Design Better Podcast: Henry Modisett – Perplexity’s VP of Design on Embracing Ambiguity and Leading with Curiosity

Date: September 3, 2025
Hosts: Eli Woolery and Aaron Walter
Guest: Henry Modisett, VP of Design at Perplexity

Episode Overview

In this episode, Eli and Aaron dive into the world of designing for AI with Henry Modisett, Perplexity’s VP of Design. The conversation explores how AI-native products are fundamentally shifting design paradigms, why curiosity and embracing ambiguity matter, and how Perplexity is approaching trust, brand, and practical UX innovation. Henry offers rich insights into blending design and engineering mindsets, the power of writing, and the designer’s opportunity to shape culture in a rapidly changing tech landscape.

Key Discussion Points & Insights

Henry's Origin Story: Art, Engineering, and Design (04:04)

• Background: Started as an artsy, music-focused teenager, but chose engineering at university based on his mother's advice.
• Empowerment through Engineering:

  "There's a worldview... that everything was made by somebody... You can dream it up and make it happen." – Henry (04:48)

• Design vs. Art:
  Henry sees a distinction between art as personal expression and design as a utility-driven contribution for others, combining his artistic sensibilities with a maker’s mindset.

Lessons from Quora: Designing for Trust and Information (06:38)

• Quora’s Mission Impact:
  Quora emphasized organizing knowledge, not just collecting ephemeral information from the Internet.
• Designer as Coder/Product Thinker:
  At Quora, designers were expected to code and think holistically about product mechanics and user experience—all informed by data and experimentation.
• Learning Culture:

  "We were like, maybe we're closer to game designers than other software designers." – Henry (07:16)

Learning How People Learn: Personal Empowerment and AI (09:27)

• Self-Teaching Focus:
  Henry enjoys building tools that make people realize they can learn skills they previously struggled with—AI can remove barriers.
• Personal Anecdote:

  "I never was good at math until I had tutors... I didn’t understand object-oriented programming until I rendered a circle on the screen and made it red." – Henry (09:53)

• Democratizing Knowledge:
  Designs should encourage a hunger for learning and show people that failing under rigid systems isn’t a personal failing.

AI’s Role: Accelerate or Enable Laziness? (11:30)

• Designing for Empowerment:
  Perplexity is intentionally removing tedium, freeing people to focus on greater achievements.
• Optimistic View:

  "With more time, we do greater things than we do more things... I’d like to believe... there will be people from different backgrounds that will surprise you." – Henry (11:42)

Perplexity’s Approach: Robust Information and AI (13:17)

• Not Chat, but Answers:
  Perplexity started by rethinking what AI products should do—emphasizing reliability, accuracy, and removing needless “fake human” personality from responses.
• Reliability and Trust:

  "We’re trying to build an AI-powered answer engine... AI is not the product. AI is what makes the product work." – Henry (14:39)

• Habitual Trust:
  It’s about building a habit—users trust the output and don’t need to second-guess everything.

Launching Comet: The Browser Reinvented (16:21)

• Why a Browser?
  Most people don’t distinguish much between browsers and search engines. By owning both, Perplexity seamlessly integrates powerful agentic features.
• Human-Centered Patterns:
  The familiar interface helps users feel comfortable, while AI introduces surprising beneficial outcomes.
• Aha Moments:

  "Everyone’s getting these aha moments... It’s fun to have brought in something actually quite novel to one of the most common pieces of software." – Henry (18:14)

Designing Magical Agentic Moments (18:38)

• Real Examples:
  From annotating spreadsheets to ordering green juice via a plain command, Comet can translate vague intentions into concrete actions on the web.
• Design Philosophy:
  Comet isn’t locked into 10 use cases, but is extensible—users discover new applications and workflows themselves.
• User-Driven Discovery:

  "People show us what they’re doing with it. Everyone has workflows on the Internet that you can’t imagine." – Henry (19:39)

Building for Trust in Autonomous Agents (21:02)

• Transparency and Control:
  The agent narrates actions, provides visual logs/screenshots, and allows interruption—users can always intervene.
• Trust = Consistency:

  "The most important way to create trust is just for it to actually work." – Henry (21:58)

• Design Principle:
  Show the “work in progress” so users understand and can oversee AI’s autonomous actions.

Evolving Design Workflow in the AI Era (27:32)

• Designing in Code:
  Because AI products have infinite states, Perplexity’s team prefers React and live data over static mockups.
• Empowering Designers:
  Coding gives designers the power to immediately iterate and test ideas, making for a more effective and satisfying workflow.
• AI as a Coding Partner:

  "There’s this kind of explosion in output happening... you can use AI to generate a lot of your code." – Henry (29:17)

• Dynamic Designer-Engineer Roles:
  Less rigid division between designers and engineers, allowing more fluid collaboration.

The Role of the Designer: Vision, Brand, and Conviction (32:32)

• Founding Designer Experience:
  As the only designer early on, Henry shaped both UX and brand, arguing for a sophisticated, serious presence to differentiate Perplexity in a crowded space.
• Design as Company Strategy:
  Brand, product, and UX are tightly integrated—telling a coherent, contrasting story to win over users.
• Valuing Design Leadership:

  "There’s way more outcomes than you can imagine if you just let somebody run with an idea..." – Henry (34:40)

• Supportive Leadership:
  Appreciates co-founders who truly support design without micromanaging the outcome.

Design and Engineering: The Big Picture vs. the Details (37:10)

• Microscope & Telescope Analogy:
  Engineers handle detail; designers envision entirely new compositions and possibilities, preventing copycat stagnation.
• Consumer Product Focus:
  Design must shape both functionality and market perception, with millisecond-level attention spans.

Writing’s Power in Design (40:08)

• Concise Vision:
  Henry values clear, brief written documentation as a way to align teams and avoid wasting effort on extensive mockups.
• Culture Fit:
  Prefers pithy, strong framing over lengthy essays—writing is an anchor, not an obstruction.

Exporting Perplexity’s Design Culture (41:41)

• Problem-Solving, Not Visualizing:
  Warns against design teams acting purely as option visualizers for leadership anxiety. Instead, designers should be empowered to make decisions and ship real outcomes.
• Faster Cycles:
  Product development must now match the pace of code generation—planning needs to be more frequent and adaptive.
• Unique Designer Value:
  Designers are best positioned to navigate infinite choices with conviction.

Big Company vs. Startup Design (45:11)

• Preference for Startups:
  Frustration with big company timelines—Henry finds satisfaction and efficacy in fast-moving startups.
• Iterative Speed:

  "There’s just nothing more satisfying than actually making a thing and giving it to people..." – Henry (46:10)

What’s Inspiring Henry Now? (46:52)

• Dogfooding Perplexity:
  Henry mostly uses Perplexity to find product gaps, but draws inspiration from broad brand storytelling in other industries (cars, watches, cereal).
• Market Opportunity in Brand:

  "It doesn’t seem like most tech companies think about brand at all... there’s a huge opportunity for us." – Henry (47:55)

• Constant Reinvention:
  Energized by the ability to challenge how people interact with software and bring novelty to established categories.

Notable Quotes & Memorable Moments

• On Engineering Mindset:

  "Everything around you... somebody had to figure out how to do it... That is a wonderful perspective to gain." – Henry (04:48)

• On Learning & AI:

  "My favorite example is... people say, 'I'm not very good at math.' I bet you just haven't had it explained to you in a way that resonates." – Henry (09:34)

• On Robust AI Answers:

  "We should also strip out all the silly personality. You’re asking a question, you want to read the answer. You don’t want to have a conversation with a fake human." – Henry (14:05)

• On Magical Moments in Comet:

  "Order me green juice to the office... it will go and buy it for me and send it to the office, and it will show up. All I did was type in a sentence." – Henry (19:04)

• On Trust:

  "We only have a few chances to prove ourselves. And if it starts doing the wrong thing, then you’re probably gonna be scared to try it again." – Henry (21:59)

• On Design’s Exportable Value:

  "If I could export anything, it's like, hey, what if designers actually solved problems?" – Henry (43:11)

• On Speed and Satisfaction:

  "There’s just nothing more satisfying than actually making a thing and giving it to people and seeing them use it..." – Henry (46:10)

• On Brand Opportunity:

  "It doesn’t seem like most tech companies think about brand at all... there’s a huge opportunity for us." – Henry (47:55)

Important Timestamps

• Origin Story & Worldview: 04:04–06:06
• Design and Learning at Quora: 06:06–09:18
• AI and Empowering Learners: 09:27–12:49
• Perplexity’s Core Differentiator: 13:17–15:48
• Comet Browser Intro & Agentic UI: 16:21–22:25
• Design Workflow with Code & AI: 27:32–31:34
• Product/Brand Vision at Perplexity: 32:32–36:05
• Design vs. Engineering Roles: 37:10–39:51
• Writing for Design: 40:08–41:41
• Exporting Good Design Culture: 41:41–44:25
• Big Company vs. Startup: 44:32–46:34
• What Inspires Henry: 46:52–48:47

Further Resources & Contact

• Perplexity: perplexity.com
• Comet Browser: perplexity.com/comet
• Henry Modisett: Twitter @HenryModisett

The episode offers a compelling look at the evolving landscape of design in an AI-driven world, blending deep technical insight with a passionate call for curiosity, courage, and human-centered product thinking.