📆 Monthly Milestone Map

Step into the time machine and review the highlights and hurdles of the past month. Reflect on what powered us forward, the missteps we faced, and map out our improvements for the next month's adventure. Let's make progress our tradition!
60–75 min
4-10 people
Based on: What Went Well, What Went Wrong, What We Want to Improve
📆 Monthly Milestone Map
Template Columns
✅ Peak Achievements

Celebrate the accomplishments and successes that defined this month.

Base column: What Went Well
â›” Challenges & Storms

Examine the hurdles and difficulties that slowed us down this month.

Base column: What Went Wrong
🔧 Room for Elevation

Identify areas of opportunity to elevate and improve for the month ahead.

Base column: What We Want to Improve
About this template

The Monthly Milestone Map retrospective reflects on the past month's accomplishments, challenges, and areas for improvement to build a stronger team and plan for future success.

When to use this template

This template is ideal for teams conducting monthly retrospectives to review their accomplishments, address challenges, and set actionable goals for continued progress.

How to facilitate
1

Start by welcoming the team and reviewing the purpose of the retrospective: to reflect on the past month, celebrate achievements, address challenges, and plan for future improvements.

2

Introduce the columns of the template and explain how each guides the reflection process: Peak Achievements (celebrations), Challenges & Storms (address obstacles), and Room for Elevation (areas for enhancement).

3

Allow team members time to individually contribute thoughts to each column. Encourage specificity and actionable insights.

4

Once contributions are made, group similar ideas together and discuss each column collaboratively, emphasizing both acknowledgment of success and understanding of challenges.

5

Focus on the Room for Elevation column to derive specific, actionable steps the team can commit to for improvement over the next month.

6

Agree on next steps, assign ownership if necessary, and close the session by revisiting positive highlights to end on an uplifting note.

Pro Tips

Encourage team members to prepare thoughts prior to the meeting to maximize discussion time.

Use visuals, such as icons or charts, to highlight standout achievements or complex challenges.

Maintain a balance between celebrating success and addressing challenges to ensure a constructive tone throughout.

Prioritize action-oriented outcomes, ensuring each challenge discussed leads toward a tangible solution or plan.

Rotate facilitation duties among team members periodically to keep perspectives fresh.

FAQ
How can I keep the session focused and on time?

Set and enforce time limits for each section, kindly reminding participants to stay concise and relevant if discussions drift.

What if team members are hesitant to share challenges?

Create a welcoming environment by appreciating honest feedback and stressing that challenges are seen as opportunities to grow.

How should we prioritize actions from Room for Elevation?

Discuss and evaluate each suggestion based on impact, feasibility, and alignment with team goals, then collectively decide on the top items.

Can this template be adapted for shorter cycles, like weekly reviews?

Yes, focus discussions more narrowly on weekly highlights and make adjustments to fit a shorter timeframe.

At a glance
  • Duration

    60–75 min

  • Team Size

    4-10 people

  • Columns

    3 columns

  • Base Format

    What Went Well, What Went Wrong, What We Want to Improve

Tags
monthly retrospective
achievements
improvement planning
team bonding
action-oriented
Ready to get started?

Use this template to run your next retrospective