Technology

Master Claude Chat, Cowork, Code

The era of treating AI as just a chatbot is over. Beyond Prompting is a podcast for developers and technical leaders ready to make the shift from conversational AI to operational AI. Join us as we explore how to turn Claude into an active, system-level agent that executes code, automates desktop workflows, and integrates directly into your CI/CD pipelines. Our core philosophy is simple: Execution over explanation, context over scale, and workflow over conversation.
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Latest Episodes:

13. Curing AI Amnesia (CLAUDE.md and Rules) Sep 30, 2026

Show notes

In Episode 13 of Beyond Prompting, author Sho Shimoda breaks down how to configure persistent repository instructions using CLAUDE.md and rule files. Rather than treating CLAUDE.md as a generic style guide or dumping ground for historical bugs, this episode focuses on treating instruction files as a concise briefing for a capable colleague. We cover:

The 200-Line Rule: Why CLAUDE.md should be kept concise (under ~200 lines) by focusing strictly on non-derivable facts, build environments, and explicit boundaries—leaving out generic advice and formatting rules the model can see for itself.

Concatenative Inheritance: How instruction files concatenate rather than override across four scopes: managed enterprise policy, user-level ~/.claude/CLAUDE.md, project ./CLAUDE.md, and uncommitted ./CLAUDE.local.md.

Scoped Rules (.claude/rules/): How to split large instruction sets into modular files inside .claude/rules/ using paths: frontmatter globs so that topic-specific rules (like frontend React conventions) only load when matching files are opened.

Deterministic Tools vs. Reasoning Context: Why mechanical syntax and formatting rules belong in deterministic linters and git hooks, reserving CLAUDE.md for architectural context and edge-case rationale that static analysis cannot check.

Preventing Instruction Sediment: Using CLI commands like /init, /memory, and /doctor to audit, prune, and maintain instruction files like code.

(Note for listeners: This episode covers Chapter 13 of Sho Shimoda's book RUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code).

12. Safe Refactoring of Legacy Code (Characterize, Change, Verify) Sep 29, 2026

Show notes

In Episode 12 of Beyond Prompting, we tackle one of the most high-stakes tasks in software engineering: letting an AI agent refactor an existing codebase. Author Sho Shimoda breaks down why asking Claude to "modernize this module" in one giant prompt usually results in hundreds of changed lines, broken production, and hours spent untangling regressions. In this episode, we cover:

The "Big-Bang" Trap: Why a single commit touching twelve files leaves you with twelve suspects when tests go red, and why working in small, single-purpose steps makes debugging instant.

Characterization Tests First: How to lock down the current behavior of legacy code by generating tests before refactoring, creating a behavioral safety net when no specification exists.

The 4-Step Refactoring Loop: Forcing Claude into a disciplined cycle—list distinct changes smallest first, execute one change, verify against characterization tests, and commit before moving to the next.

Reviewing Agent Diffs: How to review AI-generated code for subtle failure modes (like changed return contracts or deleted code paths) and using /code-review as a mechanical first pass.

Checkpoint Rewinds: Using Esc Esc or /rewind to instantly restore conversation and file state to an earlier checkpoint when an exploration fails.

(Note for listeners: This episode covers Chapter 12 of Sho Shimoda's book RUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code).

11. Securing Autonomous Agents (Permissions, Auto Mode and the Sandbox) Sep 28, 2026

Show notes

In Episode 11 of Beyond Prompting, author Sho Shimoda breaks down the permission and governance architecture that protects your host machine while allowing Claude Code to operate autonomously. As session defaults shift toward classifier-driven execution, understanding how actions are evaluated is essential for safe operation. In this episode, we cover:

First-Match Resolution Order: How proposed tool calls evaluate in a strict, fixed sequence—Deny rules first, then Ask rules, then Allow rules, before falling through to session permission modes and the classifier.

The Six Permission Modes: Navigating session postures—Manual, Accept Edits, Plan, Auto, Don't Ask, and Bypass Permissions—and understanding how settings merge additively across scopes rather than replacing team defaults.

Auto Mode & The Classifier: How a Sonnet 5 classifier evaluates proposed tool calls in real time while enforcing protected paths (like .git, .vscode, and .claude) and critical deletion paths regardless of user allow rules.

The OS-Level Sandbox Boundary: Distinguishing between client-side permission controls and true operating system isolation (Seatbelt on macOS, bubblewrap on Linux/WSL2) that constrains shell command execution even if prompt injection occurs.

(Note for listeners: This episode covers Chapter 11 of Sho Shimoda's book RUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code).

10. Governing Claude Code with Invisible JSON Files (The .claude Directory and Settings) Sep 22, 2026

Show notes

In Episode 10 of Beyond Prompting, we explore how to configure and govern Claude Code through the .claude directory and JSON settings files. Author Sho Shimoda breaks down how configuration is structured, which files take precedence when rules conflict, and how settings merge across scopes. In this episode, we cover:

What Lives Where: Distinguishing between committed project configuration (.claude/settings.json, rules/, skills/), personal overrides (.claude/settings.local.json), user-level global settings (~/.claude/), and organizationally enforced managed-settings.json.

The Five-Tier Precedence Ladder: How settings resolve from strongest to weakest: managed settings, --settings flags, .claude/settings.local.json, .claude/settings.json, and ~/.claude/settings.json.

Why Lists Merge Instead of Override: Why permission rules like permissions.allow combine additively across files rather than replacing team defaults, preventing local tweaks from silently wiping out team guardrails.

When Edits Take Effect & Workspace Trust: Which settings reload live mid-session versus which require a session restart, and why sensitive permissions wait for workspace trust before taking effect.

What Claude Code Writes About You: Managing session transcripts, rewind checkpoints, prompt history (history.jsonl), and transcript retention periods under ~/.claude/projects/.

(Note for listeners: This episode covers Chapter 10 of Sho Shimoda's book RUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code).

9. Sessions and the Interactive Loop (Steering Claude Code in the Terminal) Sep 21, 2026

Show notes

In Episode 9 of Beyond Prompting, we enter Part IV of our journey and step directly into the terminal with Claude Code. Author Sho Shimoda breaks down how Claude Code operates as an autonomous CLI agent rather than a passive text generator, working directly inside your repository. In this episode, we cover:

Getting it Running: Installing Claude Code via the native installer or @anthropic-ai/claude-code, running claude doctor to verify setup, and establishing scoped working directories.

The Interactive Loop (Gather, Act, Verify): How Claude Code gathers context, executes file or shell actions, and autonomously verifies its work against test suites and diagnostics to close the loop.

Sessions as Units of Work: Managing persistent transcripts stored on disk under ~/.claude/projects/, resuming past work with claude --continue or --resume, and branching or forking conversation histories using /branch and /fork.

Steering Over Restarting: Utilizing mid-turn corrections, rewinding checkpoints via /rewind or Esc Esc, compacting context with /compact, and knowing when to use /clear for new subjects.

(Note for listeners: This episode covers Chapter 9 of Sho Shimoda's book RUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code).

8. Scheduled and Delegated Work (Automating Recurring Processes with Claude) Sep 20, 2026

Show notes

In Episode 8 of Beyond Prompting, we examine how to turn Claude Cowork from a manual tool into a background operator that executes recurring tasks on a schedule. Author Sho Shimoda breaks down:

Remote Cloud Cadence: How scheduled tasks fire on Anthropic's cloud infrastructure whether or not your computer is open or awake—unless the task specifically requires local disk files or screen access via the desktop app broker.

Session Ephemerality: Why every scheduled run starts as a fresh, standalone session with no memory of prior runs, and how to give a task persistent memory using small, human-readable state files that are read at start and updated at completion.

Briefings People Actually Read: Designing recurring digests that ask for judgment rather than raw dumps, enforce strict brevity, and instruct Claude to "say so and stop" when there is nothing new to report.

Automation Governance: Establishing habits to quarterly review scheduled tasks, pruning obsolete automation, and ensuring failures are visible so background tasks don't quietly rot.

(Note for listeners: This episode covers Chapter 8 of Sho Shimoda's book RUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code).

7. Files, Connectors and Approvals (Safely Extending Cowork's Reach) Sep 19, 2026

Show notes

In Episode 7 of Beyond Prompting, we examine how to extend Claude Cowork's reach across local directories, cloud services, and desktop applications without sacrificing security. Author Sho Shimoda breaks down the essential controls and permissions that protect your host environment while allowing AI agents to run complex operational tasks. In this episode, we cover:

Scoping File Access: Why you should grant access to narrow project folders rather than your root home directory, and how local file access relies on an active desktop application acting as a local broker.

Connectors Call Outward: How enterprise cloud connectors issue requests from Anthropic's cloud servers directly to public SaaS APIs, and why internal services behind a corporate firewall require a local MCP server instead.

The Three Approval Modes: Navigating Manual (confirming every individual action), Automatic (pre-approving familiar action types), and Skip (zero-prompt execution for bounded tasks) as trust in a workflow develops.

Computer Use Security: Why driving your desktop screen and pointer operates directly on your live machine without a sandbox—and why it should be treated with the same caution as handing an unlocked laptop to a colleague.

(Note for listeners: This episode covers Chapter 7 of Sho Shimoda's book RUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code).

6. Cowork Today: Cloud-First, Four Surfaces (Safely Letting AI Run Work) Sep 16, 2026

Show notes

In Episode 6 of Beyond Prompting, we explore the major architectural evolution of Claude Cowork. Moving beyond simple text generation, Cowork handles operational file and document workflows—and now operates on a cloud-first architecture. Author Sho Shimoda breaks down how this transition changes where your work runs and how your local machine stays secure. In this episode, we cover:

Cloud-First Execution: Why agent loops and code execution now run in ephemeral cloud sandboxes on Anthropic's servers rather than inside a local desktop virtual machine.

One Session, Four Surfaces: How Cowork sessions sync seamlessly across desktop apps (macOS, Windows, ChromeOS, Linux), web browsers, mobile devices, and the Chrome side panel.

The Desktop App as a Broker: Understanding the desktop app's updated role—acting as a secure local broker that lets a cloud session access specific local folders, browsers, or screens only when authorized.

What Still Needs Your Machine: Identifying constraints around local disk files, live screen/computer use, and local network services, and why cloud-only tasks keep running even when your laptop lid is closed.

Session Ephemerality & Observability: Managing ephemeral sandbox state, persisting durable outputs back to disk or connectors, and using enterprise OpenTelemetry tracking for full operational auditability.

(Note for listeners: This episode covers Chapter 6 of Sho Shimoda's bookRUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code)

5. Artifacts (Turning Conversations into Shareable Tools) Sep 15, 2026

Show notes

In Episode 5 of Beyond Prompting, we focus on turning conversational outputs into persistent, interactive deliverables using Artifacts. Rather than leaving code or tools buried in a chat transcript, Artifacts create standalone, shareable components that live beside the conversation with their own addresses. In this episode, we break down:

The Artifact Boundary: Distinguishing between temporary chat messages and deliverables with a "second life" (such as calculators, diagrams, and dashboards). Note that Python code blocks inside artifacts serve as code listings rather than executable scripts.

Supported Formats: Generating HTML pages, React components, SVG graphics, Markdown documents, and Mermaid diagrams for system architecture and flowcharts.

Sandbox Security: How Artifacts run as self-contained pages inside an isolated sandbox that blocks outbound network requests, requiring inlined CSS, JavaScript, and embedded data URIs.

Standalone Publishing & Viewer Permissions: How published Artifacts live at dedicated URLs and operate using the viewer's credentials and connector permissions rather than the creator's.

Terminal Publishing & Repository Graduation: Publishing Artifacts directly from Claude Code CLI sessions using the /artifacts command, and identifying the exact signal when a prototype outgrows the Artifact sandbox and needs to graduate to a formal repository.

(Note for listeners: This episode covers Chapter 5 of Sho Shimoda's book RUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code)

4. Projects and Persistent Context (Curing AI Amnesia) Sep 15, 2026

Show notes

In Episode 4 of Beyond Prompting, we tackle the most frustrating bottleneck in AI collaboration: starting every conversation from a clean slate. If you find yourself repeatedly re-explaining your organizational domain, terminology, and conventions, Claude Projects provide a persistent container to turn disposable chats into an ongoing working relationship. In this episode, we break down the core mechanics of context persistence:

The Three-Layer Architecture: How Projects separate Custom Instructions and the Knowledge Base (which persist across sessions) from Conversations (which remain disposable and unshared).

Instructions That Earn Their Place: How to draft high-impact custom instructions that focus on non-derivable rules, target audience descriptions, and standing conventions without wasting context on generic filler.

Curating the Knowledge Base: Why uploading pattern-defining specifications beats dumping entire document trees, and how to prune superseded files so conflicting context doesn't confuse the model.

Diagnosing Project Failures: Recognizing the failure modes of Projects that are either too broad or too fragmented, using the "5-minute re-explanation test" to know when your setup needs refactoring.

Shared Institutional Memory: How shared Projects serve as automated onboarding for new team members, establishing consistent organizational context without manual runbooks.

(Note for listeners: This episode covers Chapter 4 of Sho Shimoda's book RUNNING CLAUDE: The Operator’s Guide to Chat, Cowork and Claude Code, available on Amazon as the successor book to Master Claude: Chat, Cowork and Code).

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