For years, most productivity tools were the domain of power users and productivity whizzes, people willing to do the work to get more work done. (Or, in many cases, noodle endlessly in their to-do list app without ever actually accomplishing anything.) But over the past 18 months, those tools have become crucial to the work lives of people around the industry and the world. Colleagues can't hash things out at lunch or around a computer, and bosses can't check in on a project by walking down the hall. Everything had to be digital.
That transition forced people like Michael Pryor, the head of Trello at Atlassian, to rethink their tools. With new kinds of users coming into the system, Pryor said he and his team fundamentally reimagined Trello's place in the world — and built a framework for a new kind of productivity in a new era of work.
Pryor joined the Source Code podcast to talk about the new Trello, but also why work tools need to be more flexible, why too many collaboration apps fail and why the future of work might involve VR headsets. Eventually.
You can hear our full conversation on the latest episode of the Source Code podcast, or by clicking on the player above. Below are excerpts from our conversation, edited for length and clarity.
I've spent a decade evangelizing that people should use to-do list apps and care about their digital calendars. And lots of people do, but many more don't. They're just like, "I write stuff down, or I hold it in my head, and I do my job." And then all of a sudden, thanks to the pandemic, this stuff is mission critical. And when you have to go from designing your product for people who want it, to designing for people who have to use it because there's nothing else to do, it seems like the headspace you have to be in would be very different. How has that been for you?
One of the things that we did about six months ago was rethink, what's our place? What's Trello's place within this world of all these apps that people are using? That used to be something that we talked about a couple years ago: "Oh, there's all these tools, how do I make sense of this?" But that got turned up to 11 on the dial. It became this really important, mission-critical goal, to bring synthesis amongst all these tools.
It used to be, you talked about integrations. That was a big story, what other tools to integrate with, and I think that was kind of the lowest bar for that: How do I play well and plug in other tools? Now, because the entire way that people are working has shifted in this digital world, it's much more about recognizing that this collection of tools is our way of working. It becomes our office. And that physical space used to represent a whole bunch of things that we just sort of took for granted. You invite someone new, you have a new hire, and they show up at the office. And it's like, here's your computer, and, oh, come to lunch, and we're going to talk about these things. All these rituals that people used to do in the office, the things that they did about building trust and understanding amongst your teammates, and gluing you together so that you could do work together and be able to see what everyone else was doing and talk about it.
Now, that's all happening digitally. So the bar for bringing those tools together and making them work in a way that is customer-first, instead of just, "Hey, I add some integrations, you have to plug them in." And I think that bar got raised much higher than it was before.
I'm curious to know more about the process of thinking through how Trello fits into this new space. Because to your point, everything changed all at once. You built this thing a long time ago that was deliberately flexible, it can be lots of things, people use it for lots of things. But then on the one hand, everyone else who makes software has spent the last decade ripping off the board structure. And on the other, every new work behavior is different. So it wouldn't totally shock me if you sat in that meeting and talked yourself into building, like a Microsoft Teams competitor. What is that deliberation process like?
We started thinking about, what's the evolution of the app? How do we react to this and build for the future? We went back to this core thesis, that the reason people really engage with Trello is because it's a visual organization system. It can be applied to project management, but actually, the reason why people first get into it is because that's the behavior that we do in our normal workspace: the Post-it notes on the wall.
There's something about the spatial representation of things that allows us to remember and understand, and feels very organic, and it's kind of rooted in our sensory system, right? Versus a database that lets you query it and show you the results. So I think that's the difference.
Even if you look at Excel, for example, Excel is really just a glorified table. And that's why people use it for so many different things. It's a grid, and all the cells already exist. So you could put something in the top left, something in the top right, put something in the bottom left — that spatial relationship is really important. So when we thought about that, it's like, yes, there's a lot of tools popping up. People are copying Kanban, we weren't the first to do Kanban anyway. The reason that people gravitated towards us was that that visual organization was really powerful.
So for us, it was like, how do we take that and apply that to all this other information that exists elsewhere? In Trello, we have cards that are in a list on a board. How do we make the card represent not just a task in Trello, but represent work that lives outside of Trello? This card actually represents a Figma document or this card represents a Loom video. How do we bridge the gap between that, and apply our visual organization to all that work, no matter where it lives. That was sort of the goal there.
So you're thinking about it as partly the work itself that people do, but also like the work about work. You see all those statistics, people waste half their time trying to find stuff in their email or search for information, or whatever it is. Is that kind of the space that you're trying to help people solve?
Why do you feel like that hasn't been done by others? There are so many digital tools that could do this.
There have been a lot of attempts to do it. And most of the attempts that I've seen have been these notification streams. So essentially, you take all your tools, which are generating notifications, and you put them into one stream. So you can go to this place that shows you, "Oh, someone commented on a Google Doc. Someone replied to your Slack message."
I think part of the problem there is that when you think about that notification stream, you've now taken these messages or these alerts out of the context that they're relevant to you. And so I think the system that is better able to do that is the system that also allows you to apply your own context to it. I think search plays a big role in that, but I also think so does allowing people to curate and put the information into the format that makes sense to them. Instead of imagining that you're going to have a system that just does it automatically for everyone in the same way.
There's actually a cool little app that I use called Workona that does that for tabs in the browser. It allows you to organize your tabs and kind of collect them together and give them a context that's relevant to you and stuff like that. I think people have been applying that concept to a lot of different tools and trying to figure out what's going to stick. You can build the tool, but it also has to be easy for people to understand.
In fact, if you build collaborative collaboration software, you always realize that the biggest hurdle to getting adoption is that one person on the team that isn't gonna use it. How do you bring that person in? That's the Achilles' heel if you build team tools: You have to be able to bring in the whole team or it won't work.
If you build collaborative collaboration software, you always realize that the biggest hurdle to getting adoption is that one person on the team that isn't gonna use it.
The chat tools actually did really well at this because deep down we're all gossips and voyeurs. You just want to consume the messages from other people. And so I think there's already a built-in human desire to eavesdrop and read and stay up-to-date on things. And then the question is, how do you do that for other tools? What is the mechanism that you can bring those people in, so you don't end up with the one advocate going, "Come on, let's use this collaboration software." And then everyone else is like, "I'm fine. Email and spreadsheets are good enough for me."
The other part of this kind of systemization versus personalization thing is automation. The idea that we can, and should, and will automate away most of the work that people do. Where do you feel like we are on that front? Is automation the future of everything?
There's a funny story about trying to imagine the future that my co-founder Joel Spolsky used to tell me. Fifty years ago, or 80 years ago, when people would imagine the future, they'd draw these pictures of what the future would look like, and they would talk about a robot that washes your dishes. And it would have all these arms, right? And it'd be like scrubbing the dishes. Or you go to the bank, and instead of having a teller there would be a robot. You'd say, "I'd like to withdraw money," and it would put it in. Then, when you think of a dishwasher or an ATM machine, they don't look like what we imagined they would look like, but they have the same role and solve the same problem.
I think that's a little bit of what is happening now. When we talk about AI, we're like, "Oh, it'll be amazing, we just won't even work." But it's this step by step thing that happens over time. And it's not this world in which we're just all riding around, like in "Wall-E," where they're in their chairs, and they're sipping their sodas. We're going to occupy our time, but we're going to focus on higher-level things, instead of the lower-level things, we're going to try to take out that monotony with AI.
I think the next step is this idea of quantifying the data and understanding what's changing. So at Trello, we've introduced this concept called Dash Cards: You make a card, and it's actually a metric that's watching a bunch of information inside Trello. And it can represent data on other boards or whatever. The beautiful thing is that then you can set alerts when that information will change to a level that you really want to make sure that you care about. You might want to know if there's less than 10 unopened tickets on this board. But being able to set an alert so that you get a message when that hits 10, now you've set up a system that allows you to be a little bit lazier, right? You've codified something to protect yourself.
It's like the water sensor in your basement: You're not looking down the basement all the time, but you know if water's down there it's a problem. And sure, you can just wait until you get out of the basement and see the water. But that's not what you want to happen. And so I think that melding automation with metrics, and the ability to understand your data and allow you to describe what this data represents to you, and then put the automation on top of that, is super powerful.
It seems like the last big idea we had about how to get things done was the Kanban board. That as a structure was a big, cool, new, exciting idea … a long time ago, and it doesn't feel like we've had a better idea since then. A, am I missing something? B, why not? And C, is there one coming?
I don't think these things were inventions, they were things we already did. And then they were just encapsulated into a software. The idea of creating lists: That's been around since the beginning of time, right? This is not a grand invention. Things that are really powerful and have staying power are rooted in customs that we already have in the real world and we've been doing for years and years and years, decades, before software even existed. You see those concepts having that staying power.
Things that are really powerful and have staying power are rooted in customs that we already do in the real world.
Whether it's Confluence or Google Docs or Notion or whatever, it's just a piece of paper, right? You're writing words down, you can draw things, you can add images or whatever. They're not new, per se. It's just, what's the affordance? How do I relate to it? What's the ease of use, the speed, all those different things that go into whether somebody decides to continue using it or goes back to the original thing and they're sticking Post-it notes on their computer screen again.
Shouldn't we have gotten past that by now? There should be something better than all of the stuff that we used to do on pen and paper. Are we ever going to get past that? Is there anything past that?
I think once you get enough people accustomed to those things in the digital world. In some ways, the pandemic forcing everyone to work remotely actually presents a new opportunity, because now you've set the bar for everyone's level of understanding. Go back to the iPhone 10 years ago, and look at the ability for people to navigate that system 10 years ago. It was kind of difficult. Now people are growing up with technology; my kids, when they were 4, were able to use an iPad and figure it out.
The software is getting better, but also the time spent using these tools and these abstractions is now encoded into people's brains, and the way that they're thinking and working. And so as you get more and more people doing that, then you're able to go to the next step.
It's slower than you might think, because you're talking to people that are kind of at the head of the pack. And you're like, let's go faster, let's go faster, but you're actually restricted by the movement of the entire base, because we all have to work in companies and teams and groups that encompass everyone.
I think we're going to see a huge wave of innovation right now and over the next couple of years, because now everyone gets Zoom. Everyone gets videoconferencing. They're not on the phone, they're on video, video has now become kind of like default. When you get those baseline things happening, it allows you to make assumptions in your software about the vast majority of people that are using it, and then lets you go to the next leap.
We're all gonna be wearing VR headsets, I'm telling you. You get the Oculus and play, like, mini golf, and your mind is blown.