Collaboration, Kickoffs and Ideation — Atlassian

One of the hardest things as an Illustrator is allowing people to be part of the journey. I always thought it was because I struggled with believing that designers or engineers could never truly understand. Although through my work with design systems, this thinking only limited my scope to allow people into the narrative to create illustrations. 

The biggest collaboration project I worked on for illustrations was for Stride. Stride was an Atlassian product that allowed teams to communicate with one another within the company. Previously the name of this product was called HipChat. This brief was a huge ask, as it required a lot of onboarding, empty state, and system messaging illustrations. I was quite familiar with these UI experiences as I've done previously for Jira, Confluence and Bitbucket, except these were usually much simpler asks and jammed on with the other illustrators. However, for this work, I was going to be the sole Illustrator on this project. 

Yes, it sounds somewhat overwhelming; but yet I was so excited. The most beautiful thing about this project was that I used Stride day in and day out; I knew what I loved and how it made me excited; I wanted to share my love for the product with its users. 

The first task at hand was running the kickoff. I look back and remember how chaotic this was. I was based in Sydney, Australia, the marketing team was based in San Francisco, California, and the Stride team was based in Austin, Texas. Honestly... I had no idea how we did it. But after some severe calendar searching in advance, bumping around times, and telling myself, "you got this, you're only doing your best, no one will be angry at you with setting up some ridiculous times", it happened. 

Kickoffs are so important. Learning from Design Systems running these kickoffs thoughtfully really put a face to the team, instead of random requests thrown into a black void. In the past, kickoffs were typically going through the brief talking about goals, types of spot illustrations/icons, due dates, restraints etc. But I wanted this kickoff to be more framed as an ideation session mixed with some journey mapping. I really wanted the designers and engineers to be part of this journey with me. Illustrating their ask takes me 50% of the way, but I firmly believe that working on this product for many quarters can take me to the next 50% of the way. I want to think my role was to bring their ideas to life. It's the ability to make it human, meaningful, thoughtful, and anchored with understanding the user's emotional state at that time for that illustration. 

Given that these meetings were remote, I wanted to make the ideation sessions interesting and engaging. I used Trello (another Atlassian product but I’m not here trying to sell it, I genuinely do love using Trello) and started forming columns as discussion topics, deep-diving into what metaphors, stories, and ideas we could bring to light when thinking of Stride. It was key to set the expectations that these were just ideas and something would always iterate overtime. Interestingly, it allowed people in the room to really empathize with an Illustrator's journey and how important it was to carve ideas at the start.

After this session, I was able to jam out on some beautiful and thoughtful ideas. You can see the actual hot mess of my Illustrator file. I loved finessing on all these things here; I was able to foresee the personality of Stride. We were making communication feel at ease, simple, fun, and considerate for teams. 

Once we start seeing the illustrations in-context, you begin to see how they work, break, and all the funky stuff you don't expect. This example looks at how I was able to push the style further and really find those unique Stride motifs and build better fidelity. The speech bubble began to be this symbol across the board for this communication product!

And then, we started using that speech bubble across the illustrations as a subtle nod to this particular product. My favourite ones are camping and flying through space spot illustrations. There was a unique charm that we haven't seen yet for an Atlassian product. 

But you know, not all ideas were great. Some were quite a cliche, like an ice cream falling over for a 404 page. Or some ideas that I tried incredibly hard to hone and get right, but look, not all ideas work. This is all part of the illustration journey. 

The biggest learning here was that we've never run these kinds of sessions ever at Atlassian, but I could see the potential with this style of kickoffs for future work. The sense of passion and excitement it brought across multiple working partners really allowed others to be part of this mysterious (or maybe foreign) journey. Most importantly, I was able to find that people were empathetic to the Illustrator's role. Ideation can be tricky. But I was able to make a beautiful body of work because of the Stride team.

Collaborative Partners: 

• Stride Designers: Nichole Burton & Joel Ugner

• Marketing Designer: Sara VanSlyke