Sidecar Blog

Organizational Culture

An illustration of a sunlit greenhouse with thriving plants in one section and empty pots in another, representing the environment needed for growth.

5 min read

Why Your AI Culture Is Your Greatest Competitive Advantage

When association leaders discuss the future of artificial intelligence, the conversation almost inevitably turns to talent. The instinct is sound:...

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Sidecar Sync Episode episode 137 cover featuring Amith Nagarajan and Mallory Mejias

45 min read

The 4 Modes of Working with AI, The Transformation Paradox, & Building a Learning Organization | [Sidecar Sync Episode 137]

Summary: In this jam-packed “mini” episode, Amith Nagarajan and Mallory Mejias break down a whirlwind of recent AI model releases—from Anthropic,...

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Flat illustration of a tuning fork being struck near a wine glass, with visible vibrations rippling through the glass.

5 min read

Stop De-Weirding Your AI: Why Enterprise Logic Kills Innovation

This post draws on Wharton professor Ethan Mollick's recent article, "The IT department: Where AI goes to die," which we analyzed on a recent episode...

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digitalNow 2025 featuring a cartoon plane leaving a cartoon Chicago landscape

5 min read

The Deeper Questions digitalNow 2025 Is Really Asking

I'm sitting here on Day 3 of digitalNow 2025 in Chicago. Over the past few days, we've seen incredible sessions on implementation, infrastructure,...

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digitalNow banner featuring a robot

6 min read

What digitalNow 2025 Reveals About Where Associations Are With AI

Day 2 of digitalNow 2025 just wrapped in Chicago. Over the past two days, we've seen incredible sessions from association practitioners, AI experts,...

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Illustration of a traffic light with icons: a sparkling laptop in a green light, two people talking in a yellow light, and a padlock in a peach light, on a dark pole against a light background with subtle geometric shapes.

4 min read

Your AI Guidelines Should Be a Green Light, Not a Stop Sign

Most AI policies read like a list of don'ts. Don't share confidential data. Don't trust AI outputs. Don't use unapproved tools. Don't, don't, don't....

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Cartoon-style naval battle in fog: left ship fires multiple cannonballs, one glowing shot arcs across water and hits right ship, causing a peach-colored explosion.

4 min read

From Bullets to Cannonballs: Why Your Association's AI Experiments Aren't Scaling

Year one: Let's experiment with AI! Education staff use AI for course descriptions. The membership department uses AI to draft renewal emails.

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Photo of four business professionals in a modern lab interacting with labeled beakers representing AI, Disruption, and Transformation.

7 min read

The Thought Experiment Every Association Leader Should Try: Build a Competitor to Your Own Organization

Here's the reality: There's a version of your association that costs less to run, serves members faster, and delivers personalized value at scale....

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Overhead view of a business professional at a desk using a laptop, casting a robotic, circuit-patterned shadow symbolizing AI integration.

8 min read

The Leadership-Lab-Crowd Framework: A New Model for AI Transformation in Associations

Here's a frustrating reality: Your team members are quietly achieving 2-3x productivity gains with AI, cutting tasks that used to take hours down to...

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