The jump from solo operator to employer is one of the biggest structural changes a service business makes, and it's usually made under time pressure — too much work, not enough hands, an offer made faster than the paperwork behind it. A short list, worked through in advance, prevents most of the expensive surprises.
Before you post the job
- Confirm your business structure can legally run payroll (this is a five-minute call to an accountant, not a guess)
- Get workers' compensation coverage in place before the first day, not after
- Decide employee vs. subcontractor honestly — the tax and liability difference is real, and misclassifying it is one of the most common (and costly) new-employer mistakes
- Write down what the role actually does day to day, even informally — it becomes the job posting, the interview questions, and the 90-day check-in
Before the first day
- Set up payroll (a service that handles tax withholding is worth the monthly cost at this stage)
- Have a simple written pay agreement — rate, overtime, what expenses get reimbursed and how
- Decide who trains them and on what schedule, rather than assuming it happens by osmosis on the truck
What actually goes wrong
The failure mode isn't usually the hire — it's the business owner still trying to run every job personally while also managing someone else's schedule. The value of the first employee only shows up once you actually hand off work, not just supervise it more closely than before.