Last week, I had the privilege of sitting down with Kristi Pihl, a former COO, a Northwestern-trained mechanical engineer, a two-decade strategic tech advisor, and one of the most clear-eyed thinkers I know on what AI actually is and is not. Her work earned a TIME Best Invention in AI in 2019 — and she has been building with this technology since 2017, long before most of us were paying attention.
In just under an hour, we covered something I have been thinking about ever since: AI isn’t exposing your organization’s weaknesses. It’s amplifying whatever was already there.
The great decisions get made faster. The poor ones do too. We talked about FOMO-driven boardrooms, the judgment-suppression risk no one is discussing, why the “point of decision” is the only unit of analysis that actually matters, and what it really means to lead with humanity in this moment.
Kristi also shared the personal story behind her pivot from two decades inside the machine to writing, teaching, and angel investing — and why she thinks the next generation of truly exceptional leaders will be the ones who can hold both their quant brain and their human one at the same time.
If you missed it live, here’s your guide to the conversation:
Timestamped Guide
0:00 Welcome and introductions
3:00 The central thesis: AI as a mirror, not a tool
5:00 AI as amplifier and accelerant — going faster in the wrong direction
7:00 The judgment-suppression risk and what it means for succession planning
10:00 What Kristi sees inside organizations right now: FOMO, board pressure, and the performance narrative
14:00 Why acting from fear almost never produces good strategy
15:00 AI as a path back to our humanity — the unexpected case for reconnection
19:00 OpenAI as a case study: when the “point of decision” goes wrong
21:00 Why judgment alone isn’t enough — and what the actual base unit of strategy is
25:00 The three intelligences: human, algorithmic, and artificial — and how to lead across all three
29:00 The limits of quant leadership and what AI is forcing us to reckon with
34:00 The next generation of exceptional leaders: holding the quant brain and the human one together
38:00 How to cut through the noise: slowing down as a competitive advantage
40:00 Kristi’s “humanity checker” and the case for trusted, low-stakes voices
42:00 The return of third places — and why shrinking your world might be the wisest move you make
47:00 Kristi’s career pivot: from the inside of the machine to writing, teaching, and investing
51:00 Why she’s considering teaching AP Physics and AP Calc to high schoolers
53:00 Angel investing, women founders, and seeing problems differently
57:00 What Gen Z already knows about AI — and the wisdom in their skepticism
58:00 Where to find Kristi: Systems and Spines on Substack and LinkedIn
Stay in touch with Kristi Pihl through her Substack: Systems and Spines and on LinkedIn.
