You Don't Have an AI Problem. You Have a Governance Gap.
Everyone deployed AI agents. Most companies can't govern them. Governance isn't a model setting — it's decision rights, escalation paths, and accountability. In other words, operations.
The Most Valuable Thing AI Can Do for Your Operation Isn’t Replace People. It’s Remember Them.
A friend sent me Pam Didner’s recent piece in Inc., “Forget Prompting. The Most Important AI Skill of the Next 5 Years Is Something Else.” Her argument stopped me because it lands exactly where I’ve spent my career living: the gap between what your best people know and what your organization can actually reproduce.
Her thesis is simple. The next real AI skill isn’t better prompting or vibe coding. It’s writing a skill file — a one-page document that tells an AI tool how to do a specific task your way, every time. Not a style guide. Not a prompt library. One task, your standards, your format, written down so the work runs the same whether or not the person who mastered it is in the room.
I’d put it more bluntly, from an operator’s chair: a skill file is institutional knowledge that finally stops walking out the door.
AI-Augmented Operations: A Field Guide for Founders Scaling Past Early Stage
There's a moment in every growing company where the founder realizes the operating system they've been running on — the spreadsheets, the founder-in-the-loop approvals, the tribal knowledge living in three people's heads — has quietly stopped scaling.
The team is bigger. The compliance surface area is bigger. The customer base is bigger. And the founder is spending more time on operational maintenance than on the strategic moves that actually grow the business.
This is the moment when most founders start thinking about hiring an operator. It's also the moment when a lot of them get distracted by a different question: “Can AI just do this instead?”
The honest answer is more interesting than either yes or no.
AI cannot replace operations. But AI can — and should — fundamentally reshape what operations looks like inside a company scaling past early stage. The companies that figure this out get a multiplier on every dollar they spend on operations leadership. The companies that don't usually end up paying for the lesson twice.
This guide is for founders trying to figure out the right way to integrate AI into their operations — without making the mistakes the early movers just made at scale.
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.
Good Process Is Invisible
Say the word "process" in the wrong room and watch what happens.
Screens don't go down. Eyes don't light up. What you get instead is a specific kind of stillness — the kind that means everyone in the room just added something to their mental list of things they're going to have to tolerate.
That reaction is data. Not about process. About what people believe process is.
They believe it's a rulebook. A stack of requirements. A manager's way of adding friction to work that was flowing just fine. They think of process as the ten-page document that nobody reads, the approval chain that slows everything down, the form that has to be filled out before anything can move.
Good Fences Make Good Neighbors: The Operational Case for Structure in a Flat Organization
There's a misconception that's been quietly costing growing companies for years. It usually surfaces around the time a startup hits 30–50 people. Leadership has worked hard to build a flat, collaborative culture, and they get nervous about anything that smells like “process” or “structure.” They worry that defining roles, building operating cadences, or writing things down will somehow undermine the culture they've built.
So they hold off. They keep doing what worked at 10 people. And then engagement starts slipping, execution gets sloppier, and the team that used to feel agile starts feeling chaotic. Leadership diagnoses it as culture drift and tries to solve it with more all-hands meetings, more values posters, or louder “we're a flat org” messaging.
The actual problem is upstream. The team doesn't need more flatness. They need clarity.
Operations Isn’t the Back Office. It’s the Growth Strategy.
There’s a moment every growing company hits. Revenue is climbing, the team is expanding, and the CEO is busier than ever — yet somehow everything feels harder. Decisions stall. Hiring is reactive. Compliance is a someday problem. The founder is in every meeting because nothing moves without them.
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.
Operations Is the Goalkeeper Position. Here's How AI Made Me the MVP.
Operations is the goalkeeper position — nobody notices the saves until one gets missed. How AI sharpened my goalkeeper instincts, and why sharing those wins with your team is the real MVP move.
Why Operations Is the One Role AI Can't Replace — and Why Founders Keep Trying
There's an assumption baked into a lot of early-stage thinking right now: that the operations function — the people who keep the company running — is the next obvious target for AI replacement. Founders are looking at their org chart, seeing the cost of an experienced operator, and quietly wondering if they can skip the hire and let AI cover it.
I understand the temptation. The tooling is impressive. The economics look good on paper. And there's no shortage of voices on LinkedIn telling founders that "ops is the first to go."
It isn't. And the companies finding that out the hard way are already starting to reverse course.
This is the piece I want every founder scaling past early stage to read before they make a workforce decision they'll spend a year unwinding.
The AI Layoff Reversal Has Started. Here's What Operations Leaders Should Take From It.
The companies that cut hardest in the name of AI are quietly rehiring. Here's what the data says — and how operations leaders can make the case for building over cutting.