Support Change Rollout: Automated Retrospective Bot Implementation

GitLab Support: Process Change Rollout Plan

Retrospective Notification Bot for Closed GitLab Issues

The Story

There are two update notifications:

Retrospective Bot:

Based on the approved RFC in RFC: On Implementing a Retrospective Bot Across all RFH sections and groups, we have implemented an automated retrospective bot that will trigger when GitLab issues are closed. This bot will prompt issue authors to provide insights and learnings from their issues, helping us build a culture of continuous improvement and knowledge sharing.

When a GitLab issue is closed, the bot will:

  • Post a standardised comment prompting the issue author for retrospective thoughts
  • Add a ~"retrospective::started" label to track the retrospective process
  • Provide a structured template for capturing learnings

The issue author can then:

  • Respond with their retrospective insights
  • Update the label to ~"retrospective::completed" when done
  • Or mark it as ~"retrospective::not needed" if a retrospective isn't applicable

The bot notification looks like the following:

image.png

This approach has already been successfully implemented by the Security team and will help us:

  • Ensure consistent retrospective practices across all issues
  • Capture valuable learnings that might otherwise be lost
  • Create a discoverable record of insights for future reference
  • Reduce the cognitive load of remembering to conduct retrospectives

New Slack Notifications for Missing Closure Labels RFH issues

Aligned with this we have also created a new Slack Channel #spt_rfh-missing-closure-label where an automated bot will provide notification to end users who have not applied a Closure Label to Closed RFH issues. Full details on this approach and other approaches can be found in the ReadMe under the section Closing RFH Issues: Required Actions

The Roles

Role Description
Champions @jlyttle
Users All Support Engineers and Managers who create and close GitLab issues
Impacted Non-Users Any GitLab Users who author or collaborates on GitLab RFH issues

Schedule

  • Rollout to begin on Monday 24th November 2025
  • Will the rollout be phased? No - global rollout
  • Adoption complete by Today + 2 weeks

Training

No formal training is required. The bot will provide clear instructions in its automated comment.

What users need to know:

  • When you close an issue, the bot may post a retrospective request comment
  • Review the prompts and add your insights as a comment
  • Update the label to ~"retrospective::completed" or ~"retrospective::not needed"
  • The bot won't trigger again once a retrospective label is applied

Retrospective prompts will include:

  • What went well? What worked effectively?
  • What could be improved? What challenges did we face?
  • Action items: What specific changes should we make?
  • Documentation: Should any handbook pages be updated?

Success Determination

What will success look like?

  • Issue authors consistently provide retrospective insights when prompted
  • Valuable learnings are captured and discoverable
  • Reduced number of missed retrospective opportunities
  • Increased documentation improvements based on retrospective findings

How will we track change adoption?

  • Monitor issues with ~"retrospective::started" label
  • Track completion rate (~"retrospective::completed" vs ~"retrospective::not needed")
  • Review quality and actionability of retrospective comments

Targets:

  • 70%+ of prompted issues receive a retrospective response within 1 week
  • Identification of at least 3-5 actionable improvements per month from retrospectives

Action Plan

  1. Create an item in the SWIR to announce the change and include Things to Know About - Support Change Rollout: Automated Retrospective Bot Implementation Monday 24th November
    • NOTE: On the SWIR form, add the Manager Attention tag for policy changes and action items for Support Managers specifically (you can add multiple tags to a SWIR item)
  2. Post a message in the #support_team-chat (https://gitlab.slack.com/archives/CCBJYEWAW/p1764000937426689) Slack channel announcing the change and pointing to the SWIR announcement on Monday 24th November
  3. Announce the change and tell The Story in Team meetings by 12-01-2025
    • EMEA team meeting
    • AMER team meeting
    • APAC team meeting
  4. Other communications channels
    • Discuss in 1-1s, telling The Story, by date
    • Post in relevant Slack channels (e.g., #support_leadership)
  5. Report back on change adoption, concerns, etc. by 12-01-2025

Manager Acknowledgement Section

Expectations

For Managers:

  • Review this change and the RFC #7295
  • Discuss the retrospective bot with your team in 1-1s
  • Encourage team members to provide thoughtful retrospective insights
  • Lead by example by completing retrospectives on your own closed issues
  • Monitor retrospective completion rates within your team

Due Date

Check off your name by midnight UTC on: TBD

Names

Support Managers

Sorted alphabetically by region / GitLab handle

AMER

APAC

EMEA

Staff Support Engineers

Senior Management team

Follow-Up Plan

How will results be captured?

  • Create a follow-up issue 30 days after rollout to review:
    • Retrospective completion rates
    • Quality of insights captured
    • Actionable improvements identified
    • User feedback and concerns

What is the plan for considering and making quick improvements?

  • Monitor the first 2 weeks closely for any issues or confusion
  • Adjust bot comment template if needed based on feedback
  • Iterate on which issue types should trigger the bot

What is the plan should the change be deemed unsuccessful?

  • Rollback is feasible by disabling the triage-policies bot configuration
  • If unsuccessful, conduct a retrospective (meta!) to understand why
  • Consider alternative approaches such as:
    • Different trigger conditions
    • Modified retrospective prompts
    • Integration with existing workflows

Related Issues

Edited by John Lyttle