Off the Record, On the Mark: Why We Need More Honest Conversations About Generative AI

I’ve spent considerable time behind the scenes preparing for these events—especially when law firms are involved. The redaction process is real. And honestly, it makes sense. When you’re speaking publicly or being recorded for eternity, caution is only natural.

But that caution creates a dynamic that feels more like a job interview than a learning opportunity. Even the “challenges” are carefully reframed—because in a high-stakes setting, it feels safer to keep things vague.
“One of our biggest hurdles was change management… but we managed to get everyone on board with training and communication.”

The result? Stories that sound polished but often skip the messy middle—the part where real learning lives.

Meanwhile, 88% of generative AI pilots fail to reach production (CIO), and innovation leadership roles are turning over fast, with 32% holding on to these positions for more than 3 years (LinkedIn). Clearly, something’s off—and we need to talk about it.

Have you noticed that the best insights at conferences don’t happen on stage? They happen in the hallway. Over coffee. During the walk to the next session.

It’s in these unscripted moments that people get real—sharing what didn’t work, what surprised them, and where they’re still struggling. That’s where the learning happens.

To bring more of that honesty into the open, we’re launching small-group Generative AI roundtables—intimate sessions where candid conversations can thrive.

No recordings. No posturing. Just real talk about:

• What fell flat
• What no one saw coming
• What success looks like (spoiler: it’s messy)
• What to never do
• What is worth trying

These roundtables are designed for those in the trenches—trying, testing, and figuring it out as they go. In other words: people like you.