective.
• Emphasise the importance of capturing both positive and challenging events.

3. Individual reflection (10-15 minutes)

• Ask each team member to think about the key events, milestones, and challenges they experienced during the OKR cycle.
• Encourage them to write these events on sticky notes, using different colours for positive and challenging events.
• Ask them to consider the following aspects:
  • Major accomplishments and successes
  • Obstacles or setbacks encountered
  • Key decisions or changes made
  • External factors that influenced the OKRs

4. Populate the timeline (15-20 minutes)

• Invite team members to place their sticky notes on the timeline, aligning them with the appropriate intervals.
• Encourage them to add brief descriptions or labels to the events.
• If necessary, ask for clarification as team members add their events to the timeline.

5. Review and discuss (30-45 minutes)

• As a group, walk through the timeline from start to finish, discussing the events and their impact on the OKRs.
• Encourage team members to share their perspectives, insights, and lessons learned.
• Facilitate a discussion around the following questions:
  • What patterns or trends did we observe?
  • What worked well, and what contributed to our successes?
  • What challenges did we face, and how did we address them?
  • What could we have done differently to improve our progress?
• Capture key points from the discussion.

6. Identify learnings and action items (15-20 minutes)

• Based on the timeline review and discussion, facilitate a brainstorming session to identify key learnings and areas for improvement.
• Encourage the team to propose actionable steps to address the challenges and build on the successes.
• Prioritise the action items and assign responsibilities and timelines.

The Timeline Retrospective is a great way for teams to look back on their journey and improve. By putting everything on a timeline, they can see what happened, when it happened, and what was challenging. This makes it easier to spot patterns and figure out why things happened. Plus, everyone can join in and share their own experiences, which helps the team understand each other and work better together.

4. Mad, Sad, Glad Retrospective

The Mad, Sad, Glad Retrospective format encourages team members to categorise their experiences and feedback from the past project or quarter into three emotional categories: Mad, Sad, and Glad. By reflecting on what made them feel mad, sad, or glad, team members can gain insights that help them make better decisions in the future. 

How to facilitate the Mad, Sad, Glad Retrospective meeting format

1. Preparation

• Schedule a dedicated time and space for the retrospective.
• Prepare three sections on a whiteboard (or digital collaboration tool) labelled "Mad," "Sad," and "Glad."
• Provide the team with sticky notes (or digital equivalent).

2. Set the context (5 minutes)

• Explain the purpose of the Mad, Sad, Glad Retrospective and its focus on emotional reflection.
• Emphasise the importance of honest and constructive feedback.

3. Individual reflection (10-15 minutes)

• Ask each team member to reflect on their experiences during the OKR cycle.
• Encourage them to write down their thoughts and feelings on sticky notes, categorising them into Mad, Sad, and Glad:
  • Mad: Frustrations, annoyances, or things that made them angry.
  • Sad: Disappointments, missed opportunities, or things that caused sadness.
  • Glad: Positive experiences, successes, or things that brought joy and satisfaction.
• Prompt them to consider aspects related to their OKRs, teamwork, processes, and any other relevant factors.

4. Sharing and categorisation (15-20 minutes)

• Invite team members to share their sticky notes and place them in the corresponding Mad, Sad, or Glad section.
• Encourage brief explanations or context for each note, if needed.
• Create space for clarification questions and initial reactions.

5. Discussion and analysis (30-45 minutes)

• Review each section (Mad, Sad, Glad) individually, focusing on the most prominent or recurring themes.
• Facilitate a discussion around the following questions:
  • What patterns or common issues did we observe?
  • What are the underlying causes or contributing factors?
  • How did these experiences impact our progress and team dynamics?
  • What can we learn from the positive experiences (Glad) and replicate them in the future?
  • How can we address the frustrations (Mad) and disappointments (Sad) moving forward?
• Encourage open and constructive dialogue, ensuring everyone can share their perspectives.

6. Identify action items (15-20 minutes)

• Based on the discussion and analysis, facilitate a brainstorming session to identify actionable improvements.
• Focus on addressing the issues raised in the Mad and Sad sections while leveraging the positive aspects from the Glad section.
• Prioritise the action items based on their impact and feasibility.
• Assign responsibilities and timelines for each action item.

Teams can use the Mad, Sad, Glad Retrospective to explore and process their emotions and experiences from the previous project or quarter. By sorting feedback into these three categories, teams can learn from setbacks, celebrate achievements, and identify areas that need improvement. It encourages open and honest communication, creating a safe space for team members to share their thoughts and feelings. Through discussing points raised in each category, teams can identify patterns, uncover root causes, and generate actionable ideas to address challenges and build upon successes. 

5. The Start, Stop, Continue Retrospective

The Start, Stop, Continue Retrospective is a simple and effective format that encourages teams to reflect on their processes, behaviours, and practices and identify areas for improvement. The goal is to determine what the team should start doing, stop doing, and continue doing to enhance their performance.

How to facilitate the Start, Stop, Continue Retrospective meeting format

1. Preparation

• Schedule a 60-90 minute meeting with your team, ensuring that all members can attend.
• Create a shared document or virtual whiteboard with three columns labelled "Start," "Stop," and "Continue."
• Send out a meeting invitation with a clear agenda and instructions for team members to come prepared with their ideas and observations.

2. Set the stage (5-10 minutes)

• Briefly explain the Start, Stop, Continue Retrospective format and its purpose.
• Emphasise the importance of open, honest, and constructive communication during the meeting.

3. Individual brainstorming (10-15 minutes)

• Ask team members to spend a few minutes silently brainstorming ideas for each category:
  • Start: Things the team should begin doing to improve their processes, collaboration, or outcomes.
  • Stop: Things the team should cease doing because they are ineffective.
  • Continue: Things the team is doing well and should keep doing.
• Encourage team members to write down their ideas on sticky notes or virtual cards.

4. Sharing and grouping (20-30 minutes)

• Invite team members to share their ideas individually, placing their sticky notes or virtual cards in the appropriate column on the shared document or whiteboard.
• As ideas are shared, look for common themes or suggestions and group them together.
• Encourage team members to ask clarifying questions or provide additional context as needed.

5. Discussion and prioritisation (20-30 minutes)

• Once all ideas have been shared and grouped, facilitate a discussion around the key themes or clusters that have emerged in each category.
• Encourage the team to explore the reasons behind each suggestion, the potential benefits or challenges of implementing them, and any resources or support needed.
• Guide the team in prioritising the ideas within each category based on their potential impact and feasibility. You can use dot voting, ranking, or any other prioritisation technique that works well for your team.

6. Action planning (10-15 minutes)

• Focus on the top 2-3 ideas in each category (Start, Stop, Continue) and help the team develop specific, measurable, and time-bound action items to implement these changes.
• Assign owners to each action item and establish a timeline for completion.
• Discuss how progress will be tracked and how the team will hold each other accountable for following through on their commitments.

Tools to run retrospective meetings

Tability

Tability’s retrospectives feature is a simple way to reflect on your progress and share thoughts with your team by pulling data directly from your OKRs and goals. 

You can also share a link with your team or download a PDF in one click. 

Confluence

Confluence makes it easy to document and share information with others and may be a practical option for some teams. However, it is not specifically designed for running retrospectives and may require a more manual setup and input. 

Notion

Notion is highly customisable and flexible, and offers a range of templates, including those for retrospectives. Like Confluence, however, it is not purpose-built for retrospectives, so it may be more complicated to configure. Notion also lacks a good table structure for voting.  

Conclusion

Teams should set aside dedicated time for reflecting on their work, accomplishments, and obstacles. This helps them identify areas where they can improve. While the Classic Retrospective model is effective, exploring alternative meeting formats can bring new ideas, enthusiasm, and viewpoints to the discussion. Experiment with different options and find the right fit for your team.