Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft)

Oct 15, 2023 Episode Page ↗
Overview

Katie Dill, Head of Design at Stripe, shares insights on leading hyper-growth design teams, operationalizing quality, and proving design's ROI. She discusses building trust, fostering team alignment, implementing a "Walk the Store" quality review process, and hiring for taste and courage.

At a Glance
21 Insights
1h 34m Duration
16 Topics
5 Concepts

Deep Dive Analysis

Katie Dill's Background and Early Leadership Lessons

Pivotal Leadership Moment: Earning Trust at Airbnb

Advocating for Design ROI and the Value of Quality

Stripe's Focus on Quality as a Driver for Growth

Defining Great Design and the Role of Beauty in Products

Operationalizing Quality and Design Excellence

Lessons from Diverse Organizations on Building Quality

Stripe's 15 Essential Journeys for Holistic UX Understanding

Product Quality Review (PQR) and Calibration Process

Prioritizing Quality and Impact in Product Development

Leadership Formula: Performance = Potential - Interference

Strategies for Building and Managing Large Design Teams

Case Study: Reducing Interference and Re-organizing at Lyft

The Importance of Embracing Bold Ideas and Vision Work

Key Qualities to Look for When Hiring Designers

Stripe Press: Mission and Notable Projects

Beauty enhances functionality

Functionality is important, but beauty makes things easier to use, more approachable, and more compelling. It also increases user trust, signaling meticulous attention to detail.

Quality is growth

The idea that focusing on quality is not separate from growth, but directly drives it. Making a product easier to use and more understandable increases adoption, usage, and positive user experience, which in turn fuels business growth.

Performance = Potential - Interference

A leadership formula suggesting that team performance can be improved by both increasing the potential of individuals (through hiring and development) and by decreasing interferences (obstacles, inefficient processes) that hinder their ability to do great work.

Meticulous Craft

An operating principle at Stripe emphasizing painstaking care in all aspects of work, from designing physical spaces and APIs to building interfaces and handling support calls. It signifies a commitment to excellence expected from everyone in the organization.

Design as Intention

At its core, design is about bringing intentionality to decisions. It involves thinking deeply about who a product or system is for and making deliberate choices to serve their needs, whether designing a doorknob, an organizational structure, or a strategy.

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How does beauty impact product functionality and user trust?

Beauty enhances functionality by making products easier to use, more approachable, and compelling. It also increases user trust, signaling that painstaking detail and care have been put into the product.

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How can design demonstrate its ROI and contribute to business growth?

Quality improvements driven by design directly lead to growth by making products easier to use and understand, increasing activation, conversion, and overall user satisfaction. For example, improving checkout flow quality can significantly increase revenue.

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What defines 'great design' or 'beauty' in a product context?

Great design and beauty are not opposite to functionality; they enhance it. They make things more useful, accessible, and enjoyable, leading to better user outcomes and building trust, often aligning with a shared understanding of what is aesthetically pleasing and effective.

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How can companies operationalize and maintain high product quality over time?

Operationalizing quality requires a group effort, clear vision and alignment, a strong editing function, and the courage to say 'no' when something isn't good enough. It also involves understanding the product from the user's journey perspective to identify and address quality regressions.

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How should leaders approach improving team performance?

Leaders should use the formula 'Performance = Potential - Interference,' focusing on increasing team members' potential through effective hiring and development, while simultaneously decreasing obstacles and inefficient processes that hinder their great work.

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What key qualities should one look for when hiring a designer?

Prioritize taste and character over tools and process, as these are harder to teach. Look for great talent, high craft, humility (to listen to users and teammates), and 'chutzpah' or hustle—the courage to create, fight for great, and execute rapidly.

1. Implement Journey-Based Quality Review

Establish “Walk the Store” reviews for your most critical user journeys, assigning engineering, product, and design leaders to regularly (e.g., quarterly) friction log and score the end-to-end user experience from an empathetic user perspective. This process increases awareness and accountability for product quality across the organization.

2. Define an “11-Star” Ideal Vision

Counter the tendency for incremental changes by sketching out an “11-star” ideal version of your product or experience. This comprehensive North Star vision guides development, allowing teams to work backward and make measured, thoughtful progress towards a truly transformative outcome.

3. Apply Performance Formula (P=P-I)

Use the formula “Performance = Potential - Interference” to guide leadership efforts. Focus on increasing team members’ potential through effective hiring and development, while actively decreasing interferences (e.g., faulty processes, misalignment) that hinder their ability to perform.

4. Prioritize Bold Vision Work

Fight against the fear of bold ideas and the seduction of easily measurable incremental changes. Instead, prioritize vision work that considers the entirety of the user experience and aims for comprehensive, transformative improvements, even if shipped in phases.

5. Make Quality a Group Effort

Recognize that product quality is not the sole responsibility of one person or team (e.g., QA or design). Foster a shared commitment to quality across the entire organization, ensuring internal communication and standards reflect this collective ownership.

6. Cultivate Courage to Reject “Good Enough”

As a leader, develop the resolve to say “no, this isn’t good enough” even when teams have put significant effort into something. This courage to push for excellence is critical for achieving truly great products and maintaining high standards.

7. Reorganize for Co-located Teams

Break down physical and organizational silos by co-locating cross-functional teams (engineering, product, design) to foster better alignment, faster iteration cycles, and clearer communication. Simultaneously, protect dedicated creative spaces for focused design work and community building.

8. Establish Clear Vision and Alignment

Ensure there is a clear vision for what the product should look like and how all its pieces fit together. Without this alignment, even talented individuals may produce great components that don’t form a cohesive and high-quality whole.

9. Appoint a Product Editor

Designate an “editor” (like a GC or architect for a house) who oversees how all product components fit together. This person helps narrow, reduce, and remove elements that don’t align with the overall vision, ensuring cohesion and quality.

10. Listen to Build Trust

When joining a new team or implementing change, prioritize listening to understand what individuals care about and what motivates them. Earning trust by listening is crucial for bringing the team along and making positive, collaborative change.

11. Foster Dual Team Communities

Encourage team members to identify with two “t-shirts”: their cross-functional product team (e.g., marketplace) and their functional discipline (e.g., design). Building community in both areas is important for different reasons, supporting both collaboration and craft development.

12. Quality Drives Growth

Understand that quality is not separate from growth; it is growth. Making products easier to use and more understandable directly drives user adoption, increased usage, and positive word-of-mouth, leading to better business outcomes.

13. Highlight Quality’s Business Impact

Actively identify and communicate examples where quality improvements have led to measurable business outcomes (e.g., reduced support calls, increased conversion). This demonstrates the direct ROI of quality and inspires other teams to prioritize it.

14. Embed “Meticulous Craft” as a Principle

Make “meticulous craft” a core operating principle for the entire organization, not just design. This sets an expectation that everyone, regardless of function, should approach their work with painstaking care and attention to detail.

15. Share Work-in-Progress Regularly

Implement a low-maintenance system (e.g., shared Google Slides deck updated monthly) for designers to share screenshots or prototypes of their work in progress. This increases awareness across the company, helps identify overlaps, and prevents redundant efforts.

16. Prioritize Taste and Character in Hiring

When hiring designers, prioritize their inherent taste, judgment, and character over their mastery of specific tools or processes. These intrinsic qualities are harder to teach and are more indicative of long-term success and fit.

17. Hire Humble, Empathetic Designers

Seek out designers who demonstrate humility, respect, and empathy for both their users and their team members. This ensures they are curious about user needs and collaborative within a team environment.

18. Look for Courage (“Chutzpah”) in Designers

Identify candidates who possess the courage or “chutzpah” to propose bold ideas, challenge the status quo, and fight for great design. Creation is scary, and this resolve is essential for pushing boundaries.

19. Early Startup Design Hiring Strategy

For early-stage companies, hire a design “doer” who can execute, but also consider bringing on a senior design advisor. This combination ensures immediate execution while establishing a user-focused strategy and organizational structure from the start.

20. Approach All Work with Intentionality

Bring intentionality to every decision by asking “who is this thing for?” This applies to everything from product features to organizational structure, ensuring that all efforts are purpose-driven and user-centric.

21. Show Trust by Giving Space

As a leader, actively demonstrate trust in your team by giving them the space and autonomy to take on challenges, even when it feels risky. This empowers individuals and fosters their growth and confidence.

Functionality is important. And actually beauty enhances functionality because it does make things easier to use, more approachable, more compelling to use.

Katie Dill

Quality is growth.

Katie Dill

Performance equals potential minus interference.

Katie Dill

The object isn't to make art, it's to be in that wonderful state, which makes art inevitable.

Robert Henri

Reach for the stars and land on the moon.

Katie Dill

It's easier to teach tools and process than it is taste and character.

Katie Dill

One of our greatest freedoms is how we react to things.

The Boy, the Mole, the Fox and the Horse

Tomorrow is today.

Katie Dill

Stripe's 15 Essential Journeys for Product Quality

Katie Dill
  1. Identify 15 critical user journeys that matter deeply to users and must be executed with the highest quality.
  2. Assign engineering, product, and design leaders to be responsible for the quality of each journey.
  3. Leaders 'walk the store' (review the journeys) on a regular cadence, putting themselves in the user's shoes.
  4. Friction log experiences, noting what's working and not working, filing bugs, and reaching out to relevant teams.
  5. Score the journey based on a rubric that considers usability, utility, desirability, and surprising greatness.
  6. Calibrate scores in 'PQR (Product Quality Review)' meetings with multidisciplinary leaders to ensure consistent understanding of the quality bar across the company.
pretty dramatically
Decrease in use of the word 'beauty' in digitized books (1800s-2000s) Aligned with the idea that 'functionality is king' in product development.
99%
Percentage of top e-commerce sites with checkout flow errors Errors hinder seamless checkout and higher conversion rates for customers.
10.5%
Increase in businesses' revenue from improving checkout experience (older to newer form) Achieved through quality improvements in small and large details of the checkout flow.
15
Number of essential user journeys Stripe initially focused on A somewhat arbitrary number chosen for manageability and breadth, not comprehensive of all important things.
20 years old
Age of the book 'Poor Charlie's Almanack' when re-printed by Stripe Press An anthology of Charlie Munger's words, assembled by Peter Kaufman.
4 times
Number of times Katie Dill has read 'How to Win Friends and Influence People' Recommends it as a timeless read for leadership and interpersonal skills.