Your AI Rollout Is a Change Management Project. That Makes It the COO's Job.
Most teams with AI licenses split three ways: a few power users, a lot of email drafters, and everyone who quietly stopped. Here's how a COO closes that gap.
What a New Chief of Staff Needs From You in the First 90 Days
A Chief of Staff borrows their authority from you. In the first 90 days, how much they can borrow is mostly up to you. Here's what to hand over, month by month.
How to Go From Chief of Staff to COO: Moving From Borrowed Authority to Your Own
A Chief of Staff makes sure decisions get made. A COO makes them and answers for them. Four moves that build the ownership before the title changes.
Don't Automate Out the Governance: What a COO and Chief of Staff Keep Human When AI Takes Over a Process
In an AI rollout, the Chief of Staff and COO decide which steps stay human. Here's how to automate a process and keep the approvals that make it trustworthy.
Automate the Workflow, Not the Role: Why AI Rollouts Need a Chief of Staff and a COO
Every founder wants AI to make the company faster. The people best placed to make it work are the ones who already know how the work runs.
Fractional Chief of Staff: What It Is and When It Fits
A Chief of Staff runs on being close to the CEO. So how do you rent one two days a week? Here's what you're actually buying, and when it's the wrong call.
How to Go From Executive Assistant to Chief of Staff: The Move Nobody Promotes You Into
Being a better EA won't make you a Chief of Staff. The move runs on a different kind of authority, and you can start earning it before the title changes.
Chief of Staff vs. Executive Assistant vs. Operations Manager: Three Jobs Founders Keep Hiring Into the Same Seat
Hire an EA and expect a Chief of Staff, and you'll be disappointed. Hire a Chief of Staff and use them as an EA, and they'll be gone in a year. The difference isn't seniority.
Chief of Staff vs. COO: Which One Does Your Company Actually Need?
Founders describe one role and name the other. The difference isn’t seniority or scope — it’s where the authority sits. Four questions that settle it.
Fractional Was the On-Ramp. Full-Time Is the Destination.
Why the operator role keeps getting rented — and why the smartest founders eventually buy.
The fractional operations wave was one of the healthiest things to happen to growing companies in years. It let founders who couldn't yet justify a full executive hire get real operational leadership on a schedule they could afford. It worked. I've done it, and I've watched it change how companies run.
But I want to say something that cuts against my own business model: for a lot of companies, fractional was never the destination. It was the on-ramp — the thing that finally showed them the role was load-bearing.
What I Actually Do in My First 90 Days
Most executives spend their first 90 days listening. I spend mine fixing.
That’s not a brag. It’s a structural reality. When a founder brings in a fractional COO or Chief of Staff, they’re not hiring someone to observe. They’re hiring someone because something — often several things — has quietly broken, and the company is scaling faster than its operating system can handle.
The “listen first” advice exists for a reason: premature action based on incomplete information is a real failure mode. But there’s another failure mode nobody talks about. It’s the executive who spends 90 days in discovery while the team keeps bleeding, the process debt keeps compounding, and the founder keeps wondering when they’re going to see a return on the hire.
Here’s what I actually do.
Where AI Actually Helps in Your Role: A Field Guide for Operations, HR, EAs, and Chiefs of Staff
The most common mistake I see people make with AI is starting with the tool.
They sign up for ChatGPT or Claude or Copilot, stare at the blinking cursor, and try to think of something to do. A few half-useful prompts later, they decide AI is overhyped and go back to their day.
That's a tooling mindset. And it's the wrong way in.
If you actually want AI to make a dent in your work, you have to start with your role, not with the model. Here's the framework I use, and how it plays out for some of the most common operational roles I work with.