Alex Komoroske

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Alex Komoroske is a strategic leader who merges the practice, theory, and mindset necessary to tackle complex problems. He spent 13 years at Google, where he worked on Search and DoubleClick and led Chrome’s Open Web Platform. He also spearheaded Augmented Reality in Google Maps and developed toolkits to align companywide strategy from the ground up. After serving as Head of Corporate Strategy at Stripe, he is now co-founding a startup aimed at reimagining the web for the AI era. Alex created the popular “Slime Molds” deck, which offers fresh insights into organizational dynamics. He is also the author of the widely read “Bits and Bobs,” a collection of thought-provoking reflections.

In our conversation, we delve into:

• “Organizational kayfabe”

• “Gardening” vs. “building”

• How AI will soon change how we build product

• How and why to embrace the adjacent possible

• The power of reflection and how to build it into your workflow

• How to create emergent properties in organization

• How to run effective “strategy salons” or “nerd clubs”

• Much more

Some takeaways:

1. Embrace a gardener’s mindset instead of a builder’s: While builders meticulously plan every step to achieve a specific goal, this structured approach can stifle unexpected, innovative breakthroughs. In contrast, Alex champions the gardening philosophy, which emphasizes planting seeds—representing ideas and projects—and nurturing them as they grow organically. This perspective recognizes that not every seed will take root, but those that do can surpass initial expectations, often resulting in groundbreaking innovations.

2. Reflection is crucial for deep thinking and insight generation. To make reflection a regular habit:

   1. Create a dedicated space (like a Google Doc) to capture notes from meetings, articles, and spontaneous insights. Commit to updating this document daily to keep your ideas organized and accessible.

   2. Block out three hours on a specific day—say, Friday afternoons—where you won’t take any meetings. Use this time to review your notes, distill insights from the week, and identify patterns. The goal is not just to go through your notes but to find actionable insights that can save you time in the future.

3. Organizational kayfabe refers to the phenomenon where everyone within an organization pretends that certain false narratives or overly optimistic assessments are true, even when they know they aren’t. To avoid this:

   1. Encourage radical transparency

   2. Create safe spaces for honest feedback

   3. Gather real data rather than relying on optimistic reports

   4. When issues arrive, involve team members in brainstorming solutions

4. Instead of trying to force everyone into a rigid structure, adopt a “slime mold” approach by embracing the organic, flexible nature of your organization—much like slime molds do. Pay attention to ideas that capture interest from diverse groups, iterate on them using feedback, and promote autonomy for innovative exploration. In doing so, you’ll unlock creative potential and enhance collaboration without getting bogged down in bureaucracy.

5. “Strategy salons” or “nerd clubs” can be powerful tools for generating ideas and fostering innovation. Use your nerd club as a safe space to explore half-formed ideas. Limit it to a few engaged individuals who genuinely want to participate. Set ground rules for discussions, like using “yes, and” to build on ideas and leaving negative feedback aside. These informal groups allow participants to share thoughts in a low-pressure environment, encouraging creativity and innovation.

6. Instead of chasing grand, untested ideas, focus on the adjacent possible—the small, actionable steps within your reach. Start by defining a clear North Star: a long-term goal that everyone can agree is plausible and exciting. Then, identify the next incremental step that aligns with this vision. Each step should feel safe and reasonable, allowing you to adapt and pivot as you learn from the outcomes.

7. Treat AI tools as your brainstorming buddy. When you’re wrestling with a concept, dump your thoughts into the tool. Ask it for examples, critiques, or different angles to explore. This will help clarify your thinking and generate new ideas quickly.

Where to find Alex Komoroske:

• X: https://x.com/komorama

• LinkedIn: https://www.linkedin.com/in/alex-komoroske-6597336/

• Website: https://www.komoroske.com/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Introduction to Alex

(01:53) Alex’s Bits and Bobs document

(06:20) The Compendium and note-taking process

(10:10) The impact of AI and LLMs on product development

(14:24) Skills to lean into as a product manager

(19:02) How AI makes us better as individuals

(23:04) Organizational kayfabe

(31:48) Gardening vs. building

(34:46) Emergence-oriented thinking

(41:55) Slime molds and organizational structure

(45:15) Identifying resonant ideas

(47:05) The power of metaphors

(48:02) Strategy salons and nerd clubs

(52:30) Building and sustaining communities

(55:59) Productivity hacks and self-control

(01:01:04) Life philosophy and personal insights

(01:07:52) The adjacent possible

(01:15:56) Lightning round

Referenced:

• Bits and Bobs Google Doc: https://groups.google.com/g/komoroske-updates/c/2rPJ9EyKVYY?pli=1

• The Compendium: https://thecompendium.cards/

• WebSim: https://websim.ai/

• Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

• Anthropic: https://www.anthropic.com/

• Claude: https://claude.ai

• Steve Jobs on Why Computers Are Like a Bicycle for the Mind (1990): https://www.themarginalian.org/2011/12/21/steve-jobs-bicycle-for-the-mind-1990/

• Kayfabe: https://en.wikipedia.org/wiki/Kayfabe

• Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012

• How Perplexity builds product: https://www.lennysnewsletter.com/p/how-perplexity-builds-product

• Slime Molds: https://komoroske.com/slime-mold/

• Ken Stanley on LinkedIn: https://www.linkedin.com/in/kenneth-stanley-3a159b/

• Evolution through the Search for Novelty Alone: https://www.cs.swarthmore.edu/~meeden/DevelopmentalRobotics/lehman_ecj11.pdf

• Tim Urban’s X post on “idea lab” culture: https://x.com/waitbutwhy/status/1639003239801602049

• For self-control, “always” rules are better than “sometimes” rules: https://medium.com/@komorama/for-self-control-always-rules-are-better-than-sometimes-rules-4c38be32f318

• How to Stop Procrastinating on Your Goals by Using the “Seinfeld Strategy”: https://jamesclear.com/stop-procrastinating-seinfeld-strategy

• The Iterative Adjacent Possible: https://medium.com/@komorama/the-iterative-adjacent-possible-af3e7038357d

• “The Hallmark Card Fallacy” on Infinite Loops: https://www.youtube.com/shorts/7IgApdfBjNI

• Tim Urban’s website: https://waitbutwhy.com/

• Adnan Ahmad Sheikh’s post on LinkedIn: Happiness = Reality - Expectations (by Tim Urban): https://www.linkedin.com/pulse/happiness-reality-expectations-tim-urban-adnan-ahmad/

• The Origin of Wealth: The Radical Remaking of Economics and What It Means for Business and Society: https://www.amazon.com/Origin-Wealth-Remaking-Economics-Business/dp/1422121038

• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557

• The Green Knight on Prime Video: https://www.amazon.com/Green-Knight-Dev-Patel/dp/B09CP1FMJK

• OpenAI Just Released Its Long-Awaited “Strawberry” Model: https://futurism.com/openai-released-strawberry-o1-preview-model

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Lenny may be an investor in the companies discussed.