Posts - Convictional

Are We Pigeons?

by Aryan Gupta · May 21, 2026

On humanity, the role of humanity, and why being human first is important for companies in the future.

The Power of Knowledge Bundles: Just-in-Time Compression for Better AI Deep Research

by Matt Chequers · May 6, 2026

I ran an experiment to see if 'knowledge bundles' assembled on-the-fly could replace pre-computed knowledge graphs. Here is why this dynamic approach beat our baseline, and how smaller models kept the costs in check.

Souls Only

by Bill Tarbell · May 4, 2026

On the value of human-authored communication in an AI-saturated world, and why companies need new ways to signal that the words came from a person, not an AI model.

Aligning Motives and Goals

by Roger Kirkness · Apr 30, 2026

Explores the difference between motives and goals and their relationship to AI agent alignment.

Decision Struggle

by Roger Kirkness · Apr 7, 2026

An essay that discusses the notion that in order for groups to preserve knowledge, they must struggle with decisions and record that struggle somewhere widely accessible.

Why 'Searching' Can't Solve Business Complexity: Common Search vs. High Entropy

by Matt Chequers · Jan 29, 2026

I ran an experiment to see if scoping our AI search to specific topics would improve accuracy, and it performed worse than doing nothing. Here is why 'High Entropy' data breaks standard search engines and why we had to build a community graph to fix it.

Delegation Loops

by Bill Tarbell · Dec 2, 2025

AI has made it effortless to generate work. The real challenge now is applying judgment. Delegation Loops is an operating technique that has leaders delegating work, assignees surfacing work quickly and leaders evaluating quality in a rapid cycle.

The Ethosystem: What your company wants may soon be what matters most

by Bill Tarbell · Nov 19, 2025

As AI agents master execution, your company's ethosystem becomes your only defensible advantage. The collection of judgment, taste, and values living in your people is what sets you apart.

The Cognitive Cost of Constant Connection

by Adam McCabe · Oct 23, 2025

Research-based exploration of how Slack and real-time communication platforms fragment attention through network effects and constant context switching.

Launching Collaborative Email

by Roger Kirkness · Oct 15, 2025

Announcing Convictional's collaborative email product that addresses the erosion of workplace communication caused by chat tools and AI spam. We're building tools that restore email as an effective collaboration platform while solving goal alignment within organizations.

Vibe Marketing

by Bill Tarbell · Aug 6, 2025

How we migrated from Webflow to a Claude Code-powered static site, enabling rapid development and empowering our marketing team with developer tools

Founder Mode: Reviewing and recruiting

by Roger Kirkness · Aug 5, 2025

Exploring how founders can scale their impact through two key activities: review and recruit. While extroverted founders like Brian Chesky use extensive meetings, introverted founders can achieve similar results through mastery of email communication and written updates.

How I Do Email

by Roger Kirkness · Jul 11, 2025

A comprehensive guide to using email as a productivity system, covering inbox management, task prioritization, and strategic email workflows for handling 150-200 emails daily.

Bridging the Data-Decision Gap

by Adam McCabe, Matt Chequers, Jake Beresford · Jul 7, 2025

Our journey from naive natural language to SQL targeted at business users to our current production implementation using semantic layers and MCP tooling.

The Human-AI Workforce: How Trust and AI Capability Could Reshape Our Teams

by Adam McCabe · Jul 4, 2025

A mathematical model exploring how trust in AI and capability factors could transform workforce composition, with interactive visualizations showing potential evolution paths.

From Transcripts to Decisions: A Research Project in Applied AI

by Matt Chequers · Jul 1, 2025

Explore a technical applied AI research project at Convictional focusing on extracting structured decisions from meeting transcripts, including insights on decomposing complex tasks and the importance of data representation.

Why Convictional implemented four day work weeks

by Roger Kirkness · Jul 1, 2025

How AI's evolution and its impact on work led to implementing a permanent four-day work week at Convictional to maximize team productivity and adapt to AI-driven changes.

Leading Machines, Not People

by Ben Crouse · Jun 30, 2025

As software engineers become tech leads of coding agents, discover the essential skills for guiding AI: communication, architecture, context management, review, and project management.

From Organized Anarchy to Judgment: The Garbage Can Model and the Future of Decision Making

by Bill Tarbell · May 7, 2025

How the classic organizational theory model helps explain modern decision-making challenges and points toward solutions.

Strategic Board Meeting Preparation for CEOs

by Becca Crandall · Apr 25, 2025

Transform board meeting preparation from time-consuming information gathering to strategic insight delivery using Convictional's AI-powered context synthesis and narrative building.

Weekly Team Updates Can Help Solve the Decision Context Problem

by Bill Tarbell · Apr 8, 2025

Discover how implementing weekly team updates in Convictional helps solve the Decision Context Problem by breaking down silos, capturing tacit knowledge, and maintaining organizational alignment as companies scale.

The Decision Context Problem: Why Company Performance Suffers Despite Your Best Efforts

by Bill Tarbell · Mar 14, 2025

Discover why companies lose millions annually to the Decision Context Problem—when teams lack crucial business context, clear alignment with goals, and effective decision-making processes.

Culture Shift: How AI Maturity Requires Workplace Culture Transformation

by Bill Tarbell · Mar 11, 2025

As organizations advance through AI maturity levels, workplace culture must transform from valuing execution to prioritizing judgment, transparency, and authenticity. Explore how AI adoption fundamentally changes what creates value in modern organizations.

AI-Powered Customer Development

by Bill Tarbell · Mar 6, 2025

A comprehensive guide to modern customer development using AI to enhance problem validation, solution testing, and product iteration. Learn how to leverage AI tools while maintaining human judgment in building products customers actually want.

The Future of Leadership: Why AI is Your Competitive Edge, Not Your Replacement

by Jake Beresford · Feb 14, 2025

Learn from Kasparov's Centaur Chess how AI enhances rather than replaces human leadership, combining machine precision with human creativity for superior business decision-making.

Rethinking Leadership Offsites: Why Decision Making Shouldn't Be the Focus

by Bill Tarbell · Feb 6, 2025

Learn why traditional leadership offsites fail at decision-making and discover a better approach that leverages asynchronous work, AI tools, and face-to-face time for building trust and strategic thinking.

Convictional in the Age of AI Agents

by Adam McCabe · Jan 16, 2025

As AI agents prepare to join the workforce, organizations need new infrastructure for human-AI collaboration. Learn how Convictional maintains human judgment at the center while leveraging AI to accelerate knowledge work and ensure alignment with organizational goals.

Engineering Time Reclaimed: Automating R&D Documentation with AI

by Matt Chequers · Dec 20, 2024

How Convictional transformed a multi-week R&D tax credit documentation process into an automated AI pipeline, saving engineering time while improving documentation quality. A practical case study on using LLMs to extract and organize technical knowledge from Github repositories.

Context Entropy

by Adam McCabe · Dec 12, 2024

An in-depth analysis of how business knowledge distributes across documents, based on 3,200+ entities from real organizations. Discover why 95% of entities need only 5-6 documents for complete context and when to choose RAG vs. entity pre-processing for your knowledge systems.

Context is a Fluid: Permissions in an AI World

by Roger Kirkness · Nov 26, 2024

Why traditional document-based permissions fail in the age of AI and how context-aware permissions can balance security with intelligence. Learn how organizations must evolve from binary to probabilistic access control to harness AI's full potential.

Quantum Business Planning: Understanding Direct Effects

by Roger Kirkness · Nov 19, 2024

Explore how AI enables quantum business planning by predicting all direct effects of decisions, allowing companies to maintain multiple planning scenarios and make faster, more confident choices.

Business Decisions About the Coming Tariff Changes

by Bill Tarbell · Nov 13, 2024

A practical guide for businesses facing 20-60% tariff increases on foreign goods. Learn how to assess impact, evaluate mitigation strategies, and make coordinated decisions across pricing, suppliers, products, and operations to navigate major supply chain disruptions.