The AI Workweek

Chapter 3 Identifying Automation Opportunities

When I first started automating my workflow, I made the same mistake almost everyone makes. I chased the big, flashy wins first. I thought the bigger the automation, the bigger the payoff. I wanted the kind of thing I could show off in a meeting and have people say, “Wow, how did you do that?” Those game-changing projects eventually paid off. But they also took weeks of setup, testing, and tweaking. Some stalled halfway because urgent work pulled me in another direction. More than once, I looked at an unfinished automation and realized it had been sitting untouched for months.

Automation is not about starting with the biggest thing you can find or picking off the easiest task just to check a box. It is about balance. You need wins that show up fast enough to prove to yourself and sometimes to your team that this actually works, and you need longer-term projects that have the potential to fundamentally change how you operate day to day. Without those quick wins, the motivation to keep going fizzles out before you ever get to the good stuff. Without the bigger projects that take more time and thought, you will never move past surface-level improvements that look nice but do not really change anything.

I started thinking of it like building a portfolio. Quick wins were the cash flow—they paid off immediately, kept me moving, and built trust in the process. Game changers were the long-term investments—slower to mature but capable of ...