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OP #323: The Hard Part of AI Isn't the Technology

OP #323: The Hard Part of AI Isn't the Technology

Change management, W&W, and why your 65-person team isn't ready

Darren Herman
April 14, 2026

Happy Tuesday, OP Community.

I'm writing the majority of this OP in Manchester, CT, between dances at my daughter's dance competition (Turn It Up Dance Challenge). If any of you are dance moms or dads, you know there is plenty of downtime at these events. One bonus of attending these competitions: I always come home with a new song or two for the playlist. The winner of this event in my eyes was a small group dance set to one of the main songs from Sinners. They won the crowd over. Phenomenal execution.

On to watches: this week is the Super Bowl of the watch world, known as Watches & Wonders. It takes place in Geneva, Switzerland, and is both a B2B and B2C show. I'm not there, but I'll absolutely be following along. There were a ton of predictions circulating ahead of the show and I've compiled many of them here. My call: a complication gets added to the Rolex 1908. We shall see.

Excitement is building for our May 18th Flagship event for Silicon Alley Sports. I put a couple more pickleball tickets up for sale, but golf is beyond sold out at this point. If any of you want to come as Schmoozers (skip the play, enjoy the food, networking, and festivities in the afternoon), let me know or sign up here. We recently announced our 2026 Impact Partner: Sandy Hook Promise, our 2025 partner as well. We look forward to welcoming them back.

Here are a few links to get us started this week...

Rolex Certified Pre-Owned: The Quiet Revolution Transforming the Pre-Owned Watch Market (Revolution Watch)
Universal Genève Is Back! Introducing Four Collections, With The Famous Polerouter Leading The Way (Fratello Watches)
Enamel 101 (Hairspring)
The Solo Founder's Playbook: Building a Startup Alone in 2026 (Entrepreneur Loop (Substack))
I Went Shopping For Grey & Secondary Market Watch Deals (This Watch, That Watch)

I hope you enjoy the OP. I had a ton of fun writing this one and am pulling from some recent experiences.

Be well, do good.
Darren

When It Comes to AI for Enterprises, Technology Isn't the Barrier... Change Management Is

I've been spending a lot of time on AI strategy and execution for enterprises, specifically how they're rethinking their marketing, digital, and commerce layers. My enterprises are middle-market companies, usually in the mid-to-high hundreds of employees, if not thousands. These companies have existed for at least a decade, and for many of them, several decades. Most were not born modern.

If you're at a born-modern company, a native AI startup, or something similar, this may feel irrelevant. For everyone else, here's what I've found.

AI adoption is not primarily about the frontier model, the interface, or anything technology-related. It will rise or fall on organizational change management. I'm seeing this play out over and over again, and hearing it directly from the front lines.

Let's work through it.

You run a 65-person marketing team. This team has defined processes, culture, and ways of working embedded over years. A technological revolution has arrived, and we're expecting teams to change how they work overnight. That means rethinking existing processes, adding agents to augment humans, and orchestrating a layer that may not exist yet in the enterprise.

It's easy to assume this lives or dies with the technology you choose. Technology matters, and choosing correctly is important. But it can always be course-corrected (at a price) later.

What I can guarantee: your 65-person team is not going to adopt your AI vision without a change management plan.

Humans are starting to fear for their jobs. Humans are uncomfortable with new technologies. Most humans aren't visionary and cannot see the future. Humans gravitate toward comfort, and doing what we did yesterday is easy to carry into today.

These are the truths we need to break through. You need to ready your organization to embrace this moment. Not push back on it.

How? Let's take them one by one.

Humans are starting to fear for their jobs.

Change the frame. AI isn't here to replace jobs. It's here to build a 100x Marketing Department by making 10x marketers. Embraced, AI gives everyone superpowers.

Humans are uncomfortable with new technologies. Most humans aren't visionary and cannot see the future.

I'm bundling these. Remember when the Internet emerged in the 90s? Everyone had access to build websites and apps. Very few did. The ones who did went on to become web architects, Chief Digital Officers, and similar roles. They saw the future and participated in building it. Most people didn't. They used the web. They just didn't build it.

I expect the same thing to happen with AI. Not everyone needs to build with AI. Most people aren't visionary, and they're uncomfortable with new technologies. That's OK. It's how the world works. We shouldn't expect everyone on the team to be writing new prompts or vibe coding in the evenings. What we should expect: they don't resist applying AI to their workstreams, once they've had the right training.

Humans gravitate toward comfort, and doing what we did yesterday is easy to carry into today.

We like our routines. AI is going to rewrite many of them, and we have to be OK with that. Here's my hot take: the best AI will fit into our lives and force us to change less. We adopt things that minimize disruption. Comfort is the adoption curve.

So: do you have a change management plan for your organization? How are you going to lead from the front and make everyone comfortably uncomfortable?

Lots of questions. We're all figuring this out at the same time. One thing I've found useful: bringing a talent management professional into these conversations early. There are organizational development tools they know well that translate directly to this problem.

If you're still not sure what this looks like in practice, watch these two videos, then ask yourself how you get your team to actually adopt this.

The Hiring System Is Broken. A Reader Built a Fix.

An OP community member reached out after a recent edition, and what he's built stopped me in my tracks. His name is Dave, and his project is called Nepworking.

The premise is simple and the problem is real: the hiring system is broken at both ends. Job seekers are sending hundreds of applications into a void, getting screened by bots, and ghosted. Companies are drowning in AI-optimized resumes and reverting to hiring through personal connections, which is a terrible outcome for everyone who doesn't already have the right network. If you aren’t familiar with this, read this timely article from Bloomberg.

So he did what any good operator does when they see a broken system... he wrote the playbook. A website, a free downloadable guide, and a chatbot tuned as a virtual career counselor that actually pushes back when you ask it to do the work for you.

As a dad of two teenagers who aren't far from the job market, I felt this one in my chest. Check it out at nepworking.com, take the survey if you have a minute, and share it with anyone who's navigating this mess.