Prayerson's Newsletter & Podcast

why ai tools feel exhausting to use

listen now | how to design ai products that reduce friction and actually fit into real-world workflows

Apr 12 • Prayerson

52:40

workflow integration in ai products: designing ai systems for real user workflows

designing ai systems that align with real-world workflows, reduce friction, and improve reliability through task-level integration

Apr 12 • Prayerson

March 2026

how to track success in ai products

listen now | how to measure success in ai products beyond accuracy, speed, and model performance

Mar 30 • Prayerson

36:58

ai product metrics for product managers: measuring success in probabilistic systems

measuring uncertainty, user effort, and workflow outcomes in ai systems

Mar 29 • Prayerson

why ai products fail even when the code works?

listen now | the product design challenge of probabilistic software

Mar 16 • Prayerson

1

46:08

ai product design for product managers: designing around probabilistic software

a structured guide to designing reliable products with probabilistic ai systems

Mar 16 • Prayerson

February 2026

when is an ai feature ready to launch?

listen now | a product manager’s guide to ai reliability, guardrails, and continuous evaluation

Feb 28 • Prayerson

34:06

how to evaluate ai products: a reliability framework for product managers

the decision model for shipping, monitoring, and trusting ai features in production

Feb 28 • Prayerson

1

ai product reliability: a guide for product managers

understanding probabilistic software, evaluation, and trust when designing and shipping llm products

Feb 14 • Prayerson

ai evals for product managers

listen now | why reliable ai products require testing, monitoring, and guardrails beyond prompts

Feb 8 • Prayerson

34:17

ai evals are becoming the most important layer in ai products

how evaluation determines reliability, trust, and user adoption in ai software

Feb 8 • Prayerson

1

January 2026

how i built ask lenny in a weekend

designing a grounded ai research assistant with mcp, retrieval, and lenny's podcast transcripts

Jan 26 • Prayerson

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