⭐️ Overview

Outline is really nice to use — it’s fast, has all the building blocks needed to organize a complex hierarchy of documents, and generally feels very constrained in what I’m allowed to do so that I can focus more on writing than on organization. To me, this is a big benefit over competing tools in the space which seem to offer a myriad of organizational tools, at the cost of helping me get words on the page.

Here are some areas where I think there is the most room for improvement:

1. Managing permissions is confusing

Overall, Outline is very intuitive and easy to organize. However, as soon as I entered the flow to manage groups, members, and permissions for a collection, I was lost. I think we should spend more time together working on this, but I have a couple quick recommendations that might help.

Recommendations

• The full-screen dialogs in this multi-step flow are very disorienting. I was constantly confused “where in the stack” I was, and it wasn’t easy to predict what would happen any time I clicked Back or moved forward through the flow. I think we should find ways to combine these dialogs, or even stack them in such a way that you can see multiple dialogs at a time, because it’s more important to know where I am in the flow than it maintaining visual simplicity.
• The flow is particularly odd because it seems to work in reverse: you enter a screen to add team members to a group, and when you click add they disappear — then when you go back to the previous dialog, you see the results of your additions. Ideally, flows like this are always additive: when you add things, they shouldn’t disappear from a list.

2. Improve visual signifiers, key lines, and targets for discrete actions

There is room to improve the hierarchy of compact elements and components (like the sidebar, or the document list items) by taking advantage of consistent key lines for text, adding better visual signifiers on-hover for nested actions (like starring a document, or expanding/collapsing a section of the sidebar).

Recommendations

• See Loom + Figma.

3. Dialogs take users out of context and break spatial awareness

This is rehashing the same problem above, but I wanted to call it out as a specific problem worth solving: I think more dialogs should be inline and overlaid on top of the user’s current position in the app. The full screen + white background styling is disorienting, especially in contexts where the user would want to see what they’re modifying or taking action on. For example, when deleting a document, it would be very helpful to see that document in the background of a dialog to preserve that context of what is being destroyed.