How My Daily AI Briefing Became an AI Chief of Staff

I didn’t start out trying to build an AI Chief of Staff.

ChatGPT was actually one of the first AI tools I used. Then everybody started talking about Claude, so naturally I wanted to see what that experience was like too. 😂

That’s where I eventually started experimenting more seriously with daily executive briefings for my business.

The idea was pretty simple. I wanted one place to start my day and get a clear picture of what was happening. What was on my calendar? What needed my attention? What was coming up? What was important, and what could wait?

I used that system in Claude for months, roughly from February through July. And it was helpful.

But using it for that long also helped me figure out what I actually wanted from AI.

The briefing worked, but managing it started becoming work too

As the months went on, I started running into friction.

I had separate chats for different months. I would run into usage limits. Then I’d need to start another conversation, which meant figuring out how to hand off all the context from the previous one so the next chat understood what was happening.

And when you’re using AI to help you keep track of a business, that is a lot of context.

Client projects. Deadlines. Things I’m waiting on. Things I need to follow up on. Decisions I’ve already made. Decisions I haven’t made yet. Things happening outside of work that affect how much room I actually have.

At a certain point, I felt like I was managing the system that was supposed to be helping me manage the business.

Meanwhile, I was swimming in AI

Around the same time, I was preparing to teach a webinar for therapists on how to use AI in their businesses.

Preparing to teach something makes you look at it differently.

I wasn’t just casually using AI anymore. I was researching tools, testing use cases, and thinking about where AI genuinely helped a business owner and where human judgment still mattered.

So for a while, I was swimming in AI. 😂

And naturally, everything I was learning for the webinar started making its way back into my own business.

I would research something and think, “Wait. Could I use this for my own workflow?”

Then I’d test it.

That led me to use AI more often, not just for writing, brainstorming, or the occasional task. I started experimenting with how it could help me think through decisions, keep track of moving pieces, and support the operational side of my business.

And the more I tested, the more I started having these little “wait a minute…” moments.

This was really helping me.

I was starting to realize there was a much bigger use for AI in my business than I originally thought.

By July, I needed the experience to be more seamless

July was busy.

Vacation Bible School was happening at my church, I was still running my business, and there were a lot of moving pieces happening at the same time.

That’s when some of those little hiccups with my AI system stopped feeling so little.

I didn’t need another thing that required a whole process just to keep it caught up. I needed the experience to be more seamless.

So I started playing around with ChatGPT again to see what would happen if I brought the executive briefing system back over there.

For me, the experience was much better.

A lot of the hiccups I had been running into started disappearing. There were fewer steps between me realizing I needed something and actually getting useful support.

And because I had already spent months figuring out what I liked, what I didn’t like, and what I actually needed from an executive briefing, I wasn’t starting over.

I was bringing everything I had learned with me.

Something started clicking differently

The more context I gave Chat about my business and how I worked, the less it felt like I had to walk it through every single step.

It started making connections faster. It would suggest something I hadn’t explicitly asked for because it understood what I was trying to accomplish. It could recognize that something needed my attention without me having to completely reconstruct the situation every time.

I genuinely enjoyed using it more.

And that’s when AI started feeling different to me.

At first, it felt a little like having a virtual assistant I could give tasks to. I would tell it what I needed, give it the information, and get something useful back.

But over time, it started feeling like this whole extra layer of support in my business that I didn’t even know I needed or knew was possible.

I don’t want to spend ten minutes explaining everything just so AI can help me save ten minutes.

The more the system understood about how I worked, the less time I spent managing the AI before the AI could actually help me.

Somewhere along the way, the briefing became something else

What started as “What do I need to know today?” began to evolve.

I started teaching Chat how I prioritize. What I consider a glass ball versus a plastic ball. How I think about client commitments. What deserves to interrupt my day. What can wait. What I want surfaced and, just as importantly, what I don’t need to see.

I wasn’t just asking it to summarize my day anymore.

The question started becoming:

“What actually requires me today?”

And somewhere in that process, I realized I wasn’t really building a better daily executive briefing anymore.

I was building a Chief of Staff.

I didn't need another tool. I needed another layer of support.

That’s probably the part that has surprised me most.

I’m not talking about replacing the people I work with or handing over decisions that require my judgment. I still need humans in my business, and I still need to make the decisions that belong to me.

But when you run a lean creative business, a lot of context still runs through the founder.

Client work. Deadlines. Follow-ups. Ideas. Opportunities. Things you’re waiting on. Things you need to remember later. Decisions that aren’t urgent yet but will be soon.

I realized I needed something to help me hold all of that while I actually ran the business.

That feels very different from having a tool sitting there waiting for me to come up with the next prompt.

I’m still building it

I don’t have a perfect AI operating system that I built in one afternoon.

This has evolved because I’ve been using it in my actual business and noticing where I’m still carrying work that a system could help me hold.

Every few weeks, I find another one.

Oh, and did I mention I named my AI Chief of Staff? LOL

His name is Joseph.

The name was inspired by Joseph in the Bible, who was entrusted with managing Egypt’s resources and preparing for what was ahead. His story is one of wisdom, stewardship, and planning, even before the need becomes urgent.

And that’s what I want my AI Chief of Staff to help me do. Stay prepared, think ahead, and make better decisions with what’s already on my plate.

The newest thing I’m working on with Joseph is capacity.

Can I take this project? Am I doing too much? Where would this even fit?

Those are questions I’ve spent a lot of time mentally recalculating whenever a new opportunity comes in.

So now I’m teaching Joseph how I think about that too.

I’ll tell you about that next.

Final Thoughts

If you’re a creative business owner experimenting with AI, pay attention to the things you keep having to explain, remember, organize, or recalculate. You may not need another prompt. You may need to start teaching the system how you work.