An interview with Michael Pryor

Michael Pryor, Co-founder and Head of Trello at Atlassian

Trello embraced hybrid work long before the pandemic. What drove that?

A lot of times, you have somebody super talented on your team, and for whatever reason, they have to move: Their spouse got a different job, or they had to relocate. That's how it started for us. We had somebody that needed to move to Hawaii and we said, "You know, you're too valuable to lose. We're going to make an exception here. And we'll just figure out how to make it work."

It started to spread. In 2014, I wanted to hire a head of marketing and head of sales, and I found two amazing people: a woman in Chicago and another woman that lived two hours outside of New York City, where we were based. I said: "This is a big step, because we're hiring leadership roles in remote positions now." We decided to go all the way and start developing a culture for remote work — and that was largely driven by those first remote employees.

We're coming up on Trello's 10-year anniversary. How has your approach evolved as the rest of the world embraces hybrid? What do you see as Trello's role?

Not much has changed drastically for us; prior to the pandemic, 80% of the team was already remote, so we were already used to working together in a hybrid environment. Now we're 100% remote, working from our offices at home, but we had already put a lot of remote work best practices into place. Years ago, we saw the benefits of working that way. When we would put job listings up, we would get probably five to six times as many applicants when they were remote than if we had just put them up for New York City-based workers. Being able to attract and hire really amazing talent all over the world gave us a leg up on the competition, and was a catalyst and driving force behind our growth.

Atlassian acquired Trello in 2017. How have you helped Atlassian as a whole embrace hybrid work?

We decided to do the deal in the first place because we had such a great match between our values and Atlassian's values. I remember, when we were doing the acquisition, the co-founder of Atlassian, Mike Cannon-Brookes, made it very clear that this wasn't just a moment for us to adopt the ways of Atlassian. It was also for Atlassian to learn from Trello.

When we became part of the team, we became spokespersons for that remote way of working. There were already people in Atlassian working remotely, but the organization didn't have a strong muscle for remote work. They saw that we had amazing retention on our team, that the product that we're building was loved across the world and the team was really happy. So we wrote down our best practices for creating a remote-equal culture, shared it with Atlassian and then actually published it for the public to use.

How would you advise companies navigating this transition for the first time?

The number one thing that people ought to be mindful of when all of your communication is filtered through some kind of digital medium, versus face-to-face communication, is that the message is altered in ways that you don't even realize. You have to be more purposeful about communicating and understanding the context, because the kinds of nuanced communication that you get in the office doesn't translate well online unless you purposely translate it.

For example, let your coworker know on Slack that you are juggling tasks but will get back to them. Or let them know that your responses are short at the moment because you're typing on mobile, rather than leaving them wondering why you are unresponsive or not providing more detailed replies.

Meeting fatigue is rising. How does Trello tackle that? What role do you see for async collaboration?

We're seeing a lot of new tools pop up whose aim is to boost async communication so that meetings can be reserved for discussion, instead of status updates. In async communication, communicating context is especially important, since you can't see someone's facial expressions. For example, a lot of note-taking apps or document collaboration apps have now added features where you can add images to the header. Before, when you'd write a document, it'd be something of a wall of text. It can seem like a small change, but I think even just being able to add an image throughout or in the header goes some way to setting the expectation for the document: "Oh, is this a fun document? Is this a serious document?" That's why emojis are so popular and why we've built them into Trello — along with GIFs and stickers — to help communicate tone in async communication.

One of the things that becomes more important in this asynchronous way of working with people is communicating that context, and understanding the emotional presentation of the work. Trello's entire product design is based on that visual style of communicating context around the work that you do with others.

What are the pinch points businesses are facing as they move to a hybrid work model? How does Trello help alleviate them?

There's never a straight transition from the physical to the digital. A lot of the culture does carry over, but you just have to be clearer about what you're doing. For example, we used to have meetings once a month for the whole team: Trello Town Hall. We would do that in a big conference room, and at the end of the meeting people would talk to each other in small groups before heading back to their desks. When we moved to town halls over Zoom, we realized the content was still there but what was missing was that connection piece after the meeting, which is, "Hey, there was naturally a moment where people would gather and talk to each other. Now we have to create that moment purposely." Now, after virtual town hall meetings, we have "Mr. Rogers" sessions where we break out into smaller virtual rooms and people can socialize or catch up on non-work stuff.

The transition from doing things the "in person" way to the "digital" way is hard. We've had to be very intentional about how to create the cultural environment to be a productive team when we are able to work from anywhere. This thinking also extends into the tool that we've built (and the others that we use). We are always asking: What type of company personality do we have? How are we going to solve these needs in a way that feels unique to our team, with tools that feel natural to use?

Thankfully, Trello has filled that gap for our teams to transition to remote, by providing one place for everything from project management to team brainstorms and 1:1 meetings with managers. Paired with Confluence, Slack, Jira and Zoom, we have a solid tool stack that everyone shares.

Supporting a culture of inclusivity and collaboration can be particularly challenging in a hybrid environment. How is Trello approaching this?

Starting at the executive level, you have to do work to standardize collaboration practices or they'll fall by the wayside and won't happen. You also have to spend a lot of time listening to your employees. Whether it's through surveys or leaning on your network inside your company to suss out what people are feeling, be open to change what is and isn't working.

A million different problems will come up and they will vary from person to person, company to company. Hearing when remote workers feel treated differently than in-office employees, for example, or vice versa and making adjustments to ensure everyone knows that an equitable policy is a top priority — that's what has made it work for our team, for the long term.

What are some of the unexpected things that Trello helps enable or unlock?

Trello is very flexible for a lot of different use cases. The unit of work in Trello is a card and that card can be used for many different things: It can house a single task, or it can be used to represent a team's project, with checklists for individual tasks within it. So, it's not just a piece of work that exists in a tool–it's a broader concept that your team can apply and evolve to tackle the work as it grows and changes.

That flexibility means Trello ends up being used by a lot of different departments within a company, where it becomes a great bridge between all types of teams. It's a connection point for technical and business teams, say engineers and marketers for example, that unlocks a shared collaboration space. Once everyone isn't in the same office anymore, it's important to maintain those open places where teams can see each other's work.

What you need today to facilitate remote work will change over time, so having a tool that can grow with you creates stability. Trello fills in that space between the gaps. I used to explain it like this: A lot of the vertical tools that people use within their own departments are like rocks on a beach, and Trello is the sand that fills the space in between.

Trello talks a lot about the challenge of context switching. How are you helping organizations cut down on that?

When Trello first moved to remote work, we had to adopt all these different tools — and each of them each served a distinct and important purpose. Fast forward 10 years, and now the product of our work is in a bunch of different places. So the challenge of all-digital asynchronous work for the long run is about unifying under a system or tool where people can expect to find that work and access it with the right level of permissions.

Trello does all that by being your hub to manage all the work, no matter where it lives and what tool you want to use to accomplish it. For example, when you paste a link to a Google Workspace document, YouTube video or Dropbox file, you will see a preview of it on the Trello card. In some cases, you can edit it directly from that card without having to log into another tool or open another app. It helps immensely with context switching and keeps your work organized in an easy-to-parse, visual way.

What's next for Trello?

We just released a new plan called Standard, a lower-price option for small teams. We want to make sure that there are price points and features for all different kinds of teams and companies.

We've made Power-Ups unlimited so now you can add as many integrations and added functions as you want on your boards.That is great for users because they can now connect any and all of the tools that they use to get their work done — and many of those Power-Ups are free. It's also great for our ecosystem of developers because they can create a business on top of the Power-Ups they build, creating more tailored options for users who want to customize Trello for their organization's specific needs.

We've also upped the automation limits for all of our plans. We're thinking about how people are building their digital office and how they're using Trello to do that — a lot of the tedious, repetitive work should be automated — so we've made it easier for users to teach Trello to handle those tasks for them.

We're doubling down on our Enterprise tier, which gives organizations wall-to-wall security on Trello, by listening to our biggest customers to dial into what a powerful Trello experience at scale means to them.

And, maybe most importantly, we're evolving boards and cards. That is going to be something that we continue to invest in heavily because hybrid teamwork is only going to get more complex.

We need to help people break down those silos between their teams at work, and make it easy to find the work that's relevant to them. At the end of the day, it's about helping people manage the insane amounts of information coming at them and enabling them to quickly make sense out of chaos, so they get through their workday smoothly and hopefully, with a little fun.