The Slack/Asana hybrid of my dreams — and yours?

Hello there, gentle reader! Given that you’re glancing at this post, I’m going to go out on a limb here and guess that we’ve got a couple things in common: We both rely on web apps to collaborate with our colleagues, and we’re both a little frustrated, feeling like the tools could serve us a whole lot a better.

I’ll talk about apps in a second, but first there’s something you need to know about me: I’m really easily distracted. I’ve always found it hard to focus, and easy to lose my train of thought. Some folks like to say that they’re great at multitasking: I’m shamelessly, openly terrible at it. (Science says I may be in good company, but that’s another story.)

I work at Upturn, a small team based in Washington DC, and we started using Slack for office chat in October 2014. It quickly became our main tool for working together online.

Here’s a picture of how much Upturn uses Slack. The top of the y-axis is 1,000 messages per day, and we are (usually) a team of four.

Slack (the web 2.0 update of a 1980s technology called Internet Relay Chat) is compulsively usable and fun. It offers the same blend of enjoyment and addiction as the social media apps we use at home. There are channels for each project, and the app constantly alerts you to whatever your teammates have just said.

Slack is like a party that’s always happening — or, maybe it’s more like a meeting that never ends. Samuel Hulick nailed what’s wrong in a break-up note to the app last month:

With you in my life, I’ve received exponentially more messages than I ever have before. And while it’s been awesome to have such a connection with you, it has been absolutely brutal on my productivity.
I’m finding that “always on” tendency to be a self-perpetuating feedback loop: the more everyone’s hanging out, the more conversations take place. The more conversations, the more everyone’s expected to participate. Lather, rinse, repeat.
Someone just said something — to me! And I haven’t seen it yet! Should I take a peek? Might it be important?

Others have chimed in — there’s even a more complete list of the seventeen (!) downsides of heavily using a chat app like Slack in the workplace (“5. Implied consensus. … You know how it goes — people talk about some work in the chat room and nobody objects. That leads people to [wrongly] assume everyone read that discussion and agreed”).

Slack is a constant enticement to switch gears and interrupt oneself. It’s great at getting us to spend more time chatting — and terrible at empowering us to be the masters of our own attention.

There’s got to be a better way. And we already have it — sorta.

Here’s an Asana task.

What I need is a smooth, elegant, well designed web app that allows easy, flexible conversation — but keeps the focus on what’s most relevant, not necessarily most recent. The right tool does not interrupt, except in extraordinary cases of true urgency. And we already almost have that, with Asana.

Asana organizes each project in terms of the different tasks that need to get done, rather than the most recent things people have said about the project. Each task can have an exchange of messages attached to it, which the company calls a “conversation.”

Classy, elegant. Organized. So why does our team rarely use it?

Asana’s dirty secret is, too often, it actually looks like this:

I’d like to work through my checklist at a human being’s pace. But it’s no fun watching my software do the same.

In other words, it’s slow. Slack is immediate — an instant reward — but Asana keeps you waiting. It’s ironic: Relying more on Slack is actually profoundly inefficient, but because the chat interface snaps right to attention, it feels more efficient. And Asana, which respects your attention and helps you focus, feels as if it’s slowing you down.

To be fair, Asana’s speed problem isn’t really a secret: the company recently announced on its blog that speeding up the app is “a massive project, and our highest priority.”

How bad is Asana’s speed problem? Well, the imminent new version is supposed to load in one sixth of the time it takes today. Which is the same as saying, launching the app today takes six times longer than it should. That might only be a few seconds, but the psychology of the experience — against the backdrop of instant chat apps like Slack — is profoundly unlovely. You feel yourself waiting for the app to catch up, every time you try to use it. So, sure, it might be better to use Asana and leave a note for my colleague to read when they’re ready. But why should I wait around? I can jump on Slack right away, and I’ll even get a response sooner! Human nature favors the more interrupting, less efficient approach.

The right thing might be hard to build, but it’s easy to imagine. It’s a faster version of today’s Asana, plus real-time cues that let you use any given task’s conversation as a Slack-style chat.

Making Asana faster is a good start, but there’s one other critical thing that it needs to add in order to become our team’s natural, real-time hub for work: The threaded conversations it provides for each task need to include real-time presence indicators and real-time updates, so that people can, where and when they want to, treat any given conversation as a real-time chat. Right now, in Asana conversations, you can’t see who else is looking or whether they’re about to post. The conversation about a given task ought to be a place where people can connect in real time — where you know if a colleague has the same task open, and can see that “so-and-so is typing.” At the same time, those conversations will naturally stay organized. Related material stays together, and if you’re not there in real time, you really can, easily and naturally, review the relevant information whenever you’re ready.

That’s what I’d like to see, anyway. What do you think?

Thanks for reading — I’m new around here. I’m also @dgrobinson on Twitter.

If you’re into technology, you might want to check out Upturn’s blog on civil rights and and tech, Equal Future, which is also a newsletter. I recently wrote on there about the Beware® “threat scores” some police are now assigning to people who call 911.