I bought the binder anyway

What a binder I never used taught me about meeting people where they are, and why it matters for AI transformation

I’ve spent over 25 years in digital operations and change management, and I’ll be the first to admit: I roll my eyes at slide culture as much as anyone.

So, you can imagine my surprise when I realized that the most important communication lesson I’ve learned in years didn’t come from a leadership framework, an organizational behavior study or an AI implementation post-mortem. It came from a comedian talking about making little booklets for her kid.

The Booklet Principle

A few years ago, I heard Jessi Klein (comedian, author, fellow Vassar alum) talk about a technique one of her son’s teachers had suggested: making small, illustrated booklets to help him process complicated things like doctor visits, changing routines and even big life shifts. The booklets didn’t just explain the what — they met him where he was, in the format that worked for his brain.

I remember thinking: this is PowerPoint for kids. And then, almost immediately: we do this every single day in business and almost never in our personal lives.

That realization has quietly reshaped how I think about change enablement in the context of AI transformation. Because the challenge we face as organizations adopt AI isn’t primarily a technology challenge. It’s a people challenge. And people, whether they’re six years old processing a new routine or a senior leader processing a new operating model, need to be met where they are.

The Uncomfortable Confession

I’ll just say it: I once made a slide deck to explain something to my boyfriend.

We’d had the same conversation multiple times. He genuinely cared and was trying to pick up what I was putting down, but something fundamental wasn’t landing. Then I remembered that he’d mentioned being a visual learner. So I made a few simple visuals, sat him down and walked through them.

Jokes were made and he was probably concerned I’d book a conference room for our next date, but he got it in a way that weeks of conversation hadn’t achieved.

The change leaders I most respect right now are the ones who are building genuine curiosity about individuals into their enablement approaches and not just segmenting by role or seniority or function.

What struck me most wasn’t that it worked. It was what the process of making it taught me. Translating an emotional, complicated thing into a visual format forced me to clarify my own thinking. To consider his perspective. To be precise about what I actually wanted him to understand. The medium changed the message and changed how I understood it too.

This is exactly what good change enablement requires.

The Harder Story

The personal lesson deepened in ways I didn’t expect, and in circumstances that were far less lighthearted.

My father, who passed a few months ago, had auditory processing challenges that had worsened over the years. He was a successful corporate litigator — sharp, confident, commanding in a room — but in conversation, especially as he aged, he was often not tracking what people were saying. I knew this for years and mostly compensated for it instinctively, without ever really naming it or adjusting systematically.

After his first spinal surgery left him with unexpected paralysis in both arms, the stakes of communication became acute. Doctors and family explained his situation to him dozens of times over the first several days. My mother once explained it to him every ten minutes for over an hour. He could not absorb it. He grew agitated, then despondent. It was only when I wrote it all out — in a simple, linear written explanation — that he understood. He read it once and the fog lifted.

A few months later, I tried to explain to him why he was running out of Google storage. I explained it to him 4-5 times, in person, with both of us laughing through his persistent confusion. I finally grabbed a pen and paper and drew it. Problem immediately solved. We made a pact: when he was confused about something, we’d write or draw it. Every time.

When he fell in January and spent nearly two weeks in the hospital, in and out of consciousness following complications from pain medication and multiple surgeries, I coped the way I always do — by distracting myself with something productive. I made a visual narrative: where he was, what had happened, the key decision points, the reasons behind them. I printed it and planned to put it in a binder with plastic sleeves so he could hold it easily. I was going to stop for supplies the next day.

But that day, the situation changed. I never got to show it to him.

But I bought the binder anyway.

What This Has to Do with AI

Everything, actually.

We are in the middle of one of the most significant workplace transformations most organizations have ever navigated. As I have acknowledged in previous posts, AI isn’t a feature update or a platform migration — it’s a fundamental shift in how work gets done, how decisions get made, and how people understand their own value and role. The change management and enablement demands are enormous.

And yet, in so many organizations, the playbook looks like this: send an email, run a training, post a FAQ, hold a town hall. Use the same standard approach (the one that requires the least energy) and hope it lands.

That won’t work for everyone and maybe not even for most people.

Because the people we’re trying to reach are not a monolith. They are individuals with distinct ways of processing information, different relationships to ambiguity, different fears about what AI means for them personally. A senior leader who processes best in narrative conversation needs something different than an analyst who wants a structured framework, who needs something different than a frontline worker whose first question is simply: will I still have a job?

Meeting people where they are is not a soft skill sidebar to the “real” work of AI transformation. It is the work. The technology will do what it does. The question is whether the humans around it can absorb, adapt and ultimately shape how it gets used. Will we be able to reconcile the pace of these changes with variables of the “human equation?” (A favorite phrase of my Dad’s when he was imparting life lessons!)

Curiosity Is the Core Competency

What the booklets and the binder and the boyfriend’s slide deck all have in common is this: they required someone to stop and actually ask, how does this particular person take in information? What do they need in order to understand? What’s getting in the way?

That’s not a question we ask often enough. In organizations moving fast on AI, it’s almost never asked.

The change leaders I most respect right now are the ones who are building genuine curiosity about individuals into their enablement approaches and not just segmenting by role or seniority or function. They are asking the kind of questions that reveal how someone actually processes change, what makes them feel seen versus steamrolled, what would help them feel genuinely capable rather than just compliant.

We tend to make things more complicated than they need to be before we land on something that actually works. The elegant solution is almost always the human one: understand the person in front of you, then figure out how to reach them.

There are many exciting new ways to utilize AI to offer more customized support to people as we move through stages of the transition but that still requires us to understand the people we need to reach.

My father couldn’t hear the thing I was trying to tell him. But when I wrote it down, he understood immediately.

That is the whole job.