Leadership in Tech
Leadership in Tech
#352 – October 04, 2026
under uncertainty decisions require better sensemaking before choosing between options
How can I make better decisions when facing uncertainty?
17 minutes by Andi Roberts
Better decisions under uncertainty require better sensemaking before choosing between options. Three trialectics from Dave Snowden's work help leaders examine what they notice, what they know, and how they reason: salience, sapience and sentience; explicit, tacit and entangled knowledge; and deduction, induction and abduction. The aim is not to eliminate uncertainty before acting. It is to see more, assume less, act to learn and adapt to what you discover.
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Working with AI feels more like leadership than coding
2 minutes by Allen Bargi
AI is less predictable than traditional software. The same request can produce different results, which makes sharing context and intent more important than writing perfect prompts. Working well with AI looks less like issuing commands and more like leading a conversation. The skills needed are not new, but they matter more now.
The sea squirt problem
9 minutes by Mike Fisher
Young sea squirts navigate the ocean with a full nervous system, then dissolve most of it once they find a rock to attach to permanently. Organizations do the same thing after finding success, quietly cutting the customer research, frontline relationships, and market sensing that got them there because those things now look like overhead. Circuit City literally fired its most experienced salespeople to save money, then went blind to its customers and collapsed within two years. Protect your perception apparatus most aggressively when you feel safest, because that is exactly when you are most likely to dismantle it.
Tension-based prioritization
11 minutes by John Cutler
Most prioritization work is about building agreeable stories, not making real decisions. The actual signal lives in recurring tensions: the threats everyone sees but nobody acts on, the comfortable work that quietly crowds out harder bets, the projects stuck in limbo for months. A simple fill-in-the-blank exercise helps teams name these patterns out loud, so the real decisions finally surface before another framework meeting buries them again.
Playbook to manage up
13 minutes by Danielle Matarasso
Good work often goes unnoticed because nobody tracks it for you. A simple rhythm of short, regular updates sent to the right people fixes that. Danielle shares five moves to cover it: audit what you did, send a summary up, prep meetings with a short note, recap what got decided, and send an agenda the day before your check-ins. AI writes most of it in minutes.
And the most popular article from the last issue was: