Making big ideas happen with design 💡

Summary

Dive Club 🤿 Episode Summary: "Making Big Ideas Happen with Design 💡"

Host: Ridd
Guest: Ryan Scott, former Design Lead at Airbnb
Release Date: January 28, 2025

---

1. Introduction to High-Stakes Design Projects

The episode opens with a discussion on what constitutes a high-stakes design project. Ridd introduces Ryan Scott's pivotal role in redesigning Airbnb’s checkout flow—a critical component of the platform's revenue generation—right before a $3.5 billion IPO. This project stands out as the only instance in Airbnb’s history where a complete overhaul was executive-mandated.

• Quote: "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 $3.5 billion IPO?" (00:00)

---

2. Forming Alliances and Building Advisory Boards

Ryan emphasizes the importance of forming the right alliances to drive impactful projects, especially as an individual contributor (IC). He shares his strategy of creating an informal advisory board at Airbnb to garner support and insights from key team members.

• Quote: "The first thing I started with was you. All the experts. I want to ask some questions, but I really need to understand everything you know and help me understand everything you care about." (00:45)

This approach not only sourced valuable information but also fostered excitement and ownership among team members, turning them into advocates for the project.

---

3. The Role of Design as Sales

Ridd draws a parallel between design and sales, highlighting that making a significant impact within a company often requires selling your ideas and securing necessary resources. He advises against pitching everything in the first interaction, using his own experience with securing sponsors for Dive Club as an example.

• Quote: "Design is sales. Making a big impact at your company requires getting people to commit resources to your ideas." (02:04)

---

4. Mitigating Risk and Maintaining Momentum

A critical strategy discussed is the mitigation of risk upfront. Rather than seeking approval for the entire project, Ryan suggests requesting permission for smaller, manageable components such as focused research or prototyping. This tactic helps maintain momentum and reduces the perceived risk of the larger initiative.

• Quote: "Instead of green lighting this whole project, can we greenlight some investigation into seeing how risky is this?" (02:18)

Ryan shares his experience where excessive deliberation on risks led to project stagnation. By proactively addressing potential risks, teams can build trust and stay committed even when initial metrics are negative.

• Quote: "By identifying potential issues early, you're not just preparing for setbacks, you're actively building trust." (04:21)

---

5. Overcoming A/B Testing Challenges

Ryan introduces a metaphor comparing A/B testing to unlocking a vault in a heist movie. He explains that iterative testing often fails because each test addresses only a small part of the problem. Instead, multiple changes need to work in harmony to achieve the desired outcome.

• Quote: "A B testing is like one tumbler at a time... Sometimes these things have to happen in sequence. It has to be enough, right? You have to get multiple things simultaneously." (05:29)

This insight led Ryan and his team to abandon incremental changes in favor of a comprehensive redesign, ultimately leading to a more cohesive and successful user experience.

---

6. Building Trust and Executive Presence

The conversation transitions to the concept of executive presence, defined as the ability to inspire confidence in your ability to achieve outcomes. Ryan and Ridd discuss how a track record of successfully shipping projects builds the necessary trust and credibility to undertake big ideas.

• Quote: "Executive presence usually is like the ability to inspire confidence... That confidence is built from a track record of shipping and executing." (09:02)

Ryan shares his approach of consistently delivering projects, which earned him the trust of his colleagues and stakeholders, facilitating the approval of ambitious initiatives.

---

7. Conclusion and Takeaways

Ridd wraps up the episode by summarizing the key strategies for making big ideas happen within a company:

• Form the Right Alliances: Build an informal advisory board to gain support and insights.
• Design as Sales: Effectively sell your ideas by securing small commitments initially.
• Mitigate Risks Early: Address potential risks proactively to maintain project momentum and build trust.
• Comprehensive Testing: Employ holistic approaches in testing rather than incremental changes.
• Build Executive Presence: Consistently deliver results to inspire confidence and gain credibility.

He also highlights Ryan Scott’s courses on Maven, noting their impact and providing a special offer for Dive Club listeners.

• Quote: "Hopefully this gives you a framework that you can use to build that trust and make big ideas happen at your company." (09:45)

---

Key Insights:

1. Collaborative Leadership: Engaging team members as equal partners fosters ownership and advocacy.
2. Strategic Risk Management: Breaking down large projects into smaller, less risky components can facilitate approval and progress.
3. Holistic Problem-Solving: Addressing multiple variables simultaneously can lead to more effective solutions in design projects.
4. Trust and Credibility: Building a history of successful executions is essential for gaining support for future initiatives.

---

Notable Quotes with Timestamps:

• High-Stakes Design: "When I say high stakes design project...right before a $3.5 billion IPO?" (00:00)
• Forming Alliances: "The first thing I started with was you. All the experts..." (00:45)
• Design as Sales: "Design is sales. Making a big impact at your company..." (02:04)
• Mitigating Risk: "Instead of green lighting this whole project..." (02:18)
• A/B Testing Metaphor: "A B testing is like one tumbler at a time..." (05:29)
• Executive Presence: "Executive presence usually is like the ability to inspire confidence..." (09:02)
• Building Trust: "Hopefully this gives you a framework that you can use..." (09:45)

---

Resources Mentioned:

• Ryan Scott’s Courses on Maven:
  • ROI of Design in the PM Masterclass
    Access via Dive Club here.

---

Note: This summary excludes advertising segments and focuses solely on the content-rich discussions between Ridd and Ryan Scott, providing a comprehensive overview for those who have not listened to the episode.

Transcript

[A]

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 $3.5 billion IPO? Because that's exactly the project that Ryan Scott led during his time as a design lead at Airbnb.

[B]

As far as I know, this is the only time in Airbnb's history where anyone was given executive mandate to go redesign and rebuild the whole thing.

[A]

So I want to pull out a few ideas to talk about what it takes to to drive this level of impact, especially as an ic. And the first idea is you have to form the right alliances if you want to bring an ambitious project like this to life. And that's why Ryan formed kind of like an informal advisory board at Airbnb.

[B]

The first thing I started with was you. All the experts. I want to ask some questions, but I really need to understand everything you know and help me understand everything you care about. So we're aligned. I know what your priorities are, and so I kind of recruited all these people to be my advisors.

[A]

This isn't just about sourcing information. It's about getting key team members excited about what you're doing.

[B]

Tell me all your hopes and dreams. You know, like, what do you wish you could do? If you could just start over, what would that be like? How would that look?

[A]

Questions like this make people feel like equal partners in the discovery process. And when people feel that sense of ownership, they're more likely to advocate for your ideas. But eventually, you're going to have to make that ass to get buy in. And if I Learned anything selling SaaS in my early 20s, it's this. Never pitch anything in your very first message. I mean, nowadays, even when I ping potential sponsor for dive club, I'll lead with something like, hey, I have a quick idea for how we could partner. Can I send you just a short loom? Then all they have to respond with is, sure, if you ask too much too quickly, it makes you easy to ignore. It's kind of like that person that cold dms you on LinkedIn asking to pick your brain for 30 minutes. But I digress. 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.

[B]

Instead of green lighting this whole project, can we greenlight some investigation into seeing how risky is this? What would we need to know to feel more confident moving forward? And if it is risky, how would we mitigate it? And then how costly would those mitigations be?

[A]

Now that is what it looks like to make your ask as small as possible. Maybe the outcome is a more focused research project or a new type of data collection, or maybe even a day or two prototyping with an engineer. It really doesn't matter. What matters is that you've effectively maintained the momentum of your idea.

[B]

I've definitely been in situations where we spend more time talking about how risky something might be than it would take to just go ask a hundred people and find out, like, oh, no, users won't behave that way. They're very excited about this. And then you've mitigated that risk.

[A]

It reminds me of a conversation that I had with the VP of UX at Shopify. We haven't actually released the interview yet, but he said when he's assessing an idea, he's asking himself, do I want to underwrite the risk of this project? Because he's the one that's gonna be assuming the responsibility for its success. Which is why Ryan's framing is so spot on.

[B]

This is just evolutionarily, biologically how humans behave. When we assess risk, we're gonna fight or flight. We're gonna start to shut down. We're gonna start to do this mental math of, you know, what could this cost me? If. If I screw up this big product, am I gonna get fired? Am I going to not get that promotion? Right? And if there's too many what ifs, I'm going to play it a lot safer. And so by taking that intangible thing and making it more tangible, by saying, how are we tactically going to mitigate this now? How? What do we need to learn? What questions do we need to ask? How can we do that in a cost effective way that gets people out of this? I don't know. This is scary. This is too abstract mode and gets that brain into problem solving mode of, well, we just went and talked to 20 people. Then we would feel pretty confident that we're doing the right thing.

[A]

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

[B]

I think the other thing that really helped was also setting expectations going into this that these numbers may be negative. And if they're negative, here are some, like, six hypotheses. Why? And a roadmap for what we will do to make sure that those things aren't actually contributing to this being a negative test. That really helped. Say, yep, negative metrics happen. That's okay. We have a plan. But we're going to keep moving forward with mitigating those negative metrics, not back away from the entire project.

[A]

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 possible angle. If people are already aware of potential negative outcomes, you'll be less likely to be blocked by that first set of numbers that comes in. Which leads me to one of my favorite metaphors ever shared on Dive Club. Here's Ryan talking about overcoming a B tests as a part of making big ideas happen.

[B]

If you've ever watched a movie where there's like a heist, there's always someone at a vault like listening very carefully and trying to get the tumblers just right. And a lot of times a B testing is like one Tumblr at a time. You get the first Tumblr and then or like the second tumbler, but you're like, didn't unlock the vault yet. And you're like, that didn't have any value. Let's start over. And it's like, no, no, no. Sometimes these things have to happen like in sequence. It has to be enough, right? You have to get like multiple things simultaneously.

[A]

Real quick message and then we can jump back into it. So this new product called Genway has totally changed the way that I do research. It uses AI powered interviewers to help you gather rich qualitative data at basically an infinite scale. You can even interview people while they use your Figma prototypes. Just tell the AI what you're hoping to test and it will have a dynamic conversation with each person as they're going through your prototype. You should see the quality of the follow up questions that the AI asks. It is really something. And the best part is they just introduced a self serve onboarding so you can get started right away. And they're even offering two months free for Dive Club listeners. Just head to Dive Club Genway to get that special offer that's G, E, N W a Y. As if Raycast could get any better. They just released a feature that I've been wanting for years and it's called Raycast Focus. It helps you stay in flow by blocking distracting apps and websites. It's goal based, works in your browser and it's always a keyboard shortcut away. And my favorite part is they even have a little floating bar to give you a quick glance of how much time is left in your goal. I'm already using this every day and it's just another Reason why you should definitely download Raycast if you haven't already. Just head to Dive Dot Club Focus to learn more. Okay, now on to the episode. Too Many Good Ideas Die. Because we're committed to incremental progress, but expect incremental value in return. So we abandoned Chip at the first sight of negative numbers, thinking that we're on the wrong track.

[B]

Sometimes the numbers going down is, well, we should keep moving forward. We're not there yet. We haven't unlocked all the tumblers to open the vault to get to the gold inside. So what we should do is keep unlocking tumblers, not just back away. So we had done these like AB tests and we kind of like tried to like incrementally stair step our way to a better solution. Everything's negative. So I think eventually we were like, screw it. We just like made things the way we thought they needed to be and then launched like one big a B test to say, like, if we redesign the whole experience from the ground up and we got rid of like all the debt and we did all the things, instead of trying to piecemeal our way towards like bad experience. Bad experience, Bad experience, magic experience, we just tried to go to magic experience.

[A]

Tyler Angert shared the same thing when he was talking about the early days designing Replik.

[C]

When you're designing complex systems, you can't necessarily pick apart like a single component of it and ship just that, right? Sometimes you need the whole system shipped at once in order for it to make sense. I specifically pitched working on a part of this early project for three months where nothing would get shipped.

[A]

Now, hopefully these strategies like mitigating risk have sparked some ideas that you can use to pitch that next big idea internally. But at the end of the day, big ideas come with big asks. So people have to trust you or nothing else matters. I think it's why I keep referring back to when Cat Small talked about the idea of executive presence.

[B]

Executive presence usually is like the ability to inspire confidence.

[A]

So like people feeling confident that you.

[B]

Are able to reach a certain outcome.

[A]

That confidence that she's talking about is built from a track record of shipping and executing.

[B]

And then you can start to unlock that trust. You can start to unlock that credibility, and that's going to provide different opportunities.

[C]

I think people just trusted me because before that I had basically spent two years just working on things and shipping them as quickly as possible. Or at least every project before that had already shipped. And I was like, just give me some time to really break this down. And like, if I have the pressure where I need to ship it. I'm not actually going to see like all of the possibilities, and I think people just trust me.

[A]

Hopefully this gives you a framework that you can use to build that trust and make big ideas happen at your company. And if you want to go deeper into ways to make a strategic impact as an ic, Ryan Scott from this episode has a couple of the highest rated courses on all of Maven, describing the ROI of design in the PM Masterclass for designers. I was literally just meeting with someone the other day who couldn't stop talking about the impact that Ryan had on her career. So definitely check those out. And there's even a special offer for Dive Club listeners in the show Notes. That's all for now though. I will see you next.