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.