Skip to content
Lenny's PodcastLenny's Podcast

Lessons on product sense, AI, the first mile experience, and the messy middle | Scott Belsky (Adobe)

Scott Belsky is an entrepreneur, author, investor, and currently Adobe’s Chief Strategy Officer and EVP of Design and Emerging Products. He founded Behance, an online platform for creative professionals to showcase and discover work, and served as CEO until its acquisition by Adobe. Scott is an early advisor and investor in several businesses at the intersection of technology and design, including Pinterest, Uber, Warby Parker, Airtable, and Flexport. He is also the author of two nationally bestselling books and founded 99U, a publication and conference focused on productivity in the creative world. In today’s episode, we discuss: • How to strengthen your product sense • Why you should only do half the things you want • What it takes to build a successful consumer product • Why you are probably underinvesting in onboarding • The future of AI and how to prepare for it • Advice for founders and PMs who are feeling stuck • Why resourcefulness will take you further than resources • Adobe’s current priorities and their exciting path ahead — Brought to you by Braintrust—For when you needed talent, yesterday | Eppo—Run reliable, impactful experiments | Rows—The spreadsheet where data comes to life Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-on-building-product-sense Where to find Scott Belsky: • Twitter: https://twitter.com/scottbelsky • LinkedIn: https://www.linkedin.com/in/scottbelsky/ • Blog: https://www.implications.com/ • Website: https://www.scottbelsky.com/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Scott’s background (04:50) Why Scott shifted roles at Adobe (08:29) Advice for PMs looking to build product sense (10:43) The first mile (13:18) How to develop more empathy (16:33) How to build consumer products that work (20:42) Scott’s philosophy that you should “only do half the things you want to do” (26:15) Scott’s optimism about how the world will look in five years with AI (29:44) How AI will impact product teams (32:55) How the PM role will change as a result of AI (35:09) How Adobe is leveraging AI tools (36:59) What the term “golden gut” means (38:15) Advice for PMs to stay ahead of the new AI trends (41:02) How to start writing more (41:49) The messy middle (47:03) What Scott looks for as an angel investor  (50:16) Why resourcefulness will take you further than resources  (52:41) Adobe’s current priorities and the path ahead (54:58) Lightning round  Referenced: • Adobe: https://www.adobe.com/ • Behance: https://www.behance.net/ • Casey Winters on Lenny’s Podcast: https://www.lennyspodcast.com/thinking-beyond-frameworks-casey-winters-pinterest-eventbrite-airbnb-tinder-canva-reddit-grubhub/ • Crafting The First Mile Of Product: https://medium.com/positiveslope/crafting-the-first-mile-of-product-7ed25e8f1027 • Shishir Mehrotra on Lenny’s Podcast: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/ • Scott’s tweet on only doing half the things you want to do: https://twitter.com/scottbelsky/status/1441469886975279109?s=20 • Matt Mochary on Lenny’s Podcast: https://www.lennyspodcast.com/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary-ceo-coach/ • Adobe Firefly: https://www.adobe.com/sensei/generative-ai/firefly • Howie Liu (CEO at Airtable): https://www.linkedin.com/in/howieliu/ • ChatGPT: https://openai.com/blog/chatgpt • The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture by Scott Belsky: https://www.amazon.com/Messy-Middle-Finding-Through-Hardest/dp/0735218072 • Adobe Express: https://www.adobe.com/express • Build: An Unorthodox Guide to Making Things Worth Making by Tony Fadell: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067 • Cosmos: A Spacetime Odyssey on Netflix: https://dvd.netflix.com/Movie/Cosmos-A-Spacetime-Odyssey/80004448 • Vinod Khosla’s prediction: https://futurism.com/80-of-it-jobs-can-be-replaced-by-automation-and-its-exciting • Queue: https://www.queue.co/ • Tome: https://tome.app/ • Kevin Kelly on The Tim Ferriss Show: https://tim.blog/2014/08/29/kevin-kelly/ Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Scott BelskyguestLenny Rachitskyhost
May 17, 20231h 2mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Scott Belsky on product sense, AI, and surviving the messy middle

  1. Scott Belsky, Adobe’s former CPO and current Chief Strategy Officer, shares how he thinks about product sense, first‑mile experiences, and building durable consumer products, alongside his optimistic but pragmatic view of AI. He argues that great product sense comes from deep customer empathy, psychology-driven design, and ruthless reduction of scope and features. The conversation explores how AI will collapse organizational stacks, massively expand exploration surface area for PMs and designers, and shift work from workflows to flow. Belsky also unpacks his “messy middle” framework, how founders should decide whether to quit or persist, and what he looks for when angel investing.

IDEAS WORTH REMEMBERING

5 ideas

Anchor product sense in customer empathy, not attachment to solutions.

Teams often fall in love with their ideas instead of deeply understanding the user’s life and context; shoulder‑to‑shoulder observation of customers in their real environment builds intuition and reveals the real problems to solve.

Obsess over the first mile: onboarding, orientation, and defaults.

In the first 30 seconds users are “lazy, vain, and selfish,” so products must quickly make them feel successful without tours or friction; continuously re‑design first‑mile flows as new, less‑forgiving customer cohorts arrive.

Do half as much: ship fewer features, options, and markets.

Optimize for the problems you want, not completeness—focus on getting users to core value, then let them complain about missing features later; Belsky’s Behance experience shows killing features often increases usage of the core metric.

Design for surprise, delight, and clear object models in consumer products.

Users talk about what products do unexpectedly well, not what they do as expected; lasting consumer products pair a deep psychological insight or network effect with a simple, obvious model of where you are, what to do now, and next.

AI will collapse organizational stacks and expand exploration surface area.

AI tools let PMs, designers, and others self‑serve analysis, design variations, and content, reducing dependence on specialized intermediaries and allowing individuals and small teams to explore many more ideas in less time.

WORDS WORTH SAVING

5 quotes

In the first 30 seconds of using a new product, you are lazy, vain, and selfish.

Scott Belsky

People don’t talk about a product doing exactly what they expected it to do. They talk about a product doing what they didn’t expect.

Scott Belsky

Optimize for the problems you want to have.

Scott Belsky

Nothing extraordinary is ever achieved through ordinary means.

Scott Belsky

If you’ve lost conviction, you should not be doing what you’re doing in the world of entrepreneurship.

Scott Belsky

Scott Belsky’s evolving role and strategy focus at AdobeBuilding product sense through empathy, psychology, and first‑mile designDesigning onboarding and “first‑mile” experiences for changing user cohortsWhat makes durable consumer products versus short‑lived fadsDoing half the features: ruthless reduction and killing product scopeAI’s impact on product teams, roles, and cross‑functional collaborationSurviving the “messy middle” and knowing when to quit or pivot as a founder

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome