Sidecar Blog

Organizational Culture

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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Sidecar Sync podcast hosts wearing pirate hats, sitting in a cartoon rowboat under the title 'AI Knowledge for Associations'.

39 min read

Navigating AI Seas: Leadership, Lab, and Crowd | [Sidecar Sync Episode 89]

Summary: In this episode, Amith Nagarajan and Mallory Mejias dive into the world of AI agents, hackathons, and the secret cyborgs in your office....

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Smiling parking officer gives thumbs up while placing a 'GREAT PARKING JOB!' note on a car windshield.

5 min read

Building a Culture of 'Catching People Doing Things Right' in Your Association

The concept of "catching people doing things right" was introduced to us by John Spence in Episode 88 of the Sidecar Sync podcast. According to...

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2 min read

The AI Generation Gap: Strategies for Bridging the Divide in Your Association's Workforce

As AI rapidly transforms the workplace, a concerning trend has recently caught attention: a significant generational divide in AI adoption. As...

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