Field Notes / Strategy
The AI questions you don't know to ask
People use AI for recipes, travel plans, and answering email. That is surface level, and surface level is fine. It just doesn't move a P&L.
Here is a question that does: analyze my HubSpot CRM and find the highest-intent leads I've missed.
Connect the CRM, ask the question, and it comes back with: call these people, in this order, on these days. Here are the emails to send each one. That's revenue sitting in software you already pay for. I didn't even know what I didn't know until I asked.
Why nobody asks it
Because you'd have to know AI talks to HubSpot in the first place, and everyone assumes it won't. There are a lot of assumptions like that, and every one of them has money behind it. The gap in most companies isn't tooling. It's knowing what to ask.
The highest and best use
The pattern behind every winning AI question is the same: find the work that is high-touch, high-repetition, has to happen, and nobody wants to do it.
In property management, that was lease audits. A new building means 100 leases, 30 pages each, one week of a good person's time, and charges still slipped through, like parking fees that never hit the accounting system. We built an agent. Five minutes. Nothing missed.
In a law office, it was client intake: 25 pages of intake instructions, written so simply anyone could run them, and nobody ever did. The playbook was never the problem. Somebody had to build the machine that runs the playbook.
Find yours in one meeting
- Ask each department head: what's the gnarliest thing you hate doing that has to happen?
- Listen for the groan. The groan is the sound of margin.
- Rank the answers by hours burned and errors made.
- Build the top one first, inside your own systems, and measure it.
Onboarding, contract review, checks and balances, reporting: the boring work is where AI earns its keep. Master it before it masters you.
Want this running in your business, not just in your notes app? Book a whiteboard session and bring your gnarliest workflow.