The offer and the paperwork

The trial said yes. Now you make it real, and real means two things done properly: an offer in writing and a paperwork clock you actually run. None of this is hard. It is just unforgiving of forgetting, so here is the whole list.

The offer in writing

One page. The role in outcome terms, the four sentences from the role definition: outcome, measure, boundaries, buy-back, with the buy-back sentence for you, not them. The pay, the schedule, when and how they are paid, the first-ninety-days expectations including the day thirty, sixty, and ninety check-ins, and what happens if either side ends it early. Have them sign it and you sign it.

Writing it down is not bureaucracy. It is the job existing. An offer that lives only in a conversation will be remembered differently by both of you within a month, and the version in your head does not win the argument.

On the pay number itself: your instinct will be to offer the lowest number the candidate would accept. Resist it, slightly. Operators consistently report that paying a dollar or two over the local going rate for a role buys retention and care that costs far more than a dollar or two, and turnover is the most expensive line this module never puts on the stack directly. What the going rate is in your trade and town is rate-table material, and the business courses carry it lane by lane.

The paperwork clock

For a W-2 employee, these are the moves, roughly in order. Most take minutes.

Two legal edges to know while you are this small. Federal overtime law requires one and a half times the regular rate over forty hours in a workweek for nonexempt employees, so schedule a part-time first hire with the forty-hour line in mind, and do not quietly let weeks run long. And the major federal anti-discrimination statutes kick in at fifteen employees, twenty for age discrimination, so a first hire does not put you under them federally, but several states apply their own fair-employment rules from employee one. The rule that costs nothing: fair, consistent hiring from the very first person, documented the same way for everyone.

For a contractor, the list shrinks to a W-9 before first payment, a written agreement stating the scope, the rate, and the facts that support the classification, their own tools and methods and other clients, plus a certificate of their liability insurance when the work is on client property. And remember from the reporting change covered earlier: for 2026 payments, a 1099-NEC is due when you pay two thousand dollars or more in the year.

On payroll software, one honest note from the research: Gusto lists its contractor-only plan at thirty-five dollars a month plus six dollars per contractor, which is what a contractor-only first step costs on a mainstream app. Full W-2 plans cost more, and prices move; check current numbers when you set up. Whatever the price that day, it will be the smallest line in the loaded stack, and the one that prevents the most expensive mistakes.

The first week

Paperwork done, the first week is about one thing: the person believing they made a good decision, because week one is when buyers' remorse happens on both sides.

Day one, you are there. Walk the outcome statement together. Show, do not narrate. End the day early and tell them one specific thing they did well. A first day that ends with specific praise and no surprises is worth more than a day of policy documents.

By Friday, they have done the core loop of the job at least twice with you watching, they know exactly how and when they get paid, and they know who to text when something goes wrong. That is a complete first week. Anything else is decoration.

Then the real work of the first ninety days begins, and it is mostly your work.