Had a bit of success with organising the roadmap for the squad I’m running. I decided to see if good old Obsidian could help me here. I just needed something that would present each roadmap item in a table and allow me to do some basic sorting and filtering. I probably could’ve stuck it into an Obsidian note, and used the advanced-table plugin, but I was hoping for something that worked with structured data.

So far, the db-folder plugin seems promising. What it does is read the front-matter of a bunch of files in a directory, and presents it as a table. Each column in the table is backed by a particular front-matter entry. You can add new columns, assign them types (string, number, select, date) and sort by or modify their values. Changing the cell in the table also changes the cell in the front-matter. The only downside is that each row has to be a separate file, but I think I can live with that. It might actually be a benefit.

So what I’ve done is create a separate file for each roadmap item, added front-matter entries to represent the “subcategory” (frontend vs. backend) and priority of the item, and assigned them to columns in the table. Now I can order by priority and see which part of the squad can work on each item within a single view. Pretty good.

I decided to lean a bit further into this and add the Jira JQL query for all the tickets for each roadmap item to the front-matter as well. I wrote a bit of code that’ll run this query through jira-cli and generate a nicely formatted Markdown table of the tickets, which I include in the file. It’ll also use the ticket statuses to write a one-line summary status of the road-map item (“not started”, “in progress”, “ready for release”) to the front-matter, and that is also shown in the table. The whole thing is kicked-off with a Keyboard Maestro shortcut.

This is all working pretty well. I kinda wish I can paste screenshots about the setup here, but… you know, corporate secrets and all that. Plus the whole thing is still evolving as I work out what is useful to me or not. But I this approach has got legs.

Some might say this is all procrastination to avoid dealing with Jira tickets. To that I’d say… ssh, don’t tell anyone. 🤫