“What’s the best way to see what your team is working on?”

As the head of design for one of the products at Automattic, I get this question a fair bit. I have a good way to respond to that without having to do a ton of legwork. It actually has to do with task management!

Why I prioritized solving task management

As most things go, it wasn’t a big ah-ha moment, it was a bunch of little things that all added up to me thinking I needed to do something. I collected a list of observations and problems I had relating to the general issue around task management:

As a team lead ___

• there is no one place to see an accurate and up-to-date snapshot of what the team is currently working on. No single source of truth.
• who is nearing a three month sabbatical, I would like an easy way to seamlessly temporarily transfer my role to someone else.
• it’s not always clear what everyone’s workload is. Who has too much? Too little? and to re-assign things as needed.
• much of my work is “invisible” and behind the scenes and I want to make that more transparent.
• with a growing team, I’m not in the weeds with everyone. There’s a lot of work everyone does that is in-progress and not immediately visible, and it would be nice if there was a way to help surface those items. Basically: we need a system that will scale with the team.
• I was made aware through one-on-ones that some people were having a hard time managing their own individual task lists. 

What tool I went with

I’m not a fan of choosing tools over talking to people, but I decided since we are a remote team and everyone is managing their own tasks, we needed a tool! We chose to use Trello because of its simplicity and familiarity. The tool itself isn’t as important as how everyone uses this day-to-day, so I’ll jump right to that. 

How this works in practice

First, I made two Trello boards: 

1. A main board and the only board that is “active”.
2. A board we use just for archive purposes.

The Trello board has 5 columns: Backlog, To Do, In Progress, In Review, and Done!.

As the team log on at the start of every week, everyone adds their to-do’s for the current week only. They then assign it to themselves.

If something comes up during the week, it’s added to the Backlog column. Ideally, nothing is added to the current week’s to-do’s once the week gets going. 

Each Trello card is a task. Tasks should be something that takes no more than a couple days. If it takes longer, it should be broken up into smaller tasks. Meetings shouldn’t be tasks, but brainstorming and decision making should be. 

As the week progresses, items are moved from In Progress, In Review (if needed) and then to Done! (Trello has a feature that lets you filter to only see your tasks.) We also have a Blocked column for those tasks that are blocked. Ideally, all tasks should be moved from the To Do to the Done! column by the end of the day on Friday. If there’s a link associated with the finished task, its added to the card so that The Week in Design post can be easily written.

If a task has been sitting there for several weeks, something is wrong and a conversation should take place. 

The output

At the end of the week, the person assigned to the Woo Week in Design Trello card, does the following:

1. Collects the cards in the Done column that week and writes up a post titled Woo Week in Design: [Month Day-Day].
2. The post is formatted to include everyone’s tasks within the divisions five goals. This is to give greater context and meaning around why everyone is doing a particular task.
3. Move the Dones! column to the Woo Design Dones! board. This is for a couple reasons: to not clutter the board up and also have a nice history of everything that we’ve accomplished over time.
4. Renames the To Do column to include the current week. 
5. Adds a new Dones! column with the current week referenced. 
6. Assigns the next person in the list to be the writer of the Week in Design post. They get a notification.

The bigger picture

When you’re heads down working on something for so long, it can be hard to remember what its all for. Taking a moment to look up, and see the bigger picture of your work and the work around you can help put everything in context. It also question tasks that may feel like a priority in the moment but don’t actually fit within the company or product’s goals.