You hired the person. The next ninety days decide whether you bought a system or a dependency.
Days 1 to 30: understand before building
The temptation is a backlog on day one. Resist it. Small requests feel productive and they guarantee nobody ever looks at the whole picture, which is where the expensive leaks live.
What should happen instead:
- Access on day one. Read access to the CRM, the ability to create a webhook, a sandbox, the reporting. Waiting three weeks for a seat is the least defensible way to lose a month.
- Reading real records. Fifty of them, not the documentation. Documentation describes the process as designed. Records describe it as it runs.
- Sitting on calls. Sales calls and support calls. The gap between what the CRM says and what happens on a call is usually where the first project is.
- Mapping the funnel as it actually works, including the steps nobody wrote down.
The day 30 test: they describe your funnel end to end, name the biggest leak, and show you the evidence. If they cannot, either the access was late or the hire is wrong, and both are worth knowing now.
Days 31 to 60: one system in production
One. Not five. Narrow enough to finish, real enough to matter.
By day 60 it should be live, documented, with an owner who is not them, and an error route. The guidance from people who build these systems applies here too: start with the simplest thing that works and add autonomy only where it earns its cost.
The day 60 test: someone else runs it from the documentation, for a week, without calling them.
Days 61 to 90: the number moves
One number, explained. Plus a second thing in flight and a written backlog with reasons attached, which tells you they are thinking in priorities rather than in requests.
The day 90 test: they can walk you from the number back to what they changed, and forward to what they would do next and why.
What to protect them from
The ticket queue. The moment this role becomes the person who fixes things by hand, the systems stop being built. Route small requests elsewhere for the first sixty days.
Tool evaluations before the diagnosis. Vendors will find them. Nothing gets bought until the leak is named.
Being the CRM admin. Related and slower to notice. If they are the only person who can change a field, they will spend the year changing fields.
The signals it is not working
- Month two ends with nothing in production
- Only they can operate what exists
- They cannot name something they deliberately chose not to build, which usually means they are building whatever is asked
- Everything is described in tools rather than in outcomes
Any of these at day 60 is worth an honest conversation while it is still cheap.
The handover habit
The best version of this role produces things that survive its author. Ask for the runbook while it is being built, not at the end, and test it by having someone else follow it. A system nobody else can run is not finished, however well it works.
If you are still hiring
MitHub publishes open profiles with each person's deployments written out, including who operates them now.