Sidecar Team

An open padlock sitting next to interchangeable gears on a workbench.

5 min read

The AMS Fallacy: Why Buying AI is Nothing Like Buying Association Software

The process of buying an association management system is a familiar ritual. It begins with a massive request for proposals. Committees form to evaluate features, debate technical requirements, and sit through endless vendor demonstrations. The...

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An editorial illustration of a vast library archive with a highlighted pathway leading to a specific section of rare books.

5 min read

The Thomson Reuters lesson: Why Your Niche Data is Your AI Moat

Imagine a real estate professional looking for highly specific, county-level zoning regulations from two decades ago. They open a generic AI model...

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Hands covered in wet clay shaping a spinning pot on a wheel.

5 min read

The Fluency Trap: Why AI Training Fails Without 'Immersion'

Anyone who has spent four years studying a language in high school knows the exact feeling of landing in a foreign country and realizing they cannot...

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Hands using a drafting compass and pencil to draw an organizational chart with wooden blocks on drafting paper.

5 min read

The Pfizer Playbook: 3 Non-Technical Moves to Transform Your Association

Association leaders often approach new technology with a familiar playbook. They form a committee, draft a comprehensive request for proposals, hire...

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A single beam of sunlight illuminates an open ledger in a dusty archive room.

5 min read

The Spirit Airlines Lesson: How Associations Can Monetize Hidden Data

When a company goes bankrupt, its physical assets are typically the first things auctioned off to pay creditors. When budget carrier Spirit Airlines...

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A luthier adjusting the tuning peg on a wooden cello in a workshop.

5 min read

Beyond the Stochastic Parrot: Tuning AI for Original Association Research

A persistent critique of artificial intelligence is that the technology is nothing more than a sophisticated autocomplete. Critics often refer to...

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A magnifying glass focused on a ledger while a red bird sits unnoticed on the handle

5 min read

The Gorilla in the Room: How AI Cures the Association Multitasking Myth

There is a famous psychology experiment involving a video of a basketball court. Viewers are asked to watch the players moving around and count the...

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6 min read

You Are Using AI Through a Keyhole

There is a conversation that repeats itself constantly with association staff who use AI every day. They describe themselves as heavy users, and by...

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Three colorful engine blocks connect by dotted lines to the same vehicle chassis slot.

4 min read

You Can't Predict Who Leads AI in Three Months. Build Accordingly.

Consider where things stood in the middle of 2024. If your association was trying to do something serious with AI, the decision was close to...

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