Jared Sinclair’s post today about Glassboard got me to thinking about this type of app in general. I call them project collaboration apps because they deal more with discussions than planning. (Whereas project management apps deal more with planning than discussion.)

The best project collaboration apps I have found are:

• Glassboard
• Quip
• Slack
• Basecamp

The problem is that I simply cannot tell you which of these is the best because they all have issues and strengths. In short, here’s how I see these apps stacking up:

• Glassboard: Designed around the one idea at a time approach. A users posts a new message and there is a thread of other users responding to that message. It’s best thought of as a thread on a message board. The obvious benefit being that threads are usually very on topic and to the point. The down side being that there is less room for a conversation around a general topic, as messages are designed to be more specific than that. Should you want to be more general you will quickly get lost in all the comments on messages.
• Quip: Designed around files. Think of it like Editorially for Word documents. Quip is all about collaborating on documents, so if you are only sharing Word-like files, you cannot get anything better than Quip. It’s far better than track changes if you ask me.
• Slack: Designed around conversation topics. The newest kid on the block is very well received (I use it multiple times a day). You create #channels that have set topics. Everything flows like a more natural conversation in those rooms — like in chat rooms. Files can also be uploaded into a room, where files then get a specific comments thread for each file. Overall Slack excels at water cooler talk, and general discussion. Where it lacks is focus. If you wanted to talk specifically about one design element of an app (like a button, instead of the app design in general), it is quick and easy for that to be derailed, and then hard to track the conversation about just one specific element.
• Basecamp: The OG of this type of app is designed with a more traditional project management focus. Though, in recent updates, the app is slowly shifting to project collaboration. I’m of the opinion that Basecamp combines Quip and Glassboard, but doesn’t do either function better than those apps. Basecamp for the most part still lacks a freeform chat, which was previously built into the product with the help of Campfire. Basecamp excels at structure, but lacks in allowing structureless conversation.

In a nut shell, each app has strong reasons to use it, but none of them are there yet — to me this is evidenced by the fact that I use all four of them weekly (if not everyday). I’ve been trying to think about what is missing from these apps, or what the perfect app would be, and I’ve come up with some core ideas that I think are missing (in some form) from some, or all, of these apps:

1. Give me a way to have conversations around one central theme. Something somewhat general like ‘design’. Slack excels at this, and though you could do that with multiple boards in Glassboard, it’s not setup for free form conversation. Again, Slack is the perfect example of this. This type of loose conversation is ideal for brainstorming, and also perfect for roughing out where a project is. It’s the tool you want to keep to get the project off the ground, and then gives you a place to vent as the prject gets closer to completion.
2. Allow me to define a specific topic within a conversation. This is where Glassboard and Basecamp excel, and Slack suffers. Going back to my earlier example, if I want to talk about button design within a ‘design’ conversation I should be able to track just that discussion without being sidetracked by side discussions. For that the Topic > Comment framework is ideal. While you could create more #channels in Slack, that’s a hack of a solution. I’d like these specific topics to be visible within a main conversation, but then to later be able to just view the specific conversation on a topic. This is critical once a project is under way, and all the way through completion.
3. Commenting on files and images is crucial. Each of these apps handle this in some way, all different, but I think Basecamp handles this the best. I like that I can have a conversation on a topic in Basecamp and attach any file. In Slack you can do that, but then that file can have specific comments on just a file — which is confusing. If you are swapping mockups for one design element, it all needs to be maintained in the same thread — as Basecamp does. I should be able to upload a mockup, and each person responding should be able to comment on that, and upload iterations of that mockup all on the same ‘thread’. Again, crucial for most projects that are underway.
4. I need to collaborate on text. Basecamp has a really poor implementation of collaborating on text, and it’s so bad I don’t want to talk about it any more. Quip, clearly, does the best job here, but the app is so niche it is hard to assimilate into a workflow. Every project invovles writing something at somepoint — it should be natural part of such an app.
5. Private messages are a must, and Slack really does a good job at that. It’s nice to be able to talk directly to a team member in a private setting, but not be beeping their phone with each message. I want to be able to leave work when I leave work. I want to be able to use my comptuer without getting bugged by work. To that end, I want the private messages within the app, instead of IM or Text messages.
6. Notifications need to be smart. The app should be able to tell me when things are directed at me, and what I have and have not read. Again, Slack does a very good job at this. I talked above about how Glassboard doesn’t handle this well, and I personally think the dashboard view of Basecamp doesn’t handle this well either. Slack needs to centralize these notifications, but does the best job of the lot. I also need to have quiet hours, to turn off the notifications, but get a summary when I get back to work.
7. Bookmarks. Most of the apps have a way of bookmarking a topic, or message, but I always wish it went further. I’d love to be able to send different things within each topic/discussion to a reference folder of sorts. To be able to quickly cull together excellent ideas, tasks, and important notes in one place that is only visible to me. Something like a montage of important pits from all the things going on within the app.
8. Allow me to get old stuff out of my face: a.k.a. give me an archive buttons that works. I still want to be able to see it if I need it, but I don’t want to see something that just isn’t active anymore. Once we design that button, I only need that conversation for posterity and not for active discussion. Remove the mental overhead of seeing that discussion when I login.
9. Allow me to take any one message, or thread of messages (or files, etc) and turn it into a task for a team member. Most task systems ask you to create the task first, and then discuss it. I think that is backwards. I say, lets talk about the button design and then when we get it all figured out, assign the implementation to one person.

That’s my quick and dirty list of things that need to be addressed in project collaboration tools. Perhaps you don’t think this is all that important — these are niche tools — but to think that seems to be sticking yourself with the idea that going into the office will always mean: going into a physical office where all your coworkers are. That’s changing, and changing fast, and these tools are becoming vital to that change.

I hope they get better and get better faster than they are right now, because using four apps at once is tiring.