Hand me the keys

I was sitting in a conference room in Las Vegas when I watched it happen for what felt like the hundredth time. The CEO of a membership company, call him Marcus, had just finished telling me about the $30,000 annual contract his team had signed with a major CRM platform. He talked about it the way you talk about a root canal. Necessary, expensive, something you endure.

His operations team had spent six months configuring it. His sales team had spent three months complaining about it. His developers had already built three temporary workarounds that were now permanent, load-bearing parts of his business.

I asked whether it fit his process.

He laughed. It fits a process, he said. Not ours.

I have thought about that sentence for two years. What Marcus was missing was not a better CRM. It was a person whose job it was to decide. Nobody at his company owned the technology decisions, so the vendor made them, and the vendor's process became his.

The technology is not the hard part

I have run the tech and marketing side of companies for twelve years. Membership platforms, healthcare design systems, conversion programs, a lot of websites, a lot of data. The honest thing I can tell an owner is that the technology itself is rarely what is broken. What is broken is that the decisions have nowhere to land.

Should the intake process exist in its current shape. Is the case management system you bought in 2022 still the right one. What gets built next, and in what order. Those questions keep arriving on the owner's desk, and the owner is a lawyer or a CPA or a clinician, not a technologist, so they get deferred. Deferred decisions become workarounds. Workarounds become architecture. That is how a $30,000 contract becomes a root canal.

What a fractional CTO is, for a firm that already has an IT company

Most of the firms I work with are law practices, CPA firms, clinics, and owner-led businesses. Almost all of them already have an IT company, and they should keep it. IT keeps the machines running and the data backed up. That work is necessary. It is not this.

A fractional CTO is where the deferred decisions go. I hold the roadmap, the architecture calls, the vendors, and whoever is doing the building. The firm gets a technical owner without the salary line, and the owner gets their desk back.

Hand me the keys

Here is what day one looks like.

You give me access. The domain registrar, the website, the practice management tool, the email, the spreadsheet that is secretly your database. I make a list of everything that is running and what each thing costs. Most owners have never seen that list in one place.

Then I make the first decision. Usually it is small. A form that goes nowhere gets pointed somewhere. A tool with no login for two years gets cancelled. A lead that has been landing in one person's inbox gets a second person who can see it. None of that requires a strategy deck. It requires someone who is allowed to decide and willing to be answerable for it.

That is what you are paying for. Not the tools. The ownership.

Why there is no big plan first

Owners sometimes ask for the whole plan before anything starts. I understand the instinct. They have been burned by agencies that billed for a deck and disappeared.

I do not write that document. By the time I arrive, every firm's stack is custom. Off-the-shelf tools wired together in ways nobody planned, held up by one person's habits. A plan written before I have touched any of it is a guess dressed up as a document, and it is wrong by month two. The weeks spent writing it are weeks nothing got fixed.

What I keep instead is short and stays true: the list of what the firm runs on, a log of every decision and why, and a roadmap that grows as the work does. The map draws itself from what is actually there.

What this series is

Every step of how I run an engagement, in the order it happens, pulled from my own Notion workspace. The fit call and why the most useful thing I can say in it is no. The workspace a client gets before the first real meeting. The research and the house rules that keep it honest. Why I do not write the big plan first. Scope written once as cards. A proposal the client can actually read, and the signed agreement that stays in lockstep with it. Public pricing. Kickoff questions sorted by who can answer them. Blueprints locked before anything gets built. The decisions log that saves the relationship. The team of AI roles that lets one person do the work of an agency. The data layer designed before the interface. The gates that clear before anything publishes. And after launch: local search, reviews done the compliant way, being citable, monthly reporting in the owner's units, and the lessons I write down the day I make a mistake.

Clients are anonymized throughout. A personal injury firm in Metro Detroit. A CPA practice outside Boston. The mechanics are real. The names and the numbers from their books are not here.

It is not a pitch. If you read all twenty-two of these and run the process yourself, good. The whole point is that the decisions get made by someone. I would rather it be you than a vendor.

Next week: the fit call.

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