For years, I would reflect on my week on a long walk. What went well, how I could do better, what I missed. That quiet time has always given me clarity and focus.
Recently, I started bringing in AI into this practice and it has been more targeted and effective. So, sharing it here.
Recently, I pointed Claude at 18 months of my own Slack and email, January 2025 to June 2026, and asked it one thing: rank me, message by message, across all my written work against the top 10 Amazon’s leadership principles, and show me where my next growth is.
The setup was simple. I have already connected Slack and Gmail with my Claude. So, I had Claude sweep a month at a time for the past 18 months of all my communications and documents I have created. Reading that much history is the expensive part, so I had it read each month once and tag every message against all the key Amazon’s leadership principles in the same pass, instead of reading the same history 10 times looking for one principle at a time. It came back with nearly 900 dated examples, each linked to the original thread so I could open it and check the claim myself.
I got a ranked map of my own work. My strongest evidence clustered in the principles I can act on alone: diving deep, owning an outcome, delivering the result, moving before I have permission. My clearest growth opportunity sat in the principles that only show up when you lead through other people. That is not something memory would have told me. It came straight out of my own record, with the dates attached.
So I turned the read into one habit change. I keep a running note on who I am actively developing for each week as I can evaluate myself against the evidence.
This works because the input is mine and it is specific. Every ranking sits on a real thread with a date, so I cannot argue with it and I cannot inflate it. A reflection built from memory is a story I could be telling about myself, but this collected evidence by a pool of agents is the real evidence.
I am running the sweep again in three months to re-evaluate myself. I am personally ok with using AI to analyze my everyday work and let it act as the mirror for you to reflect on. I use this approach to surface the blind spots that I would never catch from memory.
Have you tried using AI for self-reflection and self-improvement? What did you learn?