Mastering Product Design With Katie Dill: Lessons from Stripe, Airbnb and Lyft

Introduction and Role of Design

• Katie Dill is the head of design at Stripe, and has led design teams at successful companies in Silicon Valley, including Lyft, Airbnb, and now Stripe (3s).
• The design team at Stripe operates by having product designers, researchers, content designers, and engineers work together to build the product, with a focus on creating a high-quality user experience (1m11s).
• The design organization at Stripe also includes a brand studio team that works on advertisements, events, branding, and the website team that manages stripe.com (1m31s).
• Design played a crucial role in the success of companies like Airbnb, Lyft, and Stripe, particularly in their early days, by making novel products more approachable and building confidence with users (2m6s).
• At Airbnb, design was instrumental in making the experience of staying in someone else's house feel safe, secure, and enjoyable, with the founders bringing thoughtful details to the experience (2m12s).
• Similarly, at Stripe, the founders cared about every detail of the user experience, which helped build confidence with users and made them feel like their money was being taken care of (3m4s).
• Katie believes that design should always come back to solving a problem and identifying who it's trying to solve it for, rather than just shipping a product (14s).
• She emphasizes the importance of sweating over every detail to make a product more approachable and build confidence with users (2m36s).
• Companies like Airbnb, Lyft, and Stripe require incredibly high levels of trust from their users, as they involve interactions with strangers or handling of money, and a well-designed product is crucial in establishing this trust (3m49s).
• Small details, such as typos or poorly laid out interfaces, can erode trust and make users question the company's attention to detail (4m20s).
• Building trust is essential for companies to differentiate themselves from competitors, as users have many options and will choose the one that is most reliable and trustworthy (4m51s).

Importance of Founder Involvement

• The role of the founder is crucial in establishing a culture that values design and attention to detail, as it sets the tone for the entire company (5m27s).
• Founders like Brian Chesky, Joe, Nate, and the Cision brothers prioritize understanding their users' needs and building products with intention and meticulous attention to detail (6m15s).
• Having a founder who cares deeply about design and user experience can create a positive feedback loop, where the company attracts like-minded employees who share the same values and priorities (6m33s).
• When design is integral to a company's culture, it can create an "X Factor" that sets the company apart from its competitors and drives its success (6m41s).
• Building a culture that allows for going the extra mile to delight users and exceed expectations is crucial, and it must be instilled in the early days of a company's culture, with leaders exemplifying its importance and making hard choices to prioritize quality over mediocrity (7m7s).
• Founders play a significant role in demonstrating courage and making tough decisions to ensure the product meets high standards, even if it means delaying its release or taking another spin on it (7m52s).

Balancing Urgency and Quality

• Balancing the need for urgency and shipping early with the importance of getting it right is challenging, and there is no one-size-fits-all answer, but considering the problem being solved and the user experience can help guide the decision (8m51s).
• Using betas can be an effective way to get feedback and improve the product while moving quickly, rather than taking too much time to perfect it and potentially leaving users waiting (9m14s).
• Knowing when to hit the bar and move on to the next thing can be subjective, but considering the problem being solved, the user experience, and the potential impact of delaying or releasing the product can help inform the decision (9m49s).
• When deciding whether to ask for another iteration of a product, consider whether it solves the user's problem and if it's a net positive, and weigh the potential costs and benefits (9m54s).

Key Aspects of High-Quality Products

• A high-quality product should be functional, usable, and have craft and beauty, with functionality being the top priority (10m29s).
• Usability is the second most important aspect, as a product that solves a problem but is uncomfortable to use will not be successful (10m40s).
• Craft and beauty are not just nice to have, but are material to increasing the utility and usability of a product and making it more enjoyable (10m52s).
• Using a checklist to evaluate a product's quality can help ensure that it meets the necessary standards, and intentionality is key in design (11m11s).
• Design should be thoughtful and consider how the product will be perceived, and choosing the most appealing and easy-to-use option is important (11m41s).
• Enterprise software often prioritizes functionality over user experience, but bringing joy to the work experience is important (12m2s).
• Craft and beauty are not just nice to have, but are essential in creating a high-quality product that inspires confidence and joy (12m18s).
• Founders without a design background can use a checklist to evaluate product quality and look for signs of great design, such as functionality, usability, and craft and beauty (12m38s).
• Using a checklist, like a pre-flight checklist, can help ensure that all aspects of the product are considered and that nothing is missed (12m59s).

Developing Design Thinking and Taste

• A helpful mindset for product design is to approach it as if something is wrong, and you're trying to find it, which requires taking a different posture and not taking things for granted (13m13s).
• When designing a product, it's essential to question every detail, including words and pixels, to ensure the product is good and functional, which can be annoying for the team but is crucial for the product's success (13m36s).
• Questioning the product's details helps identify gaps and areas for improvement, focusing on utility rather than just taste, which is also an important aspect of product design (14m13s).
• Developing taste in product design can be challenging, but it can be improved by observing and taking note of what works well in other companies' products and hiring people with good taste (14m18s).
• Technical founders are skilled at finding edge cases in code, and applying this skill to design can help them level up their design thinking and identify areas where the product might break (14m49s).
• One of the hardest parts of product design is stepping outside of one's own viewpoint and imagining how others might experience the product, which is why bringing in users and conducting ongoing user research is crucial (15m20s).
• User research involves working with users, hearing their thoughts, and observing how they interact with the product to understand their context, knowledge, and impressions of the brand (15m39s).
• Hiring well and listening to people with good taste can also help cultivate one's own taste in product design (14m36s).
• To improve design skills, it's essential to see lots of good design, interact with it, and understand what good design looks like, which can help level up one's skills (16m25s).
• Observing products, both liked and disliked, can help learn from them, and getting out into the community can also aid in improving design skills (16m40s).
• When hiring great designers, it's crucial to help them understand their role in the company and not presume to tell them how design works if you don't know how it works yourself (17m0s).
• Bringing designers on in advisory roles or coaching junior designers can help founders learn about design and improve their company's design process (17m19s).
• Meeting people, learning from them, and seeing their examples can cultivate a sense of taste in design (17m29s).
• Taste in design can be improved, but it's challenging to teach, and it's often easier to teach someone the tools or domain than to teach taste (17m37s).
• When hiring designers, it's essential to look for those who exemplify great taste, as it's difficult to teach, and it's crucial for their role in the company (17m55s).

Stripe's Collaborative Design Process

• At Stripe, the design process involves a highly collaborative environment where designers, engineers, and product managers work together hand-in-hand (18m50s).
• The company's organization and collaboration are designed to ensure a coherent user experience across all platforms and products (19m15s).
• Designers are embedded in teams with shared goals as PMs and engineers, working on projects from start to finish, which makes a significant difference in how the work gets done (19m44s).
• The design process starts by identifying the user and their needs, often learned through engagement with users who provide feedback and help develop new product ideas (19m57s).
• An example of this process is the development of Connect, a product for platform businesses and marketplaces that allows them to create relationships with other businesses and offer financial services, which was created in collaboration with companies like Lyft (20m15s).
• Another example is Workbench, a product developed in collaboration with Slack and Notion, which involved prototyping, iterating, and receiving feedback on a weekly basis to stay away from faulty assumptions and create a better product (20m43s).
• Working with a range of users and having an iteration cycle helps reveal things that might not have been thought of otherwise, which persists into the execution and shipping of the product (21m15s).
• Even after shipping a product, it's essential to continue learning and iterating, as products can develop bugs and interaction points with new products may not be great, requiring ongoing improvement (21m32s).
• To achieve this, there is a culture of using the product and doing "walk the store" exercises, where people from various teams try the product like a user would, to identify areas for improvement and ensure the product continues to evolve (21m55s).

Maintaining Product Cohesion and Quality

• When launching a product, it's essential to revisit and review it regularly, as it can change significantly over time, much like how renovating one room in a house can make adjacent rooms look outdated (22m40s).
• To maintain a cohesive product, it's crucial to consider how different parts interact and affect each other, ensuring that the overall user experience is not compromised (23m2s).
• A program called "Essential Journeys" was established to review and score the top 17 most important user flows, with designated team members reviewing and scoring these experiences every quarter (23m23s).
• The scoring mechanism is simple, using a color-coded system (red, orange, yellow, and green) to track progress, with the goal of achieving and maintaining a "green" score (24m5s).
• This program helps identify areas for improvement and encourages team members to take ownership of specific user flows, with a scoreboard providing social pressure to achieve better scores (24m9s).
• The program also allows team members from different departments to review and provide feedback on products they may not be familiar with, providing valuable insights and helping to identify potential issues (24m32s).
• A "bugs" email alias is available for anyone in the company to report issues with the product, allowing for feedback from various sources and helping to identify and address problems quickly (25m24s).
• Using the product in the real world, rather than just relying on prototypes, is essential for understanding how it will perform and identifying areas for improvement (25m15s).

Examples of Product Development and Improvement

• A product called Link was developed, which provides an extremely fast way of checking out online and also allows users to buy crypto quickly, with a user-friendly tool for buying crypto (25m42s).
• Initially, when users typed in their email address, an alert would appear before they finished typing, indicating that the email address was invalid, which was found to be annoying and was later fixed to only alert after a short delay (26m0s).
• A redesigned email that communicated more clearly to users what to do with the product after signing up resulted in a 20% increase in product conversion, due to the addition of hierarchy, visual interest, and a clear call to action (27m3s).
• The redesign of the email included thinking about the words used, what happens after the button is clicked, and making the button clearly communicate what happens, which contributed to the increase in product conversion (27m29s).
• A new product called Workbench was launched, which aims to make it easier for developers to work with integrations and maintain their flow state, by providing a more powerful and easier-to-use tool (28m2s).
• Workbench was developed in response to feedback from developers about the challenges they faced, including breaking their flow state due to constant switching between the Stripe dashboard, code editor, and documentation (28m6s).
• The Workbench tool is designed to help developers stay in their flow state and is located at the bottom of the product, allowing users to easily access it (28m49s).
• A tool called Workbench is used to debug, prototype, and make changes to integrations, providing a microscope and telescope view of what's happening with the integration (28m59s).
• Workbench offers features such as inspecting information, checking for errors, and viewing the background of an invoice, which helps build a mental model of how the API is constructed (29m35s).
• The tool also allows users to explore the API, understand what's happening, and make changes, acting as a coach to help users see how the API works (30m9s).
• Workbench provides information that would normally be found in documentation, making it easily accessible and reducing the need to switch between different sources (30m19s).
• The tool allows users to identify and fix errors, such as incorrect email addresses, and provides code snippets that can be brought into an editor (30m25s).
• Workbench has received great feedback from users, including Notion and Slack, who have provided input on how to improve the tool (31m1s).
• The tool was developed using first-principles thinking, with the goal of creating a web inspector specific to Stripe and its integrations (31m13s).
• A community called Insiders was created to allow developers to share their experiences and provide feedback on the tool, which has been used to gather commentary and improve the tool (31m37s).

User-Centric Culture and Pride in Products

• The importance of deeply integrating the entire company with users is critical in creating a product for users, as seen in companies like Stripe, where founders and employees regularly interact with users, share feedback, and use the product themselves (32m7s).
• Founders and employees at Stripe take a lot of pride in the products they put out, holding themselves to a high bar, which is a lesson that all founders can take away (32m44s).
• The level of pride and attention to detail in creating great products for users is a key factor in Stripe's success, and it's something that the company's founders, the Cs and brothers, instilled in the culture from the beginning (33m6s).
• Design is not only important for business sense, but it's also a key aspect of Stripe's culture, and the company would prioritize it even if it didn't make business sense (33m11s).
• The emphasis on design and user experience is an X Factor that enables Stripe to make hard decisions and prioritize what's worth it (33m18s).