Essay 01

Start with a bottleneck that already has an owner

You know you are supposed to be doing something with AI. Every vendor call, conference, and board conversation says so, and nobody can tell you where to start in a company like yours.

A midsize company does not usually have an AI problem. It has a work problem someone hopes AI will absorb.

At 50 to 500 people you already have departments, systems, and a few people who have tried a chatbot or turned on a vendor’s “AI” add-on. Starting with a strategy offsite, a company-wide license, or a custom model is how a quarter disappears and the old process is still the process.

Start in operations. Start smaller than that sounds.

Pick one process that happens every week. It should already have a named owner. It should produce something you can count: quotes sent, tickets closed, invoices sent, jobs scheduled, a report a person currently rebuilds by hand. If you cannot name the owner and the count, you are not ready to apply AI to it.

Then ask three questions:

Is the work repetitive enough that last week looks like next week?
Are the inputs already in a system (email, CRM, ERP, a shared inbox), or do they live in someone’s head?
In 30 days, how would you know this helped? Hours back, fewer errors, faster cycle time, less rework. Pick one.

If those answers are fuzzy, pick a different process. AI does not fix an unnamed mess.

What the first 30 days should look like

One process, one owner, one measure.
The owner keeps the job. AI is a step inside their workflow, not a side project in IT.
You retire or shrink a manual step. If the old step still runs in parallel, you did not start. You added work.
No company-wide rollout. No prompt library as the deliverable. No AI committee.

What to postpone on purpose

A firm-wide Copilot or ChatGPT purchase as the plan.
Building your own model.
An AI roadmap with a dozen workstreams.
Letting every department pick a tool this quarter.

Those can wait until one process is actually different.

The starting move is not a vendor demo. It is a one-page note: the process, the owner, the weekly volume, the measure. If you cannot write that page, you are not starting with AI. You are shopping.