A Strategic 90-Day Roadmap

Continuing Your AI
Upskilling Journey

Executive Mastery in Three Phases

01  Core Fluency · Days 1–30 02  Custom Intelligence · Days 31–60 03  Agentic Orchestration · Days 61–90

01  ·  Phase One  ·  Days 1–30

Core Fluency &
Habit Stacking

High-Signal Consumption and the "Pulse" of the Ecosystem

Habit Stack: Morning AI News Briefing

Start your morning with a 5-minute news briefing. Use your preferred frontier model to scan what shifted overnight in AI.

Get a "Pulse" Account

Pay for at least one Pro account to access frontier models — specifically Gemini Pro or Claude.

Hitting your usage quota is a success metric. It signals you are doing ambitious, high-leverage work.

Test Drive: The Strategy Audit

Upload a 50-page PDF (market report) to NotebookLM. Request a 3-bullet executive summary focused strictly on "unforeseen operational risks."

The PRD Prompting Method

Move beyond simple questions. Define the Problem, Role, and Deliverable. Add an Example of Success — explicitly tell the AI what "good" looks like and how to know when the task is complete.

Continuous Learning

Explore foundational courses to build durable AI literacy alongside your daily practice.

02  ·  Phase Two  ·  Days 31–60

Custom Intelligence
& Multimodal

Personal Knowledge Bases and Creative Presence

Deploy a Custom Assistant

Create a "Strategic Knowledge Base" in ChatGPT GPTs, Google Gemini Gems, or Claude Projects. Ingest a year's worth of your own public articles, memos, and industry transcripts to build an assistant that drafts content in your specific executive voice.

Visual Prototyping

Turn a napkin sketch into a functional web interface. No engineering background required.

Creative & Video Automation

Automate your standard updates using AI-generated video and voice.

Gemini is the premier choice for high-fidelity image and video generation. Try it for your next visual prototype.

Must-Have Tool: Voice-to-Text

Install Wispr Flow for seamless, high-accuracy voice-to-text across all your desktop applications. It removes the friction of switching between thinking and typing.

03  ·  Phase Three  ·  Days 61–90

Agentic
Orchestration

Scaling Outcomes as a Hands-On Builder

The WAT Framework

Transition from chatbots to agents. Define your Workflows (instructions), empower the Agent (coordinator), and provide the Tools (workers). This is the architecture behind every production AI system.

Momentum Demo: Collaborative Intelligence

Use Claude Cowork to act as a real-time partner in your workspace. This is the industry momentum — shifting from "asking a bot" to "working alongside an agent" that shares your context and files.

Accelerated Delivery

Use Claude Code or Cursor to oversee projects. Describe a solution and review the execution — removing the line between technical and non-technical leadership.

Computer Use

Experiment with AI agents that navigate complex browser tasks on your behalf. Delegate the repetitive; direct the consequential.

Popular tools, voices,
and curriculum.

Workflow & Productivity

Claude Cowork  ·  n8n  ·  Cursor  ·  Lovable  ·  Replit
Wispr Flow  ·  Otter.ai  ·  Fireflies.ai

Thought Leaders

Andrej Karpathy  ·  Andrew Ng  ·  Ethan Mollick  ·  Dr. Fei-Fei Li  ·  Connor Grennan  ·  Joy Buolamwini

Newsletters & Podcasts

The Rundown AI  ·  Ben's Bites  ·  TLDR AI  ·  AI Exchange  ·  TWIML  ·  Latent Space  ·  The Best One Yet

Social Media Educators

Nate B. Jones  ·  Greg Isenberg  ·  Sabrina Ramonov  ·  Nate Herk  ·  Allie K. Miller

Your progression path.

Level Focus Recommended Tools
Level 1 Foundations Claude, Gemini, NotebookLM, ChatGPT, Wispr Flow, Perplexity, Grok, Ollama, Gemma, LM Studio
Level 2 Context Claude + MCP, Google Drive / Gmail / Calendar, Slack, Notion, Figma, Canva, Asana, Pinecone, LangChain
Level 3 Multimodal Gemini, ElevenLabs, Suno, HeyGen, Veo 3.1, Midjourney, Ideogram, Kling 3.0, Runway Gen-4, Flux
Level 4 Agents & Workflows n8n, Make.com, Zapier, Claude Cowork, Claude in Chrome
Level 5 Vibe Coding Claude Code, OpenAI Codex, Gemini, Bolt.new, Lovable, Replit, Cursor, Copilot