TripAdvisor’s Sean Landry: Autonomy breeds ownership

4 min read
Kristin Hillery
  •  Jun 20, 2016
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We talked to Sean Landry, Creative Director at TripAdvisor, about breaking rules, what makes a good design portfolio, and how to build trust with your team.

How is your team set up at TripAdvisor?

The creative team is made up of product designers, mobile designers, writers, graphic designers, and presentation designers. We service different parts of the business. The product designers are embedded with their product teams, busy building web and mobile designs. The rest of the designers and writers work on the brand side, focusing on delivering marketing support to all other things TripAdvisor—including emails, promotional materials, and those fun little window stickers you see everywhere.

The TripAdvisor team.

How does your team communicate with each other? And how do you communicate with people on different teams?

HipChat, Skype, Jabber, email, and virtual meetings. I’m not a big fan of email or recurring meetings because they steal so much of your productive hours, but I do believe in communicating with your team even if it just means turning your monitor to get some feedback. Every week there’s a product review meeting where we discuss new projects. It’s a great way to get exposed to all the things happening across dozens of product teams.

“Teams should over-communicate—never let people guess.”

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Teams should over-communicate—never let people guess. Always make it crystal clear what your audience should expect. Communicating effectively builds trust with the user and with your team.Twitter Logo

How do you hand off designs to the engineering team?

Our product designers sit with their team in a pod. Throughout a sprint, the team collaborates and discusses designs. Before the designs go into production, we have web and mobile testing environments where designers can review their designs before being deployed.

Sean Landry, Creative Director at TripAdvisor.

How do you hire new people?

We start with our recruiting team, who sources great designers. They forward portfolios to me for review. If I find a strong portfolio, the recruiter will set up a phone screen with them to make sure everyone is on the right page regarding responsibilities, compensation, benefits, etc. I’ve seen tons of portfolios—I’m looking to spot product work and examples of complex problem solving. You need to know how to design software, not just web pages. A strong portfolio has several examples of form and function working in harmony.Twitter Logo

After the phone screening, there’s a in-person interview with myself and 2-3 other designers. We’re looking for smart designers with low ego and strong skills. I ask lots of questions about team dynamics. Design candidates should know how they contribute as part of a larger team.Twitter Logo 

If all goes well, we schedule an in-person interview with the people they’ll work with day-to-day, including product managers, writers, and engineers.

How do you think your design process differs from other products?

We test everything. TripAdvisor has a unique ability to A/B test quickly because of its scale. We rank #62 in the US for web traffic—we get more traffic than GitHub! With 340 million unique monthly visitors, we’re able to get to statistically significant outcomes quickly. If the test succeeds, that design becomes the new control for subsequent testing.

At any given time, we usually have dozens of tests running on both our desktop and mobile apps.

Sometimes it’s surprising to see what comes out of a test. For example, you’ll find certain pages on the desktop that have blue CTAs and some that use yellow. We know that through testing that the blue ones outperform yellow, but only on certain pages. The color of the CTA is determined by how it impacts revenue. It’s still somewhat of a puzzle to me as to why.

“Once someone falls in love with their work, egos disappear.”

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How did you get to where you are now in your career?

I started my career in the print world working for the weekly magazine Network World, where I learned the basics of layout, typography, and how to create a visual hierarchy in order to tell a good story. Those were the days of proofs, film, and light tables.

During the original dot-com boom, I transitioned my skills to the web and learned HTML and the basics of online software and principles of good usability. From there, I moved on to large-scale enterprises where I built cloud storage systems, and then to an early-stage startup where I put together a team focused on social networks and software designed to change behavior and improve well-being. I take pride in building strong brands and great teams.

How do you build trust with a team?

Purpose, autonomy, and vulnerability. I’m a big proponent of being purposeful. By providing people with meaning in their work, they can really fall in love with what they’re doing. Once someone falls in love with their work, egos disappearTwitter Logo and everyone can work together with the common goal of building the greatest possible product.

Autonomy breeds ownership. If someone feels ownership, they become invested in outcomes.Twitter Logo While autonomy can sometimes be scary, it often produces some of the most beautiful work—and since I genuinely care about developing creative professionals, I try to put them in the best position to succeed.

“Autonomy breeds ownership.”

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Last is vulnerability. Once someone recognizes that they need other members of their team to be successful, they open up and ask for help. No one member of the team is more important than the other.Twitter Logo We need each other’s expertise to build amazing things, and being able to ask for help, feedback, and ideas is a key component of the design culture we’re building here.

What do you think is the most powerful part of your design process?

We set goals right at the beginning. Establishing a list of user and business goals at the start is a simple, powerful, and effective way to keep the project focused. Once that’s in place, it’s the designer’s or writer’s job to produce work that balances all the goals. Whenever I’m in a discussion where there are disagreements, it’s often because there’s some misalignment around the goals of the project. Having the goals restated during those conversations leads to less subjectivity and better feedback.

“Understand what emotions are driving decisions—and design for those.”

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How do you use InVision as part of your design process?

We use InVision for rapid prototyping, design annotation, design approvals, user testing, and anything else you can imagine. InVision is a key piece of our workflow.Twitter Logo Being able to simulate experiences is crucial to having substantive discussions about design.

What are some of the most important things you’ve learned about design?

Context over consistency. Whenever possible, be consistent and create patterns—regardless of whether you’re working in brand or user experience.  However, always question if the situation dictates something different. Knowing when to break the rules is just as important as following themTwitter Logo in the first place.

Fill the emotional bucket. Every decision is an emotional one. Whether your target audience (or users) are selecting enterprise tools or planning their next vacation, you need to understand what emotions are driving decisions—and design for those.Twitter Logo

Simplicity is powerful. Resist the urge to add anything unless it’s truly necessary to the design. When you think you’re done designing, go back and see what you can subtract.Twitter Logo Keep doing that until everything in your design has a purpose.

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