BOB SAILS SERIESSame day, different outcome.

Phil Drills: Master Automation Through Repetition

Like Phil Connors reliving the same day until he got it right, you'll learn to identify, build, and perfect the automated loops that run your business.

  • Understand when to use rules vs ML vs LLMs
  • Identify high-value automation candidates
  • Build reliable, repeatable workflows
  • Track and measure what actually matters

The Loop Mindset

Find Your Loops

Every business runs on loops. Phil Drills helps you identify yours and make them automatic.

Right Tool, Right Job

Stop using AI for everything. Learn when simple rules beat smart models.

Measure the Loop

What gets measured gets improved. Track your automation ROI and iterate.

Perfect the loops that run your business through deliberate repetition.

6 Focused Modules

Inside Phil Drills

5 modules available

Module 1: The AI Toolkit
Module 26: Understand AI Types - Learn Rule-Based Automation, ML, and LLMs - Bob Sails Preview
60 min
Automation

AI isn't one thing—it's a toolkit. Learn the difference between rule-based automation, machine learning, and large language models so you can choose the right tool for each business need. Build your AI readiness plan and start with quick wins.

ai-fundamentals
automation
machine-learning
Module 2: How Language Models Think
Module 27: Understand Language Models - How LLMs Work and How to Use Them - Bob Sails Preview
60 min
Automation

Learn how large language models like ChatGPT and Claude actually work—what they're good at, what they're not, and how to write effective prompts that get reliable results for your business. Build your prompt library and start delegating repetitive writing tasks to AI.

llm
large-language-models
chatgpt
Module 3: Find Your Loops
Module 15: Process Optimization — Map, Measure, Improve, Control - Preview
75 min
Automation

Pick one process, map it clearly, baseline the numbers, remove bottlenecks, and lock the gains with standard work and a control plan.

process
optimization
lean
Module 4: Build Reliable Systems
Module 9: Systems, SLOs & Automation for Scaling - Preview
85 min
Automation

Document processes, set SLOs/SLIs with error budgets, automate the right work, and run with dashboards, alerts, and incident playbooks.

slo
automation
observability
Module 5: Track What Matters
Module 13: Analytics, Attribution & Decision Dashboard - Preview
75 min
Automation

Define your North Star, instrument events, standardize UTMs, and ship a weekly decision dashboard that ties traffic → CRM → revenue.

analytics
attribution
dashboard
From Understanding to Implementation

Your Automation Journey

1

Understand the AI Toolkit

Learn the difference between rule-based automation, machine learning, and LLMs. Know when to use each and why.

2

Master Language Model Fundamentals

Understand how LLMs work, what they're good at, and their limitations. Write better prompts and get reliable results.

3

Find Your Automation Candidates

Identify the repetitive processes in your business that are prime candidates for automation.

4

Build Reliable Systems

Document your operations and create automation patterns with proper error handling and guardrails.

5

Track What Matters

Measure your automation ROI with metrics that actually tell you if things are working.

6

Build Your First Automation

Capstone project: implement one complete automation end-to-end and see the results.

Same Day, Different Outcome

Phil Connors had to relive Groundhog Day thousands of times before he got it right.

You don't have that kind of time. Phil Drills gives you the framework to:

  • Identify which tasks are worth automating (and which aren't)
  • Choose the right tool for each job (rules, ML, or LLMs)
  • Build automations that work reliably without constant babysitting

Stop reinventing the wheel. Start drilling the loops that matter.

What you need before starting

Prerequisites

Bob Sails Core

Complete the core Bob Sails course first to document your business context.

Basic Tools

Access to n8n and an OpenAI API key. No coding required.

Repetitive Tasks

At least one task you do repeatedly that you're ready to automate.

What you get:
  • 6 focused modules on automation fundamentals
  • Hands-on exercises with real automation tools
  • Decision frameworks for choosing the right approach
  • Templates for AI readiness audits

Ready to drill?

Questions about Phil Drills? Let's chat about your automation goals.