5.2. Planning progress

Project management tools that make your life easier

Reverse planning

When you start building your roadmap, it is usually easier to do it in reverse: Start from final goal and from there plan backwards step for step. This helps you to identify important dependencies and to set time frames if you have an external deadline you have to keep.

Milestones

Break up the long way to your ultimate goal into smaller pieces and define intermediate goals: your milestones. Milestones can also mark important dates such es external deadlines or events (e.g. a conference where you want to present your project). As with a long road, you should add as many details (= required tasks to complete the milestone) as possible to close milestones and rather outline more distant milestones. You can always add more details, tasks and additional milestones as you work on your project.

In order to define your milestones, use the SMART method introduced to you in “Staging Your Project”, this means having milestones that are: Specific Measurable, Achievable, Realistic and Timely.

In the next step, estimate the amount of time you’ll need to reach the milestones and define their time frame. Try to be realistic and account for possible detours, problems and troubleshooting. Time planing and management is probably the hardest part of roadmap creation. That’s why we dedicated the following submodules “Time Management” and “Evaluating Risks” to these topics. The final step is to set deadlines for your milestones, at least for the close ones. However, this depends on your projects goals and your overall strategy.

The direction of your project might change as the work evolves. Return to your roadmap frequently to update, add or change milestones, and track your progress! You may want to welcome supporters or key participants into any conversation about Roadmapping, as a way of increasing their participation and sense of ownership of the project.

In short:

  1. Define the goal of your project
  2. Define several intermediate goals (milestones) and add as many details as possible
    • Development goals (specific features or resources you want to create)
    • Meetings and events
  3. Define time spans for your milestones
  4. Add deadlines to your milestones

Tools for planning progress

Luckily there are plenty of tools available which can help you to create and maintain your roadmap and plan your project. A very common and accessible tool is a Kanban board. It visually depicts work at various stages of a process using cards to represent work items and columns to represent each stage of the process. A Kanban board can thus help you to focus on important tasks and to keep track of your short, medium and long-term goals. You can set up a Kanban board with a piece of paper and some sticky notes or use one of the many online tools. Read more about Kanban boards here. An free and easy digital Kanban tool is the GitHub Project Board.

Assessing progress and monitor indicators

As we mentioned, a roadmap is an excellent planning tool and to make full use of it, you will need to constantly revisit it and compare how actual progress compares with your plans. Let’s say you planned a milestone that is due in 60 days. Checking your roadmap today, how does it look like? Is the project/team on track to hit the milestone? Did you find any unexpected issues that will delay/prevent certain points to be completed? Does this mean that your milestones deadlines need to be changed, or do you need to detour your roadmap?

If you are working with collaborators, make sure you check in with them on regular basis, ask them how they are doing in general and how they feel about the steps they are working on. Could they use external support? Could they use more time to complete the tasks they said they would work on? If they are volunteering on your project, have a think about what is the best way to keep people motivated and engaged in the project.

Assignment: “Reverse-plan” and list the milestones and responsibilities for achieving your goal

  • Pick 1-3 milestones for your project.
  • List tasks to complete for each milestone
    • Short description of each task required to successfully complete project work on a milestone.
    • Explanation why you are doing this task (one sentence). This will reinforce your vision for the project and help others see why each step is meaningful in the larger timeline.

Resources

next: Managing time  

Help us improve content and suggest changes to this page.