While Scrum does not require and discourages planning more than one sprint at a time. Most of us work in enterprises where we are dependent outside teams (for example: marketing, sales, support).
A rough assessment of the planned project scope is achievable within a reasonable time frame and resources. The goal is to have a rough plan and estimate as a starting point, not to implement "Agilefall."
Note that this is just a starting point to enable planning discussions. We expect the actual schedule to evolve and shift over time and that you will update the scope and timeline as you progress.
Delivery Plans ensure your teams are aligning with your organizational goals.
- As you complete the assessment, you can push back on the scope, time frame or ask for more resources.
- As you progress in your project/product delivery, you can highlight risks to the scope, time frame, and resources.
One approach you can take to accomplish is with stickies and a spreadsheet.
Step 1: Stack rank the features for everything in your backlog
- Functional Features
- [Non-functional Features] (docs/TECH-LEADS-CHECKLIST.md)
- User Research and Design
- Knowledge Transfer/Support Processes
Step 2: T-Shirt Features in terms of working weeks per person. In some scenarios, you have no idea how complex the work. In this situation, you can ask for time to conduct a spike (timebox the effort so you can get back on time).
Step 3: Calculate the capacity for the team based on the number of weeks person with his/her start and end date and minus holidays, vacation, conferences, training, and onboarding days. Also, minus time if the person is also working on defects and support.
Step 4: Based on your capacity, you know have the options
- Ask for more resources. Caution: onboarding new resources take time.
- Reduce the scope to the most MVP. Caution: as you trim more of the scope, it might be valuable anymore to the customer. Consider a cupcake which is everything you need. You don't want to skim on the frosting.
- Ask for more time. Usually, this is the most flexible, but if there is a marketing date that you need to hit, this might be as flexible.
You can also leverage one of these tools by creating your epics and features and add the weeks estimates.
The Plans (Preview) feature on Azure DevOps will help you make a plan. Delivery Plans provide a schedule of stories or features your team plan to deliver. Delivery Plans show the scheduled work items by a sprint (iteration path) of selected teams against a calendar view.
Confluence JIRA, Trello, Rally, Asana, Basecamp, and GitHub Issues are other similar tools in the market (some are free, others you pay a monthly fee, or you can install on-prem) that you can leverage.