A few months back I was on a call with Monica, the executive director of a nonprofit in Austin. She wanted to know how I use AI in my day-to-day.
I pulled up my screen and showed her something I call a dossier.
It was a Google Doc the AI had generated about her before our call — pulled from her LinkedIn, her organization's website, and a timeline of her nonprofit work. Nothing private. Just public context, organized nicely.
She looked at the screen and said, “Wow, that's so cool.”
The whole thing took 45 seconds to generate.
That was the meeting prep agent. But it's just one piece of a larger system.
What “Digital Chief of Staff” Actually Means
When most people hear “AI assistant,” they picture a chatbot. Something you type questions into and get answers back.
That's not what I'm talking about.
A digital chief of staff is a set of AI agents — each one handling a specific job that used to eat your time. Meeting prep. Follow-up emails. Introduction drafts. Daily briefings. Task creation from spoken commitments.
You still make every decision. You review everything before it goes out. But the legwork — the research, the drafting, the coordination — that all happens in the background.
Think of it as AI digital employees. Not a single magic tool. A small team, each one trained on one job.
The Three Jobs That Changed Everything
Here's the specific setup I use most, and the one I now help clients build.
Job 1: Meeting prep in 45 seconds
Before any first meeting, I get a Google Doc on the person. LinkedIn data, professional history, org context, sometimes a personalized visual. I scan it for 45 seconds before I join the call and I'm up to speed.
Without this, I was either going into calls cold or spending 10-15 minutes manually looking people up beforehand. For someone who has 5-8 meetings a day, that adds up fast.
Job 2: Follow-up emails before I leave the room
The moment a meeting ends, the AI has already drafted the follow-up. It pulls from what was said in the transcript and writes in my voice. I open my inbox, read the draft, make any edits, and hit send.
I built a daily briefing system for a VC friend that does something similar — normally it would take a human assistant 20 hours a week to research every person he's meeting, find old email context, and summarize the latest news on their companies. Now he gets a prep doc every morning and spends his time on strategy instead of inbox archaeology.
Job 3: Introduction emails that used to take 20 minutes
I make a lot of introductions. I care about them being thoughtful — not lazy “you should know each other” emails with no context.
That used to take me 20 minutes per email. I'd look up both people, think about what they have in common, write something personal.
Now I just mention the name. The agent knows both people from my CRM and past transcripts. It drafts the email. I review it. Done.
20 minutes down to about 90 seconds of review.
The Concept Behind It: Agent as Teammate
What makes this work is not the individual tools. It's the mental model.
Most people build AI workflows as one-off automations — “if this happens, do that.” That's fine for simple stuff.
But a chief of staff is not a flowchart. It's someone who understands your priorities, remembers context across conversations, and knows when to act versus when to ask.
That's what I'm aiming to replicate. I think of this as building an agent as a teammate — aware of who you're meeting, what you've committed to, what your calendar looks like, and what tone you use when you write.
The more context the agents have, the better the output. This is why I keep a master context document — a single file that tells the agents who I am, what I care about, how I communicate, and what my current priorities are. Every agent reads it.
What People Save When They Set This Up
The number I hear most often from people who've implemented this: 20 hours a week.
That's specifically the admin work that wraps every meeting — prep research, follow-up writing, intro emails, CRM updates, task logging.
None of that is hard work. It's just work that eats time.
And the interesting thing is, once it's automated, you realize how much of your day used to be spent on stuff that wasn't actually your job. Your job is the thinking, the decisions, the relationships. The prep and the follow-up are infrastructure.
How to Start Building Yours
You don't have to build 14 agents at once. I didn't.
I've been using Lindy since early 2025, and my current system is the result of incremental improvements over months. I built one agent. It worked. I built another. Iterated. The system I have now is not something I sat down and architected in a weekend.
A good starting point:
- Pick one meeting each week where you wished you'd been more prepared going in
- Build a prep agent for that meeting type — ask for LinkedIn and org context plus one talking point
- Run it for two weeks. See how it feels.
- Then tackle follow-ups.
One agent at a time. That's how you get to a full system without burning out or building something that falls apart.
The goal is not to automate your personality. It's to handle the grunt work so your actual personality has more room to show up.
Want to see a digital chief of staff built live? I run one-day AI workshops where we build your first agents together. Drop me a note if you want details on the next one.
