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Open roadmaps for your projects

Speaker Deck

Hands-on workshop on designing, building, and maintaining roadmaps for open-source communities and internal projects using GitHub Issues, GitHub Projects, and AI

Tags: open-source roadmaps github project-management innersource ai

Slides

Abstract

Roadmaps help communicate vision, align stakeholders, and coordinate contributions. But creating a roadmap is only half the challenge. Keeping it accurate, relevant, and sustainable is much harder!

In this hands-on workshop, Oleg will share the experiences of public roadmaps in the projects he has contributed to: Jenkins, WireMock, Keptn, CDF, etc.\ He'll share the reasons and principles that have guided creation of open roadmaps, the challenges encountered, the techniques and technologies that could be used in your projects. We’ll talk about maintaining roadmaps, common mistakes and how to avoid them.

We will use GitHub Projects and GitHub Issues to build practical roadmaps, organize initiatives, and communicate priorities. We will also explore how AI can help monitor roadmap consistency, identify stale initiatives, and detect discrepancies between plans and actual development activity.

As a part of the workshop, we will do a two-hour hands-on exercise where participants create a roadmap for their own project or a sample project provided by the speaker.

Workshop Structure#

I. Roadmap Fundamentals#

  • Why roadmaps matter for open-source and internal projects
  • Defining audiences, priorities, and planning horizons
  • Roadmaps versus backlogs and delivery schedules
  • Common mistakes and lessons learned

II. Building Roadmaps with GitHub#

  • GitHub Issues as the source of truth
  • GitHub Projects: fields, views, filters, and automation
  • Public versus internal roadmaps
  • Managing expectations and avoiding unnecessary complexity

III. Hands-on: Build Your Roadmap (2 hours)#

Participants can bring their own project or use a prepared sample project.

  1. Define roadmap goals, audience, and guiding principles
  2. Organize issues, initiatives, and priorities
  3. Create a GitHub Project with suitable roadmap views
  4. Communicate plans and manage expectations
  5. Handle changing priorities and stalled initiatives
  6. Review the roadmap and define maintenance practices

IV. AI-Assisted Roadmap Maintenance#

  • Detecting stale initiatives and inconsistent statuses
  • Identifying missing ownership, dependencies, and duplicate work
  • Comparing roadmap plans with GitHub activity
  • Using AI assistants and automation for consistency reviews
  • Human oversight and limitations of AI-generated recommendations

V. Wrap-up#

  • Roadmap reviews and feedback
  • Sustainable maintenance practices
  • Lessons learned and Q&A

Duration#

4 hours, including 2 hours of hands-on exercises. Breaks are not included.

Prerequisites#

  • Basic familiarity with GitHub
  • GitHub account and laptop
  • Optionally, an existing project to use during the workshop
  • Optionally, access to an AI assistant

No prior experience with GitHub Projects is required.

References