Estimating projects/initiatives is not easy if you don’t have a right approach. You can be in MS Project land trying to figure out little details, but those details change and then you are stuck maintaining schedules in MS Project. You spend a lot of time tweaking the tool instead of proper planning.
A lot of companies are trying to change to use the “Agile” methodology and I am putting the word “Agile” in quotes because there is no company out there that is following exactly what you are taught in ScrumMaster courses and SAFe courses. That means that companies sooner or later end up doing what works for them and that could be an approach that belongs somewhere on the line between Waterfall and Agile; for some companies closer to Agile, and for some companies closer to Waterfall.
For example a lot of companies get a list of projects/initiatives that need to be estimated at high-level, prioritized and approved by a board before projects can be worked on. Then when they are estimated and approved, you are asked to provide project schedules with milestones and deadlines with very high-level requirements. Then some of these organizations say “let’s run these projects using the agile methodology”. What does that really mean?
What does this really mean to the delivery teams if somebody already provided the high-level estimates and basically to some degree committed when the project will be delivered?
You can still stay positive about it and concentrate on understanding the requirements and properly breaking down the project/initiative into manageable pieces and ultimately calculating the true production delivery date that you can go back to the business team with.
Let me explain how I approach this. What works for me is reading the requirements document or epics and user stories and breaking down the project into a list of features and sub-features. Then if the requirements document is written in such a way that it lists the user stories, you can easily distribute these user stories into the appropriate sub-features. If the requirements document does not explicitly list the user stories, then I would put a product owner hat on and extrapolate the user stories out of the requirements document embedded in different paragraphs.
Now that I have all the user stories under each sub-feature, I can do some high-level estimating on each story and the unit for estimation is the number of days. It is not some virtual story points and it is not the hours; it is the number of days (8h=1day).
After estimating each user story under each sub-feature, you can add up the estimates and have the list of sub-features and numbers for each sub-feature.
Now that you have the list of sub-features and estimate for each sub-feature, it is all fun after this point. It is fun because I like using Trello website to perform this mapping or pre-plan all the sprints and ultimately produce the deadline (production delivery date), because that’s what business expects from us. NOTE: In this exercise, I don’t do sprint planning at the user story level; I do this exercise of sprint pre-planning (mapping) at the sub-feature level in order to produce that deadline and to have a rough idea how each sub-feature needs to be worked on throughout the project.
What are the steps to be taken before playing the drag-and-drop game in Trello?
- Decide on the duration of the sprint (let’s say 4 weeks). I understand that the 4-week sprint is on the longer side, but this is just an example.
- Take the list of sub-features and estimates and break down each sub-feature into multiple sub-feature parts that are each 5 days worth of work. For example, if you have a sub-feature that has the estimate of 20 days, then you would break that sub-feature into Sub-Feature A part 1, Sub-Feature A part 2, Sub-Feature A part 3, and Sub-Feature part 4.
- Now you are ready to plug this all into Trello backlog list and then the game of dragging and dropping starts :)
Here is how it could look like in the backlog list when you start:
Now that you have all the sub-feature parts in the backlog, it is time to gauge what the optimal number of resources is. Let’s do some simple math.
- 6 resources
- 4 week sprints (20 working days)
- if everybody is a robot, then the team should be able to chunk away 120 days (6x20) out of the estimates. Yeah right !!! With all the meetings and interactions between teammates, a reasonable number to achieve in each sprint would be 60–80 days worth of work. If each part of the given sub-feature is equivalent to 5 days worth of work from the estimates, then you should be able to drag and drop 10+ of those parts into a given user sprint.
You as the technical lead and technical project manager know best how each sub-feature is related to each other and you are deciding those things as you are loading each sprint with the list of sub-feature parts.
Here is how it may look after going through this exercise. It looks like the duration of the project would be around 14 weeks (3.5 months). If you know what the start date is, then you can easily calculate the production launch date. You also know when you need to start each sub-feature and when each sub-feature is supposed to be completed. That can help you point out some major milestones to your senior management team.
You are done. Provide your boss the duration of the project, major milestones and the production launch date that you can achieve based on these high-level estimates.
Well, now you need to share this with the delivery team and help out the team do proper sprint planning at the user story level by using this sub-feature plan. I happened to use Trello just for the purposes of “sub-feature” planning, but when it comes to sprint planning at the user-story level, your team will need to use whatever tool your company approved.
Good luck and have fun.
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