4. Be bold, be brave.

If you work on software, you might be familiar with the phrase “release early, release often.” The general idea is that it’s better to release updates as quickly as possible, and then improve on them over time.

The problem with this approach is that it can lead to half-baked ideas instead of big leaps forward. If you’re not careful, you could end up making hundreds of insignificant improvements, instead of working on things that really matter. Constant tweaks can lead to a weak design and an indecisive point of view.

Over at Airbnb, Michael Austin Sui works on the company’s big, bold Design Language System — a unified design system for all of Airbnb. “We like bold moves!” Michael says. “As a recovering, risk-averse perfectionist, I’ve grown to embrace the adventure that comes with an innovative company, inspired by the daring ideas of my colleagues.”

He tells me about what it took to launch Airbnb Trips. Instead of just focusing on accommodations, Trips focuses on the whole trip experience, bringing together where you stay, what you do, and the people you meet—all in one place.

“It was a significant shift for Airbnb’s product, guests, and hosts. After developing Airbnb Trips for about a year, when the time came to launch, we knew we had to shift hard together to give this new idea the best chance of succeeding. That was one major learning from that launch: When you make a bold shift, shift hard.”

Their big shift seems to be paying off. Industry experts are saying that Airbnb just recently turned a profit and is expected to stay profitable throughout 2017.

Think of some of your favorite designs. Do they play it safe, or do they take big risks? Chances are, your favorite designs are the ones that have big ideas and a strong point of view—the ones that take big risks. 🎲

Making big, bold moves. (Airbnb.com)

5. Don’t just build what people ask for.

There’s a famous quote from Steve Jobs where he said, “A lot of times, people don’t know what they want until you show it to them.”

When I first heard that, I always thought it sounded cocky. After all, I know myself better than anyone else. Of course I know what I want, silly!

It took me a while, but I now get what he was saying. A lot of times, we’re constrained by what we know, and we forget there might be better ideas we never even thought of.

I recently had a few Polaroid photos that I wanted to transfer to my laptop. If you had asked me what I wanted, I would’ve asked for a flatbed scanner, so I could scan them to my laptop. But then Google came along and created the PhotoScan app, which lets you scan photos right from your phone. The app turned out to be a much faster, easier solution—even though I never asked for it.

Gusto is a product that helps business owners take care of payroll, benefits, and other HR tasks. The company’s design team makes big bets on creating features that people aren’t asking for, but will make their lives better.

They recently released employee happiness surveys in which they ask employees a simple question: How happy are you at work? “The results are surprisingly insightful,” says Val Klump, a writer on Gusto’s design team. “The businesses who’ve tried it love it, but no one asked us to build it.”

They predicted what people wanted before people even realized it. 🔮

Making businesses happy with employee happiness surveys. (Gusto.com)

6. Know when to shine.

To have a strong point of view in design, you need to know who you are as a brand. What’s your personality? Are you more Beyoncé or Bublé? Coldplay or Kanye?

But when it comes to product design, knowing your personality isn’t enough. You also need to know when to show your personality, because too much personality gets in the way of usability.

Let’s say you have a button that says “Start tour.” If your brand is all hip and happenin’, you could rewrite this as “Let’s get crackin’!” This sounds a lot more fun, but it’s also confusing. It’s not clear if clicking that button will start a tour, ask you to sign up, or show you a clip from The Nutcracker.

Showing your personality helps you earn brownie points with your users, but you’ve got to know when to dial it up and when to play it cool.

A lot of people love Slack for the playful copy in its product. The team at Slack understands that words are an integral part of the product’s design, so they have a group of product writers on their design team. Sara Culver, who leads the product writing group, explains the challenge of having to juggle clarity with personality. “We want to preserve personality in the product — but we have to find the best places to do it, where a user is least likely to become frustrated, confused, or annoyed.”

Sara goes on to give me an example: “We recently had a fun session where we all wrote different versions of the same error message — a pretty obscure one that only power users of Slack will ever see, so we wanted it to be playful. We ended up not being able to choose a winner, and are going to try to implement them all in a rotating way, so a user could see a different one each time.”

Showing your personality helps you earn brownie points with your users, but you’ve got to know when to dial it up and when to play it cool. 😎

Showing personality without getting in the way. (Slack.com)

7. Believe it, build it.

Part of a designer’s job is to explore multiple ideas to solve a problem. Then, you weigh the pros and cons until you find a direction that works.

But chances are none of your ideas are perfect, and that’s when you start to make compromises. You add an extra button here. You add extra text there. You optimize for edge cases. Suddenly, your design becomes a hot mess.

So what should you do instead? Sometimes you just need to pick a direction you believe in and build it.

David Kjelkerud, a design director at Dropbox, tells me about an experiment his team ran on the Dropbox homepage a while ago. Instead of showing everyone an A–Z list of files and folders, a small percentage of people saw a list of recently viewed files with inline previews. The assumption was that people would quickly scan the previews and pick up where they left off.

Ultimately, this direction didn’t work because recent files weren’t always the most relevant files. So instead, they pursued a different direction. “But we learned a lot that we wouldn’t have unless we built and released it,” David says. “It’s important to follow your conviction even if the chance of failure is big. Even if you don’t reap the big reward, there’s always learning to be had. I encourage teams to take risks, build, ship, and learn. As long as you’re learning, you’re getting closer.”

Even to this day, their learnings from that experiment are helping to shape new projects. More than a year later, people at Dropbox are still looking back at that experiment for ideas and inspiration. ⚡️

What Dropbox could’ve looked like with inline previews. (Dropbox.com)

8. Push for what’s right.

All my life, I’ve lived in shadows. I never caused trouble. I never picked fights. I was that quiet Asian kid in the back — the one who never made a fuss. I just wanted to make sure everyone was happy.

It took me years to realize this, but I now know you can’t make everyone happy, no matter how hard you try. You can’t design for every possible use case, and you can’t please everyone in the room.

Now, more than ever, I’m learning that you need to have a point of view if you want to make progress. You need to ask questions, you need to understand “why,” and you need to fight for what you believe in.

These are crazy times we live in. When we see problems, we need to push for a point of view and push for what’s right. It’s the only way to make things that matter. It’s the only way to design.