Sidecar Team

A vintage brass key resting on a stack of leather ledgers on a wooden desk.

6 min read

The 'Brain in a Jar' Problem: 4 Steps to Turn AI into a Worker

You open a browser tab, type a question into a chat interface, and watch as a highly sophisticated response appears on your screen in seconds. The output is impressive. It might be a draft of a member renewal email, an outline for your upcoming...

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A mechanic carefully tightening a bolt on an older piece of machinery.

5 min read

The 'Computer Use' Breakthrough: Connecting AI Agents to Legacy Tech

Walk into any association board room and mention artificial intelligence, and you will likely hear the same heavy sigh. The consensus is usually that...

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A wooden workbench with high-quality hand tools and a partially built chair.

5 min read

Stop Chasing the AI Frontier: Why You Should 'Squeeze the Lemon' of Current Models

Every week brings a headline about a new artificial intelligence breakthrough. A major lab releases a model that shatters previous benchmarks. A day...

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Illustration of a bookbinder hand-stitching a leather book at a wooden workbench.

5 min read

The Waymo Effect: What Happens When AI Outpaces Your Members' Skills?

Imagine opening the door to a taxi, sliding into the back seat, and finding the driver's seat completely empty. For a moment, the absence of a human...

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A vintage brass mail-sorting scale balancing a single envelope and a metal counterweight.

5 min read

System 1 vs. System 2 AI: Why Your Association Needs a Decision Model

Look at any standard process documentation in your association. You will likely see a flowchart made of two primary shapes. Rectangles represent...

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3 min read

Three Minutes a Day: A Better Way to Build Staff AI Skills

On a recent episode of the Leading Learning podcast, JD Dillon made a point that should land hard with anyone planning AI training for an association...

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Illustration of multiple train tracks merging into a single line inside a sunlit concourse.

5 min read

Why Your Association Needs a Product Leader, Not a Technical CTO

When membership organizations decide to modernize their technology, the immediate instinct is to look for technical talent. The assumption is that...

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Illustration of a woodworker shaping a single strong beam while ignoring a pile of disjointed scrap wood.

5 min read

The End of the IT Committee: How to Ship AI Projects Like Tech Firms

The traditional association technology committee is designed to be a safety mechanism. It might bring together representatives from membership,...

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A roll of duct tape sitting on top of architectural blueprints on a workbench.

4 min read

The Vibe Coding Trap: Why AI Apps Need Architecture, Not Duct Tape

Imagine discovering a leaking pipe in the garage. A quick fix is to grab a roll of duct tape and wrap the pipe tightly. The water stops. The floor...

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