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Lessons From
Building With AI
Volume Two / WIP
Cris Pierry
Work in progress / Volume two
Snapshot through July 16, 2026
A work-in-progress collection about trustworthy systems, product leadership, discovery, and the craft of making AI-assisted work reviewable.
By Cristiano Pierry
Introduction
The first volume collected the writing that helped me understand a basic shift: AI moves more of the work toward judgment. This second volume begins where that collection stopped. It brings together the revised articles and substantial notes that were not part of the original book.
These chapters are not here because they were leftovers. Most were written later, after more of the practical questions had become visible. How do you make AI-assisted work reviewable? What should survive when a tool changes? Where should a model reason, and where should a deterministic system constrain it? What happens to the shape of a product team when more people can build?
The common thread is trust. Speed matters, but speed without evidence, continuity, or a clear owner creates fragile work. A useful system has to carry its reasoning forward. A useful artifact has to make review possible. A useful product has to translate intent without hiding the machinery that protects the user.
Read the full introduction →Contents
This draft uses the revised text while preserving each original publication date and source link. Page references are estimates for this web edition.
Part 1
AI-assisted work earns trust through evidence, evaluation, continuity, performance, and explicit human control.
Note / 01
Jun 18, 2026
p. 2
Article / 02
Jun 21, 2026
pp. 3-5
Article / 03
Jun 22, 2026
pp. 6-9
Article / 04
Jul 8, 2026
pp. 10-11
Note / 05
Jul 11, 2026
pp. 12-13
Article / 06
Jul 12, 2026
pp. 14-17
Article / 07
Jul 13, 2026
pp. 18-23
Part 2
AI changes the shape of product work, but leadership still sets the quality bar, removes friction, and owns the outcome.
Article / 01
Apr 3, 2026
pp. 24-26
Note / 02
May 1, 2026
p. 27
Article / 03
Jun 25, 2026
pp. 28-33
Article / 04
Jun 29, 2026
pp. 34-35
Article / 05
Jul 3, 2026
pp. 36-39
Part 3
Recommendation systems and AI products become stronger when they translate intent without obscuring constraints or accountability.
Article / 01
Jul 1, 2026
pp. 40-43
Article / 02
Jul 7, 2026
pp. 44-48
Article / 03
Jul 10, 2026
pp. 49-50
Article / 04
Jul 14, 2026
pp. 51-56
Part 4
Photography shows how software changes tools while leaving judgment, technique, and purposeful use in human hands.
Back matter
Alphabetical chapter index with estimated page references across 65 web-edition pages.
Copyright © 2026 Cristiano Pierry. All rights reserved. Web edition snapshot through July 16, 2026. Work-in-progress draft.
This writing reflects my personal perspectives on product management, AI, and content discovery. It does not represent the official position of my employer or any affiliated organization.