Making big ideas happen

When I say “high-stakes design project” what comes to mind?

How about redesigning your company’s checkout flow (AKA the money-making machine) right before a $3.5B IPO?

Because that’s exactly the project that Ryan Scott owned when he was a design lead at Airbnb.

So I interviewed him to uncover what it takes to drive this level of impact, especially as an IC.

Here’s what I learned about making big ideas happen 👇

1 — Form alliances

If you’re going to bring an ambitious project to life then you’ll need to rally support from the right team members.

Ryan kickstarted his checkout redesign by assembling an unofficial advisory board of people across the company.

“I worked to make sure that designers, engineers, and product managers who rarely worked together felt like part of one shared effort”
— Ryan Scott

People need to feel like they are equal partners in this discovery process. Ask big questions like: “If you could start over, what would you do differently?”

Figuring out what each team cares about is how you cultivate alignment. And when people feel a sense of ownership in the process, they’re more likely to advocate for your ideas.

2 — Make your first “yes” as small as possible

If I learned anything selling SaaS in my early 20’s it’s this… never pitch anything in your very first message.

Nowadays when I ping a potential sponsor for Dive Club I’ll lead with something like… “hey I have an idea for how we could partner, can I send you a quick Loom?”

Then all they have to respond with is “sure”.

Asking for too much too quickly makes you easy to ignore (think: LinkedIn cold DMs asking to pick your brain for 30 min).

How is this relevant? Well… design is sales.

Making a big impact at your company requires getting people to commit resources to your ideas. That’s why Ryan suggests mitigating risk up front:

“Instead of green-lighting this whole project, can we green-light some investigation into seeing how risky is this?”
— Ryan Scott

See how that makes the first “yes” smaller? Maybe the investigation is a focused research project, or a new type of data collection… the key is maintaining momentum.

You’re pitching learning, not commitment.

3 — Set expectations up front

One way to help teams feel more comfortable with your vision is to share potential failure points up front.

“It helps to set expectations going into this that these numbers may be negative. And if they are, here are some hypotheses why that might be the case”
— Ryan Scott

By identifying potential issues early, you’re not just preparing for setbacks… you’re actively building trust.

Plus thinking deeply about why something might not work forces you to consider every angle.

If people are already aware of potential negative outcomes, you’ll be less likely to be blocked by a single A/B test.

Here’s why that’s so important 👇

4 — Keep unlocking tumblers

Have you ever watched a movie where there’s some kind of a heist and a person is at a vault listening carefully trying to get the tumblers just right?

Ryan says A/B tests can feel like this sometimes…

You invest some design work, ship an update to unlock that first tumbler, aaaaaannnnd…. the door still didn’t open 😬

Too many good ideas die because we’re committed to incremental progress but expect incremental value in return. So we abandon ship at the first sight of negative numbers thinking we’re on the wrong track.

“Those numbers are going to be negative until they’re not. You have to have conviction that it’s worth moving forward”
— Ryan Scott

Ryan’s vision for the Airbnb checkout flow was to reduce a five-page flow to a single “hub” with modals that house mini-flows… not the easiest idea to achieve incrementally 🤔

Thankfully Alex Schleifer not only supported the vision but encouraged Ryan to push the idea as far as possible (even if it meant a short-term dip in metrics).

Sometimes reaching an idea’s full potential means committing to unlock every single tumbler.

Hopefully this gives you a framework you can use to build persistence at your company 💪

“The checkout redesign project was a dramatic step-function improvement that increased bookings far beyond anything the company had been able to accomplish with iterative experiments”
— Ryan Scott

Making strategic impact as an IC

If you want to go deeper, I filmed a full episode with Ryan Scott to uncover lessons learned as an early designer at DoorDash and design lead at Airbnb.

It's jam-packed with insights about:

• What it’s like presenting at Airbnb CRIT

• Ways to unlock your credibility as a designer

• How to mitigate risk when presenting your ideas

• What it takes to speak the language of the business

• Types of “PM-y” questions that designers should be asking

• How Ryan led a massive redesign of the Airbnb booking flow

• The right (and wrong) way to make a case for investing in UX debt

• How to talk about your work in a way that resonates with non-designers

• a lot more

Listen on YouTube, Spotify, Apple, or wherever you get your podcasts 👇