I've been working through where I should hand off to AI versus where I need to stay directly involved—especially in my personal knowledge management. I use Obsidian as my knowledge hub (local markdown notes with links) and Claude Code as my primary agent interface, alongside Notion as an operational hub for tasks/projects. I deliberately keep Claude's access session-based (not always-on) and set boundaries: AI can help organize, search, and triage notes, but it cannot create or modify my "permanent notes," which must be written in my own voice to preserve real understanding. I also experiment with disposable, AI-generated Obsidian vaults for exploratory research (e.g., mapping an industry or concept graph), then selectively turn what I learn into my own fleeting/reference/permanent notes.

Most people use AI coding tools to write code. I'm using Claude Code to help build a personal operating system as a CEO.

I've hooked it up to many different tools that are important to us: Todoist, Slack, Linear, Notion, Salesforce, Gong, email, and so on. I've found it to be far more useful and sticky than the vanilla ChatGPT approach.

I now think of it as a mini coach+chief of staff. Some particularly valuable ways I'm using it right now or things I'm experimenting with:

🧠 Distillation of knowledge
I have a knowledge base that auto-syncs meeting transcripts from Granola, documents from Notion, indexes them by type (1:1s, customer calls, leadership), and makes them queryable across any conversation. It syncs to my Mac hourly. This means I can go see someone at their desk, Granola the conversation, and the context is now available for any future work I want to do with Claude.

🧘‍♂️ Removing distractions
A small but useful skill I've built is the slack-cleanup skill. It scans my 170+ channels, checks 6 months of activity, cross-references Salesforce and many other tools before deciding what to leave. Keeps me focused.

💭 Self-reflection and persistent memory
It knows our yearly initiatives, quarterly targets, and I write a weekly check-in before the week starts. So when I ask "what should I focus on today?", it doesn't just read my calendar. It checks whether my week is tracking against what actually matters. It's a gentle and useful accountability system.

🧐 Thinking quality
I'm experimenting with a /frame skill that takes messy context and distils it into a one-sentence problem, the binding constraint, and the eigenquestion — the question whose answer determines the answers to all the other questions. I use it to force forward progress on hard problems.

🔎 "Cheap", one-off analyses
For example, a competitive deep-dive into win rates, backed by specific customer quotes on gaps, with Gong snippets. That was a multi-day project compressed into minutes, backed by hard evidence, so I can sense check correctness.

Ultimately, I think the most benefit comes from work that would never have happened in the first place because it was far too expensive to do, vs. making me faster at what I already do. I recommend!