Artificial Intelligence

Generative artificial intelligence is the most important new information technology since the World Wide Web. I'm exploring ways to help organizations and individuals create value using AI. I'm sharing what I learn here.

Workshops and Seminars

AI Hands-on (live)
Join me in Philadelphia on April 15 for a half-day version of my AI Hands-on workshop.

AI Hands-on (online)
Learn to tap the power of generative AI beyond the chat box. (Waitlist)

AI as a Thought Partner
A Rosenfeld Media seminar on using AI for personal knowledge management.

Projects and Experiments

Using Graph RAG for Information Architecture
How to use knowledge graphs with retrieval augmented generation (RAG) to organize large content repositories.

LLM-powered Content Tagging
An approach to re-categorizing large-scale content repositories, such as websites, using AI.

Using Embeddings to Group Content
An approach to finding patterns in content by having an LLM create an embeddings database.

LLMapper
An open source command-line tool that generates simple concept maps from Wikipedia pages.

LLMapper Skill
Gives Claude the ability to draw and manipulate concept maps, based on the earlier LLMapper CLI tool.

Handwriting Transcription Using Local LLMs
How to turn handwritten notes into Markdown — on your computer.

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Essays

• Don't Let Your Tools Distort Your Reality

  When faced with hype, consider the sources — and whether they're seeing clearly.

• AI Starting Points

  Opinionated suggestions for UX researchers getting started with AI in early 2026.

• Dabble No More: Toward Disciplined AI Adoption

  Experimenting with AI is a starting point. But creating real value requires direction and discipline.

• The Moylan Arrow: IA Lessons for AI-Powered Experiences

  How traditional structural principles can inform the design of AI-powered products and services.

• My Theme for 2026

  Making myself accountable by declaring my focus for the year.

• LLMs as Robot Arms

  How to deliver value by rearchitecting knowledge pipelines around AI constraints.

• Transcribe Handwriting Using a Local LLM

  How to turn handwritten notes into Markdown — on your computer.

• Tapping Into AI’s Conservatism

  AI favors established frameworks. Knowing that will change how you develop your information systems.

• Automate the Boring

  Delegating tedious tasks to AI is the most strategic, feasible, and humane use of the technology today.

• Introducing unfinishe 

  Announcing a new strategic consultancy focused on helping small businesses make the most of AI.

• Using AI to Illuminate My Blind Spots

  ChatGPT helps me think about what I need to improve.

• Don't Let the Drawings Distract You: AI is Not About the Output

  AI’s real value isn’t in generating flashy outputs; it’s in making sense of unstructured information to support better decisions.

• AI is Probabilistic – That's Why It Needs Constraints

  Computers used to exclusively follow rules; now they generate possibilities. Combining both approaches maximizes their potential.

• The New Leverage: AI and the Power of Small Teams

  Doing more with less isn’t just possible — it’s the future of work.

• Horsey Horseless and the Challenge of AI-native Products

  What a weird 19th century product can teach us about designing for disruptive technologies.

• The Resurgence of Plain Text in the Age of AI

  Reflections on the advantages of plain text and why it matters when working with LLMs.

• Exploring the AI Solution Space

  Unlocking AI’s potential requires broadening our understanding of what’s possible.

• The GREW Model

  A framework for leveraging the power of generative AI while keeping human oversight.

• Why I'm Excited About Generative AI

  Generative models aren't sentient entities but advanced symbol manipulation tools with vast potential.

• Empowering Information Architecture with AI: Making It Real

  An approach to using AI to re-categorize content in a 1,200-page website.

• Information Architects Must Embrace AI

  While generative AI has downsides, it also has great potential — especially for information architecture.

• LLMapper: An AI Concept Mapping Tool

  Overview of my most recent experiment with AI: a tool for drawing concept maps from Wikipedia pages.

• Five Future Roles for Designers

  Possible career directions for designers working in an AI-driven world.

• Empowering Information Architecture with AI: A Practical Experiment

  Overview of an experiment of using LLMs to categorize and tag over a thousand blog posts.

• Reality Augmentation Field

  Apple’s new augmented reality platform will change how you interact with information.

• AI as Writing Partner

  LLMs can speed up the writing process. Here’s one way they can help.

• Artificial Intelligence for Information Architecture

  Looking beyond the AI hype to explore how LLMs might help us design better information architectures faster.

• Three Roles for Robots

  Examining different ways in which AI can augment your thinking.

• The Hair Metal Disclaimer

  New tools are changing how we create. How will you respond?

• Machine Intelligence and the Design of Complex Systems

  On the balance between top-down direction and bottom-up emergence in the design of complex systems.

• Challenges in Designing for Emerging Technologies

  Thoughts raised by a new video demonstrating direct neural control of software.

• A Year of Podcasting: Editing

  A description of the tools I used to edit my podcast during its first year.

• Causes of (and Remedies for) Bias in AI

  On the potential of AI to identify and amplify human biases.

• Suggested Searches in Apple Photos

  Helping users find photos they might not know they're looking for.

• Artificial Intransigence

  Video streaming recommendation algorithms sometimes fall short.

• The Treachery of Deepfakes

  It's becoming harder to distinguish between reality and its representations in information environments.

• The Tricorder on Your Wrist

  How the Apple Watch has evolved into a essential personal health device.

• Designing for “Smart” Agents Among Us

  The emergence of AI challenges us to rethink the impact of human-agent interactions.

• When Algorithms Know

  An algorithm saved my travel plans by rebooking my missed flight without hassle.

• What Are You Working On?

  How asking designers “what are you working on?” reveals their values and engagement.

• Talking With the Information Machines

  Users can struggle as they adapt to novel semantic environments.

Videos and Presentations

• Scaling LLM-Powered Web Content Changes

  A demonstration of one way to automate LLM-powered operations while keeping a human in the loop.

• Automating AI Web Search With Perplexity

  A demonstration of how to use AI to update site content using web search.

• Using AI to Extract Structured Data From Markdown

  A video on how I'm using an LLM to extract metadata from unstructured Markdown files.

• Improving My Website Using AI

  The first video in a series on how I'm using AI to make changes to my ~1,300-page online home.

• Open-Ended Sessions: Workflow Archaeology

  A conversation about how considered use of AI can help small and medium-sized businesses thrive.

• The LLMapper Agent Skill

  A new Skill that gives Claude the ability to draw and manipulate concept maps.

• AI “Real Talk”: How Useful are AI Agents Right Now?

  An informal livestreamed conversation about a key AI concept.

• Envisioning (Near-)Future IA Design

  On the differences between using AI for automation vs. augmentation — and why information architects should explore both.

Podcasts

• Traction Heroes Ep. 15: AI for Leaders

  A conversation about the three key neurological qualities for leaders — and how AI might augment them.

• The Informed Life with Karen McGrane

  Overview of a conversation about how generative AI might affect content management.

• The Informed Life with Chris Risdon

  A conversation with a master service designer about the role of technology in delivering cohesive experiences.

• The Informed Life with Jodi Forlizzi

  A conversation with a distinguished practitioner and academic about the changing role of design in light of AI.

• The Informed Life with Rachel Price

  A conversation about how information architects can help organizations use AI more responsibly.

• The Informed Life with Emily Campbell

  A conversation on why we need a pattern language for interactions with AI-powered systems.

• The Informed Life with Michael Anton Dila

  Overview of a conversation about a new initiative that aims to redefine AI governance through inclusivity.

• The Informed Life with David Rose

  Summary of my interview with an ambient computing pioneer about augmented reality.

• The Informed Life With Mary Parks

  Delving into the hows and whats of voice interfaces.

• The Informed Life With Carol Smith

  An with researcher Carol Smith on the benefits, limitations, and potential dangers of AI technologies.