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Day 9: A One-Year Review With AI — and Eight Hard Questions

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Tomorrow is exactly one year. So I did a proper review of it — and I asked my AI assistant to help.

A real one-year review has two halves. The outside view: what the year visibly produced. And the inside view: what it cost you, what changed in you, what you avoided.

AI can sketch the first half in seconds. Only you can supply the second.

So here's what I did. First, I had it summarize what it already knew about my year from our daily work. (No AI habit? Paste in your project list or calendar highlights — same effect.) Then it walked me through eight questions. Not "what are my strengths" questions. Questions like: What was I still doing in July that I shouldn't have been — and was it trust, speed, or identity holding me back?

The one that stopped me was the last: what did I believe a year ago that I no longer believe?

My answer: Empathic leadership isn't about being nice. It's about owning respect and being clear.

All eight questions are in the carousel above if you want to use them.

The result? It was more than satisfying. After AI got my answers, it correctly did the assessment of different dimensions and gave ratings, showed what went well, and even where I have to work in priority order. It surprisingly knows me very well!!

Try it and tell me how it works for you.


This is part of my "100 Days of Year One" series. Follow along as I share what I've learned in my first year as Head of Data and Cloud.