Hello! Who are you? Tell us about yourself. What are you passionate about? What do you enjoy doing?

I’m Christopher Davis. My friends call me Chris. My mom calls be Vitamin C. I’m a self-taught designer who’s currently working at Trello.

I spend a lot of my time working. But when I’m not thinking about Trello, I’m usually cooking or working on a side project. As I’m writing this, it’s January of 2019, and I’m committed to reading more books this year. Check back in with me later, and hopefully “bookworm” will be a word that I use to describe myself. 

I live in (or ridiculously close to…) Louisville, Kentucky. It’s a town known for bourbon, but our food and coffee scenes are wonderful. Hence, my partner and I spend a lot of time eating and drinking. She and I are huge foodies! We also love to travel. We got to visit Italy, Australia, and Portugal in 2018! 

How did you get started in product design?

For as long as I can remember, I’ve been doing design work. I think it started with gig posters for my friends’ high school bands, which evolved into business cards, flyers and websites for their parents. From an early age, I was inspired by people like Scott Hanson, Joshua Davis, and James White. I fell in love with the process of designing during late nights spent with long Photoshop and Illustrator tutorials. 

I first became aware of the concept of Product Design while building an app called Over with my good friend Aaron Marshall. While I worked on growing a fanbase for the app, I got to watch the product development cycle take place. Aaron taught me a lot about building great experiences; I credit a lot of my foundation to him. 

My first role in “product design” was as an Information Architecture Director at a local agency. It’s a hilarious title, because I had almost no experience, and must have been 20 or 21 years old. But having a title to live up to forced me to grow. I bounced around a lot over the years, working for several more agencies, freelance, and eventually, in-house. 

For me, the years spent freelancing were indispensable. I had to learn to sell the value of design, and then deliver on it. In order to be competitive, I had to be a good visual and UX designer. In order to understand the client’s needs, I had to be good at communication and research. It wasn’t always product design — there were a lot of logos and pamphlets — but everything I learned helps me do a better job in my role today.

Where do you work today? What is your title?

I’m a Senior Product Designer at Trello, working on onboarding and activation.

How big is your company? How big is your design team?

Trello’s actually a part of the Atlassian family, so it’s a big company within a really big company. There are only about 15 design folks at Trello, including researchers and design managers. 

What types of things are you responsible for day-to-day?

I’m on the team that’s focused mainly on Activation, which is a fancy way of saying that I spend most of my time thinking about how to make it easier for new users to get started. It’s such a fun task! We recently redesigned onboarding to make it more fun and engaging, and we’ve seen a positive impact. These days, I spend a large portion of my time writing; often in Mural, Dropbox Paper, or Confluence. There’s a lot of think-y stuff that goes into planning experiments, pulling off user research, and analyzing data. I’m trying to spend more time in these things before touching any pixels. There’s still plenty of Figma time though, don’t get me wrong! 

Most days, I do a little bit of visual design and prototyping, and a lot of planning. Oh, and did I mention meetings? 

My desk setup

What do you love most about your work?

It’s challenging me…a lot! As is often the case in experimentation, 80% of our tests fail — which means lots of iteration. It feels amplified in the activation space, where meeting the needs of Trello’s unique audience with the horizontal use cases of our product is a pretty complicated task. I think it’s a fun challenge, and the built-in constant failures (erm…learnings…) are chipping away at my ego. I needed that. 

Above all, I love the people that I work with. We’re remote, but we feel like a family. 

What drains you at work?

It can be a bit lonely, working from home. I’m naturally an introvert, which for me means being comfortable in the quiet of my house, lost in my own head. There’s a certain energy that comes from being physically near your team, especially when you enjoy each other’s company. I do miss that. 

Otherwise, the constant process of testing and failing can be exhausting. Ending a quarter with a few 0.3s or 0.5s on our team’s OKRs feels like a miss, even though I know that’s the wrong perspective. Ongoing experimentation is new for me. I struggled a lot with imposter syndrome when I first joined Trello. My experience in agencies and freelance didn’t include a lot of regular testing. Even though I mentally knew the steps, I didn’t know what it would feel like to see so much of my work fail. It created a lot of doubt within me, and that Imposter Syndrome told me that I didn’t belong. Through personal reflection and some wisdom from my amazing manager, Courtney Drake, I was able to push those feelings aside.  

Many of the other designers on the team are excited about these failures. I’ll be that way soon! In the meantime, it’s a muscle that I’m working to build. For me, the secret is finding joy in the process and refusing to let doubt in my abilities trounce my curiosity. 

A reminder to breathe through stress and frustration

Can you walk us through your typical work day?

8:30amMy Sleep Cycle alarm goes off. I snooze it, and go back to sleep. 
Force myself out of bed and straight to the kitchen to make coffee. I’ve been trying the whole collagen peptides thing recently, so I’ll mix a spoonful into my v60. The powder has no flavor, which is nice, but I still haven’t seen any results. I’ll keep drinking it, I guess.  
9:15amMake breakfast. Monday through Friday, that’s usually some eggs, black beans, and spinach. 
9:30amEat at my desk while catching up on blogs and Dribbble. I work from home, so there’s usually at least one cat nearby. 
10:30amSketch out a post-it note schedule for the day and start by knocking out at least one low-hanging item. 
11:15amI don’t usually stop for lunch, so from now till 5:30pm-ish, it’s emails, meetings, strategy, and pixels. Sometimes I’ll take a Masterclass break. The creator of the Sims, Will Wright, just released a course on Game Design. I couldn’t recommend it highly enough. And if you’re into food, you’ve got to check out Gordon Ramsay’s and Alice Waters’ classes.
5:30pmStart winding down. Even though my partner also works from home, she and I rarely get to talk during the day. I always look forward to the hour we’ll spend catching up, draped over our office chairs at the end of the day. 
7:30pmStart cooking something for dinner. We’re trying a plant-based diet right now, so it’s usually pretty fast to prepare something delicious. 
8:30pmDinner’s done and dishes have been cleaned. Sometimes I’ll spend a couple of hours working on a side project. I’m building my first iOS app! Most nights, we’ll just sit on our computers. We’re trying to break that habit, however. We really should get that puzzle out of the closet…
11:00pmIf we’re feeling disciplined, it’s into bed with a book. Right now I’m reading two: Poor Charlie’s Almanac and A Confederacy of Dunces. I strongly recommend both! If we’re not feeling disciplined, we’ll watch TV. Right now we’re loving Terrace House. Before our diet, there might have even been a late-night Uber Eats order from McDonalds.
12:30amWash face. Breathing exercise in Headspace. Noise machine on and lights out.

Where do you turn for inspiration?

Dribbble’s still a huge source of inspiration for me. I love seeing the amazing ways that people are using motion these days.

More and more though, I’ll just go for a walk or pause and take deeper breaths. It helps me clear my mind. It sounds really lame, but I find that this simple little action gives me more capacity for feeling inspired. It’s all about the breath, friends!

And when all else fails, I’ll read something by the Basecamp team. 😄

What design or project are you most proud of? (It can be recent or older).

I feel like it’s lame to toot my own horn here, but I’m really proud of this app that I’m building. It’s a simple little mindful moments app that helps you create time to pause and reflect. I’m proud because I’ve finally forced myself to learn Swift and code it all on my own. There have been some rocky bits, but I stuck with it! It’s been about a year. But all this time later, I’m surprising myself with how smoothly I can work through new unknowns. Maybe I’m biased, but I think it’s a pretty cool app. And there’s still so much more to build!

Walk us through the design process you used for a recent project (you can pick any project).

Sure! Here’s a recent project: 

When you invite someone with no previous exposure to a Trello board, there’s no onboarding to help orient them to the product. We know that this is a challenge that can cause our members (we call users members) confusion. So, as with most new pieces of work, we started by crafting a problem statement that succinctly and clearly illustrated the opportunity. Problem statements are great guardrails, and they help get everyone on the same page. 

Next, we start asking ourselves what we already knew. We looked for data that might help us make informed decisions, and talked to other teams who have worked on similar challenges. Pretty quickly, we start to have a clearer vision into the problem space. It turns out that the Acquisition team was working on a very similar challenge, so we joined forces. In no time, we’d constructed a few strong hypothesis and figured out the leanest way to test our assumptions. 

We started small. No design needed! We created fake Trello boards and ran tests on usertesting.com to collect some early signals. It was a quick test, but we ran several variations at the same time, which gave me a solid two week’s worth of great data to analyze. It was exhausting, but I came out the other side with a huge stack of learnings. We met as a team and brainstormed ways to run the next iteration on more users. 

In the meantime, the Acquisition team designer and I worked together to craft a customer journey map, so that we could better understand how our two user types overlapped. After several refinements, we were able to find a shared solution that would be flexible enough to work for users with all kinds of permissions and experience levels. Our teams coded the next iteration, and we ran a few versions on a cohort of real users! 

We love the Lean Startup method of reviewing our data after each test and deciding as a team to pivot or persevere. The iteration continued in a similar way till we were happy with the results.

Most of the things that we build work this way. We test everything, and iterate based on our learnings. It can be time consuming, but it’s invaluable. Trust your gut, but rely on data! 

What career advice do you have for product designers just getting started?

Start talking to the people who are using your product. Visual design and prototyping skills definitely have their place, but you’ll grow enormously by talking to your users. After that, learning how to communicate your findings is critical. Keep things simple. 

If you’re just getting started but you built a portfolio of thoughtful research told in a simple and strategic way, you’ll catch some attention. If you want to turn heads, translate your learnings into delightful user experiences. It’s okay if they’re not real, too!

Most importantly, you got this. 🙂 If you ever have questions, reach out to designers that you respect on Twitter. They’re usually a pretty friendly bunch.

Where’s the best place for folks to learn more about you or follow you?

Chat me up on Twitter or give me a follow on Dribbble! My website’s a cobbler’s shoe, so set low expectations if you choose to visit www.christopheralandavis.com. I also post infrequently on Medium