AI Executive Workflow Automation: Your Blueprint for Systematic Leadership Transformation (Part 2)

From Novice Prompts to Expert Systems: How to Build AI Workflows That Run Your Routine Work While You LeadIn Part 1, we explored the foundational mindset for AI executive productivity—the shift from 80% routine work to 80% creative work. Now, in Part 2, Barry O'Reilly reveals the specific AI executive workflow automation systems that make this transformation real.This isn't theory. These are the exact workflows, prompts, and systems that Barry and leading executives use daily to reclaim their time and amplify their leadership impact.What you'll learn: The weekly business review system that takes 90 seconds instead of 30 minutes. How to audit your work with AI's help. Building your personal prompt library. And why your unlearning rate must exceed your irrelevance rate.The AI Executive Workflow Automation Philosophy: Creative Work + Automated DisciplineBefore diving into specific systems, understand the core principle driving effective AI executive workflow automation: "Every time you can automate routine but disciplined work, you're moving the needle toward having more capacity to do creative problem-solving work. That's where you get the power and real promise of what AI is—people doing the best work of their life." Barry O'Reilly The Work Category FrameworkAI executive workflow automation works by understanding two distinct categories of leadership work:Category 1: Creative Problem-Solving WorkStrategic planning and vision developmentComplex decision-making in ambiguous situationsCoaching team members through challengesInnovation and new product/service designBuilding relationships and influencing stakeholdersPattern recognition across diverse business situationsCategory 2: Routine Disciplined WorkWriting meeting follow-ups and summariesTracking action items and deadlinesSending reminder notificationsCompiling weekly/monthly reportsScheduling and calendar managementData entry and information organizationThe AI Executive Workflow Automation Insight: Humans should do Category 1. Machines should automate Category 2. The problem is most executives spend 80% of their time in Category 2.As Barry explains: "Machines essentially offer this opportunity to automate a lot of that disciplined, repeatable, routine work—like having an auto-scheduler that sends an email 5 days before a task is due. I don't want to think about it, I don't want to send it, but a machine is amazing at making sure it follows up and does that."The Self-Audit: Ask AI to Analyze Your Work EfficiencyThe first AI executive workflow automation you should implement is having AI audit where you're spending your time. This creates objective data about your current state.The Initial Audit PromptCopy this prompt into ChatGPT, Claude, or your preferred LLM: What AI Will Ask YouWhen Barry guides executives through this process, AI typically asks questions like:About Creative Work:"What tasks do you find most creative, interesting, and rewarding? List them all out.""When do you feel most energized during your workday?""What work would you do more of if you had unlimited time?"About Routine Work:"What tasks are time-sinks that feel like necessary evils?""What do you find yourself repeatedly doing that could be standardized?""What work drains your energy without adding strategic value?"About Time Allocation:"What percentage do you spend on creative work versus routine work?""Over the last year, how much time have you spent on these categories?" (You can even connect your calendar)Example: The Business Expenses AutomationBarry provides a concrete example: "Say it identifies you spend 5 hours a week doing your business expenses. Necessary, because your accountant wants those things. The machine could say to you, 'Instead of spending those 5 hours manually capturing expenses each month, why don't you try to automate it like this?'"Potential Solution: Use an app where you photograph receipts as they happ...