AI is changing how work gets done faster than most teams can absorb it. The tools aren't the hard part. The hard part is people understanding each other well enough to build the right thing and use it. That's change management, and it's becoming one of the most important skills a Chief of Staff, COO or EA can bring.
I was talking with someone this week about the Chief of Staff role, and I said something I keep coming back to.
If we don't get more human with our teams, all this AI isn't going to work.
Not because the tools are bad. Many of them are remarkable. It's because a tool only helps if the people using it understand it, trust it, and see how it fits their work. That doesn't happen on its own. Somebody has to make it happen.
The same tool, a different story
I've written before about a friend at a large tech company who hated the AI tools her company rolled out. They were handed to her with no direction and no explanation, and she filled the silence with the worst possible story.
Then we talked about it from a different angle. What it could take off her plate. How it could make her better at the parts of her job she actually cared about. Same tool. Completely different reaction.
Nothing about the technology changed. The perspective did.
Every role speaks its own dialect
Here's something I've learned working across a lot of teams. Every role speaks its own language.
A salesperson might take an hour and forty-five minutes to explain something. I can say it in thirty. An engineer can say it in five. None of us is wrong. We just speak to our role and what we do. It's almost like a dialect.
That's fine until you try to build something together.
Recently I built a pipeline dashboard with a colleague in a client-facing role. On paper it was a tracking tool. In practice it became much more than that. It pulled in the operational support she didn't even know she needed, made her work easier, and made mine easier too.
But it only worked because we put real time into understanding each other. I had to learn how she thinks about her pipeline. She had to learn what I needed from the process to support her. It was a collaboration from the first conversation to the last, and that's why it's a tool she actually uses.
Communication isn't communication anymore
What I see a lot right now is people talking without hearing each other.
You can have a conversation with someone and give them every word. But unless they take the time to actually hear it, understand it, and see it from your side, they won't get it. And when that happens with AI, they build what they think you need instead of what you need. Or what the industry needs.
That's how you end up with tools nobody uses, rollouts that stall, and teams that quietly go back to the way they've always worked.
The gap isn't technical. It's human.
Why change management is the next big skill
For a long time, change management was treated as a specialty. Something you brought in a consultant for when a big system went live.
I think that's about to change. As AI keeps reshaping how work gets done, change isn't a single project anymore. It's constant. Every month there's a new tool, a new workflow, a new way of doing something people have done the same way for years.
Somebody has to translate between the dialects. Somebody has to understand the environment, not just the software. Somebody has to bring people along with honesty and care, so change feels like support instead of a threat.
That's going to become a core part of the Chief of Staff, COO and executive assistant roles, if it isn't already. These are the people who already sit between teams, read the room, and know how a message will land before it's sent. That's change management, even when nobody calls it that.
What it looks like done well
1. Listen in their language first.
Before you build anything, spend time in the other person's world. Learn how they describe their work, what they worry about, and what a good day looks like for them.
2. Build with people, not for them.
The best tools come out of collaboration. Bring the person who'll use it into the build from the start.
3. Translate, don't just announce.
The same change means different things to sales, engineering, finance and operations. Explain it in terms each group actually cares about.
4. Show the why, and what's not changing.
People can handle change. What they struggle with is guessing. Be clear about the reason, the impact, and what stays the same.
5. Stay human through it.
Check in. Listen to the pushback. Treat hesitation as information, not resistance.
The human part is the advantage
AI will keep getting better. The tools will keep getting easier. What won't get automated is the work of helping people understand each other and move forward together.
That's the work great Chiefs of Staff, COOs and EAs already do. It's about to become the part of the job that matters most.
If you're bringing AI into your company and want someone who can build the tools and bring the team with them, let's talk.
