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Hard Boiled Software is also a newsletter. Essays on product, engineering leadership, and organizational design, written for the person who has to make the call on Monday morning. Selected pieces get pulled on-site with their takeaways attached, like Oh, Estimates and Your Requirements Suck. The full written archive is below.

"AI Saved Us Time" Is Not Enough
Jun 10, 2026 by Jess Brock

The ROI lives in what happens next.

Rethinking Learning Design with AI
Mar 29, 2026 by Dave Laribee

The training workshop finally gets tools.

AI Is Going to Disrupt Jobs. Eventually.
Mar 9, 2026 by Jess Brock

Maybe it's more turtle than hare.

Documentation Needs a Feedback Loop
Jan 26, 2026 by Jess Brock

Checking documentation the moment code changes.

How a 7¢ LLM Experiment Rescued My Inbox
Jul 9, 2025 by Jess Brock

A powerful example of how people can level up with LLMs using pocket change

Better Results Together
Jun 24, 2025 by Dave Laribee

The AI stan’s rumors of teamwork’s death have been greatly exaggerated.

Busy is the New Stupid
Jun 8, 2025 by Dave Laribee

How perpetual urgency is sabotaging your most important work.

Engineers, Don’t Fear the Vibe
May 21, 2025 by Jess Brock

The best thing to happen to engineers—or the start of a slow erosion of the craft?

Vibe Coding and Learning Debt
Apr 15, 2025 by Dave Laribee

Vibing with AI might feel productive in the short term, but watch out for the long-term consequences of trading dopamine hits for deeper learning.

Community Updates & Events
Mar 6, 2025 by Dave Laribee

A coach, a programmer, and a product leader walk into a bar...

From Technical Debt to Technical Investment
Oct 17, 2024 by Dave Laribee

Our playbook for balancing product delivery with system quality.

Your Requirements Suck
Oct 9, 2024 by Dave Laribee

But crappy requirements probably aren’t the problem.

What Product-led Means to Engineering
Aug 21, 2024 by Anne Steiner

Exploring the differences between project- and product-based engineers.